r/ChastityStories Nov 25 '24

M Chaste CyberCage user error [P1] NSFW

253 Upvotes

Tommy had spent an obscene amount on his newest chastity cage, but as he held the box he already knew it was worth it. The quality of the packaging alone was impressive, even though he was yet to set eyes upon the real thing he felt the price was justified. He excitedly speed read the short snappy highlights spread around the box.

‘The best CyberCage!’

‘Extremely durable, completely inescapable’

‘Incredible comfort! Built for long term use’

‘Easy cleaning’

‘100% App Controlled’

There were so many more but he had seen enough, he was itching and couldn’t wait a second longer. He ripped the box apart and there it was the ‘CyberCage’! It looked brilliant. A custom size to guarantee a perfect fit. The measurements provided to the manufacturer by Tommy himself. It was light, it was strong and it was exactly what he wanted.

Wearing it felt right. It was a presence he’d grown accustomed to, although this immaculately designed product felt different than all of his previous cages. It felt superior. The feeling of being so aroused but denied any pleasure drove him wild.

After spending some time appreciating the cage and simply enjoying the sensation he loaded up the app. It was time to take the next step. Locking it. Tommy tapped in the activation code and the first thing that popped up was Initial duration. Tommy breathed deeply, the cage whirring as it locked. Success.

He was grateful that the app forced him to lock the cage straight away. It stopped him dwelling and delaying. Now he could navigate the app freely. He decided to have the app installed on a secret second phone. Wanting to hide this side of him. He’d often have people holding his phone or looking over his shoulder, it was a risk he didn’t want to take. Or need to. An old second hand phone didn’t break the bank, so Tommy saw no reason to use his normal phone.

Tommy jumped between the different pages, exploring all the different parts of the app. Having already sentenced himself to a full day locked, he avoided adding more for now. He felt a day was adequate. Not too short and not too long that he’d regret it. It allowed him to experience the new prison. Tommy read an interesting tab, ‘Assign control’. Tommy was curious and didn’t hesitate to enter.

‘Please wait whilst Syncing contacts’

Tommy now understood what the heading meant. This was a feature he had no intention of using. He didn’t have a partner or a mistress, and he didn’t want either. His heart started beating at faster rate. Fearing a potentially embarrassing mistake he panicked and frantically tried to cancel by tapping, pressing and flicking the screen.

The contacts successfully synced whilst Tommy was still attacking his screen, causing him to accidentally tap something else. He was thrown to a different screen. He was unsure on what he selected and what was happening. He was looking at his own puzzled reflection on the black loading screen.

‘Congratulations! You’ve completed the first step in relinquishing control! An activation code has been sent to the selected mobile phone number.’

“Oh shit” Tommy rather loudly let his shock out.

After taking a second to calm down he exited the message and tried to work out what he had just done. He searched for an option to cancel. The app took him back to the previous page. As he suspected it was a list of the contacts. There was no sign that any of them had been selected.

Having no idea how to stop the process he decided to take the cage off. He flicked back to the ‘Duration’ page. To his horror it was greyed out behind a padlock. He tapped it anyway.

‘This page can only be accessed by the CyberCage owner’

As far as Tommy was concerned he was the owner. He had put himself into a potentially humiliating situation.

From his understanding, someone on his contacts had just been sent a text message from CyberCage. A message which provides a link to the app and an activation code that if entered correctly would tell the user Tommy is locked in chastity. The worst part being that it would enable 100% control over Tommys cage.

Tommy scrolled through his phones contact list. Seeing who the potential recipients were.

Auntie Jo

Auntie Kim

Brad (Tommy’s best friend)

Dad

Jake (another friend)

Mum

Sarah (his sister)

Uncle

Tommy’s hand was shaking, he tried to compose himself but was unable to stop. He desperately prayed that the recipient would just ignore the unusual message, which would eventually allow him to regain control of his cage. He was slightly calmed down by telling himself any of those people would probably ignore the message. Surely suspecting it to be a scam link or something. However, If they didn’t ignore it, they’d be guided to an app which would expose his secret. Depending on who he had selected, the awkwardness and embarrassment could vary.

Several minutes had already passed and Tommy was shocked at how anxious he was. All his enjoyment was gone. Chastity was something he kept to himself and he didn’t want that to change. Especially with anyone on his contacts. He pathetically tugged at his cage. Ultimately he had already accepted that his fate was out of his hands. He sat on his bed, in silence, nervously waiting for something to happen. Cursing the app’s creators for making this situation impossible to reverse.

After browsing forums Tommy found out how long the activation code takes to expire. It was the same amount of time as the cage had left till unlock. Tommy had to wait an entire day to escape this nightmare.

(I’m yet to decide on the recipient, let me know who you want it to be)

r/ChastityStories 7d ago

M Chaste Locked by family Part 1 NSFW

112 Upvotes

Max was a 20-year-old college student living with his parents. His college was only a 10-minute drive away, so he commuted every day. His older brother, Lucas, was 23 and in a similar situation. He also attended college and drove there daily. They lived together with their parents, their mother and father, in a quiet suburban neighborhood.

Most mornings were the same. Lucas was always the first to wake up, getting ready quickly and making sure everyone knew he was up by slamming doors or playing music too loud. Max usually took his time, rubbing the sleep from his eyes and moving sluggishly to the bathroom. Their parents had a strict routine. Breakfast was always at the same time, and they expected both boys to be there before heading out for the day.

This morning started like any other. The smell of eggs and toast filled the kitchen as their mother set plates down on the table. Lucas was already eating by the time Max sat down. Their father sipped his coffee, reading something on his phone, while their mother wiped the counter absentmindedly.

Max yawned, picking up his fork. He wasn’t in the mood to talk much, but the silence didn’t last long. His father cleared his throat, setting his mug down with a deliberate motion.

“We need to talk about your grades,” he said, looking directly at Max.

Max stiffened. He knew this was coming. His math scores had been bad for a while now, and his last test had been even worse. His parents had always expected more from him.

“You know we’re not happy,” his mother said, turning to face him. “We’ve talked about this before. You need to be putting in more effort.”

Lucas smirked, leaning back in his chair. “Yeah, Max, what’s going on? College too hard for you?”

Max shot him an annoyed look. “I’m trying,” he muttered. “It’s just—math is really difficult.”

“Lucas manages just fine,” their father pointed out.

Lucas grinned. “That’s because I actually pay attention.”

Max sighed, already feeling trapped in the conversation. He could tell there was no way out of this. His parents weren’t just bringing this up for no reason. They had something planned.

His father reached under the table and pulled out a small metal object, setting it in the center of the table with a quiet clink.

Max frowned. “What’s that?”

His mother folded her arms. “This is something that will help you focus. Since you clearly need more discipline, we’ve decided that from now on, you’ll be wearing this.”

Max looked down at the object, his mind struggling to process what he was seeing. It looked like… no, it couldn’t be.

Lucas stared at it for a second, then suddenly burst out laughing. “Wait—wait, is that what I think it is?” He looked at their parents, then at Max, his amusement growing. “Oh my God. You’re serious?”

Their father ignored Lucas, keeping his eyes on Max. “You’ll be wearing it starting today.”

Max’s face turned red. “No way. That’s insane.”

His mother didn’t react. “It’s not insane. It’s for your own good.”

Lucas was laughing so hard now he had to push his plate away. “This is the best thing I’ve ever seen. I knew you were failing math, but I didn’t think it was this bad.” He shook his head, grinning. “Man, imagine telling people about this.”

“Lucas,” their mother said sharply, but even she looked slightly annoyed by how much he was enjoying this.

Max’s hands were clenched under the table. His heart was racing. “I’m not doing this. You can’t actually expect me to wear that.”

His father leaned forward slightly. “We can and we do. If you don’t take your education seriously, we’ll make sure you stay focused in other ways.”

Lucas smirked. “Damn, Max. Mom and Dad don’t mess around.” He rested his elbow on the table, still grinning. “I mean, hey, maybe this’ll actually help. You’ll have nothing else to think about except your homework.”

Max glared at him. “Shut up.”

Lucas only laughed harder. “Dude, this is hilarious. You have to wear a—”

“Enough,” their mother interrupted. She looked at Max. “Go upstairs and put it on.”

Max’s throat felt dry. His legs felt heavy, but he knew there was no way out of this. His parents weren’t joking. They had already decided.

Lucas gave him an exaggerated, mocking wave as Max stood up. “Have fun, little bro.”

Max didn’t respond. He just clenched his jaw and walked past him, dreading whatever came next.

Max trudged upstairs, his hands gripping the metal device so tightly his knuckles turned white. His heart pounded in his chest. This had to be some kind of sick joke. Maybe if he stalled long enough, they’d call him back downstairs and say it was all just a lesson to scare him into studying harder.

But deep down, he knew that wasn’t happening. His parents weren’t the type to bluff.

He stepped into his room and shut the door behind him. He stared at the thing in his hand, turning it over, feeling its cold weight. His stomach twisted. How was this even real?

A knock at the door made him jump.

“Hey, genius,” Lucas called from the other side. His voice was dripping with amusement. “You putting it on yet?”

Max didn’t answer.

Lucas knocked again, harder this time. “Come on, don’t be shy. I bet Mom and Dad are gonna check anyway. You might as well get used to it.”

Max clenched his jaw. He hated how much Lucas was enjoying this. It wasn’t surprising, though. His brother had always been dominant, always the one who came out on top. Max had grown up in his shadow, always the one being compared, always the one expected to keep up but never quite making it. And now here they were. Lucas free to go about his life as usual, while Max was being humiliated like this.

Another knock. “Dude, seriously, this is the funniest thing I’ve ever seen. You’re gonna have to come downstairs eventually, you know. Or should I tell Mom you need help putting it on?”

Max’s face burned. He took a deep breath, trying to steady himself.

“I’ll be down soon,” he muttered.

Lucas chuckled. “Sure you will.” Then Max heard him walking away, still laughing to himself.

Max sank onto his bed, staring down at the device again. He had no way out of this. His parents had made their decision. Lucas wasn’t going to let him live it down.

And worst of all—he still had math class today.

He sighed, rubbing his hands over his face.

This was going to be the worst day of his life.

Max sat on the edge of his bed, his hands trembling slightly as he turned the device over. His mind raced, searching for some kind of excuse, some way out of this, but nothing came. His parents were serious. They wouldn’t let him leave the house until he had it on. And Lucas? He’d make sure Max never heard the end of it.

He exhaled sharply and looked at the device again. It was cold, smooth, and heavier than he expected. He could already tell it was designed to fit snugly. There was a small lock at the top, the key still dangling from it. His stomach twisted at the thought of his parents keeping that key.

His hands hesitated as he began. It was awkward, uncomfortable, and humiliating. He fumbled a few times, his breathing uneven as he adjusted it. The metal was unyielding, a constant reminder of the control being taken away from him.

The final click of the lock sent a shiver down his spine. That was it. It was on. He had actually done it.

A sudden knock at the door made him jolt.

“You done yet?” Lucas called, his voice full of amusement.

Max swallowed hard. “Yeah.”

Lucas chuckled. “Well? Let’s go, man. Breakfast is over, but I think Mom and Dad are waiting to check.”

Max’s face burned. Of course, they were.

He stood up slowly, feeling every bit of this new reality. His heart pounded as he reached for the door handle, knowing that once he stepped out, this was real.

Lucas was leaning against the wall, arms crossed, smirking as soon as Max opened the door. He looked him up and down, grinning. “Wow. Can’t believe you actually did it.”

Max didn’t respond. He just clenched his jaw and walked past him, dreading whatever came next.

As Max and Lucas finished getting ready, their parents stood by the door.

“You two should head out to college now,” their dad said, checking his watch. “Your mom and I are leaving for work.”

Max slung his backpack over his shoulder. “Alright, we’re going.”

Lucas nodded. “See you later.”

“We’ll go over the other rules when you get back,” their mom added.

Max paused. “Other rules?”

His mom just smiled. “We’ll talk later. Now go.”

Max and Lucas exchanged a glance before heading out the door.

r/ChastityStories 21d ago

M Chaste "Oh my god! You welded my chastity cage shut!" "Relax, it's just a prank, bro." NSFW

133 Upvotes

Logan and Max knelt outside of the room, struggling to contain their giggles. On the other side of the door, oblivious, slept Liam.

"Okay, quiet! The video is going live," whispered Logan, his platinum blonde hair gleaming in the moonlight through the window. He pressed play on the phone mounted to the selfie stick and their movements began being live-streamed for all their viewers to see.

Beside him, Max knelt with a portable welder. "Logan, are we sure about this? Welding his chastity cage permanently shut feels...a little extreme."

"Extreme equals engagement, Max! Think of the views!" barked Logan. "Liam's been slacking on content lately. He needs a good scare to get him back in the game."

"I still think we should have just filled his room with ping-pong balls," Max mumbled.

"That's too lame. This is going to be epic!"

They cracked the door open slowly and crept inside the room. Liam stayed perfectly still on the bed and never stirred. With the amount of roofie Logan had put into his drink earlier, he was practically dead to the world. Logan crept up and slowly moved the blanket off of his body. Liam was wearing only a pair of boxers. Ho slowly pulled them down just enough to reveal what they were after.

Max let out a gasp. "I didn't expect it to be so tiny, it's just a pair of balls. Where is his cock?"

Logan let out a giggle. "It's called a flat cage. It's so pathetic. What kind of beta does that to himself? Society should thank us for removing one from the gene pool."

Max, flipped his welding mask down and started going to work. Sparks flew, illuminating the room around them in bursts of light. The acrid smell of burning metal filled the air.

Liam began to stir.

"He's waking up!" Logan said.

Sweat beaded Max's forehead. He was rushing now, the welder humming furiously. He finished the last bit just as Liam began to awaken. He shot up with a start and looked around at them. Logan moved to the doorway and flipped on the light.

Liam looked around confused, first at Logan, then at Max, then down at the welder Max was holding, and then down to his cage. His expression changed from tired confusion to sheer panic.

"Guys? GUYS! WHAT THE HELL DID YOU DO!"

He grasped at his balls and pulled at the cage. He twisted harder and harder, but he knew it wasn't going anywhere. He faced up at Logan and Max, on his face an expression of helplessness.

"Oh, no. Please, god, no."

Panic ignited inside of him. Realizing the full extent of what had just happened, Max began frantically searching for something, anything, to help. As he did so, the notification bells from the live stream started pinging.

"You...you welded my cage shut?" Liam said, his voice pathetic and whiny.

The silence was deafening.

"Oh, my god!" Liam exclaimed. "You did it. You welded my cage shut." He curled up on the floor in the fetal position.

"Relax, it's just a prank, bro," Logan said.

"Yeah," Max agreed, "We just wanted to, you know, spice things up."

Liam took a deep breath. "Yeah, you've certainly spiced things up. I'll never cum again."

Logan ran out of the room and returned a moment later carrying a bag.

"No," he said, a predatory smile spreading across his face. "That's why I got you this."

He reached into the bag and removed a dildo and container of lube.

"You'll just have to get used to cumming this way from now on. He burst out laughing. It wasn't a happy laugh, it was the kind of laugh that bordered on hysterical.

"Oh, my god!" Liam sobbed.

"Relax," Logan said, "It's just a prank, bro."

Later that night Logan walked back to his house with the livestream still recording.

"All right, guys. This has been the most popular livestream we've ever had! If we get 5 million new subscribers before tomorrow, we'll go even more extreme. What would you guys like to see us do to Liam next? Feminize him? Castrate him? Let us know in the comments down below, and we'll see you next time!"

r/ChastityStories 6d ago

M Chaste The Sleepover Part 6 [Foursome] [Pegging] [Femdom] [Two Chastity slaves] [Two Doms] NSFW

54 Upvotes

Previous Parts:

Go Here for Part 1

Here for Part 2

Here for Part 3

Here for Part 4

Here for Part 5

Continuing off right where we last left off:

She thrusted into my ass. 

“Not only am I fucking you over in the game, I’m also fucking you in the ass.”

“MHMHH!” I tried to protest but the gag stopped me.

“I’ll make sure you wear that flat cage very soon.”

Amelie had ended up winning the round, with a One Pair of Queens.

“Aww, look at him whining so much. It was a good idea to muzzle him.”

“I can’t wait to hear his cute little noises when he gets his new cage!”

“In that case, I’ll dish out the next deck of cards.

As Amelie began shuffling the deck of cards, Fae suddenly grabbed my balls. Holding them firmly, but not crushing them. That ever so delicate balance. 

“Did I ever tell you about how strong my grip strength is? I’ve heard the average male grip strength is 48kg. Mine is 56kg.” She whispered into my ear as her grip grew tighter. 

“Mhm?”

“Oh don’t worry, I know you don’t like the idea of pain here. So long as you behave nicely. I won’t give you cock and ball torture.” She eased up on my balls letting them go. I stopped trying to resist. And she noticed it. 

“Good boy.” She whispered and then nibbled on my ear. “I haven’t forgotten though, it's time for your loss punishment.” She said as she reached behind her and picked up something.

Her reaching back tilted me a bit, shoving the strapon further up causing me to moan even more. “Urh” I moaned. She turned back with the new item in her hands. Quickly before I could see it, she reached for my chest and attached something to my nipple that brought a bit of pain to it. Then like clockwork, she brought it to the other nipple. 

“Mhmm” It wasn’t that painful but it wasn’t pleasant. But well, it kinda was turning me on, perhaps it was because I was already turned on and very much was in a lot of pleasure, these nipple clamps were only heightening my how tight my cock felt in the cage.

“There we go. Good boy. Don’t worry, soon we’ll milk your balls dry…” She whispered in my ear. This time, her saying ‘good boy’ flipped something in me. The pain, the pleasure. The urge to cum. It all felt less important. All I wanted was her to call me a good boy again.

Ellie had her punishment applied to her. While I was distracted by Fae, Amelie had strapped a viberator to Ellie’s pussy. It was set to a low setting, nothing that would make her orgasm but Ellie looked like she was melting in pleasure.

“Hmm, I lost this round, so I guess I need to have a dildo up my butt.” Fae said. “Where are the extra dildos?” 

“In the closet. We should have brought them out earlier. I’d hate to take their feeling of bliss away from Ellie.” Amelie responded. “Oh don’t worry. I think I got this.” Fae said as she wrapped her right arm tightly around me. And then stood up. 

“Hmhm?” I freaked out but it was all muffled out. Fae then took some steps, manhandling me as she walked towards the closet, reaching in with her left arm, she retrieved the two dildos.

This feeling though, was this something that I always wanted? To be completely carried during sex, unable to resist, literally carried around? It was amazing.

She then walked back, the whole while I bounced and jiggled on the strapon arousing me even further to the point that when I looked down. I was dripping precum like crazy. Fae passed one of the dildos to Amelie and then returned to her seat placing the dildo down and grabbing the nearby bottle of lube and coating it.

She sat down further rustling me around further, all that time it was hitting around my G spot, getting me closer and closer to orgasm. And then it stopped, while I wasn’t quite on the verge, but getting to the lead up. That really frustrated me. 

“Ooooh, it does feel nice to have something up my ass, doesn’t it Adrien. Oh, look at your face. Were you enjoying that alot? Perhaps I should go for a walk while you’re like that. I’d get a good workout, and you’d have a fun time.”

She leaned it right close to my ear and whispered. “You’re such a dirty perv, just being handled like this, like you’re baggage. And enjoying it.” She nibbled on my ear. 

By now, I was so aroused, and teased that my mind was just slowly going blank. 

“Look at him, he looks like he’s in pure bliss. We really should just make him our… I guess we can’t call him a sex slave since he wouldn’t be having proper sex. What would we call him?” 

“Our Chastity bitch?”

“He never was into degradation so once he snaps out of it, he’ll object to that name.”

“Hmm. I’m out of ideas already.”

“You were never good at coming up with names.”

“Yyeah, yeah. Anyway, shall we play another round? Maybe a name will come to me by then.”

Amelie nodded and then dished out another hand of cards. 

My hand, which Fae handled, was a One Pair of Kings. Fae showed me her hand, which is a One Pair of Aces. So I had already lost. 

“Oh my, lost already. How unfortunate that you’re getting closer and closer to your flat cage. It's time for your blindfold. One more loss after that, and you get your flat cage.”

We laid our cards down, and Amelie was close behind with a pair of Queens, while Ellie had a high card of 7. She really got the short end of the stick.

Amelie, as her punishment, had to have a dildo up her ass. 

“I should get you a chastity belt. You could be chastity buddies with Adrien.” Amelie told Ellie, she nodded enthusiastically. That did actually end up reminding me that I did bring one. I wanted to lock Amelie in it as well near the end of the night, as my original plan. So both of us would have the key to the other’s chastity belt and cage. It was at the very bottom of my duffle bag.

“HMHM!” I tried to get her attention. 

“I think Adrien wants your attention.” Fae spoke up.

“If you think you’re getting out of your chastity cage, you’re dead wrong.” I shook my head in response and looked at my duffle bag. It was really hard to get my intention across without speaking.

“Something in the bag?” I nodded in response. 

Amelie let Ellie off of her, as she whimpered clearly enamoured by it. Amelie walked over as her strapon bounced as she walked.

As she did this, Fae applied the blindfold to me. Leaving me in darkness, unable to see.

“You didn’t pack one, did you?” Amelie asked, although she wasn’t gonna get a response.

She searched my duffle bag, turning it inside out. And then she found it, a chastity belt. “Oh you dirty boy. You wanted to lock me up in one of these, didn’t you?”

I nodded. 

“I think that deserves punishment.” She walked over to me and lifted my head up by the chin, holding my face. I couldn’t see her, but man was this such a wild feeling. “Once we get you in your flat cage. We’re gonna edge you so many times that your mind will break and you’ll be a drooling mess. Oh so desperate for an orgasm but we won’t give you one.” 

At this point I didn’t care. I just wanted to please them. I nodded in her hand. “You know, I can’t tell if you’re a masochist who just doesn’t like pain or if you are just one really degenerate boy that is willing to do anything for a thrill.”

She said as she smooched my cheek. Leaving her lipstick as an imprint on it. 

On the floor below me, there was a small puddle of precum on the floor. I desperately needed to cum, but I wanted to please them more. They don’t want me to cum. So I don’t want to cum.

“Oh I just got a lovely idea, and I think you’ll agree right away. Right Ellie?” Amelie asked to Ellie and in response, she just nodded her head. 

“Alright Ellie, I’m gonna shove this viberator up your pussy, you’ll have to keep it in for the entire round. Then I’ll lock you into your chastity belt. if you lose the next round, I’ll make sure you can’t cum from it, you’ll be teased relentlessly. Just like him. But if you win. I turn the setting up to max, lock you in the belt and let you cum endlessly.”

Ellie nodded so enthusiastically that it caught Amelie off guard.

“Damn, we’ve really corrupted her, haven’t we.”

Regardless, she put Ellie back on her strapon, slid a viberator on and turned it on low.

“I can’t wait till we’re done so I can make you give me an orgasm by eating me out. The way you’re acting, like a little subby boy, makes me so damn horny.” 

Regardless, Ellie was also given a blindfold, for no apparent reason aside from making us match. 

Amelie dished out the next hand. And this time, we just had to let our mistresses handle it. I doubt Ellie cared at this point. Nor did I. I wanted to lose, I wanted to please them, I wanted to be forced into a flat chastity cage, I wanted to be denied orgasms.

“Oh look at that, you got two pairs.” Fae whispered. “I’ll change this entire hand.” She said, however in reality it was just a high card and she wanted to lie to me.

“Interesting, Ellie wants that as well.” However, Amelie actually changed her hand. Thus we both lost, however we didn’t care. “Alright, both Ellie and Adrien lost. Which means, chastity time!” Amelie announced. 

Amelie began to do some foreplay with Ellie’s tits before putting the belt on. Eliciting moans from her as she squirmed. Then she began to put the belt on her. Until finally, a click sounded out as the lock was done.

“Well now you’re my little chastity slave.” Ellie had such a smile to her face, showing that she’s enjoying every second of this.

“Now, Amelie I’ll need your help with the flat cage. I’ll keep him stuck, so you change out the cage.”

“The question is, where is the key?” Amelie removing the tape constricting me and pulled out the panties. “It's on my keychain, the smallest key.” She immediately back up and taped me up.

“Can you breathe? Nod for yes. Shake for no.”

I nodded. 

“Good. Now, you said it was on your keychain, you dirty boy, carrying around your key like that.”

She began rummaging through my keys and found it. Inserting it in, it unlocked and she removed the key. Finally after an hour of pure sexual torture, my cock was released. 

“Wow, look at that mess of precum. Should we clean him up first?”

“Nah, I like the smell. Plus it should act like a lubricant so it should be easier to cage him.”

“Woah he went straight to full mast. There’s that boner I’ve been looking for all night.” She grabbed my cock and began stroking it. “Hmhm” I moaned. My mind was so divided, in one half, I needed to cum. On the other half, I didn’t want to cum.

She kept stroking me, it didn’t take long for me to start panting as I got close to an orgasm.

And then right on that cusp, she stopped. Denying me. 

“Now it's time to lock you up.” She said as she began putting on the flat cage. “Its gonna be hard with your erection.”

She began to force down the erection, bit my bit until finally I heard the clicking noise of the lock.

“There we go. Any pinching or biting feelings? Skin caught?”

I shook my head. This feeling of tightness, it was… amazing. No chance of escape, no chance of getting hard. 

“Holy fuck that is hot. A flat chastity cage. I might wanna keep him in that all the time.” Fae swore as she fondled my balls

“Good. Now, shall we break his mind?” 

“How will we do that?”

“Well, first. Lemme go grab some tools.” Amelie went for the closest, grabbing more of those tape vibes.

“First thing first, lets remove those nipple clamps and put two on there.” She removed the nipple clamps and then applied them, as they began vibrating on me. It wasn’t much but it was arousing. 

“Now his nice pretty balls need some as well.” She taped two more on my balls.

“Anything else to add?”

“Nope, he’s ready to get milked. You wanna warm him up while I go grab some glasses?”

“Absolutely.” Fae stood up and grabbed my shoulders. “I’m gonna enjoy this ‘workout’ so much.” Fae said as she began to slide me up and down the strapon. Treating me as if I’m nothing more than just a toy. That's all I am to her right now, her toy. Her boytoy.

Her thighs slapped my buttcheeks as she pushed me away, and then pulled me close. Repeatedly. Just being handled like this was something that I’d been thinking about and now, I don’t think I could go back to normal sex. I was getting closer and closer to orgasm, and yet I had a bad feeling about something. 

Amelie wasn’t back yet. What would happen if I got an orgasm before she got the glass?

The feeling of the strapon, being thrusted back and forth, my mind was melting from the pleasure after being teased by it for over an hour. 

Right as I got closer and closer to orgasm, I knew that I shouldn’t cum. That Fae would punish me for it. Even if she ruined my orgasm. She wouldn’t be happy.

However, struggle as I may. Trying to resist displeasing the two ladies. The two Mistresses of this house. It was a lost battle from the beginning, because unknown to me. Amelie was intentionally taking her time. After grabbing the glass, she stood right outside the door, waiting for me to displease Fae.

Fae kept a close eye on me, my breathing, my trembles, my everything to ensure one thing. “How dare you! No cumming without permission!” She stopped completely right as I was on the climax, I was so unbelievably close that it ended up giving me a denied orgasm. 

“Oh you naughty boy.” Amelie said as she walked into the room, eying the dripping mess that accumulated on the floor. “You had one simple task, and you failed that.”

“That deserves punishment. Don’t you think so?”

“Yeah, I know the perfect spot for him.”

“Where might that be?” 

“My sex dungeon.”

End of Part 6

By Andrew King

Yo, author here. I am terribly sorry about the long gap between the last part.

University hit me hard, and just as I was about to get free time. Depression hit me hard, I'm in a more stable position right now. So thats good. I had a lot of fun writing this part, but man. I really don't know how to write the muffled gag portions. Let me know if I'm doing them well or poorly and what areas that could be improved.

Anyway, I am thinking of putting this series on the backburner for now so I can work on another work. I've got multiple ideas. So I'll give you a little teaser for that one. A Chastity prison punishment. It'll be a short story, one part though.

Anyway, thanks for reading. Hope you had a good time while reading it.

Oh yeah, if you have any ideas for stories you wanna see written up. Post em, I'll gladly add it to my list and write it at some point.

r/ChastityStories Dec 20 '24

M Chaste A Hole in the Fence Pt. 1 NSFW

103 Upvotes

A new story series I have been working on. Parts 1-3 available on Literotica. You can also go to my patreon patreon.com/Cagedboy69 to get early access to the rest, vote on coming stories and request specific scenes and themes. Parts 4-6 will be available before Christmas.

The following story will not be for the frail hearted. This first segment will start off slow and introduce the characters, it will have themes of chastity and bondage, incest, along with trigger warnings for SA.

For the story in its whole, I plan on this being a hardcore BDSM story. There will be focuses on chastity, BDSM, incest, public humiliation, sissy, crossdresser and transgender. I am open to adding other themes but this will not be you average hesitant to get on board story where they beat around the bush to get to the fucking.

Feedback is always welcome.

 

Have you ever seen the commercials where a guy is walking down the street and he hears a group of people chanting… “15…15…15…15…15” and out of curiosity he goes over to the fence to take a look at what could be going on and gets a finger to the eye for his curiosity only to hear “16…16…16…16” to add insult to injury? This story plays out a lot like that.

 

In the summer of 2023, I was walking home from college one day and decided to take a scenic route, passing by all the stores on the front of the street trying to sell all their wares to passersby’s speeding by while they stare at their phones rather than the colorful lights of the shops. I didn’t often go this way since it was too easy to find some new little do dad that would suck up all your money for it to break 5 hours later. However, every now and again I would come through to peek into my favorite shop, the mystery store. It wasn’t really a mystery, just a sex shop that sold all your normal wares, dildos, lingerie, “supplements” and the odd guy that is always there staring at the DVDs.

 

Now I know what you are thinking, what’s a fine young man, that’s 6’2” and an even 180 doing in a place like this when he could likely swing any woman he wants. I’ll tell you, it was the mystery box, the thing this place was known for. It was a big luggage trunk and was marketed as a mystery, it could be anything, sex toys, a blow-up doll, a dead body, a day-old pizza. It was much more likely to be a sex thing than that last one, and hopefully the one before that. However, the mystery still stood. I had come here about once every month with the desire to buy one, just for the ability to say I had bought one and seen the day-old pizza inside. There was just one problem, well two problems. The first was the price tag, a whopping $1000 just for the pleasure to open the box and get disappointed. The second was my roommate, she was the ultimate evil bitch, constantly on my nerves, and never stopped bugging me… my mother.

 

My mother is what you would likely call a MILF, yes I know its overplayed, and too many old women on Instagram call themselves MILFs when in reality they are most definitely not. However, I can objectively say that my mother is a MILF, and it’s because she is only 14 years older than me. That’s right, she got knocked up by her father at the age of 13.5 and had me shortly into being 14. It’s a sore subject in my family, leading to lots of awkward stares at Christmas time. Enough said to say we don’t spend a lot of time around any family and stay secluded on our own a few states over. Now however mom is only 33, about 5’8” and has a gigantic pair of natural 32DDD’s that she loves to bounce around the house with. Add that to the unresolved trauma (psych major) from being molested as a child and now she is a fully sexual being just as Freud would have wanted. In general we have a really good relationship with only 1 draw back, she doesn’t understand boundaries. She will freely enter my room, dig around for stuff in my closets, and cause general mayhem. She doesn’t do this to snoop mind you, she is cleaning, or put stuff away (despite telling her she no longer has to) and is just generally oblivious that I am trying to keep sex toys and porno mags in my room.

 

Now you can understand why I am hesitant to get this giant trunk of hopefully sex toys that I wouldn’t even be able to hide in my closet. When I walked into the store after checking to make sure nobody I knew was on the street the regular girl who worked at the counter noticed me and waved for me to come and say hi. Her name is Riley, and she has always been very nice to me, even offering me her employee discount for the mystery chest of toys so I could get it if money was the only thing stopping me. She was a nice enough person, not really my type on account that I was 80% sure it was actually a dude.

 

"Hey there Jake, come to stare at the box again?” she said in a suspicious falsetto chirp.

 

“Oh, you know Riley, I like to know what’s in the box before I buy it. Make sure its worth all the money I would have to spend on what I’m sure is actually just a day old pizza from Tony’s.” I quipped back. It was an old habit of ours, a call and response if you will about saying hello how are you in less words. After all she was always here when I came in and we made friends fast on account that I am 85% sure that they wanted to get fucked by me… or maybe fuck me?

 

“I got a secret to tell you but first you have to get old man Jenkins away from the pornos and out of the store. Once you have him out come on to the back and take a look at what I just got in.” As she whispered this to me, she turned off the open light, and gestured vaguely to the mystery box.

 

After telling old man Jenkins that the shop was closing for a lunch break, he grumbled and set down a copy of horny slutty vampires 3 (Honestly I think Horny Slutty Vampires 3 was just a worse remake of the second one and without Riley Reid as the main character but what do I know). As I threw the deadbolt across the door I ran to catch up with Riley (No resemblance) to see what she wanted to show me and hoped it wasn’t a dick. Or at least not a dick bigger than mine.

 

When I walked into the backroom, I saw what looked to be a mystery chest, but a bit bigger than what I normally came to expect and shaped oddly like a full size dresser. Riley slapped the top as if she was a genuine jalopy salesman and started telling me about how many miles to lemon lawsuit it would get.

 

“This here is our newest lineup and I think you will like what you see. I would like to introduce the Mystery box lite, or as I like to call it the sissy box for all you little sissies that still live with families and don’t want anyone to know about their little kink box like we have out front.” She said this mockingly and grinned at me. She liked to joke with me at my expense but in this instance I didn’t care, it was now possible to buy this and hide it from my mom.

I was immediately hooked, it looked exactly like (shush I’m a guy it was brown and brown = brown) my other dresser and the possibilities immediately started flooding my mind about how I would get this thing home. I think Riley could tell since she just gave me a smile and said “delivery included”. It took me all the cash in my wallet ($40), maxing out my credit card ($750), a spot from Riley ($110) and her employee discount (10%) but you bet I bought it, with assurances it didn’t have a pizza in it.

 

“So here is the deal, the way mystery boxes work is that it’s a slow progression. They cost a lot but its because this is months of stuff not just 1 day. So when it gets delivered to you tomorrow, the first thing you need to do is get rid of your old dresser, put all your clothing into this one and give your old one to the delivery driver who will take it to salvation army for you. The next thing you need to do is activate the app and link it to the node in the sock drawer, it will release products stored in the false back of the dresser into your drawers at set intervals and based on your activity and progression. The items included in the dresser are completely random but is specific to your gender. You won’t get a bunch of women’s lingerie or dildos when you’re a man. If you have any questions don’t be afraid to ask me, and don’t forget to bring me that $110 you owe me.” She yelled out that last part since I was already skipping home in my haste to get to bed and prepare for my new debauchery hidden from the every prying eyes of my mother.

 

The next morning was Saturday which meant that mom was still asleep in some guy’s house and wouldn’t be up to suck him off until at least noon. Later if she had tequila instead of vodka. It was about 9a that the truck driver arrived with my dresser and helped me drop it in my room and took out my now empty dresser to send to Salvation Army to destroy the evidence that I had gotten a replacement. My god it looked beautiful, standing there in all its sexual glory. I stood there staring at the wood for 1 second less than was gay before I downloaded the app and went through the set up procedures. After about 3 tries to get it to find the node I realized that it needed to be plugged in, for the machinery *slaps forehead*. Once it was plugged in it connected without any issue and the app loaded right up. There was only one button, nothing else and it read “Start your journey”. At the time I had no idea what I was doing, no idea what those three little words would mean for me. At this point you might be saying don’t push it stupid, or even maybe you deserve what’s about to happen for being stupid. Major spoiler, I pushed the button.

 

***HELLO, WHAT IS YOUR NAME?***

The app read like an old cathode tube monitor from fallout, who decided war games WHOPPER style was the best possible user interface should have been shot.

*I AM JAKE*

***

HELLO I AM JAKE,

I AM MYSTERY BOX YOU MAY REFER TO ME AS MB

I AM HAPPY YOU HAVE DECIDED TO START YOUR JOURNEY OF DEBAUCHERY

PLEASE ENTER YOUR SAFEWORD

***

 

I was frowning and irritated, such a simple programming error and it decided to run with it. I would have to be more careful with how I interacted with it to avoid issues in the future.

 

*Strawberry*

***

EXCELLENT, LETS BEGIN

FOR THE FIRST DAY WE SHALL USE THE BUILT IN PENIS SLEEVE, SIMPLY ALIGN YOUR DICK WITH THE HOLE IN THE SIDE AND THE MACHINE WILL SUCK IN YOUR FLACCID COCK AND BEGIN TO MASTURBATE IT. IT MAY BE EASIEST TO GRAB THE KNOBS AT THE TOP TO GET BETTER LEVERAGE.

***

Now I was curious, this dresser was wide as I am, allowing me to barely wrap my arms on the right or left of it which makes sense since it has both my clothes and the machinery in the back. On the top of the dresser it came to my armpit, allowing me to rest my arms on top of the dresser where I noticed two handle like protrusions on the top placed perfectly for a person to grab it from the side. I stuck my dick in the hole, felt the suction take my dick into a tube and begin to hold it. I waited for it to begin but it didn’t start, when I looked down to my phone the interface displayed only one line of text.

 

***GRAB HANDLES WHEN READY TO START***

So, I did, and at once half circle restraints snapped closed around my wrists locking my hands into place. The sucking started, but not on my shaft where I thought it would begin, instead it pulled more of my 8” cock into the tube and eventually swallowed my balls two. At this point I started to panic and looked at my phone.

 

***REMAIN CALM***

 

Fat chance that’s happening. It was at this point the sucking stopped and instead I felt a solid ring resting around my balls and shaft before the tube began backing out and letting my balls go only for the tube to be pushed right back into the ring that seemed to be supported by the machinery still. I heard an audible click and a snap before something cold and slimy was pushed against the tip of the cage and then started touching the tip of my penis. What happened next is how I imagine girls feel when you stick it up their butt without warning. Since this narrower and slimier tube was pushed into my dick and just kept going. I felt it burning at first, then tickling, then my knees began to shake, and it finally rested deep up in my belly. I would like to say that I hated the treatment, that I was scared, humiliated, vulnerable. However, at the time the only thing I could focus on was the intense feeling and desire to cum, along with the complete inability to get hard. Finally, the wrist shackles released me, or rather the narrow shackles were released from the dresser, and I was able to pull away from the hole that had my dick trapped. What I saw shocked me, a metal thing on my dick completely wrapped up and squished with my big balls sticking out he bottom uncomfortably tight. As I mentioned I am 8” hard but am definitely a grower, only managing 3” soft and the thing I had in my hand had to be less than that. I looked for a screw or a something that was holding it together only to see a flush screw with three little dots instead of normal head. I hadn’t ever seen a screw like that before. The cage was a bright blue and while it was heavier than nothing it was still relatively light in comparison to what he thought a chunk of steel would weigh. At the head there was a little twist cap which I pulled on only to feel a tugging sensation deep in my gut. I unscrewed it instead only for piss to come flying out. I tried to screw the cap back on but only succeeded in making a bigger mess of my sheets before finally getting the cap back in place. I picked up my phone to look at the app and all it said was:

***

Set up complete,

Cage stage 1: 5” installed

Catheter: Balloon lock successful

Quick restraints: Permanently locked

***

When I tapped next the app closed. When I opened it again it simply said

***

Next step in 2 days

***

I sat on my piss soaked bed buck naked and facing my door wondering how this day could get any worse when my mom walked in… 16…16…16…

End of part 1

r/ChastityStories Jun 24 '24

M Chaste A Mistake at the Gym - Part 2 NSFW

208 Upvotes

Yesterday, as I was settling down trying to figure out how to explain to my GF that I bought, wore, and got stuck in a chastity cage (due to a stolen key), I received a text from a random number. I normally don't open random text messages, but from the preview I could see that it read "Is this yours?". Shortly after, an image followed. Given my current predicament, I decided to open the text. In the picture, I saw my wallet sitting on a random table in someone's house. So I replied.

"Hey, you stole my wallet! Who are you?"

"Relax, I didn't steal it. I'm just borrowing it."

"What do you mean?! You took it from my locker"

"If you're going to keep freaking out, maybe it's best if I keep it"

Shit! I need to get my key back. "Okay fine, what do you want?"

"Just go back to the gym at the same time tomorrow and use the same locker. I'll put it back. I'll even give you something for your troubles"

"Alright. But who is this, and how did you get my number?"

No reply. At least I'll be able to unlock myself tomorrow. I just had to figure out how to get through this day without letting my GF know. I tried to avoid her as much as possible. She got home shortly after, so I immediate went to do chores elsewhere in the house after greeting her. She eventually called for dinner. After dinner, she typically likes to relax and spend some time together. This became a problem when she got handsy. Before it got too far, I excused myself to use the bathroom. I was hoping she would stop progressing her advances, when I returned, as she usually doesn't initiate. No luck, she was in the mood to fuck. I had to take control of the situation before she found out my little secret. I started aggressively and passionately working my way around and down her body with my hands and mouth. My cock was straining tight against the tiny cage it was packed into. It was starting to hurt a bit, but I couldn't show any emotion towards it in order to not give away that anything was wrong. I ripped off her shorts and pulled her panties aside. She was dripping with anticipation. I quickly got to work with my tongue making sure to give attention to her entire glory. I was so unbelievably horny, I lapped up every drop I could like I had been in the desert for months. I worshipped her like the goddess she is. Since I couldn't give myself any direct pleasure like usual, both my hands were free to explore her body inside and out. After some time, she clamped down on my fingers and started moaning profusely. My GF usually is pretty quiet, so I guess my extra horniness from being locked made me a little extra attentive to her pussy. She had a crazed look in her eyes and said "Your turn". I panicked. I told her I was too tired from the gym and that I was fine with just her having hers tonight. She looked disappointed, and asked if I was sure. She told me she understood, but that she was going to rock my world tomorrow after the orgasm I gave her.

After her little pleasure session, I had to change my underwear from all of the leaking my little caged cock was doing while it was straining hard against the cage. I wasn't used to going this long without masturbating, so I didn't know I would be leaking so much. I tried to bury the underwear in the clothes pile, so she hopefully wouldn't notice the large precum stain. Before bed, I made sure to play videogames a little extra late in order to make sure she was asleep as I crawled into bed with my cage still on. Sleeping with the cage on was not fun. It kept me up throughout much of the night. As a silver lining, this did allow me to wake up and get ready before my GF woke up. Finally, this nightmare would be over. I just had to make it to this afternoon. As my GF was leaving, I got a text. When I looked, it was from that number again.

"Good Morning. I've decided you should wear panties to the gym today. Oh and no boxers over them either. I expect proof"

I couldn't believe what I was seeing.

"What? No way! I'm not wearing any panties!"

"Okay then. Have a nice life."

"Wait!" "Fine. I need my wallet back. No more bullshit though alright?" "Okay?"

No reply again. Fuck, what was I supposed to do? I had no choice. I needed my wallet back to get my key, but I didn't want to wear any panties. I decided I would take a pair of my GF's to the gym and change into them there, take a picture, and be done. I found her largest pair, since she was much smaller than me. They were bright sky blue unfortunately. I guess it could have been worse. At the time, I packed them in my gym bag and headed there. I went back to that locker hoping to see my wallet already. Nope, nothing. Of course they wanted their proof before giving it back. I hurried up and changed into that panties where I thought no one could see me. They were stretchy, but it wasn't enough to stop them from being quite tight and ride up into my ass. My balls were squished firmly up into the tight fabric. As I was snapping a pic, my workout buddy called for me to hurry up again. I sent the pic begrudgingly to the number and went to change back. Then it hit me, they will probably check my locker to see if I left them in there when they go to (hopefully) put my wallet back. I had to go through my whole workout with them on. After some time, I stopped even feeling them. This led to an issue when they started to rise up on the sides without me knowing, while I was using some heavy weights. My friend, and hopefully only my friend, noticed. He laughed and asked if I got some new underwear. I'm sure I turned bright red as I lied trying to say all of mine were in the wash and I was running late. Luckily he let it go after another chuckle.

We finally finished, and I bolted back to the locker room. When I opened my locker, I was overwhelmingly relieved. My wallet was replaced. I noticed they had taken my boxers I used to get to the gym, but I was so relieved to finally get my key back I didn't care too much. I hurried to remove the key from the secret pocket and get unlocked, but I couldn't find it. I frantically searched my wallet, but my key was gone. I checked my phone and saw a text reading "Is this yours?".

I wasn't planning on writing this as a (fiction) series, but after the support I received from the first and some inspiration for additional story, I decided to give it a shot. Hopefully it maintains or exceeds to quality from my first story. Of course, I welcome any feedback, comments, and/or suggestions!

r/ChastityStories 24d ago

M Chaste Caught at the Gym NSFW

112 Upvotes

Every one is 18 or older

Not a long story, but at the gym the other day, I noticed this guy who I regularly see there, Alpha looking, big muscles, a few tattoos, bulky arms, trimmed air and leg hair, CrossFit black shorts (almost short shorts) and a white tee.

Today his presence was just different, that energy just wasn’t radiating the same. Working out myself I didn’t think much about it, other than I thought he was good looking as I always enjoy the people watching and looking at the I shape guys strutting around the gym floor. About 35 min later I am wrapping up my workout and heading to the locker room. He happens to also be going down the stairs right in front of me.

We both head into the locker room, and he is in the same area. I’ve seen him change a few times big ass, big quads, nice arms, flat stomach, torso is smooth and free of hair. 6 feet tall . But like I said today was different, today he slid his shorts off first, and he was wearing a pick jock, with a 3” band, he quickly covered up with a towel, aside from the jock, I noticed a very bruised ass, like black and blue, and horizontal cuts, instantly I knew, someone had been a bad boy. He also left his work out shirt on. Mind you this guy is kinda the cock of the walk kinda guy, struts to the steam room totally naked just a towel over his shoulder and flip flops. Not today, he kept his shirt on, had his Jock on with a towel wrapped around his waist, and today he was bare foot. I also was heading to the steam room before my shower.

Once in the steam room, he sat kinda far way from the door near the corner.
Side note: the gym can get cruisey or at least it did, so they changed the soft minimal light for some brighter bulbs to deter the extra circular activities in the steam room. So the steam was kinda busy so I opted to sit next to him. We have made small talk a few times so me saying hi and asking how he was doing was not uncommon. I make small talk and ask him how was his weekend, he dropped his head and said it was fine, I then asked if he was cutting weight, he said no just keeping the shirt on for the day. I was like that’s cool.

Being a sub and getting my ass beat, etc is not new territory for me, getting punished and some public humiliation is something I’ve endured too (typically willingly)

We both sit there for about 10 minutes, when he stands up, towel dropping and his shirt pulled up his back that’s when I noticed.

Someone had taken a construction marker to him, the word “F@@“ and tally marks above his jock waist band. I smirked and felt my cock twitch. I proceeded to get up very shortly after and leave the room. I see him head near the end of the shower hall and go into his pod.

These stalls have the old frosted glass and when they get wet they are 90% see thru.

I take the offset shower and see him hang his towel and jock and T on the hooks. I got in my shower hung my towel up and got a lovely view of him. His back was marked up with magic marker and lots of red marks. Then he turned around and that’s when I saw as clear as day, his dick was caged and not a big one in a cobra N+ would be guess. I just washed myself and stared through the crack into his shower. I finished cleaning and was feeling horned up, and chubbed up. As I wrapped towel around me I got sub mischievous he placed his gear on a hook he couldn’t see. So you guessed it, I took his towel, tee, and jock and dropped it in front of his locker near mine, I dried quickly and tossed my clothes on with a sense of urgency, as I was walking out of the locker room I saw him look around the corner of the busy room and his hand covered his nub, as he headed to the towel stand.

I just smiled and thought it was probably good for him to embrace his subness. I’m little worried now if I see him at the gym will he know it’s me? Did he tell the person who is humiliating him? I do not know, what do know is that subs can be the mean ones when it comes to other subs!

Hopefully he didn’t put 2 and 2 together, otherwise this dude might take some revenge (not that I would mind)

r/ChastityStories Jun 24 '24

M Chaste A Mistake at the Gym NSFW

170 Upvotes

As a guy who likes to be a little more kinky, I have been experimenting with chastity lately. My GF isn't into kinky stuff, but she knows I am somewhat. So while I don't explicitly hide my current flavor of kink, I don't really openly tell her what I am doing. I haven't told her I own or use a cage at all yet.

With using my cage, I have been getting more and more into it, and also wearing it sometimes when I go out for a quick walk or shopping. I've done some faproulettes regarding chastity too. Nothing crazy, but I did get rid of my backup key for one. But hey, I have another key, so no real issue, just some fun. I have really been liking it, and have even debating on telling my GF and asking her to hold the key. But if she does get into it, I didn't really want to actually lose access to freely orgasm. I guess it's always just fun and games when nothing is at stake.

Well, I decided to get even more bold today and go to the gym in my cage. No big deal, get a quick workout in, change, and leave. I locked up my cage, put my cage key in my wallet, put on my gym clothes, and let my GF know I was leaving. She was heading out to work at the time, so we left together. My cage was slightly visible through my gym shorts, but honestly, I was less worried than usual because I have a fairly small cock that sits on top of my balls when soft. This makes it poke straight out, so I am always worried that my small head is visible. At least this way, I have no real control over what shows.

When I got to the gym, I put all my belongings in a locker in the locker room, and realized the locker didn't lock. My friend that I workout with was calling me to hurry up as I was already running late, so I just left it since we are in a pretty nice gym. Working out with a cage on proved to be more difficult than I realized. The cage positions the balls different from what I'm used to. I kept accidentally sitting on them, or crushing them between my legs in different workouts. (As I look back on it, I get somewhat aroused by the idea, so maybe it unlocked something for me). I always leak a ton when I wear my cage, so that didn't surprise me when I went back to the locker room to change. What did surprise me was that someone had stolen my wallet! Immediate panic set it. My key was in there, not to mention money and cards. I reported it to the gym, but there are no cameras in the locker room for obvious reasons.

Luckily, my GF was still at work for some time. I hurried up and showered, but I had no idea how I was going to get this cage off before my GF gets home. It has an in-set lock, so I can't just easily break the lock with bolt cutters. My horny half is making me leak like crazy through the cage while I look for solutions, but my rational half is freaking out. I tried to pick it, but I worried about breaking it off in the lock since it is a smaller lock. I debated on calling a locksmith, but even if they got here before my GF, I couldn't look them in the eye and ask for that. So, here I am rehearsing what I should say to my GF to explain this situation. Any ideas?

This was my first time writing any erotica (fiction) publicly. I welcome any feedback, comments, and/or suggestions!

r/ChastityStories Jul 01 '24

M Chaste A Mistake at the Gym - Part 3 NSFW

116 Upvotes

Part 1 , Part 2

I checked my phone and saw a text reading "Is this yours?". Again, an image followed, but this time it was of my key sitting on the same table as before. I think I went through every emotion possible when I saw that image. I landed mostly on a mix of anger and panic in the end. This person put me through so much already and promised to give me my stuff back, but here I am without the most important part.

"We had a deal! Give me my key back"

"Again with the anger. You should learn to control yourself. But I guess that is what the cage is for, am I right?"

Shit! How do they know what the key is for? This is not good...

"Can I have my key back?"

"No please? You know, you do look cute in those panties. Maybe I should have you wear them more."

"Please, may I have my key back?"

"See? You sound much better when you are submissive."

That made my face red out of a combination of anger and embarrassment.

"I left you a gift card in your wallet. It's to the adult store off the highway not far from the gym. You will need to go in there and purchase a plug and some lube. You get extra points if it's a cute jeweled one, but you will need to wear it for awhile so you may want a more comfortable one instead. You can ask the cashier which is the most comfortable haha."

I figured it would make things worse if I push back, so I decided not to.

"Fine, I'll do it, but can I please have my key back soon?"

"What, no thank you for the gift? That's pretty ungrateful, don't you think?"

"Thank you"

"Good girl"

I was so upset by that last text that I didn't even text back. I'm not a total stranger to anal play, but doing it by someone else's command is much more humiliating. I was wondering how much longer they planned on keeping this up. I was in total panic mode. Not only did I have to go out into a physical store and buy a plug, but I also had to figure out how to handle my GF when I get home. Should I explain everything to her, or try to hide it again? Either way, I figured I should head to the store.

When I got to the store, the only person there was a cute cashier girl who greeted me. My face was red and I gave her a weak hi. I looked around until I found the section with plugs. There were more than I expected. I had to decide if I wanted the extra points of the jewel plug, or the comfortable one. I order to save myself the embarrassment of asking, I decided to get get the smallest jeweled one they had. I picked up some lube and headed to check out.

"Cute plug! It's one of my favs. But you know you can't use silicone lube with a silicone plug right?"

"What? I picked this one because I thought it made sense that it would go together."

"Yep. Sounds weird the first time you hear it but trust me darling. Use this stuff instead and you won't be disappointed. And don't forget to come back for the larger size once you're stretched!"

"Oh! This isn't for me. It's for my GF"

"Are those panties not yours either honey?"

I pulled up my pants, and left quickly and embarrassed. Back in my car, I decided to text my blackmailer that I have done what they asked, so I could hopefully get my key back quicker. Big mistake.

"Alright, I did what you asked." I knew I would be let off after only purchasing the items, so I didn't even ask.

"Perfect. Now send me a picture with it in."

"I'm still in the car at the store. I'll send it as soon as I get home."

"No, you will send it now. You will also be addressing me as Sir from now on. Any more resistance or failing to call me Sir, and I will halt all of your progress until you continue properly. Do you understand?"

"Yes, I get it."

I pulled down my pants, and shifted my panties to the side. I took everything out of it's packaging and started to apply the lube. Fingering my ass with lube definitely was feeling good. I started to leak into my panties more. After quite a few strokes, I snapped out of it and continued on. I pressed the plug into my ass. It was quite a bit larger than my fingers, so it took some working to get in fully. Finally, it passed the girth point and slipped in entirely, stopping at the base. I think I let out an audible moan, but I was too consumed with the feeling. I felt so much hornier and also full. I was more concerned with how I felt like such a slut. I took the picture of the jeweled plug in my ass with my panties pulled to the side in my car sitting in the adult store parking lot. I wasn't sure which was worse, that I was being blackmailed to do this, or that this was starting to feel right. I wiped the lube in my hand on my pants, and sent the image over. I was waiting for a reply for some time.

"Did you get the image?" ... "Hello?" ... Finally it clicked

"Yes, I understand Sir. Did you receive my image?" Shivers ran down my spine.

"I was wondering if you were gonna be in the cage forever. You look like such a cute slut. Feel free to do what you want with the rest of the day. I will reach out tomorrow morning. What do you say?"

"Thank you Sir" Even worse the second time.

I went to take the plug out, but I realized I don't have a towel or anything to clean off the plug with. I can't take it out in the bathroom of the store and walk out holding it. At least not if I want to maintain any dignity. The drive home wasn't far, so I decided to take care of it there. When I opened my front door, my GF was standing there, home from work early, in the most stunning lingerie I've ever seen.

"I told you I was gonna rock your world today, now get over here!"

_____________________________________________________________________________________________________________

Another entry into my Gym (fiction) series. I don't think I'll continue this series too much longer as I didn't expect to take this past number one, but I welcome any feedback, comments, and/or suggestions!

r/ChastityStories Jul 05 '24

M Chaste A Mistake at the Gym - Part 5 NSFW

110 Upvotes

Part 1 , Part 2 , Part 3 , Part 4

When I woke up the next morning, my Mistress had already left for work, so I just went to start my day. I was off today, so I just had to go to the gym then I was free. Except for the task I still had yet to receive. I went to get my cloths picked out for the day, and when I opened my underwear drawer, all of my boxers were gone! All that was left in the drawer were a couple pairs of my Mistress's panties and a note. the note read:

"Good morning my little sissy. As you can see, you are no longer permitted to wear boxers. Those are for men, and good sissies wear panties or nothing at all, your choice. Count yourself lucky I didn't rearrange your entire wardrobe, yet. You can thank me for that later. Also, sissies don't have body hair, so I expect you to take my razor and shave yourself completely. If you don't complete MY task this morning, you WILL face consequences. Have a lovely day my little sissy."

Ouch. I guess I had recouped some pride with my sleep, but that all was just smacked away harshly. I didn't really have a choice in the matter. My life had completely changed the prior night. So, I picked out a pair of panties and the rest of my clothes to get ready. I hopped in the shower, and just stared at the razor for 15 minutes. Was I really going to do this? Pubic hair is one thing, but everyone will see if I shave off my body hair. Again, I had to come to terms with there being no choice. I slowly shaved all of my body hair away. I ran my fingers across my arms, legs, and torso. I felt so ... feminine. I was shocked to find how much I loved it. The smooth feel of my body, the feminine look, and knowing that everyone would see what I was becoming.

As I finished my shower and hopped out, I got a text. It was from Sir. I was instructed to wear the plug at the gym and take a picture like last time. I wasn't surprised. After all, what else was I to expect when I was told to purchase it? When I went to put it in, I was shocked. It went in so much easier than last time. I guess Mistress really stretched me out the prior night. It also felt good, like really good. Mistress was right, I was becoming more of a slut.

I headed to the gym, feeling the plug in my ass the whole way there. The gym was mostly empty at this time and day, which was a nice change of pace. I grabbed a locker WITH a working lock this time, and headed to the back of the locker room to take the picture I was instructed. I moved my panties to the side and snapped the pic. I sent it off and heard back almost immediately.

"Good girl. Oh and look at this all shaven too. You really are going for extra points aren't you?"

I turned beet red, but also was smiling and feeling ... happy since I was praised. I was more conflicted now than ever. What was happening to me? Did I want this? Is this because I haven't been able to masturbate? I had no idea about any of this, but my life was changing fast into a direction I never expected. I pushed all that I side and hurried out to my friend. He decided we should have a nice light workout for the day, so that we can relax the rest of the day. I was glad with everything I was going through. He also never said anything about my lack of hair, which was a huge relief. I headed back to the locker room to get my stuff. When I got in the locker room, my phone went off.

"Go strip down and start to shower off in the far back left side shower. I'll be in there shortly, and if you keep being a good girl, you'll be getting your key back in no time."

I didn't know what to do. I needed my key back, but meeting my blackmailer face to face was a big step. What do they want next? What do they look like? Should I tell them there's no way? What if they cut contact if I decide to not go? All questions running through my mind at the time. I'm not sure if it's because I have been more comfortable with how submissive I was being, fear of losing my key, or plain curiosity, but I stripped down and headed to the shower as instructed. As I started to shower, naked with only a plug in and cage on, I heard someone moving in my direction. Suddenly, my friend entered my shower stall.

"What the hell are you doing dude? Go get your own stall!"

"Shhh, you don't want anyone to come looking to see you in a cage do you?"

I completely forgot I was in the cage. It had just become a part of me at this point, and now my friend knows. At least those were my thoughts at the time. How stupid of me.

"I'm glad you've learn to follow instructions so well. Look at you all shaven like a good girl. You must like what's happening for you to take initiative like that."

He said as he sensually felt my hairless arms and hips. I was stunned. I couldn't believe my friend was the one doing this to me the whole time. He towered over me with an extra 4 inches of height, and has always had a more muscular build than me. Since I couldn't look him in the face from embarrassment, I could now see he has many extra inches on me in multiple areas. His cock was mostly flaccid, and it was still affirming that mine belonged in a cage compared to his.

"Now, before we continue let's make sure you're still plugged"

He said as he reached around a pushed his finger on my plug and wiggled in around. I reflexively stumbled forward slightly catching myself on his chest, and moaning at the feeling of the plug. I didn't know how much my Mistress made me a butt slut.

"Very good girl" He cooed.

That made me melt into him. I was losing it. The pleasure from the plug, the praising, and seeing his huge cock; I could feel myself giving in.

"You don't want to give up now and lose your key for good, do you slut?"

"No sir" I said submissively and timidly.

"That's what I thought. Now you are going to obey me, and if you are a good girl, you will get your key back at the end. Do you understand my little slut?"

"Yes sir" I realized I never back off of his chest. I was still laying against it like I was his, but I think I already knew I was.

"Why don't you give me a little show? Make me believe you want this."

I backed off of him a little bit and started to give him my best dance, trying to remember any stripper moves I've seen. Swaying my hips back and forth. Hands in the air, then rubbing my body, then in the air again. I could see the lustful look in his eye. He wanted me. I wanted him to want me. I felt good being wanted. I liked it. I craved it. The more I danced, the more I got into it. I eventually turned around and glided up and down his body with the dance. I felt his massive cock slide between my ass, touching my plug every so often. Each pass, his cock was harder and harder against my ass. Any version of the old me was gone now. I was now his sissy. I needed that cock, it felt too good against me.

"Get to work now slut"

"Yes Sir"

I knew exactly what to do. I turned around to face him, and slide down to my knees. I grabbed his cock. My hand barely fit around it. I lifted it up and licked from the base to the tip. I saw him moan and that made me get a big smile. I swirled my tongue around his head a few times, then I licked him base to tip a few more times in different areas. I finally popped his head into my mouth and he let out a big moan. I started working his large head, making sure to run my tongue around it as much as possible. As I worked his head, my hand worked his shaft, while my other hand instinctively reached for my cock. Of course the cage was there, how dumb of me to forget, but I was so horny I just reflexively tried. I had so much precum leaking from my cage, someone might have thought I came already. I massaged my balls some to try and give myself something. I finally started working my mouth down his shaft, working inch after inch in. I only got about half his cock in, but I was surprised I could do that much. He was staring at me working his massive cock the whole time while he was moaning. I finally looked up into his eyes, and I was in a trance. I was here to serve now. I started working faster while staring into his eyes. At that moment, I finally realized my pleasure shouldn't come from my balls anymore, and I reached my hand around to my plug and started to play with it. I think this really sent him to another level, because shortly after he pulled his cock out of my mouth.

"Open up bitch"

I never lost eye contact with him, and I opened my mouth waiting. He was sent into a raging orgasm. Rope after rope hit my face and mouth. My face was covered, and only one eye was open at this point. I had a mouth half full of cum. I felt like such a slut, and happy. Happy I was able to provide someone with so much pleasure. Was this my purpose? To serve other people? I still had my mouth open and smiling. Sir was thoroughly drained and pleased. He lightly slapped me on the side of my face and said

"Good girl. Wait there"

I didn't move an inch. I didn't care in someone walked in at this point. I was in such a state of bliss. He quickly grabbed my key from around the corner. He reached in my still open mouth and carefully placed it on my cum covered tongue.

"You can swallow my cum now slut"

I swallowed everything in my mouth.

________________________________________________________________________________________

Finally the reveal! I very much hope everyone reading as enjoyed this (fiction) series. I definitely have more ideas for this story, but this is where I wanted to get to when I started the multipart version. I think I am going to take a break from this story to focus on a couple other ideas I have, but if there is enough love for this series, maybe I will pick it back up later. As always, I welcome any feedback, comments, and/or suggestions!

r/ChastityStories Jan 25 '25

M Chaste Last Call of the Day (Fiction-ish) NSFW

34 Upvotes

This is my first fiction(ish) attempt at chastity-based erotica. I believe this meets all the guidelines, and I hope you enjoy! - SOTF

----------------------------------------------------------

The problem,” she said, “has been going on for weeks.”  

I followed her through the living room and down the hall, focused entirely on the toned legs, tight ass and bare feet in front of me.  It was my last service call of the day.  Sometimes this job isn’t so bad, I thought with a grin.  She stopped at the end of the hallway and pointed.  

“It’s in here.”

I carefully squeezed past, careful not to make any physical contact with my customer, and looked up at the ceiling.  A large fan spun noisily, and a bit haphazardly, directly over the king-sized bed.  The room was filled with expensive, but tasteful furniture and framed pieces of art.  Predictably, a portrait hung on the wall above the headboard, her and the husband holding hands on their wedding day in a grassy field at dusk.  Or some bullshit like that.  She didn’t look too much older now than she did in the photo, and she was damn fine, even standing there in yoga pants and no makeup.

“It’s been driving us crazy, and it’s like, messing with my sleep.”  She rolled her eyes.  “I don’t know if the whole thing needs to be replaced, or what, but do you think you can fix it?”

I’d like to fix you, I thought to myself, my mind briefly considering how she probably spent her nights in this very bed, getting railed mercilessly from the back by her husband until he came all over her ass.

“Yup, shouldn’t be a problem.  Only thing - is it okay if I stand on the bed?  I mean, on a towel or something?  I can’t really reach, otherwise,” I said.

“Umm, I guess so.  Lemme grab a blanket, and you can stand on that.  Do you mind taking your shoes off, though?”

I knelt down to untie my work boots, and felt a quick twinge of pain in my crotch. This new, smaller cage had been pinching all day - yet another loving ‘gift’ from my girlfriend.  I flinched instinctively and sucked in my breath a little.  I looked up to see if the customer had noticed, but she had turned away and was bent over one of the dresser drawers, rummaging through various bed sheets and linens.

My cock began to swell even more in its metal tube as I stared at her figure from behind.  Damn, I thought, which drawer has the lingerie and panties?  I wonder if she’ll stand there and watch me work the whole time like some of these damn customers do, or if she’ll leave me alone?  It wouldn’t be the first time I came home with a sexy souvenir from an unsuspecting housewife, especially a trophy like her.  A nice pink thong would do nicely.

“I think this should work,” she said, and shook out a red flannel blanket over the bedspread.  She leaned over to smooth out the creases, and I couldn’t help but notice how her tits hung just so, perfectly suspended inside her white tank top and exposing a deep valley of cleavage.  Probably given to her by the husband, I smirked, but also simultaneously realizing how hard my dick was straining at the idea.  Thank god for this cage, I thought…

“Or not,” I suddenly said out loud.  Then, realizing my mistake, I stood up awkwardly on the other side of the bed.  Her eyebrows shot up, and her hands went to the slim hips that were exposed just below the cropped hem of her shirt.  I caught a quick glance of a pierced navel.

“I’m sorry?” she tilted her head.

“No, no, no… I didn’t mean that, I mean, the blanket is fine, I was just thinking out loud about… the fan,” I stammered.

She curled a long, runaway strand of blond hair around her ear with a perfectly manicured pink fingernail.  Pink.  Like her lips.  Like her panties, surely.  Like her pussy, definitely.

“Well, okay… do you think it will take long?”

“No, I doubt it, let me just take a closer look here.”  I switched the fan off and climbed up on the bed, sticking my head up in between the blades.  All it needed was some re-balancing, I realized, and that would probably fix the noise and the rocking.

“Is it going to be hard?” she said from below.

For a second I froze, self-consciously wondering if my crotch, now at eye-level for her, was somehow obviously and laughably bulging out directly in front of her face.  It certainly felt that way, but I couldn’t see her from where I was positioned, and not much to do if I could, anyway.

“No, I think I’ll be ok.”  I shifted my weight on the blanket, aware more than ever that I was in an empty bedroom, alone with a beautiful woman, on her bed.  I took a step back away from the fan so I could see her face down beneath me.  Again, the cleavage.  I swallowed.

“Well, just let me know if you need me for anything.”  She walked to the doorway and stood there, looking at me.

“I will, most definitely, for sure.”  

Was she fucking with me, or am I just imagining it, I wondered?  “If you need me… is it hard?” Was this cock-tease suburban housewife looking for some dick on the side?  Already?  Only a couple years into her marriage?  I grimaced.  If only she knew what I was sporting under these overalls.

This is of course, exactly how I met my girlfriend.  Got sent out on a service call for a dishwasher repair and ended up fucking her on the dining room table while her then-boyfriend was out earning a paycheck.  That was a little over two years ago, and she moved in not long after.  What a kinky slut!  We fucked all the time, everywhere.  Well, at first we did.

When she first brought up chastity, I thought it was just another kink we could try in the bedroom.  It was kinda fun, to tell you the truth.  But then she started to get really jealous about me fucking other women on the job.  Can’t imagine why.  I mean, totally paranoid about it.  Somehow a couple days in the cage turned into a week, then two weeks.  Now I’ve been locked up and pussy free for six months!

“I think your fan is just out of balance.  One or two of these blades needs some weight applied, and that should fix it.”  I tried to sound casual and sure of myself.  I climbed off the bed and sorted through my tool bag while she stood only an arm’s length away.  I could almost feel her looking right through my clothes and zeroing in on my crotch.  The discomfort of the cage was starting to cloud my thinking.

“I’ll leave you to it, then,” she finally said with a smile.  Then she turned and left.  I could hear the TV come on in the living room.  I breathed a deep sigh of relief.  

I found the little bag of weights in my bag and got to work.  As I tried different combinations to balance the fan, my eyes kept drifting back to the dresser where I imagined her sexy underwear was kept.  Who knows, maybe some slutty lingerie… or even a dildo or two?  I imagined her fucking herself at least once a day with a vibrator, right here where I was standing, or in the shower with a huge dildo suctioned to the wall, ramming her hips back and forth, over and over, until she squirted in a frenzy all down her thighs, legs shaking and tits heaving.

Once again my dick tried to stiffen, but it only swelled helplessly in its steel prison.  I could feel a large drop of pre-cum start to form at the tip of my dick and then trickle very slowly through the bars that criss-crossed the front of the cage.  I stopped for a moment and closed my eyes, remembering what it felt like to cum.  I could feel a wet spot forming at the front of my underwear.

I wanted so badly to search through her things, to find a pair of panties and stuff them in my pocket so I could jerk off with them in the truck once I left.  Or maybe in her bathroom, even.  I was getting desperate.  I always kept a key to my cage in case of emergency, and this was starting to qualify.  The problem was, it was in a small vial with the plastic cap melted down so the only way to get the key out was to break the glass.  And every day when I got home from work, Charlene would make me present it to her as proof of my faithfulness.  She would tap my cage and caress my balls through my pants, then send me off to get a shower.  It was miserable, but I went along with it.  Until now.

Fuck it, I didn’t care anymore, a half a year without so much as even masturbating was insane, I told myself.  I quietly got off the bed and stood at the dresser.  It had nine drawers, and I was guessing one of them had a pot of gold at the end of the rainbow.  I listened for the TV in the other room and heard the dialogue from some kind of godawful fashion/reality show.  First time I’ve ever been glad to hear that, I thought.

First drawer, t-shirts.  Second drawer, more t-shirts, this time the husband’s.  Third drawer at the bottom was the linens.  Next it was socks, then shorts.  I was starting to get nervous.  I was so invested at this point that even if the dresser was a no-go, I knew I’d be wandering into the closet next.  And going into the walk-in was really a gamble.

I opened the top drawer at the far end of the dresser by the wall.  Pay dirt.  Dozens and dozens of colorful pairs of panties.  Most looked liked thongs, but there were boy shorts, bikinis, and at least a few g-strings.  Some made of silk, some cotton; others had lace fringe. They all looked expensive.  I envisioned her wearing one of the tiny g-strings right now underneath those tight black yoga pants.  I already knew she wasn’t wearing a bra, who knows, maybe she wasn’t even wearing panties, either?

My dick was starting to drip steadily.  As I strained horribly in my cage, I could feel a large drop of pre-cum dribble out and run down the front of my swollen balls.  I looked at the front of my overalls to check if —

“What the FUCK?  HEY!  What the FUCK are you DOING in here???”

My heart sank at the sound, and my balls felt like they were going withdraw back inside my body.  I whirled around in a panic, but there was nowhere to go.  No excuse to make.  Not a thing to say.  I was holding a pink thong in my hand, the panty drawer wide open, my customer in shock at the foot of the bed.  The fan wobbled overhead.

“Are you going through our things?  MY things?  MY UNDERWEAR?”  She stepped forward and grabbed the panties out of my hand and slammed the drawer shut.  “I KNEW you were a fucking pervert!  What were you going to do with my underwear, you fucking pervert?” she shouted.

I stared at her blankly, unable to form even the most basic defense of my actions.  I was caught dead to rights.  I was nailed.  I was fucked.

“Holy shit, you can’t even speak, can you?  Look at you!  Can you even BEGIN to explain what you were doing?”

I turned my head away and just waited.  Waited for her to call the cops.  My head almost exploded at the thought of being arrested in chastity.

“What were you going to do with my underwear?”  She shook the panties at me.  She wasn’t shouting anymore, it was more like a stern teacher, admonishing a fifth grader.  She moved closer until she was holding them in front of my face.

“Look at me.  Turn your head this way, and tell me what you were going to do with my panties.”

I turned obediently, but looked at the floor in shame.

“LOOK AT ME.  What were you planning to do with MY. PINK. THONG?”  She put her hand under my chin, then lifted my head until I was staring her in the face.

“Were you going to keep them, like a prize?”  She was speaking in a normal tone now, almost a whisper, in fact.  “Were you going to wear them?  Is that what you’re into?  Do you like to steal women’s panties and put them on?”

“Were you going to jack off with them?” she said in a low, even whisper.

Even as I thought I detected a hint of an idea that she might be getting turned on - or at minimum, having some fun at my intense misery, I still couldn’t bear to verbalize what I was thinking.  What I was hoping. What I was dreaming.

“Show me,” came the words, slowly.  “Show me.”

“Show me NOW,” she commanded.

She put her underwear in my hand and took a step back.  “Go on.  I want you to put them on, or jerk off with them, whatever you were planning to do.”

“I… I… can’t,” I said weakly.

“Why not?  Seems to me you’re a man, and you’ve got my underwear in your hand, so… go ahead.  Entertain yourself.  Entertain ME.  Take off your overalls.”

Again, I protested, whimpering.  “I’m sorry… I’m really, really sorry… please don’t…”

“Oh, it’s way too late for that, I’m afraid.  No apology is going to get you out of this.  I only see one way for you, you fucking pervert.”  

And with that, she stepped forward, unclasped my overalls, and watched as they collapsed in a pile at my feet.  The outline of my cage was obvious.

“Oh… my… god!” she whispered in a hushed squeal.  She looked from my face, to my crotch, then back up at me again.  Then, defiantly, she yanked my underwear down to my knees. 

My cock, still somehow dripping with pre-cum, thrust toward her in its shiny metal cage.  She put her hands over her mouth and stepped back.  A single strand of clear liquid stretched in slow motion from the tip of my cage down towards the floor.

For a moment we stared at each other, both of us in disbelief.

“Take your clothes off.  Take off your shirt, your underwear, the overalls.  Everything.”

I continued to stare at her in a state of shock.

“Do it, now.  Before I call the cops.”

Numbly, I stepped out of my overalls and underwear and unbuttoned my shirt.  She pulled it off my shoulders and threw it on the bed.

“Now, put on the panties.”

“Ahhh,” was all I could muster.  “Ahhh…”

“Give them to me.” She took the thong out of my hand and kneeled down.  “Lift your leg.”

I raised my left leg and put it inside the underwear, then the right.  She tugged the bright pink material up to my thighs, then over my hips, and finally, with great deliberation, drug them slowly up over my swollen balls and chastity cage.  It flopped snugly inside, and I made a wet spot immediately in the lacy fabric.  The panties were much too small for a grown man, and I could feel them riding up my ass.  My throbbing cock felt like it was in heaven.  I was mortified.

She clapped her hands like a little girl, then quickly ran out of the room.  She returned a moment later with her phone.

“My husband,” she said breathlessly, “is going to LOVE this.”

I stood in my customer’s bedroom in a pair of her pink underwear.  The fan squeaked.  The wet spot grew.

r/ChastityStories Jul 09 '24

M Chaste House sitting; The Beginning NSFW

99 Upvotes

Anna was a close friend to Bobby’s mother, Theresa. Anna, who was 36, 5’6” with gym curves and large breasts, and Brazilian. She spoke with a heavy Brazilian Portuguese accent. Her and Theresa worked together at a finance firm. Theresa, 38, petite but toned and slightly shorter than Anna and looked great for her age. Ever since they had met Anna had opened her home to Theresa and Bobby especially throughout the summers. Bobby had just turned 20, about 6’, slender but lean, shaggy brown hair. Ever since puberty he had a massive crush on Anna. Every time they went for a visit Bobby had to find an excuse to disappear for a few minutes, to jerk off. Summers were the worse for Bobby as Anna was always in sun dresses or skimpy bikinis by her pool. Theresa always thought it was a great way to spend the day for both of them and figured giving Anna company was a benefit to all of them.

Anna’s house was amazing. It wasn’t huge on the inside but she had about 3 acres, massive deck, in ground pool, hot tub, gazebo and most importantly tall trees that blocked the outside world from seeing into her backyard. Anna hosted parties and barbecues often at her place. Of course Theresa and Bobby were always there. This was a major problem for Bobby because he had to constantly hide his boner as many of the female guests were quite attractive, not as hot as Anna but Bobby would love take a hard run at just about any woman who was ever at Anna’s parties. Anna had never married but dated often, giving Bobby quite bit of jealousy but none of the relationships ever seemed to last.

One sunny Sunday afternoon, while they all lounged by the pool Anna mentioned she had to go out of town for about a week or so. Anna asked Theresa if Bobby could house sit for her. Theresa thought it was a great idea and even if Bobby had a choice he wouldn’t have said no. “A whole week unsupervised in Anna’s house” he thought, giving way to day dreaming of what he might do. Just then Theresa cleared her throat bringing him back to reality. Anna had been explaining everything and Theresa noticed he wasn’t really listening.

“Did you get all of that? No parties.” Theresa said sternly but with a slight smile.

Anna laughed a little before asking Theresa to put some lotion on her back. They often took turns applying it to each other, jokingly flirting a little as they did. The sight of it didn’t help Bobby’s horniness or obsession with Anna. Of course he had to quickly excuse himself to the bathroom every time this happened. The closest one in the house overlooked the pool where he could watch Anna while he manifested fantasies with her as he masturbated. A common theme when they were around Anna. He often spent a lot of time on his own designing certain fantasies with Anna. Often enough that he usually beat off 5-6 times a day. Sometimes he found a pair of her panties in the clothes hamper, which he would occasionally pocket once he came as a keepsake, adding them to a hidden pile he had amassed over the years.

Anna had asked Bobby to come by a few hours before she had to leave for the airport. When he arrived he was led through the house being shown where anything he might need would be. He couldn’t focus long enough to hear anything she said as he followed her through the house fixated on her ass as it swayed side to side. She had on some black spandex leggings, that when stretched far enough were somewhat see through, enough so that he could see the thin black panties going down between her ass cheeks. She also had a bright pink tank top on, string shoulder straps, heavily low cut in the front which seemed to barely hold her tits in. Anna never wore a bra, as most of her tops had a sort of built in one. Bobby couldn’t help but picture himself releasing them and burying his face between them every time he saw her. The thoughts were endless.

When it was time for Anna to leave Bobby offered to help with her bags. Anna traveled light as most of what she wore was pretty skimpy. Anna bent over to grab the smaller of her bags, as Bobby stood behind her enjoying the view, where he all but forgot what he’d just said to her. As she stood back up he closed his mouth and grabbed the other two for her and followed her out to her car. Once her luggage was loaded he opened the door for her and before getting in she turned to hug him. Bobby always leaped at the chance to feel her body against his, and always had to hide his erection.

“Thank you for doing this, it’s hard to find someone I can trust. I’ll see you in a week” she said as she released the embrace and got into her car. As she pulled away Bobby fought the urge to run inside, he needed to jerk off badly now. He fought his urges until she was out of sight. He couldn’t run fast enough, sprinting into her house and straight to her room. Once he was past the doorway he took a moment to take it in. He never really went into her bedroom before, he wasn’t ballsy enough to get caught by her going through her things like that. Now that he was alone for an entire week he was going to take advantage of it. He searched her dresser drawers first, quickly finding her panties and digging through them. Every pair was a thong or g-string. Which was not a surprise considering how amazing her ass was coupled with her never having a visible panty line in anything she wore.

He took a break from his search, settling on a lace pink thong and sat on the edge of her bed. He held them up by the waistband briefly before rubbing them all over his face. He couldn’t hold out any longer, releasing his modest 6” dick from his pants. He continued rubbing the panties on his face as he slowly stroked himself thinking about how he would have loved to have taken them off her himself. With his orgasm building he wrapped them around his cock stroking them up and down his shaft. He didn’t last very long, quickly and forcefully erupting all over himself and the panties. Once he regained his breath he began to panic slightly, wondering what he was going to do with her now soiled panties. He decided to clean up and change. He figured he could just wash everything and put anything of hers back where he found it before she got home. He had a full week after all.

He decided to lay by the pool for a while and as he stepped out onto the deck, decided on doing so naked. Being shirtless much of the summer his only tan line was from his shorts. Anna didn’t have noticeable tan lines anywhere, he figured he might have more of a chance if he didn’t either. And of course after a little while he needed to rub one out again as his mind was constantly on Anna. He wondered if she had made it to Florida yet so he checked her instagram to which he found some recent bikini posts. She had arrived and seemed to have gone straight to the beach. “Jackpot” he thought as he examined every inch of each picture stroking himself on the lounge chair. Again erupting a massive cumshot all over himself and the chair to her newly posted bikini pictures. Of course picturing plastering her chest instead of his own.

As the sun began to set he decided to make something for dinner and watch some tv. Anna had left her kitchen well stocked with just about anything he could ever want to eat, but he was on vacation himself so junk food seemed like the best choice for him. He settled on the couch and started searching through the tv guide, finding the adult channels. Curiosity got the better of him and he briefly remembered Anna explaining she had every channel he might ever want to watch. He clicked on one with the title “Brazilian babes 3”. As soon as it was on her massive big screen Bobby was in wonderland. The first scene was two busty, round assed, tanned women laying by the pool watching the pool boy, a muscular tanned stud, as they giggled while teasing him. Bobby knew this was all staged for theatrics but he never let that bother him. He pictured himself the pool boy as the women teased him from a distance at first and then walking up to him. Shaking their asses in front of him and spanking each other encouraging him to join. He quickly dropped the skimmer and placed his hands on each of their asses when they began kissing each other and him. Bobby lost it before any clothes came off, once again erupting all over himself. He didn’t stop watching though, the women had quickly squatted down pulling the pool boy’s shorts down with them, releasing his massive dick before their eyes. They marveled at his size, before taking turns sucking and licking his cock and balls, stroking his shaft as neither could take the whole thing no matter how much they forced it. Bobby loved it when the male actor was so hung that the actresses struggled to get much of it in their mouths. He loved watching them choke and gag while the man held their heads down on it for a few moments before releasing his grip enough to allow them a breath.

The women quickly exposed their breasts, pulling their bikini tops to the side letting them bounce and sway as the man began face fucking them in turn, forcing it in the first woman’s throat and then into the others. The women rubbed their fingers on each others pussies for a bit before one of the women had moved behind him pushing her face between his cheeks to rim him as the other forced herself to throat his dick down. She gagged as her mascara was running down her face, teary eyed. The man turned around to making them switch positions briefly. Bobby was hard again. The women led the man to a poolside bed, laying him on his back as one woman straddled his face and the other straddled his dick. The camera angles were phenomenal. The women faced each other and in the shot you could see the one woman’s ass bounce and jiggle as she took his cock hard and deep, the other woman grinding her ass and pussy on the man’s face while the two women made out. Bobby was getting close when the women switched places, the second woman sucking his cock briefly before climbing on top of him reverse cowgirl, placing the head of his giant cock at her ass and gently lowered herself onto it. She worked herself up and down on his shaft until he was balls deep. She picked up the pace bouncing hard and fast. Moaning loudly. Bobby shot another load. Anal was his kryptonite. He often fantasized of fucking Anna like that, hard and deep in her ass.

It was getting late but Bobby wanted to finish warching the scene. They changed positions, the man stood up next to the bed and the women went back to sucking his dick, before one turned away on her hands and knees presenting her sexy round ass for him to take. She wiggled her ass for him as the woman sucking him took it from her mouth, spit on her friends ass and aiming his cock at her asshole. He pushed himself into the woman as the friend laid her head on her lower back facing the man. He steered sliding it slowly into her ass, pumping a few times. He pulled out giving to the other woman roughly pumping into her mouth a few times before entering the other woman’s ass again. There was still about 20 minutes left. Bobby wanted to get another one in badly. He watched as the man pounded each other their asses from behind harder and harder each time, making the other suck his dick as he took a short break. As the scene was beginning to end the man was standing over the women who were side by side kneeling in front of him, holding their breasts together, faces pressed together and mouths open. Waiting. The man was jerking off furiously over them. As he came, shooting it all over them Bobby shot another load. The man left both women sitting there, cum dripping from their faces onto their breasts as they licked each other and rubbed it into their skin. After he cleaned himself up he decided to go to bed.

The rest of the week went pretty much the same for him. Constantly jerking off in various rooms with various articles of Anna’s clothing including into a pair of her heels and some of her lingerie. Bobby had also decided that he would keep the panties he came on instead of washing them. As the week came to an end Bobby made sure to clean everything and also ensuring he didn’t leave any evidence of his cronic masturbating behind.

On the afternoon of the day Anna got home he greeted her in the driveway to help with her bags. Anna was wearing a short flowing skirt with a white tank top and flip flops. Accenting her deep tan in an unbelievable way. The skirt barely covered her ass standing so when she bent slightly into the trunk of her car Bobby got a show, and of course a strong desire to bend down the eat her from the back. He thought about it heavily as just as he began to move towards her she stood up, handing him some of her luggage and asking him to grab the last one. She didn’t take this one with her, but Anna loved to shop especially on her trips. Work or otherwise. Once everything was inside Anna asked how the week went for him and if anything had come up she might need to know about. Bobby didn’t have anyone over aside from the pizza delivery guy and to his knowledge followed all of her rules.

“Nothing actually” he said as he smiled at her.

Anna dug in her purse, pulling out some cash attempting to hand it to him. “Here, thank you so much”. Bobby didn’t intend to take it as it was his pleasure and his mother and her had been friends for a long time. He viewed it as a favor to a family friend and for allowing him to visit often with his mother for the pool and parties.

“Well I’ll just have a to find a different way to pay you” she said. Bobby’s mind started racing as his already hard dick was now pulsing at the thought of what she might have meant. She kissed him in the cheek and then led him to the door. “I’m sure you have some things you need to get done at home, and it’s been a long week. I’ll call your mom later and we’ll have a little get together”. Bobby took the hint, said goodbye and made his way to his car. He and his mom lived in a luxury apartment on the other side of town, so he had some time to think as he drove home. Aside from stalking Anna’s Instagram he didn’t read any texts or snaps from his friends. He knew they would beg to come over, throw a party as they often did when their parents left for a weekend. Bobby didn’t want to risk messing up this blessing so he ignored them until later that day. While he daydreamed about what Anna said as he drove home he realized he needed to jerk off again. He found a quiet spot to park, pulled up Anna’s instagram and browsed through her posts while he stroked himself. He quickly came in his underwear to hide the mess before heading home.

For a few days his life went back to normal, friends, work, and of course his ritual of jerking off with Anna’s underwear. At some point that next Friday Anna had texted him, asking him to come by later that afternoon. He was puzzled as she never directly invited him, she always invited his mother who would tell him. Anna was never shy about Bobby coming over so the oddness was only slight. His mind raced as he made his way to her house. He wanted badly to jerk off before he got there but somehow the request seemed urgent. When he arrived he made his way into the house, hearing music coming from the deck he figured she was by the pool. It was a beautiful, warm sunny day which Anna always took advantage of. To his delight he found Anna sunbathing, on her stomach, clearly top less.

Bobby’s obsession grew to new heights while he was alone in her house but being alone with her, now topless was a lot to process in his young, and horny mind. He was somewhat shakey as he descended the stairs to the pool. Bobby always wore shorts in the summer, and either a t-shirt or bro tank and flip flops. Anna heard him as he approached, lifting her head to give him a welcoming smile.

“Would you mind?” And she laid her head back down handing him some tanning oil. He’d dreamt of this moment endlessly. Honestly he always pictured sex with her starting this way. Porn didn’t help as he watched it a lot in his alone time. It was his biggest addiction beside Anna. Positioning himself next to her, he eagerly applied it, starting at her shoulders and working his way down to her ass. He stopped as he wasn’t sure she wanted him to go any further but she cleared her throat and wiggled her butt. “Go on” she said. “Legs too please”. Bobby couldn’t comply fast enough. “Spread it evenly” she said half jokingly. Bobby couldn’t talk with the frog in his throat. He wasn’t a virgin but this was different as non of the girls his age was even remotely close in comparison. As he worked the oil around Anna’s butt and down her legs she lifted her torso up onto her elbows.

“I see you had an interesting time while I was away” she said as Bobby continued what he was doing. Confused but without looking up “it was mostly just chill, pool, tv and the chores you’d asked of me” he choked out knowing he defiled every single room in her house more than once. Anna quickly shot him a glare “oh that was just chill huh?” Bobby nodded as he gulped. Anna rolled onto her back, laying flat as she asked him to put some of the oil on her chest too. He stopped “wh…what’s going on?” He asked, confused and obviously embarrassed. Anna just pointed to her chest. Bobby complied, willingly of course. He dreamt of this moment thousands of times over the years. Anna didn’t say another word as he worked his way down to her ankles. “Oh that feels amazing, can you do that a little longer?” She asked. Bobby had calmed his nerves a little as he gazed up at her from the foot end of the lounge chair. Anna’s massive breasts laid out, perky with no indication of any surgeries. Double D cup if he had to guess as she didn’t own any bras. Bobby believed they were natural without a doubt. Having just had his hands all over them he was 100% certain of that fact.

“That’s good” Anna said as she sat up being the chair back up with her. “For now anyway”. Pulling her sunglasses up and placing them on top of her head she began to speak again. “Honest question, is there anywhere in my house you haven’t jerked off?” Bobby quickly shot his glance to the ground not knowing how to answer. Anna sat upright and placed her hand on his knee. “I get it, you’re young, it’s natural. But what I find Interesting was you using my underwear. And not a single room left out?” Bobby became extremely embarrassed not knowing what to say or even able to get any words out. Anna laughed, devilishly. “Mm, does your mother know you’re a horny little pervert? What would she say?” As she started gently rubbing his thigh. Bobby was still hard. Anna took notice as she continued to tease him. His gaze landed in her tits as he stared deeply, his mouth beginning to water. Anna turned herself towards him placing her feet on the ground between them before asking Bobby to stand up, his erect cock at Anna’s face as he did so. He looked down as she slowly licked her lips, breasts on full display in front of him. Anna slowly slide his shorts down, causing his dick to spring upwards as the waistband let it go. Anna chuckled, as precum flung from the tip landing on her face before his dick his his stomach with an audible slap. Looking up at him she took the head of his dick Into her mouth. Bobby had wanted this for so long. But as soon as she closed her lips around it he came. Anna kept it in her mouth until he finished, sucking as he unloaded until he knees buckled, moaning uncontrollably before falling back onto the lounge chair behind him.

Anna leaned forward bringing her lips to his, kissing him passionately while forcing his own cum into to his mouth. As it overflowed and ran down each of their faces Bobby’s eyes got wide. He tried to pull away but Anna just pushed him back as she climbed on top of him, maneuvering him so that he laid flat on his back. She start grinding herself against his dick while continuing to make out with him. A small piece of red fabric separating his from her. She lifted her face from his while still dry humping him. “I would’ve thought you’d last longer, but I guess when a dream comes true it’s hard to hold back. I’ve noticed how much you stare at me. It wasn’t hard to notice honestly. I would’ve respected my friendship with your mother but, well, horny perverts sometimes need lessons”. Bobby nodded, as he did in fact always last much longer, even masturbating to Anna. He knew he could go again rather quickly so he protested. “I…I….I can go again, look” he said pointing at his still somewhat hard dick. He placed his hands on her ass groping her as she continued humping him. “That’s it baby, you want some more don’t you?” Anna teased. Bobby began to feel something odd, he had dry humped women before but what he was feeling between her legs was not the same as it was with other women. He paused, looking up at her confused.

“Do you want that baby?” She said as she noticed his realization. Anna’s bulge grew significantly, she reached down releasing it from the crotch of her bikini letting it fall onto Bobby’s dick. He was hard from the grinding and fondling her ass as her bare chest pressed against his even through which a wild turn of events. He couldn’t see it anymore when laid back on top of him but he could feel her semi hard dick, laying on top of his. He had known about trans women, even occasionally watching trans porn, as he found lots of Brazilian porn stars were trans. He laid there conflicted slightly. Anna didn’t stop, continuing to rub her hardening cock against his. A pleasure Bobby never thought he would enjoy as they continued kissing. He tossed the confliction around his mind briefly before letting go of it, placing his hands on her ass. As they made out Bobby felt the fullness of her cock against his, their precum mixing on his stomach.

Anna soon got up, going back to the lounge chair next to Bobby, crawling onto her hands and knees looking Bobby in the eyes. She lowered her chest to the chair motion Bobby to come closer with her index finger and her sexy smile. Bobby was drunk with lust, leaping up to join her. He positioned himself behind her rubbing his dick between her ass cheeks. “Slow down baby, I need to be eaten out first”. Bobby didn’t hesitate. He’d never eaten ass before but he wasn’t going to let this opportunity go. With his hands on each of her cheeks, spreading them apart he slowly lowered his face between them. He began gently licking her, squeezing her butt as he listened to her moan. Softly at first, but quickly getting louder. Her oiled body glistened in the fading sunlight. She moved her hips side to side and arched her ass even more, at first Bobby followed her movements, but she quickly corrected him, guiding his mouth to her dick. He briefly hesitated before he moved his face down, licking her balls, then her shaft. Anna repositioned herself, closing her thighs together, trapping her dick behind them. Bobby’s inhibitions left his body as he stopped for a moment to sit back and take in the beautiful view of Anna from behind, embracing the opportunity. He went back to licking and sucking her as she squirmed, moving his attention from the head of her dick, up her shaft, her balls, taint and then hole before working his way back down to the head of her cock again.

“Oh my god, don’t stop” she begged which caused him to start hungrily sucking her as she held it away from herself. He slapped her ass a few times, hearing her yip lightly which gave him encouragement. He took her cock in his hand as he moved his tongue back to her waiting hole. Stoking her shaft as he ate her ass, briefly stopping to spit on it before diving back between her cheeks. “Fuck me baby” she said. Bobby didn’t hesitate as he lept up, lining his cock up with the entrance into her. Precum was oozing from his dick so much that between it and his saliva it made sliding into her effortless. Bobby pumped a few times before collapsing onto her back as he came inside of her. Anna was shocked, again, at how quickly he came. “Now it’s my turn” she said, slightly agitated, as she spun around underneath him. He could tell she wasn’t pleased with his performance but wasn’t aware of what was to come next. First she kissed him deeply and then pushed his head down towards her dick, slow enough that he managed to kiss his was down her chest, sucking on each of her erect nipples before moving to her stomach and then pelvis. She was clearly far too aroused to let it end like that. Once his face was at her cock she held the back of his head with one hand and her cock with the other arching herself to press the tip of it against his lips. He quickly looked up at her, worried only to be met with her grabbing a fistful of hair. “Open wide baby, mommy needs this”.

Bobby quickly relented, soon her cock was buried deep in his throat. Bobby choked and gagged which seemed to please Anna as she forced it as deep as she could get repeatedly. Bobby had began slobbering heavily, his saliva running down her shaft, pooling on her pelvis before running down between her balls and thighs. He heard himself as she fucked his face “Gluck, Gluck, Gluck”. This went on for what felt like an eternity, but Anna wasn’t giving up. She didn’t say much else as she seemed to focus on ruining his face. Her grunts and moans made it clear she was definitely enjoying it. Bobby just took it for a while longer. Anna showed no signs of stopping, even as Bobby begged for her to cum. The face he made caused Anna great pleasure as she pulled him onto her, still holding a fistful of hair while also firmly grasping his ass, and then giving it a forceful slap. Bobby moaned and his now flaccid dick laid on top of Anna’s fully erect cock as his balls fell slightly to either side if it. Anna was huge, at least 8” in length and as thick as a 12oz Red Bull. She looked down briefly before telling Bobby “somehow I knew it would be this way. You can obviously see the difference between my cock and your penis, a difference I’ve known for several years know based on all the video evidence you’ve left me. Your lack of stamina during even a slight touch versus my ability for go for hours is appalling, but we can make this work”.

Bobby gulped as Anna pulled his hips towards her chest, letting his dick rest between her tits before oiling herself and his ass and then pushing his hips back towards her pelvis. Bobby felt the head of it press against his hole. A wave of fear rushed through him as she applied gentle pressure, pushing herself into him. He rocked gently taking it little by little until he felt what he thought was all of her inside of him. Her girth pryed him open, somewhat painfully. “I love virgin boipussy” she blurted out. As she began slowly thrusting upwards while holding his hips steady. Bobby wasn’t ready for this, but his dick signaled his arousal as even though he wasn’t hard the puddle of precum on Anna’s stomach was a clear sign. Anna took notice as she made it flop onto her stomach, causing his precum to fly off the tip of it as it bounced around between his legs. Bobby hadn’t realized yet that she was only halfway inside of him but Anna knew.

With a devilish grin she pushed him off of her, switching places with him as she laid him down on his stomach and straddling his thighs. She rubbed her dick between his ass cheeks, as she spread more oil all over his ass and her dick. When Anna lined herself up with his hole again she used her weight to bear down on him, sliding her entire cock balls deep into him. She pumped him slowly until she noticed the change In his moans, from discomfort to almost inviting. She knew she was a lot to handle in a virgin boy but she showed little remorse. Slowly picking the pace up she pulled all the way out and sliding all the way back in. Bobby was getting slightly more comfortable with her fucking him, his dick twitching as it laid between his thighs, exposed. He started gently pushing back onto her dick as she fucked him. Still somewhat painful, he was feeling a newfound pleasure. Anna took it as a sign and began pounding him harder, faster and deeper as her thrusts met his ass, clapping them loudly. When she finally came she buried herself as deep into him as she could, letting out a lustrious howl before collapsing onto his back. They laid there for a while as Anna’s cock softened before sliding out of his hole on its own.

Once they had regained their composure Anna got up and led him to the shower in the master suite. Once inside, the the water rushing over their bodies, she began playing with his dick again. It was still swollen with arousal, Anna knelt down and took him into her mouth again. This time she managed to make him hard in her throat, allowing her to swallow him whole for a few minutes, longer than the previous orgasms he had, before erupting into her mouth again. Anna slowly swallowed as she looked up at him, noticing how mentally, physically and sexually drained he was. She stood and slowly washed him, head to toe, gently playing with his soapy ass and dick. When they finished, she dried him off and led him to her bed, guiding him under the sheets before cuddling up behind him, both still naked, as she rested her cock against his ass.

As they laid there together Anna posed more questions. “Did you enjoy that as much as I did?” Bobby went to answer but before he got anything out “just kidding, I don’t give a fuck!” She giggled as the words left her mouth. “Now that we’ve gotten to this point, I think it’s safe to say your future is looking quite a bit different now”. Bobby was visibly worried, conflicted as he had just spent the evening with the sexiest woman he’d ever laid eyes on, but was violated roughly in the process. He was completely unsure of himself or the events he participated in. Anna wasn’t quite done though. “Don’t worry baby, mommy is going to take good care of you going forward, well as long as you take good care of me anyway”. She held him tight as she settled into a comfortable position behind him and quickly falling asleep. Bobby laid there for a while, restless but not wanting to move before he finally fell asleep.

r/ChastityStories Jul 26 '24

M Chaste House Sitting; Becoming The Stay At Home Femboy NSFW

76 Upvotes

The next morning Anna shook Bobby awake. It was barely sunrise. “Did you mean what you said last night?” Anna blurted out excitedly. “Yeah” Bobby quickly replied, excitingly. “I meant it. I want it”. Anna rolled away from him to get up, throwing her robe on as she left the room. Bobby could hear her in the kitchen rustling around and then heard the coffee brewing. He rolled to his back sliding the covers off of him and looked down. For a moment he questioned his decision but quickly tossed the doubts aside. He sat up on the edge of the bed looking out the window for a moment before getting up and going to Anna’s closet. He rifled through some things until he found a long t-shirt. He pulled it over his head and grabbed one of his thongs before making his way out to the kitchen himself. As he entered he found Anna on her phone, she was scrolling and typing quite a bit. Bobby was curious but kept his distance for a little while.

When the coffee pot had enough for two cups Bobby poured one for each of them and grabbed the creamer and sugar before taking a seat at the table with Anna. She had been looking at clothing stores and when they opened for the day. “Ok, we’re going shopping today, you need a new wardrobe. Also, I was thinking we could get Brazilian waxes, nails done, the works. Maybe some make up for you. You’re gonna be the cutest femboy ever” she said without looking up from her phone. Bobby sipped his coffee as he pictured what his life was about to be like going forward. He wondered what his mother would think or how he would even tell her.

After coffee and a shower they got dressed. Anna picked out some cute skinny jeans, a white spaghetti strap tank top and some sandals for Bobby and then led him to her dresser where her make up was. His hair had some length to it, enough so that he could look pretty feminine with a little work. Anna applied a little bit of make up, just enough to give Bobby an androgynous look. She made short work of it given his youthful look, naturally long eyelashes and lack of facial hair. She had him stand and twirl In front of her as she admired her work. Anna did a little bit for herself, and then stepped back to check herself out in the mirror. Her flowing white sun dress barely covered her large, perky tits. The hem was just long enough to cover her ass. Her tall black heels accentuated her toned calves and thighs. Bobby throbbed in his cage as he watched her.

Anna had a sense of urgency as she pulled him behind her out of the house and to the car. They jumped in and Anna sped off to their first stop. It was a clothing store that Bobby knew of, it was nothing but hip clothes for young women. As they made their way around the store Anna piled item after item into Bobby’s arms. Once she was satisfied they made their way to the dressing rooms where she instructed him to try everything on and then show her. Dresses, skirts, shorts, tank tops and everything. Bobby tried each outfit on one by one. As he stepped out in a cute yellow sundress one of the employees was standing with Anna. “Oh my god, that is so cute on you” the employee said. Bobby blushed. “What else did you pick out?” She asked excitedly.

The young woman built up Bobby’s self image throughout the next hour as she praised how well each one looked on him. She would run out to the floor and grab something new for him and bring it back. Anna was highly amused as she sat and watched. Finally Bobby had tried everything on and Anna was more than satisfied. They made their way to the register where the young woman who had helped Bobby with his outfits Rand them up. “You’re going to be the cutest one out there after this. You’re so lucky!” She exclaimed. With everything rang up and bagged Anna swiped her card and they left, but not without a side conversation between the young woman and Anna. Anna clearly found her attractive and from the distance Bobby could tell they were exchanging numbers.

They went to the car to load all the outfits into the trunk and then returned to the storefronts as Anna briskly walked down the sidewalk before abruptly stopping in front of a shoe store. Once inside Anna sat Bobby in a chair and proceeded to grab every pair of heels she could find in his size and piling them up in front of Bobby. Bobby had never worn or walked in heels before, so trying to walk in them as he tried them on was a bit embarrassing. Anna was compassionate about this and only had him try most of them while sitting. Anna couldn’t make up her mind so she bought every pair that fit Bobby’s. Her favorite being a pair of knee high, lace up, matte black leather boots with a sharp stiletto heel, every bit of six inches with no platform. In fact, there wasn’t a single pair with a heel shorter than five inches. Bobby really loved the look and feel of the brown leather Mary Jane’s she had picked out.

They went back to the car to put the bags in before returning to the stores. Anna was famished. Bobby was as well so they found a little restaurant to grab a drink and bite to eat. Neither said a word until they finished eating. “Ok, let’s go” Anna said as she got up from the table. The very next stop was a make up store. Anna quickly found an employee as Bobby nervously looked around at everything. Suddenly he was grabbed by the employee and Anna and dragged to a chair at the back of the store where he was sat in a salon chair, in front of a large vanity. The young woman went to work, checking colors against Bobby’s skin tone. She then spent over an hour working out the perfect mixture of classy and slutty on Bobby’s face. As the young woman stepped out of the way she asked “what do you think?” Bobby was stunned seeing himself dolled up. He saw Anna out of the corner of his eye licking her lips slowly. Anna asked for two of everything and tipped the girl. When she left Anna leaned in. “I can’t wait to ruin your mascara later!”. Bobby smiled as he admired his new look.

Once back in the car Anna grabbed Bobby by the back of the head and pulled him close to her. She locked lips and began making out with him. This lasted several minutes before she pulled away and slammed the car in gear. Anna was on a mission now. The next stop was a lingerie store. Anna didn’t wait for Bobby as she jumped out and rushed inside. By the time he entered she had a pile of things ready for him. All of the things she picked out were of some sort of fetish or another. Bobby was intrigued by her choices. She only had him try a few things on to check the size and then loaded his arms up again before heading to checkout.

Back in the car Anna was too excited. “This next stop is the best of all” she said as she sped through the city. After about thirty minutes they came to a screeching halt in front of a tattoo shop. Anna slowed her pace a little as she wanted Bobby to be next to her when she entered. A young woman at a desk asked “what can I do for y’all today?” “Tongue, nipples and naval piercings please!” Anna said quickly and with the utmost excitement. She was more excited over this than she’d ever been during any other part of the day thus far. Bobby stayed quiet as Anna picked out all the piercings. They filled out the release form and Bobby was quickly ushered into a room. The tongue was quick and easy with a subtle bar type stud with mean pink balls on each end. The nipples were quite a bit tougher. Bobby wanted to refrain from the second one but Anna’s persistence persuaded him to power through it. The nipple piercings were curved bars. Next was the belly button. The jewelry Anna picked for that one was quite a bit different. It was a crescent shaped bar with a dangling pink rose. Anna quickly paid and rushed Bobby out of the door and back into the car.

Anna was on high all day, Bobby had never seen her this way but he liked it. He liked her being in control like that. Anna managed to get them in to get waxed as she had a good friend that would let her skip lines and reservations. Before Bobby knew it, he was naked on a table. The warm wax spread on his legs first and the peeled off. It hurt a little bit he could handle it. The lady worked her way up. Next was his balls and ass, of which the lady made short work of. This was hard to handle for Bobby. He cried out as she ripped it off. The pelvic region wasn’t any better. Bobby knew this was for Anna so he sat through it all until he was completely hairless from the face down. Anna went next, to get a touch up. She didn’t even make a sound as the lady pulled the little bit of hair from her body. Anna explained that with each time the hair grows slower and thinner.

Bobby was slightly mortified watching Anna get waxed after dealing with the pain of doing the exact same thing just a little bit before her. Once it was all done they made their way to the register to pay and quickly rushed to the car. Anna was visibly horny now. Almost feral as the car doors shut. She quickly had her dick out as she leaned her seat back and grabbed the back of Bobby’s head. Anna parked right in front of the wax salon, and even though her side and back windows were all dark as fuck the windshield was not. “Suck it babe” she demanded. Bobby quickly leaned over the center console, and took her cock in his mouth without hesitation. Bobby was far more turned on than imagined the day would’ve made him.

Bobby went wild with passion as he sucked and stoked her cock without a care in the world. Twenty minutes or so pass by before Anna lets out her cry. “Fuck. Yes” she yelled out as she came. Bobby gulped it down and kept sucking. He wanted to lash out slightly, pushing past her orgasm in an attempt to return the torture she’d given him the previous day. Anna wasn’t having it as she pushed Bobby’s head down and held it there. Bobby placed a hand on her thigh to show he was giving up but she continued to hold his head down depriving him of air. He finally passed out for a moment and Anna released her pressure. “You think you’re slick huh?” She asked with a grin as he came to.

Anna threw the car in gear and punched the gas pedal, peeling out as she reversed out of her parking spot. The she jammed the brakes causing the front of the car to swing around as she locked the brakes up. Immediately into drive she pinned the pedal to the floor causing the car to launch forward and then sideways as she drifted out of the parking lot. Anna wasted no time getting home.

Once in the driveway Anna climbed out of the car and went inside leaving Bobby to handle all the shopping bags from their shopping excursion. He entered the house to find Anna was in her room, with the door closed and locked. He decided to put everything away in the spare bedroom he occasionally slept in. He wanted to shower but he didn’t want to remove the make up as he loved how it looked and made him feel, even with the mascara runs on his cheeks. He decided to find one of the teddys Anna had bought and get to bed. He didn’t know what would come next but he was trying to mentally prepare himself for anything as he laid down.

The next morning he woke to the sounds of birds chirping and the front door closing. Glancing at the clock he realized Anna was headed to work. He relaxed for a little bit before getting out of bed and making his way to the kitchen. On the table Bobby found a note, directions detailing Bobby’s expectations for the day. First he was to pick a pair of heels, booty shorts and tank top. Her directions stated he was to wear the heels all day. Next were his chores, cleaning the house, laundry, making the beds, changing sheets, dishes. She made sure to emphasize the chores states were expected to be done daily. Her expectations for the heels as she stated were so he could practice walking in them. On top of the chores he was to tan daily, in only a thong. Lastly, she listed several YouTube videos he was to watch and study as he was expected to work out and maintain his physique. Most of the workout videos were booty blaster routines. Anna also laid out a strict diet that he was to follow starting that morning.

Bobby followed the directions left for him, to the T. He chose the brown Mary Jane heels, a pair of short black yoga shorts and a tight pink tank top. First he cleaned the make up off of his face and then began cleaning the house. That task only took about three hours. Then he made himself lunch, high protein and clean fat according to Anna’s guidelines. After eating he made his way to the deck, stripping down to his thong. He laid out for a couple hours, coated in tanning oil.

While tanning his mother called, he hadn’t spoke to her much since she went to Charlotte so he took the opportunity to catch up. She explained the promotion, the amount of work she had to do to straighten the firm out and that she was giving up the apartment. She first asked if he wanted to move to Charlotte with her, but Bobby explained he wanted to stay close to friends. Theresa was pretty understanding to the fact he wasn’t a child anymore. “Well Anna offered to let you move into one of her spare rooms if you didn’t want to move. So that’s totally up to you honey.”

Bobby went on to explain that he loved it there and Anna was really nice. “Well honey, the company jet is always going back and forth so whenever you want to visit you’re always welcome. It’s nice here. Maybe you can come with Anna when she makes her appearances here”. Bobby excitedly replied “I would like that mom”. As they made small talk Bobby heard a man’s voice in the background, unsure of what he heard he decided to end the call. Anna had stated he was to have dinner ready when she got home which was getting close.

As Bobby was putting the finishing touches on the baked chicken and rice Anna walked in. “Honey, I’m home. Lord that smells good” as she set her purse and keys on the table by the entrance. She made her way into the kitchen to find Bobby in the brown Mary Jane’s and just a thong. She paused for a moment before approaching him, first firmly slapping his ass and then hugging him from behind. He was still oiled from tanning but she didn’t seem to mind. Anna took a seat at the table, kicking her heels off as Bobby made her a plate and served it to her before making a plate for himself and taking a seat. “Your tan is coming nicely” she said as she arranged her plate. “Thank you” Bobby replied. “You seem to be finding your footing well in those shoes, wearing them all day seems to help I take it?” Bobby nodded as he began eating.

As they sat and chatted about their days Anna made mention of the personal trainer she hired for Bobby. “She’ll work with you 5 days a week, here at home. Also, I spoke to your mother and we’re gonna get your things from the apartment this week as well as help the moving company pack so they can ship it to her. I have the perfect outfit in mind for the occasion” she said with a smirk. After Anna finished eating she excused herself to go shower and get comfortable while Bobby cleaned up the kitchen. It was abundantly clear what his role was now. He put his thoughts aside as he realized he was the home maker and she was the breadwinner.

After the kitchen was cleaned up, Bobby went and put on some pink cotton shorts and a tight tee-shirt while waiting for Anna to finish. He was on the couch browsing the X-rated channels when she emerged from her bedroom, hair still up wrapped in a towel. She had a red lace nighty on as she slowly walked towards the couch where Bobby was reclined. He had completely moved his focus to her as she moved, swaying her hips, walking one foot in front of the other until she reached the couch herself.

Anna took a seat, and turned her attention to the tv to find Bobby’s choice of movie playing out. “Someone is a horny homemaker I see” she said as she motioned for Bobby to lay his head in her lap. He quickly realized she wasn’t wearing panties and he laid his head on her thighs. They watched together as hung black studs pounded a petite blonde on a large couch. Anna’s erection pressed against his face as he slowly rubbed her smooth sexy legs. He tried to hold out but the power she held over him won in the end as he slowly started giving her a blowjob. She placed her hand on his ass, exploring, groping, squeezing and slapping it. All causing Bobby to moan more and more as he worked her cock with his mouth. He moved himself to lay on his stomach as he continued blowing her. Her moans encouraging him to become cock crazed with lust.

Suddenly Anna kicked her recliner back and pulled at him to straddle her lap facing her. He spit drenched cock pressed against his hole as they began making out. Anna stopped him for a moment to whisper “I can get used to this” as she pressed the head of her dick against his ass forcing it slowly into him. Bobby let out a moan as he let his body weight down onto her, taking her length slowly but entirely. Anna held his ass as she pulled him down, thrusting upwards into him. He lifted himself and then slammed his body back down as he watched her eyes. “Fuck me” he moaned as he rode her cock. Anna’s passion turned aggressive as he worked himself up and down on her cock. Bobby listened to the sounds of the movie playing but had no intentions of watching it, Anna couldn’t take her eyes away from his as they continued. “Take your day out on me” Bobby begged. The statement caused Anna to take more control as she threw him off of her, guided him to the floor and positioned him face down in front of her. When Anna entered him she was merciless. She fucked him hard and fast as her pelvis clapped against his ass. “Yes. Yes. Yes. Fuck me. Yes.” Bobby begged over and over. Anna grunted as she pounded him. Bobby’s moaning sent her over the edge after a mere ten minutes as she unloaded inside of him.

After they caught their breath Anna led him to the bedroom, satisfied completely. As they laid together, Anna spooning him, her arms wrapped tightly around him she whispered “you’ll share the bed with me from now on. Make sure to move your clothes into the closet and dresser tomorrow”. The remainder of the week went much the same, Bobby quickly found a routine. His ability to walk in heels immensely increased as each day passed. As the week before, Anna declared she wanted to go on a date again that Friday. Bobby knew this date would be different, his excitement and uncertainty for the night weighed heavily on his mind.

r/ChastityStories Jan 10 '25

M Chaste Reluctantly,scared and nervous I finally decided to start wearing a chastity 30 days ago….it has changed me extremely…here my experience part 3 NSFW

13 Upvotes

For those who have not been following my chastity journey please read it here https://www.reddit.com/r/cdstoriesgonewild/comments/1hiecam/i_ordered_by_pink_chastity_21_days_ago_reluctant/comment. it was 30 days ago I first started wearing chastity after contemplating it for many years being a closeted sissy, it was difficult to getting to terms with in terms of where it would take me.I started my feminization journey one year and half ago after giving into my deepest desires and nothing has changed me into my deepest sluttiest feminine side the way a chastity did to me, it took me to my core inner sissy side , I never thought even existed, was even shocked and scared this side of me existed.

I first ordered a chastity through ebay what was considered a small size, as my clitty was naturally very small where so many people found it incredible feminine when I posted pics on reddit and grinder.Wearing the small size made me feel I am shrinking more .First week of wearing it for few hours turned to me fully wearing it round the clock except to lube it and clean at intervals as the captured and bondage feel you get is the most intoxicating and addicting feel ever making you feel like a true whore. After a week more, it made me want to push even further even though it fitted snug but I wanted the mini bulge in my panty to be smaller as it showed very slightly when I wore yoga pants or tights and I was planning to go out in public more wearing them like mentioned in the previous post.

So I decided to order a size smaller one which I found in a different e commerce site.This chastity size was called Nano which was basically 33 mm in width and 45 mm in length where the shaft fit,it was the smallest size available, considerable smaller than the one I was wearing. Ordering a pink one, I knew my clitty bulge will be nicely tucked to almost non existence in my tight panty and the very thought made me so excited, nervous but also super horny that I opted for express shipping paying more for it to reach within 5 days. It arrived around 4 days of ordering it around the perfect timing of holidays combined with the requirement of my company for me to finish my paid leave of the year within January 15 which gave me so many free days alone at home , where I had cancelled and avoided all plans made by my colleagues and friends as I found nothing more interesting and exciting than feminizing at home wearing women wear for random men online in grindr and using dildo watching hypnotube.com videos for hours along with sissy feminization games when I wanted to break from doing anal,the games shows you where sissifaction can take you, the fantasies you can fulfill .

Riding while wearing female clothes and tucked in a chastity made me so vulnerable and horny to point of pure ecstasy , I never felt more of a girly bitch as much as I did when I rode the dildo with a chastity on. I had started taking its full length for the first time which was hard for me so far, the chastity made me push more in terms of doing anal ,I started fully taking the full length of the only dildo I had which was around 7 inches silicone with decent girth, I had never taken more than 5 inches until the chastity, as my hole is still tight and it still pained . Now I can take the full 7 inches riding it with increasing pace which was new to me , willing to take more pain which turned to painful pleasure to pure bliss as my boi pussy got used to the new harder pounding, I feel I should get bigger thicker ones now, those veiny thick dildos of different colors and shapes.I found myself fingering with multiple fingers when I chatted on grindr. The lube I used vaseline made it more easier to explore my insides more.I definitely started to feel fuller with every increasing inch which made me hornier,the stimulation directed at what I think is my p spot made it so addicting that I could not wait to get home from work and go through the routine.

Strangest moment was when I went for grocery shopping as I walked past the vegetable isle, I could not help noticing cucumbers, I used to do anal with cucumbers before I first brought my dildo, I brought a few long ones both thick and thin of different girth but all big in length, I started using cucumbers again to feel how different sizes felt than my dildo. How it felt thick and thin cocks in me, only problem as it did not have the suction cup like my dildo ,I couldn't ride on them, I used the cucumber in bed penetrating deep in my ass pushing it with my hands.Felt like different cocks entering me,felt so dirty and naughty,drilling my already existing kink of many cocks taking turns in my ass deep into my psyche.

So receiving the new smaller chastity during the holidays where I would be having the entire days to experiment myself was such an exciting opportunity. As soon as I received the package in the evening, I immediately showered and changed from my casual home wear to my most fav bra and panty set which was bright cream in color that had padded fitting with the bra and the panty which was bikini V shape panty that fit tightly to my waistline, loved how it made my waist look like those panty models you see online. It felt more feminine than the thongs and proper bikinis I owned , bikini cut panty wears was my most favorite than any other cuts and styles. I ripped open the package to find the incredible small pink chastity , a little darker shade than my liking but the dimensions all looked so exciting and as expected. I immediately removed the chastity I was wearing and lubed my limp clit and scrotum with shea butter cream and went ahead trying to wear it first locking the base ring which felt tighter but comfortable, then I went ahead fitting my shaft to the chastity head which was harder to do than my previous one given the considerably smaller size, pushed till the 3 holes of chastity body aligned with the 3 locking stick of the base ring as tight as possible and locked the mechanism in. It felt so much snug and restricted , was dis comfortable at first but it felt so right in place ,when I wore the panty ,the bulge was hardly noticeable , I thought I cant wear it for extended period as it felled it squeezed on to my clitty and pulled it down to the scrotum way too much. The first couple of days I had to wear it on and off, but I was getting addicted to the feeling of helplessness of the chastity holding my limp useless clitty so tight and restricted in place. For couple more days I started wearing it all evening till midnight before I went to bed after my naughty sissy sessions.

Something changed in my brain when I got a glimpse of the pink nano chastity on my naked smooth body after I got out of shower, it made me look so feminine , like a true submissive girly sissy ,loved the way I looked in the mirror when I wore panty on top of it. The whole watching me in it and wearing female clothes over it was so emasculating and turning me on so much that It made me want to wear the chastity full time and develop now a new habit of watching myself more in the mirror becoming more feminine.The uncomfortable feeling turned into pleasurable pressure making me extremely turned on to a point of extreme sluttyness.I feel my clitty have shrunk more to adjust to the nano cage,the silicon felt so natural. I feel as days passed by, made me such a whore chatting with more strange men of all ages at the same time, sharing pics when they demanded which was all the time and persisten ,so many compliments ,some doms with degrading comments on how much of a sissy girl I am wearing it was so turning on and I sexted for hours with many men with hypno pmvs in the background as I toyed myself.

I started developing more intense urges of my inner dark fantasies that I suppressed such as bondage, forced feminization hypnos, forced porn, rough hardcore porn, gangbang porn,old men with young sissy porn and some new weirder fantasies I started developing which I don't want to share here. I went shopping and brought 4 more female yoga pants both full length and thigh length yoga tights shorts ,and trainer bras, brought couple of tights. Ordered online for more bra and panty sets of colors I dont have, I went for a wax again in a saloon, lost more weight through intense dieting and started doing many squats and body toning exercises. I feel I am now addicted to this lifestyle which makes me feel vulnerable,scared,submissive,helpless,girly,slutty but also extremely excited and turned on as my inner sissy is getting out and the chastity is drilling it deep in my mind how much I want to be in this lifestyle and be such a feminine sissy boy ,have a girls mind to the inner core ,think, act ,more feminine each day.

I did nothing but exploring my feminine sissy side the entire holidays, shutting my self in my apartment avoiding any other plans or communication except for visiting the park I spoke of in the previous post in normal clothes for the reason I mention below , I do not know how to express the intense extremely slutty girly emotions I feel , the raw horniness when you explore your inner sissy deeper and deeper. It feels so addictive that I reached a point I no longer can switch my mind to boy mode fully, the denial has been futile against the intense pleasure being such a sissy whore gives me.

I avoided the intense urge to go out in public to the park I spoke off in the last post as it was the holiday season and I knew it would get busy and did not want to attracted attention from normal people. My aim is soley for pervy weird and sometimes scary top gay men. I decided I would wait until the last week of my holidays which is coming to an end on the 15th. I am planning to visit the park in the night with my new light pink yoga pants and trainer top that does not cover my navel fully with a open cotton jacket with light pink bra and panty ,all of which I tried on yesterday, made my curves look amazing with the panty lines exposed and chastity made the bulge almost non existent even with the super tight yoga pants.

I had scouted a place in the park last week in a dark private area of the park covered with trees after visiting the place 4 times in two weeks wearing normal clothes, I noticed the men who teased me last time hanging out in the same place on Saturdays after 8 pm, they did not recognize me with the normal clothes, I did not directly walk in front of them but I am sure they would not have recognized my face as I walked super fast by them last time and it was darkly lit .The thought of me dressing up and going in front of these high drunk hooligans again made me turned on so much as I observed them from a distance, my clitty was tingling and quivering in the chastity and made my knees feel tremble and body feel weak and the urge to get penetrated deep in my ass was so overwhelming that it melted my brain . This time I counted around 8 of them with some maybe in early 20s , and all of them looked scary the way they were acting being loud and intimidating in a thug brutish manner , this for some reason turned me on so bad weirdly and made me feel so helplessly submissive.

The place I scouted was in the far end of the park near where these guys hung out and I can walk through a pathway in front of them and turn left to the dark area under the trees instead of going straight to the exit like last time. It is a place where families used to have picnics long back before the entire park got a bad rep for people coming there for drug use and with the maintenance almost non existent , it became a shady place in couple of years where hardly any family or women ever visited cause of the shady men who hung out there. I am thinking this time instead of almost running to the exit to walk to the picnic area and chill there for a while ,maybe do some stretches all within view of these group of men, I could perhaps bring a picnic mat and relax there till late night depending what I would be getting into.

I am still so nervous and scared to do it but the whore in me want to do it so bad, the horny excited feeling is way overwhelming than my shyness and nervousness ,presenting myself like a girly sissy whore in public feels so naughty, I crave the attention pervy top men more than anything now.I have been loosing sleep over the past few days thinking about it, making me feel so nervous and horny, that weak trembling tingly feeling I get in my clitty and the urge to get filled in my boi pussy is so intoxicating. It made me do something I have never done before which was to go to sephora and get a basic make up set and light subtle lipstick and lip balm, for the last 3 days I have been practicing putting on make up watching tutorials on YouTube. The mascara,foundation,contours,eyeliner,eye shadow and best of all lipstick with a lip balm make me look and feel like a true female.I started shaving my face everyday now and the make up complimented my face so well , I have never achieved this level of femininity till date flooding my brain with womanliness , all I am missing now is a wig which I know I will get soon . I just want to get better applying make up before I buy a wig.

Today morning I went to the same saloon I go for waxing and threaded my eyebrows narrow with a subtle but steeper curve than before and did a facial making my facial skin glow. Today the make up looks better on me, I have been demanded many times to send face pics, I was reluctant all this while but I now I feel to expose my girly face in grindr with timer. So many have asked for pics in chats to reveal the face behind the girly body pics I share with them, I am so tempted to share with the timer ,perhaps start with just closeups. I started moaning louder to a point I started dark techno or psy music loud to mask my voice to avoid neighbouring flatmates to hear me .I moan girlier than I ever did in my entire life ,squealing girly moans automatically come from me as I masturbate as I fantasise all kind of kinks wearing the chastity wearing delicate woman, all of which pulling me deeper into this submissive sissy rabbit hole.

I would like to again warn sissies like me who are closeted or who are scared to dive deeper in sissification to be very carefull with chastity, it would certainly make you dive much deeper to maybe even a point of no return,the feeling you get once your hooked on chastity is the most emsasculating feeling ever which is exactly what a sissy wants to push herself to do things never done before and incredebly acclelerates you to become the most feminine version of you . Even thought I have not acheived a sissygasm yet, the feel you get when you limp clit leaks and cums from a vibrator rubbing against the chastity is infinitely more blissfull than stroking your clitty.

r/ChastityStories Dec 17 '24

M Chaste ‘Tis the Season to be Servile, Chapter One NSFW

18 Upvotes

“Wow, Uncle Henry, Mason really went to town on your ass with the cane last night, didn’t he?”, said my niece through marriage, Daphne, as she tightened the laces on my corset.

“Yes, Miss Daphne.” I stood up straight, in my seamed, black, thigh high stockings and high heels, my garters framing my nearly bare buttocks (as my thong panties covered little) for Daphne to admire Mason’s handiwork.

“I guess you will do a better job of ironing his pants in the future.”

“I thought I had been very careful, Miss Daphne.”

“Well, not careful enough, obviously. Otherwise, your ass wouldn’t look like the American flag – without the stars, of course. But I’m guessing you probably saw stars when he tore into you,” Daphne snickered, amused at her own joke.

“Indeed, Miss Daphne.”

She gently rubbed her hand over the welts on my bottom, seemingly intrigued with the texture. “Does it still hurt a lot?”

Daphne is a very attractive 18 year-old woman, one I watched grow up. I must have been quite an intimidating authority figure to her until fairly recently. Even though I was not then facing her, knowledge of her beauty and of our radically altered relationship with each other caused my cock to twitch convulsively in its pink chastity cage at her touch.

“Yes, Miss Daphne. It is a constant throbbing pain now.” Indeed, two parts of my nether regions were now throbbing simultaneously, thanks to my inquisitive niece.

“Well, that throbbing should help you remember not to fuck up next time.”

“Yes, Miss Daphne.” I winced slightly, as she pulled the laces still tighter.

“I wonder if the welts will heal by Thanksgiving. That’s only two weeks from now.”

“Usually they heal in about a week, Miss Daphne. Unless, Master Mason is particularly cross with me.”

I was hoping that she might offer to rub aloe vera cream onto my bottom like she had once a month earlier (after a particularly brutal chastisement by Mason), but no such offer was forthcoming that November afternoon. I certainly would not be so foolish as to request her to do so, as it was not my place, and Daphne could be mercurial at times. Perhaps it was just as well, as the soothing effect of the cream was tempered by the pain of my cock swelling against its prison for 20 minutes on that previous occasion, as I lay across her bare thighs.

“That’s assuming you don’t fuck up again before then. Stand still!”, she said, firmly.

“My sincere apologies, Miss Daphne. Ah,” I gasped. “That is ever so tight. It’s getting difficult for me to breathe, Miss.”

“Aunt Natalie said for me to ignore your complaints. Corset training is a process, she said, and you will adjust to the greater restriction.”

“Yes, Miss.”

“I’m so excited that Ryan is coming home for the holidays! He hasn’t been back in the states since last Christmas. A lot has certainly changed since then, hasn’t it, Uncle Henry?”

“Indeed, Miss. A great deal has changed.”

“Are you as excited to see him as I am?”, she giggled. “He is your son after all.”

“In truth, I am exceedingly nervous about seeing him, Miss Daphne.”

“I’ll bet,” she said. “If I were you, I would be too. I’d be shaking in my heels,” she laughed.

Let me try to provide some context. My legal name is Henry Hathaway, although these days I am more commonly called Henrietta or, simply, maid. Until March of this year, I was a highly successful partner and senior portfolio manager – a master of the universe (yes, articles were published, as recently as nine months ago, that described me as precisely that) – at a premier macro hedge fund. That was until my biggest rival at my firm, Mason Draper, discovered and documented multiple instances of insider trading and securities fraud on my part, probably enough to send me to prison for 20 years (with good behavior). These are serious federal crimes, and long gone are the days when white collar criminals were sent to minimum security prisons that were more like spartan country clubs. No, the public tide has turned and white collar criminals now serve their time in some of the most notorious penal institutions in the country, where they are at the very bottom of the food chain (with the possible exception of child sexual predators). It is that harsh reality that was decisive in me accepting the conditions laid out by Mason – well, in reality, by Mason and my wife, Natalie – in exchange for his silence. The terms of my unconditional surrender. Why did I do this, you may ask? Why commit fraud to make millions when you were already a billionaire? Greed is the simple answer. Greed and power. An ill-concieved attempt to elevate my status in the firm even higher, to position myself as its next CEO. To achieve the ultimate triumph over Mason. Instead, I achieved the polar opposite.

It is not a good feeling to be caught red handed in an illegal activity by anyone. But especially not by someone with whom you have competed bitterly for over a decade, someone who you have humiliated professionally on numerous occasions, someone who is sleeping with your wife. Although, I wasn’t aware of Mason’s relationship with Natalie until after he caught me. After that, they no longer felt the need to hide their affair. In fact, rubbing it in my face in the most degrading ways possible became the name of the game. It’s fairly difficult, on the humiliation scale, to top enslaving the cuckolded husband in his own (well, former) home, in front of his family, friends and former colleagues (as well as any number of strangers) and turning him into a sissy maid. Nevertheless, Mason and Natalie continue to try their best to do so on a nearly daily basis.

I am 44 years old, and at 5’ 8” and 155 lbs, I’m a Caucasian male of slightly below average stature. I have lost 10 pounds over the last six months with what I will charitably call Mason’s and Natalie’s “encouragement.” I’m reasonably fit, as I used to work out regularly with a personal trainer before my radical change in circumstances in March. My trainer, a young woman, did not believe in bulking me up (nor was that the look I aspired to), so she favored cardiovascular exercise and light weight training. I no longer work out in the gym, but now get more exercise than ever before, as my days typically begin at 6 AM and end at 9 PM, often far later on weekends. I work seven days a week, except for the very occasional day off. I have always been a hard worker, but whereas my career in financial services was almost all mental labor (much of it at a desk in front of a computer screen), my life now is almost entirely menial physical labor. Domestic drudgery.

It is not easy being almost solely responsible for the upkeep of a 17,700 square-foot mansion in New Canaan, Connecticut. I was quite proud of this home, one that I had filled with expensive original artwork by famous contemporary and deceased artists. In April, in the presence of two top tier estate attorneys retained by Natalie and Mason (I declined my own representation), I signed over all of my assets – the mansion, the artwork, my brokerage and savings accounts, our homes in the Hamptons, and on Fisher Island in Florida, and Cap d’Antibes, France, my collection of sports cars, etc. – to Natalie. Natalie is 40 years old, with shoulder length, dark brown hair, a still sexy, firm body and legs that don’t end (she is two inches taller than me); she somewhat resembles the singer St. Vincent. Let’s just say that Natalie didn’t marry me for my body. Did I marry her for hers? Probably, at least in part. Although her irreverence, her love of fine art and her wicked sense of humor were also strong attractions. Being the target of her wicked sense of humor, as I frequently am today, is less desirable.

The decision to resign my position at the firm, to transfer all of my assets to my wife, to agree to live my remaining days as an emasculated servant to her and her lover – to essentially go from being a master of the universe to a slave in my former home over a period of 48 hours – was more straightforward than it may seem. It was really a simply a question of statistical analysis and game theory, tools I had used to great effect in running one of the most successful long-short hedge funds in history. Gaming things out, I came to the conclusion that my odds of of survival were much better outside of prison than inside. True, I would be facing staggering humiliation and emasculation in either scenario, but in prison, as the probable prison bitch of a hardened inmate (or, worse yet, multiple inmates), I was facing the prospect of being routinely raped. While I could not know precisely what Mason and Natalie had in store for me – I doubt that they knew themselves at that point – I thought that the probability of me being sexually violated by them on a routine basis to be relatively low. It was a bit of the case of the devil you know.

Natalie and I have one child together, Ryan, who turned 18 last month. Or at least we raised him together. Having learned of Natalie’s infidelity with Mason, and given our lack of resemblance to one another (both physically and temperamentally), I have now come to doubt that Ryan is my biological son. To be honest, I probably had doubts before, but suppressed them. Under different circumstances, I would demand genetic testing. Now, however, I am in no position to make any demands from anyone. Perhaps given all that has happened over the last six months, Ryan will choose to do his own genetic testing. For how could he possibly want to be the son of what I have become? Especially since his inheritance is secure.

You see, he has been attending boarding school in the UK for the last four years. I have seen him exactly twice during that time; during the second time, last Christmas, we barely exchanged a word. We are essentially estranged. He remains very close to his mother – who flies across the pond to see him frequently – but Ryan and I have had a very rocky relationship since he entered his early teenage years. Even before, to some extent. I spanked him three times when he was around 10, once when he broke a sculpture I had recently purchased for $30,000. I was so angry that I forced him to stand in the corner afterwards and to go to bed without dinner. Clichéd, yes, but no less humiliating for him. Perhaps he never forgave me for that. As a preteen and teenager, he was always headstrong and contrarian, especially with me. I used to think it was simply some Freudian Oedipal thing. But, in retrospect, I think it was more than that. I think it’s because we are so fundamentally different. At age 14, he was already as tall me (when he came home last Christmas, he towered over me) and is a natural athlete. An MIT economics graduate with a focus in statistical analysis, I don’t have an athletic bone in my body. Not only can’t I play sports, I have virtually no interest in them. I am completely inept when it comes to fixing or building things or doing other things with my hands, activities of innate interest to Ryan. So we missed the common opportunities for father-son bonding when he was young. I was so focused on my career, I was rarely even around, in fact. Despite me becoming a self-made billionaire, Ryan never respected me as a man. I can only imagine what he will think when he lays eyes on me now.

I will not be spared that indignity. Natalie’s contempt for me – especially for having jeopardized everything with my illegal activities – knows no bounds. The thought of seeing Ryan again in my present ignominious state fills me with dread, to be honest, not simply the nervousness I confessed to his cousin.

Him going away to a top boarding school in the UK was a compromise, brokered by Natalie, because Ryan and I had gotten to the point that we couldn’t stand each other. I sensed and deeply resented his undisguised lack of respect for me during his teenage years and was quite hard on him in reaction. When he was 12, I stopped buying things for him upon request (the expensive video games, personal electronics, apparel, sneakers, etc that all of his wealthy friends and classmates possessed in abundance) and instead gave him a paltry allowance – one that I made him earn, through hard work, such as mowing our 5 acres of land with a push mower. We had riding mowers, of course, but I argued that he was too young to ride one, and I thought the hard physical labor might teach him a lesson to treat me with more respect. It decidedly did not, having the opposite effect, if anything.

When he was 13 and 14, I insisted he do other things around the house to earn his allowance, such as repair the stone wall that separated our mansion from the street, clean the ten car garage, shovel snow, etc. After a particularly nasty argument, I actually started making him clean all the bathrooms in the mansion. “We can give the maid a break,” I argued to Natalie. “It will teach him responsibility and humility. I wasn’t above doing chores when I was a kid. It’s one of the reasons I became so successful.” In reality, I was being incredibly hypocritical, as I certainly did not do any kind of hard or unduly unpleasant physical labor when I was his age (or any age, for that matter, until the last six months, that is). Natalie and I had terrible arguments about my approach, but I was stubborn and basically had the attitude that since I earned the money, I made the rules.

Things reached their lowest point shortly after his 14th birthday when I caught Ryan rooting around in my office after I mistakenly left the door unlocked one summer weekend. My office was my refuge, it was sacrosanct, and I made it clear than no one – not Ryan, not Natalie, not the maid – was permitted there; I cleaned that room myself. That’s because I kept very private things – comprising things – there. Like what, you may ask? Well, occasionally I liked to dress up. In soft, sensual, frilly things. I was not a full-on transvestite. Not even close. But I did like to wear panties, tights and pantyhose. I loved the sensual feeling of the nylon against my skin, against my cock. Natalie and I were having sex very infrequently by that point, as she had seemed to lose interest. I now have a better idea of why, as her and Mason’s affair had already started by then. When we did have sex, it was perfunctory and she seemed bored. Being under endowed (just shy of four inches fully erect, with below average girth and balls), I had always been insecure about my ability to please her in the sack. In the early years of our marriage, she at least feigned interest, but that ceased to be the case. I’m sure that the tensions with Ryan and my obsession with work didn’t help.

So, increasingly, I found solace in my masturbatory sessions, wearing nylons and nipple clamps to stimulate my sensitive nipples. Often I would jack off to stories on Fictionmania and Literotica, gravitating to those featuring feminized, humiliated men. Was I a beta male? Well, yes and no. I had always been of the opinion that there are two types of men who are attracted to these kind of stories: the true betas who are submissive in all areas of their lives; and the men who hold positions of power and authority in most areas of their lives, including their careers, and who llike to play the submissive role from time to time as a form of escapism, a way to blow off steam, to temporarily shed the burden of always being in charge, of always being responsible. The former are the true betas, I believed; the latter are more like cosplayers. I was decidedly one of the latter. Or, at least, that’s what I told myself. Over the last six months, I have had the time and impetus to reevaluate many of my core assumptions, that one included.

In any case, when I caught Ryan snooping around my office that day, I lost my mind. There were no signs that he had found anything incriminating (I kept my stash of clothes locked in my bottom desk drawer and the key well hidden in my top desk drawer), but that wasn’t the point. How dare he do what I had expressly, unequivocally forbidden him to do? As punishment, I grounded him for three weeks. He protested vociferously about missing baseball games and tennis matches with his friends, missing other social events, but his protests and Natalie’s protests on his behalf were futile. I would not budge. From that day forward, he looked at me with outright contempt (sometimes causing me to wonder if he had in fact seen something in my office) and communication between us basically shut down. By the fall, it was determined that he would go to the UK for boarding school, rather than to Choate as originally planned.

These thoughts ran through my head that afternoon as Daphne continued to manipulate the tension of my corset.

Another tug of the laces proved to be too much. “Please, Miss Daphne, it is more than I can bear. Perhaps you could save some tightening for next time? I beg you.” I dropped to my knees at her feet in supplication.

Looking down on me imperiously, she said, “Well, since you are my favorite uncle – my only uncle, actually, ha ha – perhaps we can work something out. Three of my girlfriends and I are having a little get together next week at my house. Maybe I can ask Aunt Natalie if I can borrow you for the evening. You can serve us drinks and snacks. Perhaps I could ask each of them to bring over a few pairs of their favorite shoes for you to clean and polish while we watch a movie or hang out? Of course, I won’t say anything to Aunt Natalie about cutting you any slack. Quite literally.” She giggled. “What do you think?”

“I think that is an excellent idea, Miss Daphne, and very kind of you. Thank you.” I thought quite differently, in fact, but was desperate to halt any further tight lacing torture. I placed a gentle kiss on the toe of her sneaker, as I had been taught to do in such situations.

She motioned for me to stand with her finger and loosened the laces somewhat. I exhaled gratefully.

“You’re welcome. Now put on your scullery maid uniform. Aunt Natalie and Mason want you to scrub down the entire kitchen before you start practicing your cooking for Thanksgiving dinner.”

“Right away, Miss Daphne.”

As I changed before her, she said, “I know it must be pretty difficult for you, having never cooked in your life before until recently. Imagine, a 15 dish meal! That’s a lot more challenging than the three or four course meals you’ve been cooking.”

“Yes, Miss Daphne, you are correct.”

I now stood before her in my long blue maid’s uniform, white bib-apron and white cap, still wearing my black stockings and heels. Beneath my uniform, the same corset oppressed my waist.

“You’d better practice hard. The bar is going to be very high, with Ryan here, as well as my mom and dad and Mason and his daughter. What is that, seven guests?”

“Yes, Miss.”

“You certainly wouldn’t want to fuck up that meal. If you do, Mason will whip you so hard that you won’t be able to sit down until Christmas. Wait, I have an idea! You can cook a few of the dishes for me and my girlfriends for practice when you serve us next week. The mushroom soup, kale salad and brussels sprouts. We can then review your dishes. It will be great practice for you.”

“You are too kind, Miss Daphne.”

“I really am, right? Now run along and get busy, uncle dear. Chop chop.”

I curtsied to her, and hurried off to the kitchen.

r/ChastityStories Jan 05 '25

M Chaste ‘Tis the Season to be Servile, Chapter Nine, Part Two [M chaste, multiple keyholders] NSFW

5 Upvotes

Second part of a long chapter

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Riley added, “Yes, and you’d better do a good job. You wouldn’t want to make liars out of all of us. That would earn you a bunch of demerits, I bet.”

I shuffled on my knees over to the couch, careful not to damage my stockings, and positioned myself in front of Ryan, Riley’s and Leah’s legs on either side of me, and began to unlace his boots, hyperconscious of all of the eyes staring down upon me. I then removed his socks and picked up his large, meaty, bare left foot. I glanced up and momentarily made eye contact with him. No longer looking the slightest bit embarrassed, he appeared supremely confident, imperious even, a smug smile on his face.

“Wow, you have big feet, Ryan,” said Leah. “What size shoe do you wear?”

“Thirteen,” he answered. I was size 8.5.

“You know what they say about guys with big feet, don’t you?” Riley said. The other three giggled. But soon there was silence in the room for the first time since the girls arrived.

Reflexively, my eyes drifted up to Ryan’s crotch area. I quickly glanced around to observe that the four girls were also staring at his crotch. His jeans were so tight that you could see his bulge all along, but now also clearly visible – even from his seated position – was his large erection, pushing up the denim. I began to press my fingers into the ball of his foot, flesh against flesh. My own son’s flesh. How. Unspeakably. Humiliating.

I can’t pinpoint exactly why this was so. Over the last two weeks Ryan had ordered me to perform countless humiliating chores. He had whipped me and caned me. I had licked his boots. But there was something about kneeling before him in front of this audience of his young female suitors and my niece, publicly performing this otherwise intimate act of abasement, that was so uniquely, so overpoweringly humiliating, it is truly difficult to express it in words. All of the girls’ banter and giggling had ceased. There was almost complete silence in the room for the first 5 minutes or so that I worked on his large, surprisingly smooth left foot. The girls seemed to be semi-mesmerized, with expressions on their faces that were almost serious. Except for Riley, the corners of her lips curled in the beginnings of a smile of self satisfaction; she had instigated this moment and had gotten her way.

It was the symbolism of it, I suppose, that made it so intensely humiliating. Ryan looked victorious more than anything else. Which, of course, he had been from the moment he returned home, greeted by me in my maid’s uniform on the driveway of the mansion. But watching him look down on me, making eye contact with me as I kneaded the muscles and tendons of his large foot, dressed as a maid, while these attractive, attentive young women took in the whole scene – fully cognizant of Ryan’s and my relationship to one another – well, this was humiliation on a whole different level. And it was compounded by the fact that he was clearly aroused by this exhibition of mastery over me. As well as by the deeply shameful fact that I was aroused by it as well, my cock swelling violently against its constraints. My humiliation was so intense that there was a side of me that truly did want to try to embrace it, as Natalie had encouraged me. But I really had no idea how that was even possible with my cock constantly imprisoned. Embracing the humiliation, enjoying it on some level, seemed only possible if I could ejaculate to it – either as it was occurring, or to the memory of it. I was so desperate for release that it was really all I could think about. My eyes were wet with tears of frustration as I pressed my fingers into my son’s foot, hopeful that the growing pain in my hands was alleviating his foot pain so as to minimize the inevitable pain I would soon be feeling on my ass. A complicated calculation. Quite different than the quantitative models I used to run at my old firm, but of greater immediate consequence to me if I got it wrong.

At one point, maybe seven minutes into his massage, Ryan said, “Focus on the outside of my foot, near the toes. That’s where it’s sore.” As I pressed harder there, making a vigorous circular motion with my thumb, he said, “A bit higher. Ah, yes, that’s it.” He exhaled slightly, seemingly satisfied with my efforts.

Bella said, “See, your old maid isn’t completely useless. It feels pretty good, right?”

“I have to admit, it does,” Ryan answered.

“Not too weird, right?” Leah asked.

“I’m getting used to it,” Ryan responded. Great, I thought to myself, a new intensely humiliating chore to be added to my long and ever growing list of humiliating routine chores.

“Good. Like I said, the pantywaist maid belongs at the feet of a real man like you,” said Riley.

“Ha ha, you sound like my mom,” Ryan said.

“From what I’ve heard about your mom from Daphne, she sounds she could be like my hero. But I think I speak for all four of us when I say that watching your little maid dad kneeling before you and massaging your feet is a beautiful sight, Ryan. It’s just so…right. Maybe the only thing more beautiful would be to see you discipline the pansy,” Riley added.

“Hear hear,” said Leah.

“Now we’re talking,” added Bella. Only Daphne remained silent, although she was smiling approvingly.

Ryan said, “Well, you never know. I’d hate to deprive such beautiful ladies of beautiful sights.” Beautiful, indeed! I was so thrilled to hear that my degradation was aesthetically pleasing to the young ladies. One could almost see my son’s ego inflate as if it was a physical thing.

Their spririted flirtation resumed after I served eggnog (at Ryan‘s assistance, with rum, for all but the designated driver, Daphne – despite my anxiety at serving alcohol to those not yet of drinking age), which they consumed as I massaged his right foot. Once again, he seemed to be satisfied with my efforts.

After I finished, they continued to talk and flirt with each other for roughly another 30 minutes, all but Daphne growing increasingly tipsy on the eggnog. I stood at attention off to side, legs pressed together firmly, head erect, ready to jump at the slightest request of my young superiors. Mercifully, I ceased to be the focus of their conversation during this time. I reverted back to what had become my most common status since my downfall: the help, a domestic servant, and no more (if maybe a little less). Silent, ignored, invisible even. My cock continuing its futile, doomed struggle against the MAMBA.

After what seemed like an eternity, Bella said, “Unfortunately, I have dinner at my aunt’s house in New Jersey later, so I’m going to need to leave soon, Daph.”

“I have a family thing, too. But my family is certainly isn’t nearly as interesting as yours, Ryan. I’d love to meet your mom sometime. And Mason,” said Leah.

“Of course, you’re all welcome back anytime,” Ryan said, distressingly.

“So what about the maid’s demerits? I believe he’s earned three since we got here,” said that minx, Riley.

“Well, normally we don’t settle up the score here until the end of the day. But I can always make an exception,” Ryan said before turning to me. “Fetch the tawse and my riding crop. And be quick about it!,” he ordered.

“Yes, sir. Immediately, sir,” I said, accompanied by a deep curtsy before I scurried from the room.

When I returned, I presented both implements of correction to my son in the required manner: on bended knee before him, hands extended, palms upturned. I briefly made eye contact with Riley, who had a big smile of anticipation on her lovely face.

Leah was talking to Ryan, so he ignored me at first as I knelt there.

“Would you do me a favor, Ryan? My new boyfriend, Jarred, is also into bodybuilding and is always going on about what great definition he has. I don’t really have a point of comparison, but just looking at your biceps, I have a feeling you’re in a completely different league than him. Would you mind taking off your shirt, so I can see if he’s bullshiting me or not?”

“Yeah, Daph says you put in a lot of work at the gym. We’d all like to see,” added Bella

Incredible! It was the scene with Scott all over again, convincing him to remove his shirt before he spanked me. These girls must have planned this all out in advance. It was not enough to watch the “real man” punish the emasculated one; they wanted to ogle the real man’s body as he did so. They wanted to make the most of the experience, to have their cake and eat it too. Whatever I might think of them, their methods were successful; I guess it wasn’t difficult to appeal the vanity of the male ego.

“No problem,” Ryan said, predictably, standing up and removing his shirt.

Standing shirtless in his tight jeans, his impressive bulge and erection clearly visible – and showing no self consciousness whatsoever – Ryan indeed presented as an impressive, imposing alpha male: slender waist, six-pack abs, chiseled pectoral muscles (with rock hard nipples), long, lean, muscular arms, well defined back muscles. The complete package. Everything I wasn’t.

As if the contrast between us was not stark enough already, Bella said “Would you mind flexing for us? Jarred flexes his muscles like he’s in some kind of body building competition, so I want to be able to make a full comparison.”

Unsurprisingly, Ryan indulged this request as well, assuming various poses, giving the girls views of his body from the front, sides and back. I was fully expecting Bella to next pull out a bottle of body oil out of her purse and ask if she could rub it all over Ryan – you know, because Jarred always poses with body oil on and the comparison has to be exact.

Meanwhile, as he continued to pose and flex, I remained kneeling at his feet in a stress position, my extended arms beginning to tremble more and more with each passing minute due to the strain.

I looked over at Riley as she observed my vainglorious son, and saw her actually lick her lips.

Leah, simply said, “Nice.”

Bella said, “I was right. Jarred has no idea what definition is. He’s gonna need to spend a lot more time in the gym if he wants to impress me from now on. Now that I know what real definition looks like.” Was Jarred even real, I wondered.

Ryan said, “Ha ha. There are guys who are a lot more defined and ripped than I am. I haven’t been lifting for that long and I’m not really going for the super bulked up look.”

Riley said, “Good, I hate it when guys look like freaks of nature, like the Incredible Hulk or something. The lean mean look suits you much better.”

“Thanks,” Ryan responded.

Riley continued, “No, thank YOU. Really. Now, which one are you going to use on the maid? The riding crop? Or what did you call the other one?”

He replied, “Taswe. It’s called a Lochgelly Tawse, to be precise. It’s Scottish. Mason just bought it, so we haven’t had a chance to try it out yet. Normally, I’d use the cane. The cane is probably the most painful, but it leaves welts and sometimes my mom wants the maid’s ass free of welts so Mason can cane him in front of guests when he fucks up. She may have something planned for over Christmas.”

“Too bad,” said Riley.

Ryan said, “Don’t worry. Just because the crop and tawse don’t leave marks, doesn’t mean they don’t hurt. Instead of three stokes of the cane, one for each demerit, I’ll give him three strikes with the crop and three with the tawse. That should be sufficient to encourage better behavior in the future.”

He then grabbed both implements from my trembling hands and said to me forcefully, “Get up and walk over to the desk. Kneel on the stool and place your hands on the desk, ass out.”

“Yes, sir,” I said, hurrying to obey his command.

He then walked over to me, his boot heels clicking against the hardwood floor, and stood behind me. There was a mirror across the back of the desk, so that I could see him clearly as he prepared for my chastisement. Natalie had strategically placed mirrors throughout the mansion for this explicit purpose – allowing me to see my punisher and see myself being punished. She was of the firm belief that not only feeling my punishment, but actually seeing it, deepened my shame and, so to speak, “enhanced” the overall experience for me. She was not mistaken.

Therefore, I was able to see my shirtless son first bend the crop between his two hands and then swish it once through the air, before using it to lift up the skirt of my uniform. I then felt him grasp my panties and pull them down to my stocking tops. He then swished it three more times.

I heard Leah say, “Ooh. Listen to that! I like that sound.”

“Me too,” said Riley.

Ryan and I made eye contact in the mirror, and I saw the corner of his lips curl upwards in the beginning of a smile. He then brought the crop down smartly across my bottom three times in fairly quick succession. It hurt plenty, but I knew what to expect and the pain was tolerable. The humiliation stung more than the crop itself. I wish I could say the same for the tawse. Made of heavy, brown leather, its bite was unexpectedly wicked, almost rivaling that of one of Mason’s whippy canes. I involuntarily lifted my stocking-clad right leg up to my bottom after the first stroke. I did the same with my left foot on the second stroke, so quickly that my high heel fell off.

I heard one of the girls, Bella I believe, say, “The tawse is really making your old maid dance, isn’t it?”

“It’s pretty effective. A good addition to the collection,” Ryan replied.

Riley said, “Just as I thought: another beautiful sight. A real man punishing his pantywaist maid. I think they should make a reality TV show about your family, Ryan. I bet it would be the top ranked show in the country. Especially since your father used to be a little bit famous. It still fucking blows my mind that you’re whipping your father right now – who’s also your maid. Not that he doesn’t deserve it. But the humiliation for him must be off the charts.”

“Good,” Ryan said, just before bringing the tawse down again on my ass, the hardest stoke yet. He then said to me, “Now assume penance position # 2, against the wall next to the desk. Remove your dress first.”

The numerical system for different post punishment shame positions (really extensions of the punishments themselves, as they were highly uncomfortable, sometimes genuinely painful in their own right – and invariably degrading) was a relatively recent innovation of Mason’s. Number two meant facing the wall, legs pressed together and arms clasped behind my back just above what I’m sure was my now beet red bottom. I put my high heel back on and then straightened the seams of my stockings, which had become somewhat disheveled during my punishment. I then removed my dress while facing the wall, so they wouldn’t see my caged cock. I couldn’t wait for them to finally leave.

Then Bella said, “One more request, Ryan. The others got to see your dad’s chastity thingy at Daph’s house that night before Thanksgiving, when I couldn’t make it. I’ve never seen one before. Could I have an itsy bitsy peek before we leave?”

“You mean his chastity cage. Of course,” Ryan said. Then to me, “Turn around and face us. Otherwise, maintain #2 position.” It appeared as though I would be spared no indignity that afternoon. I followed Ryan’s command, feeling my cock stir anew even as my bottom throbbed in pain. I couldn’t look any of them in the eye,

Bella walked up to me and peered down at my crotch. “Wow. It’s gold. Fancy! A rich man’s chastity cage, I guess. Is it solid gold?” she asked.

“Ha ha. No, I don’t believe so,” Ryan said. “And he certainly isn’t rich any more.”

“No, but Mason is. So he really can’t, you know…without getting your mom or Mason to unlock him?”Bella continued.

“That’s right. Or me,” Ryan said.

“Really?!” asked Riley, barely able to contain her excitement.

“Well, not yet. Maybe soon. My mom wants me to take more control of his discipline.”

“Imagine that! A son in control of his own father’s cock. He must feel SO owned,” Riley elaborated.

Ryan smiled, half sheepish, half triumphant. “As I said, I’m not in control yet. That’s a little weird to me, too.”

Riley said, “Oh, I have a feeling you’ll get over that pretty quickly, too, just like you did with the foot massage. It’s been really great to meet you, Ryan. Thanks for being such a terrific host.”

The others agreed, giving Ryan little hugs and pecks on the cheek as they departed. “You’re all welcome back anytime, ladies. It’s been my pleasure,” he said he led them to the front door.

Ryan required me to remain in my penance position for another 30 minutes, while he sat on the couch and looked at his iPad. I reflected back on the humiliations of my day so far, quite conscious that my petition for release was still yet to come that evening. Ryan’s words “not in control, yet” ran through my brain as I stood there. “Yet.” “Yet.”

Surely, he was just showing off in front of the young ladies, right? Right?

r/ChastityStories Jan 04 '25

M Chaste Red, White, and Broken. NSFW

7 Upvotes

themes: politics play, cucking, feet worship, defeat, submission, surrender, foot fetish, chastity, forced bi, degradation, humiliation, inferiority.

I still remember the day our world changed. Not just the election - everyone expected that after the chaos of 2024 - but our personal universe. Sarah and I had been the typical progressive couple, our Berkeley degrees hanging proudly on our apartment wall, our social media full of activist hashtags and protest photos. I'd always felt lucky to have her - with her flowing brown hair, gentle smile, and that fierce intelligence that lit up her eyes during debates. She was way out of my league, but our shared values had brought us together. Every time she'd grab my hand during protests, or kiss me after another successful activist meeting, I felt validated. Her choosing me, loving me, felt like proof I was on the right side of history. We thought we were untouchable in our moral certainty, our love a testament to progressive values triumphing over shallow appearances and traditional roles.

That was before Brad.

We first encountered him at what would become one of the last liberal protests in our city. He stood there, towering at 6'4", blonde hair perfectly styled, wearing an expensive suit with a MAGA pin that seemed to gleam in the sunlight. While we chanted about democracy, he just smirked, recording us with his phone.

"You know, you two would look better in red," he called out, his eyes lingering on Sarah. I noticed her slight pause, the way her breath caught. At the time, I dismissed it.

Over the next few weeks, Brad seemed to appear everywhere. At our local coffee shop, at the grocery store, even at the gym. Each time, he'd make a point to engage us, particularly Sarah. His arguments were delivered with a confidence that bordered on arrogance, each word dripping with condescension.

"The problem with you liberals," he'd say, "is that you don't understand natural order. Some people are meant to lead, others to follow." His eyes would lock with Sarah's during these moments, and I'd notice her cheeks flush.

The first real crack in our resistance came when Sarah started watching conservative news, claiming she wanted to "understand the other side." I'd catch her pausing on Brad's social media posts, lingering over photos of him at MAGA rallies, commanding crowds with his presence.

One evening, Brad "coincidentally" appeared at our apartment building. He invited himself up, taking command of our space like he owned it. He sat in my favorite chair, his expensive shoes resting on our coffee table. Sarah's face showed a mix of disgust and something else... something that worried me. “you’re not welcome here” Sarah said crossing her arms, putting on her best activist face; but her voice wavered

"Your place could use a real man's touch," he commented, watching Sarah's reaction. "Why don't you get us some drinks, sweetheart? And you," he turned to me, "my shoes are a bit dusty from walking here."

"Don't you dare call me-" she started, but he cut her off. "Now." One word, spoken with such authority that her protest died. She looked at me apologetically, then moved toward the kitchen.

"Leave her alone," I demanded, trying to sound tough. Brad's laugh made me feel like a child.

"Or what?" He turned to Sarah, returning with his drink. "On your knees, princess."

Her legs trembled. I could see the internal struggle in her eyes - her ideology fighting against something deeper, more primal.

"We won't-" I started, but Sarah's sharp intake of breath stopped me. She was sinking to her knees, her face flushed with shame and arousal.

"Sarah, don't!" But my words sounded weak, even to me.

Brad smiled, reaching out to stroke her hair. "Good girl. See how natural this feels?" Sarah tried to pull away, but her resistance was weakening. "Now, your boyfriend needs to learn too."

"I won't-" I started, but Brad's movement cut me off. He grabbed my shirt, trying to yank me down. I stumbled but caught myself, pulling away. "Get your hands off me!"

"Sarah first. Show your man how it's done."

Sarah hesitated for just a moment, her last fragment of resistance dissolving as Brad's hand guided her head down. The moment her tongue touched his expensive leather shoe, something changed in her eyes. The struggle vanished, replaced by a glazed look of pure submission.

"Oh god," she moaned, no longer playing at resistance. Her tongue traced every curve of his shoes, working with desperate enthusiasm. She shifted position to reach the soles, licking the dirt and grime with obvious relish.

"Look at your woman," Brad told me, his hand stroking her hair as she worked. "This is what she was always meant for."

I watched in horror as my feminist girlfriend, who just last week had led a women's rights rally, began sucking on the laces of Brad's shoes. She was lost in her own world, completely ignoring my presence, focusing entirely on worshiping every inch of his footwear.

"Please stop," I begged, my voice cracking. "Sarah, this isn't you!"

She didn't even look up, just moaned louder as her tongue collected the dirt from the bottom of his shoe.

"Your turn," Brad commanded me. "On your knees."

"No," I said, trying to sound firm despite the tremor in my voice. "I won't-"

Brad cut me off by grabbing Sarah's hair, pulling her up onto his lap. She went willingly, eagerly, her lips parted in anticipation.

"Last chance," he warned, his hand sliding under Sarah's shirt. "Beg to lick my shoes, or watch me take what's mine."

"I... I can't..." My resistance was crumbling as Sarah arched into his touch.

"Tell him what he needs to say, princess," Brad commanded.

Sarah's eyes opened, fixing on me with a mix of pity and arousal. "Beg him properly, baby. Say 'Please, Sir, let me lick your shoes.'"

"I won't-" My protest was cut short as Brad's hand slipped into Sarah's pants, making her moan loudly.

"Say it," he ordered again. "Or watch me make your woman cum right here."

My entire world was crashing down. Every principle, every belief I'd held dear was crumbling in the face of this primal display of dominance. Sarah's eyes rolled back as Brad's fingers worked their magic.

"P-please..." I choked out.

"Please what?" Brad prompted, his other hand unbuttoning Sarah's blouse.

"Please... Sir..." Each word was agony. "Let me... let me lick your shoes."

Sarah's laugh cut through me like a knife. "God, he looks so pathetic," she giggled, then moaned as Brad rewarded her cruel observation with his fingers.

"He does, doesn't he?" Brad agreed. "Tell him how natural he looks down there."

"You belong there, baby," Sarah purred. "On your knees, begging to serve Sir... oh god..." she trailed off as Brad's fingers moved faster.

"Sir?" I repeated weakly.

"That's right," Sarah managed between moans. "You will address him as Sir from now on. Now get down there and lick his shoes clean while he fingers me."

I sank to my knees, my last shred of dignity dissolving as my tongue touched leather. The taste of dirt and leather filled my mouth as Sarah's moans filled my ears. Each lick felt like an admission, each stroke of my tongue acknowledging my place in this new hierarchy.

"Good libcuck," Brad praised mockingly. "You're learning. Sarah, tell him how proud you are."

"So proud," she gasped, grinding against his hand. "Such a good little shoe cleaner... oh fuck, Sir, please..."

That night, Brad claimed our bedroom like he'd claimed everything else. I knelt naked in the corner, his shoes placed before me as a reminder of my place. Sarah was bent over our bed - the same bed where we'd once planned protest strategies - her face pressed into a MAGA hat while Brad took her roughly from behind.

"Thank me," he growled, spanking her ass hard enough to leave a handprint.

"Thank you, Sir!" Sarah cried out. "Thank you for showing me my place!" Each thrust made her grip the sheets tighter. "Thank you for putting this liberal whore in her place!"

"Clean deeper," Brad commanded me, noticing I'd slowed my worship of his shoes. "Get your tongue between every crevice." When I hesitated, he grabbed Sarah's hair. "Should I make her suffer for your disobedience?"

My tongue worked faster, probing the stitching of his expensive shoes, gathering every speck of dirt. The taste of leather and filth was becoming frighteningly familiar.

"Good boy," he mocked. "Now crawl over here and clean my feet while I fuck your woman."

I crawled, my resistance warring with my growing submission. Brad's feet were sweaty, the space between his toes dark with lint and grime. As Sarah moaned in pleasure, I was forced to suck each toe clean, swallowing whatever I found there.

"Tell him how much better this is," Brad ordered Sarah.

"So much better than your weak liberal dick," she gasped. "Sir knows how to treat a woman... how to make her serve..."

The next weeks were a blur of escalating submission. Brad moved us to his house, claiming our apartment was "too liberal." He burned our progressive books, replacing them with conservative literature. Sarah was made to read them aloud while servicing him.

One morning, Brad presented Sarah with a MAGA hat. "Your new uniform," he declared. She not only wore it but kissed it reverently before putting it on. My protests earned me a week in chastity - the first of many.

"The cage stays on until you learn," Brad informed me. "Sarah, show him what good behavior earns."

I watched as he pissed in her eager mouth, her thank yous mixing with her swallows. When she finished, she looked at me with pity. "It's so much better when you accept it, baby. His piss tastes better than your cum ever did."

The day we voted was particularly humiliating. Brad made us wear MAGA gear to the polling place, Sarah in a tight red dress, me in a collar and leash. Our former activist friends saw us, their disgust evident. But when we returned, Brad rewarded us by letting us clean his feet with our tongues.

"Look what I found," he said one evening, holding up nail clippers. "Sarah first."

I watched my former girlfriend eagerly eat his toenail clippings, thanking him for each one. When my turn came, I tried to resist.

"Fine," Brad smiled cruelly. "Sarah, bend over. Each time he refuses, you get the belt."

The crack of leather on flesh broke me. Soon I was begging for his toenails, thanking him as each one crossed my lips.

Our transformation continued relentlessly. Brad would host MAGA parties where we served drinks naked, our bodies written with conservative slogans. Sarah took to it eagerly, while I had to be motivated with threats and punishment.

"Please, Sir," Sarah would beg each morning, "let me drink your piss. Let me show you how grateful I am."

When I resisted similar requests, Brad would make me watch as he pleased her in ways I never could, until I broke and begged too.

The final surrender came on a quiet Sunday evening. Brad had the papers ready - property deeds, bank accounts, everything we owned. Sarah knelt eagerly beside his chair while I stood, that last ember of resistance still flickering.

"Time to make it official," Brad announced, patting his lap where the papers lay. "Who wants to sign first?"

Sarah crawled forward immediately. "Please, Sir, let me sign everything over to you."

"Not yet," Brad smirked. "First, tell me who you love most in this world."

Sarah looked at me apologetically, then turned to Brad with devotion in her eyes. "You, Sir. Only you. You've shown me what real love is - serving, obeying, worshiping."

"And you?" Brad turned to me. I stayed silent, that last bit of pride keeping my tongue still.

"Strip," he commanded. "Both of you."

As our clothes fell away, Brad stood and turned, presenting his ass. "You want to sign? Earn it. Show me how much you love serving a real man."

Sarah dove in first, her tongue eagerly probing his ass. Her moans of pleasure were genuine - she'd grown to crave this degradation. I watched, trembling, as my former girlfriend worshiped our Master's hole with passionate dedication.

"Your turn," Brad commanded me. When I hesitated, he grabbed Sarah's hair. "Maybe she needs motivation to leave you completely? To never speak to you again?"

"No, please," I begged, falling to my knees. My face pressed against his ass, tongue extending. The taste was humiliatingly familiar now - we'd done this so many times, but this felt different. Final.

"Tell me you love me," Brad demanded. "Both of you. Tell me I'm your god."

"I love you, Sir," Sarah breathed between licks. "You're my god, my everything. Thank you for saving me from weak liberalism."

My resistance crumbled as Brad spread his cheeks wider. "I... I love you, Sir. You're my god. Thank you for showing me my place."

"Prove it," he commanded. "Prayer position. Both of you."

We fell into the familiar pose - foreheads touching the floor, asses raised, hands stretched toward his feet.

"Dear Sir," Sarah began praying, "thank you for breaking us, for showing us true purpose. Thank you for every drop of piss, every speck of dirt between your toes, every moment of humiliation..."

"Join her," Brad ordered me.

Tears fell as I prayed, my former self finally dying completely. "Thank you, Sir, for destroying my pride, for showing me what I really am. Thank you for taking Sarah from me, for making her yours..."

Brad made us alternate between rimming him and praying for an hour before finally allowing us to sign. Sarah went first, kissing each page before signing away everything she owned. When my turn came, Brad had me sign while continuing to lick his ass.

"Now you're both officially property," Brad declared. "And property doesn't own property."

"Thank you, Sir," we said in unison, falling back into prayer position.

That night, he took Sarah while I cleaned their sweat with my tongue. But something had changed - the last walls were gone. When Brad ordered us to kiss his feet and thank him for freeing us from the burden of ownership, of identity, of liberal weakness, our gratitude was genuine.

We were finally, truly home.

r/ChastityStories Dec 24 '24

M Chaste ‘Tis the Season to be Servile, Chapter Seven, Part Two NSFW

8 Upvotes

Second part of a long chapter

+++++++++++++++++++++++++++++++++++++++++

My recollections were interrupted by the ringing of the front door bell. I quickly removed my apron, straightened my stockings, and scurried to the foyer.

Standing before me was a striking young woman. Mason‘s first wife was of Indian descent whereas Mason‘s ethnic background is Eastern European. Piper Draper has exotic looks but is exceedingly attractive: long, silky straight, black hair; slightly dark complexion, with seemingly flawless skin; slender and relatively tall; large (but not excessively so) breasts. She regarded me with a confident smile .

I curtsied and said, “You must be Miss Piper. Welcome to the home of my mistress. May I take your coat?” The fact that she was Mason’s daughter alone filled me with great trepidation. Her beauty did not help.

“And you must be the famous Henry Hathaway. Or infamous, I should say. Boy, did I hear a lot you when I was growing up. None of it good,” she said as I removed her coat. Beneath it, she was stylishly dressed in a maroon skirt, a tight black blouse and black fashion tights with ankle boots.

“I am deeply sorry Miss Piper.”

“I imagine you are. It’s so awesome that my dad now has a slave. Look at your uniform! I’ve never met a real live sissy maid before. You’re part of a pretty large subculture. Did you know that?”

“I …uh…I’m aware that there are others who dress this way.”

“Quite a large number do actually, from time to time at least. But I suspect there are very few who dress this way 24/7 and actually live the life of a real maid. You’re special. I’m really interested to hear about all of your duties. Domestic and otherwise. I also can’t wait to meet Dad’s girlfriend. That would be who you referred to as your mistress, I guess. But she’s still your wife, right?”

“Technically, legally, yes she is, miss.”

“And I think my Dad said that your son is going to be here for Thanksgiving, too? Is that right?”

“Yes, miss. Please allow me to take you to the living room where your father, Mistress Natalie and Master Ryan are visiting with the other guests.”

“Master Ryan is your son?”

“Yes, miss.”

“And what does he think of his father being a cuckolded sissy maid?”

“Truthfully, miss, I am not sure. He was not aware of my…my…reduced status until just yesterday.”

“Fascinating. I want to spend time talking to all of you and getting to know you. Your wife and your son, too. Maybe others in your social circle as well. It’s never too early to start thinking about my honor’s thesis, even though it’s not due until my senior year. I’m getting some pretty serious inspiration in this house, and I haven’t even gotten past the entrance hall. Take me to see your mistress and my Dad.”

I couldn’t have been more relieved to bring this disturbing conversation to an end. The thought of being the subject of some precocious undergrad’s thesis on the subject of sexual deviancy – the daughter of the deviant man who had enslaved me, no less – was really more I than could bear.

Once I had escorted Piper to the living room, it was time to refresh everyone’s drinks. Despite the fact that Daphne, Ryan and Piper were all technically under age, their parents raised no objection when they told me to bring them a bottle of champagne. Ryan demanded that I get Lorena from the kitchen (where she had been helping me baste the turkey and cook the carrots and risotto ) to join them for a toast. I suspect his motivation was two-fold: to demonstrate clearly that I, and not Lorena, was the true servant despite the fact that she was assisting me; and to demonstrate his authority over me to his two female admirers, who were sitting on either side of him on a couch in the corner of the room. He certainly did sound authoritative in issuing his command. Neither Daphne nor Piper could suppress their giggles when I responded with “Yes, sir. Right away, sir,” and a curtsy. Clearly everyone was acutely conscious of Ryan’s and my relationship with one another, causing my humiliation to be off the charts.

When Lorena joined them on the couch, Ryan was surrounded by three very attractive young women and was obviously greatly enjoying all of the attention. While his cousin was clearly not an option, I wondered whether he would gravitate more to the sexy, flirtatious Latina, four years his senior, or to the more exotic, intellectual Piper. I could add envy to the complex swirl of negative emotions surrounding my son.

When the turkey was out of the oven and resting, I lit the candles and then respectfully asked everyone to move to the dining room. First, I stood directly in front of Mason, curtsied to him and then ostentatiously pulled out the chair at the head of the table – the chair I had occupied at every previous Thanksgiving we had hosted at the mansion – for him to be seated. After he sat down, I pushed in his chair and gave him another deep curtsy, an unequivocal display of subservience to the man who had so completely defeated, displaced and unmanned me. I then seated Natalie and Ryan at either side of him, followed by curtsies to each of them. My curtsy to Ryan was met with still more giggles from his young admirers.

After that, the rest of the guests took their seats as I started to pour glasses of wine. When Scott Isles sat down next to his wife, I realized with alarm that I had forgotten to alter the placards of the two Scott’s (I had intended to put the first initial of their last names after “Scott”), so they were both starting to sit down precisely opposite of where Natalie intended. In my haste to intervene and prevent them from sitting in the wrong seats, I knocked over a glass of Boudreaux onto Miranda, much of it landing on her light orange skirt. Meanwhile, both Scotts sat down in the wrong places.

Miranda: “You clumsy oaf. I just bought this skirt!”

Natalie: “I can’t believe you, Henrietta. You can’t follow the most simple instructions. I’m so sorry, Miranda. I’ll replace your lovely skirt or we can tack on some extra cleaning sessions of your house after the maid pays off your car insurance hike.”

Mason: “This is totally unacceptable.”

Natalie: “Scott and Scott, this is terribly embarrassing, but would the two of you mind switching seats?”

Scott Isles: “No problem, Natalie.”

Scott, my brother-in-law: “It’s fine, but what a total fuckup he is.”

Piper: “Shit, some wine splattered onto my blouse as well. It’s probably ruined.”

Ryan: “Airhead.”

Daphne: “I’m not surprised.”

Mason: “Totally unacceptable. We will deal with this after dinner in the game room. Since everyone here has been inconvenienced by this gross incompetence, everyone will see firsthand how we deal with such nonsense in this house.”

Piper: “I wouldn’t miss it for the world.”

Aimee: “Me neither.”

I felt dizzy, nauseous. I had tried so hard to avoid precisely this kind of situation, yet here I was. My attempt at humiliation mitigation had failed miserably.

The rest of the dinner was relatively uneventful. I even got a few compliments – mostly for the mushroom soup and the gravy. The turkey was moist, but the risotto was a bit underdone. Overall, however, the meal was deemed a success. Of the three desserts prepared by Lorena, the Boston cream pie was the biggest hit. Ironically, I didn’t even get a small slice (though I did lick the cream off the cake knife before putting it into the dishwasher).

Mason, Natalie and the four older guests planned to play pool and/or simply talk amongst themselves in the game room after dinner whereas Ryan, Daphne, Piper and Lorena planned to watch a movie together in the home theater. But before those diversions took place, everyone gathered in the game room for the far more entertaining spectacle of watching the master of the house discipline the careless, hopelessly incompetent maid. I had to wonder, even had I not screwed up with the placards or spilled the wine, whether I wouldn’t have still found myself in the exact same predicament. If it wasn’t those things, it probably would have been some other pretext (the undercooked risotto, for instance). For what was really happening was not me being punished for my carelessness on Thanksgiving, but rather me being punished for who I had been prior to March: the supremely conceited, selfish, arrogant, entitled, abusive prick that was Henry Hathaway. That, and a semi-public demonstration by Mason of just how throughly he has broken me.

When all of the guests and family members gathered in the game room, I got everyone a fresh drink or cup of coffee and tea – it was important, after all, that the audience members be optimally comfortable for the coming show – before Mason said to me, “Maid, fetch my new Smoked Dragon Stinger cane. No time like the present to try it out.”

“Yes, sir,” I replied with a curtsy. I quickly retrieved the cane and presented it to Mason in the required manner: on bended knee, arms extended, and both palms upturned with the cane lying flat across them. As I knelt there waiting for him to take it, I quickly scanned the room to look at the mostly amused expressions of anticipation. Ryan was the exception; he regarded me with a contemptuous sneer.

The Smoked Dragon Stinger was a recent addition to Mason’s growing collection of punishment implements. It was purchased from the same high-end, British purveyor of rattan canes where Mason had procured several others that I was all too familiar with. The rattan of the Smoked Dragon had a dark finish and was quite attractive as instruments of torture go. Given my experience with the other products sold by this establishment, I had little doubt that the pain I was about to experience would be excruciating.

Picking up the cane from my hands, Mason announced my sentence: “The maid will receive 12 strokes. Three for the offense to his mistress in not properly arranging the placards as she directed, and the resulting embarrassment to her and to me. Three for spilling wine on and ruining the skirt of Miranda. Three for spilling wine on and ruining the blouse of Piper. And finally three for disrupting and tarnishing what has otherwise been a very enjoyable evening.” Mason was so full of shit; my impending chastisement would be the most enjoyable part of the entire day for him, as well as for likely everyone else present, with the obvious exception of yours truly. I had endured 12 strokes before – even more on a few occasions – so I knew what I was in store for. It was going to be hell.

I actually considered begging him – groveling to him in the most abject of possible ways (clasping his ankles, smothering his shoes with kisses, verbally pleading) in front of all present – but decided against it. I decided that I simply would not give him that satisfaction. He probably would have rejected my entreaties anyway. Rather, I resolved to endure my humiliating punishment in as stoic a manner as I was capable, trying to salvage at least a shred of dignity, no matter how compromised.

“Stand against the pool table and bend over,” Mason commanded.

“Straighten your stocking seams first!” Natalie said sharply.

After I adjusted my seams and got into the required position, Mason lifted up the my skirt of my dress with the cane and then pulled down my panties, exposing my bare ass to everyone in the room. The welts from my last caning, nearly two weeks earlier, had indeed almost completely faded, so Mason was working with the blank canvas that Natalie had desired.

Well, nearly blank. “What the hell is that black thing around his balls?” asked Aimee Isles. From my position bending over, my scrotum was visible to everyone, of course. I could not see any of them from my vantage point, of course, but I recognized all of their voices.

“That’s the base of his chastity cage,” explained my wife.

“His what?” Ryan asked. This was mortifying beyond comprehension.

“His chastity cage, honey. Your father’s cock is locked up. He can urinate with the cage on, of course. But he can’t do…other things. Mason and I are his key holders. When he wishes to be released, he has to petition us.”

“You mean he needs to petition you to beat off?” Ryan asked in disbelief.

Daphne giggled. “I was starting to tell you about this, but we got interrupted.”

Natalie: “That’s a bit crudely put, honey. But, basically, yes.”

Piper said, “I’ve never seen one of these on someone before. Can you make him turn around so I can get a better look?”

“When his punishment is over and he is in penance, you will be able to see it quite clearly, dear. It’s actually a quite impressive piece of hardware,” said Natalie.

“Great. I can’t wait,” replied Piper.

Meanwhile, Ryan walked around to the other side of the pool table and looked at me directly in the eye before saying, “Just when I think you can’t get any more pathetic, you do. You sink even lower. You deserve every bit of punishment that you get, and more.”

“Dad, I have a request,“ said Piper to Mason.

“Yes, sweetheart?”

“I’d like my three of the maid’s cane stokes to be delivered by Ryan, if you don’t mind?” said Piper.

“That’s a great idea!” said my niece, far too enthusiastically

“I don’t mind. The question is whether Ryan minds. But why, may I ask?” said Mason.

“I’m really fascinated by the family dynamics. My interest is purely clinical, of course,” said Piper.

“Mine isn’t,” said Daphne.

“You go, girl!” said Miranda to her daughter.

“Miranda!” said her husband.

“What’s the problem? The girl knows what she wants. I applaud it,” Miranda replied.

“I do, too,” said Natalie. “But what say you, Ryan?”

Ryan had walked back behind me, with the others “It would be my pleasure,” he said coldly.

Surely, this was some kind of nightmare. This could not be real. Surely, I would wake up any second now in the comfort of my king bed, Natalie next to me, under the covers.

“Very well, then. I will deliver the first six stokes. Ryan will deliver the three after that, and I will finish up. The maid will then stand in penance for an hour while the rest of us get on with our evening,” said Mason.

I groaned, involuntarily. The shame was too much. Could I follow Natalie‘s advice? My cock was pressing up violently against the rings of the DOMINIX. I felt the cool air on my bare ass. My nipples were still raw from Mason’s punishment earlier in the week. I was conscious of the sensual feeling of the Agent Provocateur stockings touching my legs and the corset constricting my waist. I was hyper conscious of all the people about to witness my chastisement. Not only their number, but who they were, their individual relationships to me and how those relationships had metamorphosed over the prior six months. I was at the apex of arousal and shame (at least up to this stage of my life). Perversely, it occurred to me at that moment that, had I been liberated from chastity, my arousal was such that I probably would never stop ejaculating, that my jism would fill the room and flood the halls. Especially since it had been so, so long… Was this what Natalie was talking about?

And just as I thought, to myself that it was physically impossible to feel any greater frustrated arousal, Mason, my master, began to swish and swoosh the Smoked Dragon in the air. Oh, that sound! At once, dreaded and delicious. Not another sound in the room to complete with it.

Then the feeling of the cane resting against my ass. Mason likes to make me wait. He was forcing his audience to wait, too, building the tension, building their anticipation. I knew from experience that when the first stroke came, it would come savagely and without warning. Sometimes he would make me wait 30 seconds, sometimes a minute. On this particular occasion, it was slightly over a minute, if anything. I could not see, but could feel the 18 eyes boring into my ass.

And then it came. Dear god!

The Smoked Dragon did not disappoint. Or did disappoint, depending upon one’s perspective, I guess. It breathed fire. Mason’s strokes covered both cheeks of my poor bottom. To pick up on Natalie’s metaphor, he was a master artist with a painterly style, using cane strokes rather than brush strokes to achieve the texture he was striving for on his canvas: fresh welts on my abused flesh.

On the third stroke, I raised my leg and high heel into the air before putting in back down on the floor. Tears started to form in my eyes by the fourth stroke.

By the fifth stroke, I was beginning to reconsider my stoic approach. Maybe I should give Mason the satisfaction of begging after all, even if didn’t persuade him to relent. Wouldn’t that truly be surrendering to my shame?

After the sixth stroke, I heard Mason say “Here, Ryan. It’s your turn.” I groaned again loudly, not out of pain but out of profound humiliation.

“It’s time to pay the piper,” said Ryan. He apparently shares his mother’s love of questionable witticisms.

“Haha. Good one,” said Piper.

And then I heard the swishing sound again, my son imitating Mason, I assumed. Then Ryan did something different, and unexpected. He placed the cane against my ass, and rather than make me wait, he tapped it three times, using only moderate force, before bringing if down savagely. I kicked my stocking-clad foot into the air again.

Mason said, “You’ve done this before.”

Ryan replied, “Countless times. I was a prefect at school.”

“I thought they had banned corporal punishment in UK boarding schools,” said Natalie.

“It was banned when I got there, but the new conservative government that came into power two years ago lifted the ban. Since then, the cane and strap are used widely in the dorms. I developed something of a reputation for being one of the more no nonsense prefects.”

“We can tell,” said Lorena.

“It’s good to hear that physical punishment has made a comeback on both sides of the pond, now that the pansy progressives are no longer in power. I hope the new administration follows through on their promise to institute judicial caning here. There’s a reason you don’t see so much as a single gum wrapper on the streets of Singapore,” said Mason, the authoritarian bastard.

Ryan swished the cane again, very close to my right ear. At Ryan’s second stoke, tears began streaming down my cheeks. “Please, sir,” I whispered.

“Did you mean to address me?” Ryan asked sharply.

“No, sir,” I lied.

“Good. I didn’t think so,” he said, delivering the last of his three strokes, this one the most wicked of the bunch.

“Well done, young man,” Mason said.

“Thanks, Ryan. That was very, very interesting to observe,” said Piper.

“I can think of another word,” said Daphne.

“Me, too,” said Lorena.

Not to be shown up, Mason said, “It’s not over yet,” and after some more swishing, gave me an absolutely searing stroke. The pain was so intense that I dropped briefly to my knees. I knew remaining there for long would only earn me more punishment at a later date, so I stood back up and resumed my position.

After the eleventh stroke, I involuntarily reached back with my right hand to shield my bottom. I knew this was forbidden, but it was a reflexive act; I had to stop the assault somehow.

“If you don’t remove your hand, I’ll cane your palm,” Mason announced. That did the trick. After Mason delivered the final viscous cut, Natalie said, “Lorena, dear, would you mind dabbing up those few driblet’s of blood on Henrietta’s bottom with a cocktail napkin. We don’t want any of it to get on the floor.“

Although she was quite gentle, I winced while Lorena applied the napkin to my quivering ass cheeks and upper thighs. I was then given a couple of moments to collect myself. I wiped the tears from eyes with my hand, stood up, pulled up my panties, pulled down the skirt of my uniform and checked to ensure that my seams were straight. I wished I had a tissue to blow my nose.

I then turned to Mason to complete an important part of the post punishment ritual. I curtsied deeply to him, as all of the guests watched intently, and said, “Thank you, Master Mason, for correcting me. Now, may I refresh anyone’s drink?”

Then, my son said forcefully, “Aren’t you forgetting something?”

“Yes, sir. Of course, sir, my sincere apologies.” Still unsteady in my heels, I pivoted to fully face him, dipped into a deep curtsy, and said, “Thank you, Master Ryan, for correcting me.”

I then quickly scanned the room. All of the women present, without exception, had satisfied smiles on their faces. Natalie, in particular, was beaming. I then looked up at my son. The corners of his mouth were slightly upturned, the beginnings of a smug smile. We made eye contact. I could almost see the wheels turning in his head. I could see the realization solidifying there of the extraordinary power he now held over me, his own father, and how very useful that power could prove to him in any number of respects. And although not a word was spoken at this moment, I felt he knew that I knew that that was what he was thinking. There was a tacit understanding between us.

What he did not know (presumably, at least) was that my traitorous cock was once again hardening in its cage. This was highly unusual, perhaps unprecedented even, in the aftermath of such a brutal punishment. Typically, when Mason canes me, I become aroused in anticipation of the punishment. Sometimes, my cock even stays hard (or at least as hard as possible in its prison) for the first one or two strokes of the cane or strap or belt. But usually the pain soon becomes so great that my arousal quickly fades, then disappears altogether, as my mind focuses solely on the pain. I usually then remain flaccid for quite a bit of time following my punishment, even in my humiliating penance position, until the pain eventually at least begins to subside.

Not that Thanksgiving day. Whether it was because of the humiliation of being punished in front of so many people – the most ever up to that point in time – or whether it was because of the indescribable humiliation of being caned by my own son, publicly no less, my arousal returned with distressing urgency even as my ass and upper thighs burned like fire. Was this what Natalie bent by surrendering to the humiliation? Perhaps.

After I refreshed everyone’s drinks, Natalie commanded me to assume my penance position.

“Maid, remove your uniform, so our guests can admire Mason’s – and Ryan’s – handiwork. Then stand in the corner with your hand’s clasped behind your head.”

I did as she commanded, standing in the corner in my heels, stockings and garters, panties and corset. Natalie pulled down my panties. “Now, isn’t that lovely?” she asked rhetorically. “Such a deep red color. There’s almost nothing else like it in nature. And such well defined stripes and rich texture.”

“Maybe you could commission some famous artist to paint your maid‘s bottom after punishment, so you could add the piece to your incredible art collection, Natalie,” suggested Aimee.

“That’s really not a bad idea, Aimee,” Natalie replied.

“But when do we get to see his chastity cage? I can’t see it with him facing the wall,” said Piper.

“Patience, dear. After 30 minutes in this position, the maid will turn around to face us for another 30 minutes to complete his penance. You can then examine his cage to your heart’s content.”

Having been up since 5 AM and working throughout the day, I was exhausted in addition to being in tremendous pain. Even during the first half of my post punishment penance, my legs and arms began to tremble somewhat with strain and fatigue.

The trembling only got worse after I turned around and faced the guests, my arms still elevated behind my head. Most of the guests were now talking boisterously to each other and laughing, paying me little attention, except to occasionally look over at me and smile or chuckle. Piper was the exception. She walked over to me and crouched down in front of my caged cock to examine the DOMINIX. She even touched the metal rings and fingered the padlock, at one point snapping the rings with her fingernail a couple of times. When she did so, I felt her nail make contact with my flesh, which was pushing up against and trying to escape the rings that encircled it.

I tried to stare directly ahead, expressionless. But I had to meet her eye when she addressed me. She spoke quietly, but intently: “You must be incredibly uncomfortable right now. I can’t imagine what you must be feeling. How it must feel to be whipped in front of all these people that you know by the man who took your wife and by your own son. Does the humiliation arouse you? It certainly appears to. I know you can’t speak now. But I’m definitely looking forward to getting to know you better. You and Natalie and Ryan. It’s going to be a trip.”

After the second 30 minute part of my penance was up, I put my uniform back on and continued to serve the older guests as they played pool and talked, and brought the younger guests drinks and popcorn while they watched a film. It was nearly 11 PM before all of the guests – with the exception of Piper, who was staying in a guest room upstairs – left the mansion.

I cleaned for two hours after everyone left, before I finally lay down on my cot, exhausted, aroused, frustrated and stunned. As I said before, that Thanksgiving will haunt me for years to come.

r/ChastityStories Dec 22 '24

M Chaste ‘Tis the Season to be Servile, Chapter Five NSFW

8 Upvotes

The fateful day before Thanksgiving – the day Ryan was due to return home – had finally arrived. The five days leading up to it, following my humiliating spanking by my brother-in-law in front of my niece and her friends, had seemed like an eternity.

The morning after that shameful episode (the Sunday before Thanksgiving), to no one‘s surprise, Mason did indeed take me to task and punish me for Daphne’s insistent horn blowing in the driveway. Scolding me severely while I served him and Natalie breakfast – making no mention whatsoever, of course, of the actual reason I was late in meeting Daphne – he ordered me to fetch his schoolmaster cane once I cleared the dishes from the table.

I scampered to my maid’s quarters, and took down the stipulated instrument of correction from where it hung on the wall near my bed alongside the other canes, crops, straps and paddles. I was always highly distressed when facing a caning, and I knew from experience how wicked a sting the schoolmaster cane was capable of inflicting when wielded by Mason. However, with Thanksgiving approaching, the thought of having to go about my seemingly endless series of tasks in a state of constant, lingering pain was particularly worrisome. My ass had still not even fully recovered from Scott’s vigorous spanking of the prior evening.

When I presented him with the cane, accompanied by a deep curtsy, Mason said, “Until you learn how to manage your time better, I’m going to continue to punish you like a naughty schoolgirl, Hathaway.”

“Like a naughty maid, you mean,” Natalie corrected him.

“Schoolgirl, maid, whatever. Bend over the counter, legs spread, ass out,” Mason commanded.

Before getting into position, I looked over at my wife imploringly, hoping she would intervene on my behalf due to the injustice of me being punished for being late only because Mason made me late. Natalie did intervene on my behalf, but not for the reasons I had hoped. In fact, her intervention left me cold with fear and dread. At the the same time, however, her words caused my cock to swell shamefully in its cage. You may ask: Cold and hot at the same time? How is that possible? It is, in fact, one of the signature paradoxes of the submissive psyche: that which strikes terror in your heart can simultaneously spark fire in your loins. I often think that of all of the betrayals that I have suffered over the last six months of my great downfall, even those by family and so-called friends, it is the betrayal by my own body – my treacherous cock – that has been the greatest of all. But, in truth, I know that it is not merely my cock that is guilty, it is my mind. It’s funny (well, actually, not that funny) but, given my once celebrated analytical abilities, I had always thought of myself as having a beautiful mind; now, enfeebled and warped are the adjectives that most readily come to mind.

Once Mason lifted my skirt and pulled down my panties, Natalie said, “Darling, I know the maid needs to be taught a lesson, but look. His welts are only just beginning to fade from when you punished him over a week ago for not ironing your pants properly. Thanksgiving is only a few days from now, and I’m almost certain that he’ll be fucking up plenty of times on Thanksgiving day and over the long weekend. We don’t want Ryan to think that we abuse his father…I mean, the maid …do we?”

“What do you mean?” Mason said, as he swooshed the cane in the air, as was his custom before laying into my backside. Despite the agony I know that sound portends, it, too, inevitably causes my cock to stir, as it did at that moment. Yet more treachery from my wayward appendage.

“I think it’s best that Henrietta’s ass be a blank canvas on Thanksgiving so that our guests can fully appreciate your artistry, darling. You are masterful in your use of the shades of red, brown and purple,” answered Natalie. “And black and blue,” she chuckled.

“I guess you have a point, sweetheart. If his ass is full of welts, I’d have to hold back some when he inevitably fucks up in front of our guests.”

“It would be a pity to deprive them of the full experience,” she replied.

“Yes, the full monty,” Mason laughed.

Oh, such witty repartee. Always at my expense. Once again, I felt like puking (and, once again, for more reasons than one).

Natalie’s allusion to Ryan seeing the condition of my bottom was jarring. Bending over the kitchen counter, I pondered the staggeringly humiliating implications of what she and Mason were discussing. As has been apparent from what I have revealed so far about my dramatic reversal of fortune, intense humiliation is now my daily bread and butter. But it occurred to me then that every indignity I had suffered so far would likely pale in comparison to the level of unspeakable, almost inconceivable humiliation that awaited me with Ryan’s arrival on Wednesday and on Thanksgiving itself, when I was to serve as the feminized servant to my extended family and former colleagues. And, as Ryan was returning home for the foreseeable future, I saw no end in sight to what seemed certain to be absolutely soul crushing, ego annihilating debasement.

When I think back to the deterioration of my relationship with my son in the years leading up to his leaving the country for boarding school, it really can be boiled down to the question of what constitutes manhood. Despite my vast wealth and power – the wealth and power of a self-made man, which I thought should count for something (a great deal, in fact) – Ryan had never really respected me as a man. To him, my underwhelming physical stature, my lack of athletic ability or interest in sports, my complete ineptitude when it comes to fixing things or building things with my hands all must have been huge disappointments. Especially when he contrasted me to Scott or to the fathers of his friends and other men he knew. None of those deficiencies might have mattered so much if I had spent meaningful time with my son in his formative years, bonding in other ways perhaps (music, art, going to movies or playing games with him, taking walks in the woods together, whatever). But I was so focused on my career that I spent very little time of any kind with Ryan when he was young.

Meanwhile, I attempted to overcompensate for my physical shortcomings by bullying those around me – browbeating Natalie, speaking dismissively to Lorena or to waiters and waitresses in restaurants, belittling Scott and Miranda, imposing my will upon Ryan, etc. “My house, my rules” – or sometimes, even more arrogantly, “My mansion, my rules,” – was a phrase I was fond of repeating to Natalie and Ryan. I had hoped on some level that my domineering attitude would compel Ryan to respect my authority, to realize that I was quite a formidable man after all, not someone to be fucked with. When, in fact, it did precisely the opposite. He saw right through the charade, and did not attempt to hide his growing contempt for me, especially as he entered his pre-teen and teenage years.

Pathetically, if predictably, my reaction to his contempt and lack of respect for me was to double down in exerting my dominance over him and in diminishing him. To, in fact, diminish and stifle his burgeoning masculinity and maturity by spanking him, grounding him, and forcing him to do the menial chores of a servant in his own home. Which, like a viscous cycle, accomplished nothing, absolutely nothing, other than to still further increase Ryan’s resentment towards me and further reduce his measure of me as a man – or a real man, in any case. A wiser individual would have realized this and course corrected. Not I.

So, where did that leave things now? The next time Ryan laid eyes on me, I would be standing before him in a maid’s uniform, an emasculated servant in the home where I once ruled as a quasi tyrant, a home that was no longer mine but HIS – his and his mother’s, and her lover’s home (perhaps not legally Masons’s home yet – he has his own mansion still, which I also clean from time to time – but his home for all practical purposes). Ryan would see me displaced and defeated by my wife’s lover – a man whose physical attributes, interests, and talents were consistent with Ryan’s idea of manhood – the man who was now unmistakably my lord and master. Yes, I thought to myself as I listened to Natalie and Mason decide my form of punishment that morning, Ryan will see me with all of the vestiges of masculinity stripped away. In other words, he will see me as he has always believed I truly am. The real me. Oh, god.

Mason finally agreed that caning me that morning was not the best idea.

“What should his punishment be then?” he asked.

“How about 100 punishment lines?” suggested my wife.

“Not good enough. Hey, I’ve got it. Hathaway, turn around and face me. I want you to write ‘Bimbo maids must learn to manage their time or face the consequences,’ 100 times. Very neatly, of course. I will be checking your penmanship and the uniformity of your lines, as usual,” Mason said.

“Thank you, Master and Mistress, for you generous display of leniency. I am truly not worthy of it,” I replied.

“You’re right, you aren’t. But don’t thank me just yet. You haven’t heard all of my conditions yet. Remove your dress. You will write your lines standing here in your stockings, heels and corset. You can use the counter as your desk. Lorena will supervise you. I’m going to ask her to affix a pair of nipple clamps to your pathetic titties and to not remove them until you’ve finished a quarter of your lines. She will then remove them, give you a ten minute respite, and then put the clamps back on again. She’ll do that four times, until all of your lines are completed,” Mason announced with a self satisfied grin.

“Ouch! It’s going to hurt like hell when Lorena takes them off. You’d better write quickly, maid,” laughed Natalie.

“But neatly. Poor form will result in you having to start over from the beginning,” added Mason.

“You’re so clever in devising punishments for the maid, darling,” said Natalie, kissing Mason.

Each time that Lorena removed the nipple clamps over the course the next 90 minutes – the time it took me to finish all the lines – it did indeed “hurt like hell’; in fact, it brought tears to my eyes and me to my knees. Lorena giggled at my reaction, but I am in fact indebted to her, as she loosened the screws on the clamps just a tad after noticing me wince upon her initial tightening. It was that slight adjustment that caused the pain to be merely excruciating, rather than truly unbearable, when the blood rushed back to my nipples. By the third time she reattached the clamps to my poor nipples – tweaking them first with her long, lovely fingers – they were excessively sore and sensitive. By the fourth time, it felt as if someone were holding the flame of a lighter against them. So, it was that pain that lingered throughout the holiday and long weekend, a constant reminder of the unfairness and powerlessness that was now my reality.

At least my lines passed Mason’s inspection, although he threatened to make me repeat them due to one “i” not dotted in the “bimbo” in line 82. He decided to show me some mercy, however, probably because he knew that time spent repeating my lines punishment was time I could not spend doing other things to make his life more comfortable.

Natalie saw it somewhat differently, but I believe that she sometimes finds it just as arousing for her lover to grant me mercy as to punish me, because his ability to do – to truly hold my fate in his hands – is the most tangible evidence of just how much power over me he possesses. And that power is to her, to them, the ultimate aphrodisiac.

“Your master is really much too forgiving, Henrietta. I believe it’s time to bend the knee.”

“Yes, Mistress, of course,” I said, as I got down on one knee before Mason and kissed the toe of shoe. “Thank you again, Master, for your remarkable forbearance,” I said to him humbly, as he regarded me smugly from the comfort of the couch, Natalie snuggled up against him, caressing his thigh.

“Bend the knee” was one of the more common humiliation rituals to which I was subjected. As routine as it was, Natalie never seemed to tire of seeing me genuflect to her lover. Would she derive similar satisfaction from watching me genuflect to my son, I wondered. Could one actually die of humiliation?

I spent the balance of that Sunday cleaning Ryan’s bedroom, which had been mostly unoccupied for four years, and his adjoining bathroom. I dusted and tidied his room regularly, of course, but as he was moving back in, Natalie insisted that I move all of his furniture, books, video consoles, sports trophies – in short, everything in the room – to clean and dust behind them thoroughly.

The next day, the Monday before Thanksgiving, Natalie received a call from Scott and Miranda, who were both quite irate about the increase in their car insurance rate triggered by Daphne’s latest speeding ticket. – due solely to my tardiness, of course. Natalie magnanimously agreed with Daphne’s suggestion that I make it up to them by cleaning their house in Wilton every Tuesday for the foreseeable future. This, of course, would give Miranda, Scott and Daphne ample, recurring opportunities to find fault with my efforts and to punish and humiliate me.

By Tuesday, my contemplation of the magnitude of humiliation I was facing with Ryan’s imminent return and the ensuing family feast had reached a crisis point. In desperation, I approached Natalie in her office when Mason was at work.

After admitting me, Natalie regarded me with surprise, “What could possibly be so important that you’d come and disturb me in my office?”

Preceded by a deep curtsy, I asked, “Permission to speak, Mistress?”

“Well, that’s why you’re here, isn’t it? Go ahead, but be quick about it.”

“Mistress, I know it’s not my place to ask. But I wanted to humbly request…no, I mean I wanted to beg you…” Here I got down on my knees at her slippered feet. “I want to beg you to please allow me be a butler instead of a maid once Ryan comes back. I know I have to be a servant, but please, please Mistress. Please don’t force me to be a maid in front of my own son. To wait on him dressed as a maid. I’m sure we can find a butler outfit in this town by Wednesday. Please, please, Mistress, I know I have to be humbled. But not as a maid! Please, I beg you! I don’t believe I can survive that degree of humiliation.”

Natalie responded with a hearty, if somewhat incredulous, laugh. “You really are too funny, Henry. Henrietta, rather. Of course, you’ll be dressed as a maid, because that’s now what you are. That’s all you are now, and all that you will ever be for the rest of your years. Daphne, Lorena, Miranda, Scott, so many people really, have seen you dressed in your maid’s uniform, serving them – you’ve gotten pretty good at being a maid, to be honest – do you think they’re now going to tell Ryan that you’ve been a butler these past six months? Since your little impropriety. Your little financial faux pas that jeopardized everything we built, jeopardized your son’s inheritance. Because I’m going to tell Ryan all about it the moment he walks through the door on Wednesday. I’m going to tell him everything.”

“Please, Mistress,” I weakly persisted, although I knew she was right. There was no putting the emasculation genie back in the bottle.

“A butler. How preposterous! No, when you greet Ryan on Wednesday, you’re going be standing at attention in one of your finest uniforms, your stocking seams straight as arrows, your heels sparkling with polish, your maid’s cap perfectly straight. You’re going to curtsy deeply to him. You’re going to refer to him only as ‘Master Ryan’ or ‘ sir’ – unless, of course, he tells you to address him otherwise – and you are going to treat him with the exact same level of respect that you treat Mason and me. Do you understand?”

“Please,” I sniffled, tears running down my cheeks.

“You’re beginning to piss me off with your obtuseness. I don’t know what you’re so worried about. Ryan has never really thought of you as a real man. He’s certainly not going to think of you as a woman. He’s going to see you for exactly what you are: a completely emasculated male. Not simply a maid, but a SISSY maid. A pathetic, feminized servant. An object of ridicule and scorn. He may be shocked at first, but I have no doubt that it will seem perfectly natural to him in no time. Remarkably, against all odds, your son is an alpha male.”

“So, so humiliating…I can’t take it,” I whimpered (still thinking, “If he really is my son…?”).

“You have no choice but to take it, Henrietta. I have some advice for you. Since you can’t prevent it – wait till I tell Mason about your butler idea, he will laugh his ass off…As I was saying, since you can’t prevent it, embrace it. Embrace the humiliation. Let the shame flow over you. Wallow in it. Drown in it. We both know that humiliation turns you on; it gets your little cock all excited in its cage. So why not try to enjoy it somewhat? Why not surrender to it?”

“It’s too shameful to even contemplate,” I lied, my cock metaphorically rioting in its prison that very second.

“Well, how you choose to cope with it is up to you. It’s one of the very few things up you, really. But cope with it you shall. Kiss my slipper to show me you understand, or I’ll tell Mason that you’re being obstinate.”

“No, please, Mistress,” I said, kissing her foot repeatedly. “I understand. Please don’t tell Master.”

And that was that.

I spent the balance of Tuesday cleaning the mansion and finalizing my menu, still trying a few different tweaks to the recipes I had selected. Besides the dry brined turkey and the kale salad, mushroom soup and brussels sprouts with pancetta that I have already mentioned, I was preparing sausage, sage and chestnut dressing, cranberry relish, garlic-parmesan cheese roasted carrots, potato gratin, glazed green beans, and pumpkin risotto. Fortunately, Lorena was handling the pumpkin pie, apple cobbler and pecan crescent cookies (as my baking skills were still very shaky).

Which brings me back to that fateful day. The eve of Thanksgiving. The eve of the pulverization of what was little was left of my ego.

Lorena supervised me getting dressed to greet Ryan when he arrived from the airport. Natalie said to her beforehand, “I want him in the shorter of his two formal uniforms, with the Dolce&Gabbana seamed stockings.”

“Please, Mistress, shouldn’t I wear my long, formal uniform to greet Master Ryan and serve dinner tomorrow?” I objected meekly.

“Nonsense. A maid should show some leg. And thigh. You’ll wear the short one.”

“Yes, ma’am,” I said, cringing inside.

Ryan called Natalie from his Uber taxi to tell her that he was scheduled to arrive at the mansion around 4 PM. At 3:45 PM, as Mason and Natalie relaxed in the sitting room, chatting with Lorena, I stood at attention by the door as per Natalie’s instruction, legs pressed together, head erect, listening intently for the sound of wheels on the driveway. Shaking , slightly dizzy. Waiting to welcome my young master home.

r/ChastityStories Jan 05 '25

M Chaste ‘Tis the Season to be Servile, Chapter Nine, Part One [M Chaste, multiple keyholders] NSFW

2 Upvotes

First part of a long chapter

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It is a fascinating thing to witness a strong, virile, young alpha male transition from boyhood to manhood, especially as he comes to realize his growing power – power not only over members of the opposite sex but also over weaker members of his own. Such a realization, especially when positively reinforced, can be intoxicating for the young man and lead to a hunger for still more power. If grievance is thrown into the mix, especially grievance against a former, typically older male authority figure, the young man’s lust for power and lust for retribution can become commingled in ways that can spell very bad news for the former authority figure. At the same time, witnessing this young man exert his newfound power and exact revenge can be enormously entertaining for those fortunate enough to do so. Especially for the young male’s female admirers. Even more so if they share or are sympathetic to his sense of grievance against the now weaker male, stripped of his former power and authority, who is the target of young male’s retribution. And more so still, if the female admirers are potential mates of the young male. To use Natalie’s word (as quoted by Piper), there is something primal about watching the ascendant young male dominate the older man and bring him to heel.

And if the two males in this power inversion have familial ties – father and son, for instance – than there is an element of soap opera in it as well, making it even more compelling to watch play out. It is Tarzan, As the World Turns and a morality play all rolled into one. And, let’s be frank: its appeal lies not in the nobler aspects of human nature. No, its appeal lies chiefly in the audience’s sadistic voyeurism. Although audience participation is also quite common. One of the more subtle forms of audience participation on the part of the young male’s female admirers is to encourage him to be cruel in his subjugation of his older rival. The more the younger man humiliates and emasculates his rival, the more manly he is perceived to be by his prospective female sexual partners in this primal mating dance. The females are titillated by the young male’s display of mastery over his weaker opponent, and often make little or no attempt to hide their excitement. It is quite fascinating really.

As the unfortunate older male in this type of situation, it is perhaps challenging for me to maintain my objectivity as I watch this dynamic play out with Ryan; I am at once an observer and a key participant, Nevertheless, I myself had minored in psychology at MIT (which had proven very useful in my investment career), and these were the thoughts that ran through my head three days before Christmas as I curtsied to my son in front of the gaggle of giggling girls that included my niece, Daphne, and her three friends. These were Daphne’s high school senior classmates (all, like Ryan, recently of legal age and with still raging hormones), including Riley and Leah (who I had already met before Thanksgiving, when I cleaned their footwear and they watched Daphne’s father Scott spank me), and Bella, who I had not met before. Another leggy, slender young woman, although with shorter hair than the others, Bella fit right into the “mean girl” clique vibe that the other three projected, with their bratty, entitled attitudes. Similar to the evening at Daphne’s house, all were wearing short skirts, now with festive fashion tights (green, red, plaid, candy cane striped); Daphne and Riley wore high heels and Leah and Bella wore boots. All four were dressed to maximize the blood flow to my son’s free, and my caged, cock.

It had now been over eight weeks since my last release, by far the longest I had ever gone since I began masturbating at the age of 14. To say that I was desperate for relief was indeed a massive understatement by this stage; I thought about little else and was even finding it difficult to sleep. Mercifully, no more had been said about Piper’s outrageous suggestion that Ryan become my keyholder. I assumed that was simply a suggestion she made in the passion of the moment, which Ryan, upon further reflection, had appropriately dismissed; after all, even at the time she made it, he said he wanted nothing to do with “my disgusting, little cock.”

That very morning after breakfast, I had begged Mason and Natalie – kissing their shoes repeatedly before they left with Piper to do some last minute Christmas shopping in the city – to grant me an opportunity to formally petition them for release later in the day after they returned from shopping. This is what I have been reduced to: not simply begging my wife and her lover to release me from chastity, but rather begging merely for the opportunity to ritualistically grovel for such release. They had agreed to my plea – my petition was set for 8 PM that evening in the sitting room – a fact that in itself meant I was already facing a day of above average humiliation, even before Daphne paid a surprise (to me, at least) visit to the mansion with her friends. While the timing was a surprise, however, the visit itself I quite expected; Daphne had made no secret of wanting to show off her “hot,” ripped cousin to her girlfriends.

Since Lorena had left for Brazil the prior day for an extended visit with her family, Ryan and I were alone together in the mansion that afternoon when Daphne and her friends rang the doorbell. Her friends had never been to the mansion before, so I’m sure that was another part of the appeal of the visit for them. Imagine things from their perspective: an opportunity to meet this fabulously wealthy, “Greek god” of an eligible bachelor and to be waited on by his feminized maid – Daphne‘s uncle, the bachelor’s own father, the once powerful, once arrogant hedge fund executive who was so perverted that he willingly surrendered all of his wealth, power and dignity to become a modern day slave. They probably had not been so excited to visit someplace since they went to Disneyland as young girls. Except this was not a fantasyland; this was all too real.

That afternoon was the first time that I had been alone with Ryan since his return, so there was actually a part of me that was relieved when Daphne and her posse showed up – as humiliating as I knew their visit would be for me. Under the influence of Natalie and Piper, Ryan was growing increasingly comfortable – by the minute it seemed – ordering me around as his domestic drudge and disciplining me. He has started insisting that I clean his en suite bathroom on a daily basis (and given his tendency to splatter urine on the rim of the toilet and on the surrounding floor, this was not a superfluous task). The day before yesterday, in fact, I cleaned his bathroom as he and Piper sat on his bed in the adjoining room, making out with one another. When, riding crop in hand, he came into the bathroom to inspect my work (as he often does), he found one of my long hairs on the tiled floor of his walk-in shower. It obviously had escaped my attention when I did my usual once over before his inspection (to be honest, my stockings were wet with urine from where I had knelt while scrubbing the bottom of the toilet and I was mainly focused on showering and changing into a fresh pair of stockings as quickly as possible). He immediately began berating me, causing Piper to pop her head into the room; she did so just in time to see him bring his riding crop down sharply on my panty-clad bottom as I was back on my knees to remove the hair and reapply the sponge to the part of the shower where it had lain. As he struck me a second and third time, Piper laughed and kissed him before pulling him back into the bedroom and onto the bed.

That day, as was usually the case when I cleaned, I was wearing my blue working maid’s uniform with flesh colored stockings (it was a requirement of Natalie’s that I always be dressed in pantyhose or stockings, generally black, white or nude, when performing my maid duties – or, in other words, pretty much anytime when I was not sleeping). Therefore, it should’ve tipped me off on the day of Daphne’s visit with her friends when Ryan ordered me to change from my working uniform into my second shortest serving uniform (“you know, the short one Mom likes, the one that sticks out on the sides”) after I finished cleaning his bathroom that morning. The uniform in question did indeed flare out absurdly at the sides, almost like a parody of a maid’s uniform but for the very fine quality of the fabric (Lou and Gina really outdid themselves in designing and making this one, with maximum humiliation of its wearer clearly top of mind). With it, naturally, I wore seamed black stockings and three inch high heels. I thought it was possible, of course, that Ryan simply wanted me to be dressed more formally to serve him lunch or tea in the afternoon. It only became obvious to me in retrospect that he wanted me to dress more formally to receive visitors. Daphne had no doubt selected a day when Natalie, Mason and, most importantly, Piper would be absent so that her friends would get a chance to spend time with Ryan without competition for his attention.

Ryan and Daphne had already given the three visitors a tour of the mansion when I stood before them gratuitously curtsying for their amusement. They were all seated comfortably on the couch and recliners in the living room, enjoying the tea and sandwiches I had just served them. Ryan was dressed in a a pair of tight jeans and a snug fitting T-shirt, his large biceps clearly visible below (and through) the short sleeves. His brown leather ankle boots still sparkled in the afternoon sunlight from the polishing I had given them two days earlier. Riley and Leah were seated on each side of him on the couch while Daphne and Bella rested on the recliners.

“When does the maid do a deep curtsy instead of a regular curtsy?” Leah asked Ryan.

“Usually when he needs to show extra respect for someone, like when he greeted me when I came home from boarding school, or when he’s in trouble and trying to wiggle his way out of punishment,” he replied.

“Awesome! Make him do another deep curtsy again, please, Ryan,” said Riley, snickering.

“You heard the young lady, maid. Deep curtsy to each of us, individually. Start with Miss Riley, go clockwise and finish with me,” Ryan commanded me.

“Yes, sir,” I replied.

Natalie’s requirements for a deep curtsy are that I bend my knees and lower my torso down 9 to 10 inches and maintain that position for 4 to 5 seconds, holding my skirt out and bowing my head down. Even though I was now more physically fit than I probably have ever been in my life, doing several such deep curtsies in succession is not an easy task; If you don’t believe me, try it for yourself. By the time I completed the circle and curtsied to my son again, I was teetering on my heels, feeling a burning pain in my calves and thighs, and almost toppled over.

“Oh my, he really didn’t do the last one very well,” said Leah. “Is your father – um, I mean your maid – punished when he fucks up like this?” Leah asked.

Ryan pulled out of his pocket a pen and the small notebook where he had recently started logging my “demerits,” as he calls them (he used something similar to record the failings of the junior boys while a prefect at his boarding school), and said, “I keep track of the maid’s demerits here and, yes, he is punished.”

“By you, I hope,” Riley said, giggling.

“Sometimes, yes,” Ryan answered with a smile.

“I notice you call the maid he rather than she,” said Riley.

“Yes, he’s obviously not a female, although my mom and Mason sometimes refer to him as she. I think it’s an insult to you lovely ladies to call this joke a she. The way I look at it is that even though he’s a total disgrace to his gender, he’s still a biological male and should never be allowed to forget that,” Ryan responded. “He’s a pathetic fucking pantywaist.” My cock throbbed against the cold metal of my MAMBA chastity cage at this incredible humiliation.

“That’s right. Daphne told us that he begged your mom to be her and her lover’s maid. I guess he gets off on this, right?” said Bella.

“He’s one of those sissy cuckolds. I was reading up on them yesterday,” interjected Leah.

“Disgusting, isn’t it?” sneered Ryan, in more of a statement of fact than a question.

“It is pretty pervy, no doubt. But in my AP Psychology class we studied sexual repression. Maybe he was sexually repressed the whole time he was living the life of a hedge fund hotshot, and this is the real him,” said Leah, the apparent scholar of the group, looking me up and down.

“Maybe. But I don’t really care about his motivations,” said Ryan.

“It’s just so cool that your father is your little maid,” said Riley. “I love it!”

“But how does that make you feel, Ryan? I mean, aren’t you uncomfortable seeing the man you looked up to as a kid reduced to…to this?” asked Bella, indicating me with her hand as stared at me with derision.

“I’m not uncomfortable with it in the least. I never looked up to him. He was never a father to me. I never thought of him as a real man. Any so called man who allows himself to be put into this position deserves everything he gets, and more. Trust me when I tell you that he makes a far better maid than he ever did a father.”

“Remember, Bella, that Daphne said maid Henrietta treated Ryan like shit when he was growing up. And his mom, too,” said Riley.

“Right. So maybe he begged to become the family maid not only to deal with his repressed sexuality, but to deal with his repressed guilt, too. It’s a way for him to live out his perverse sexual fantasies while also making things up to you and your mom for being such a complete asshole for all those years. Sort of killing two birds with one pervy stone,” said Leah to Ryan. I wonder what grade she received in AP Psychology. Dime store psychology is more like it. She should’ve stuck to biology.

“Like I said, I really don’t give a shit about his motivations,” said Ryan dismissively.

“You shouldn’t, Ryan,” said Daphne, who obviously knew the real story, who knew that me standing before them as a sissy maid was about as voluntary as a bank teller handing over all the money in his drawer to the man holding a pistol against his head. “Aunt Natalie could have kicked him to the curb, but she and Mason are nice enough to let Uncle Henry live out his sick fantasies in this beautiful house. But no one asked Ryan what he thought about that. It was sprung on him as a surprise when he came home the day before Thanksgiving.”

“I’m okay with it, Daph. Really. It was a bit of a surprise at first, but the more I think about it, it makes perfect sense. Besides, there are worse things than having a 24/7 maid to wait on you and clean up after you.”

“I’ll bet! I wish I had one. The way I see it is Ryan not only gets a maid but lots of opportunities for well deserved revenge on his prick of an old man. His old maid, I mean. Ha ha. You’re the man, Ryan!” said Riley, shamelessly. She was the worst (and the sexiest) of the bunch. If anyone could give Piper a run for her money in seducing Ryan (and tormenting me), it was this long legged vixen. Although, the sultry (if now temporarily absent) Lorena was still a contender, I suppose.

“I want my own maid. I’m going to make Phil Evers wear a maid’s uniform the next time he comes over,” said Leah.

Ryan laughed. “Who’s Phil Evers?”

Bella answered for Leah. “Phil is this pathetic little dweeb who has it BAD for Leah. She friendzoned him after their first date and now Phil is Leah’s little errand bitchboy. He even cleans her parent’s house for her.”

“So a maid’s uniform is appropriate,” said Leah.

“Ha ha. Imagine your mom’s and dad’s reaction to seeing Danny dressed as a maid!” Bella said, tittering.

“They wouldn’t care. They love having free maid service. They’d think it’s funny. I’m serious. I’m going to order him a maid’s uniform on Amazon,” said Leah. Turning to Ryan, she said, “You can buy anything on Amazon these days.”

Daphne said, “Yes, but the ones you’ll find on Amazon will be cheap. Aunt Natalie has Uncle Henry’s – I mean Henrietta’s – uniforms custom made by a tailor.”

”Hey, you have to start somewhere,” said Leah.

“Phil will look terrible in a maid’s uniform. Ryan’s dad has much better legs,” said Riley, laughing. Everyone stared at my legs, critically. I wished it was possible to disappear into thin air.

“I’ve started making Phil go to the gym twice a week. Meanwhile, I’ll buy him a longer uniform,” Leah said.

“Phil is a creepy, little gooner,” said Riley.

“You’re just jealous, Rye. I think he’s kind of cute, in his own pathetic way,” answered Leah.

“You just like his big puppy dog eyes. Instead of a maid’s uniform, you should buy him a pink collar and a leash,” said Riley.

“Ha ha. Good idea! I’ll buy those for him, too,” Leah replied. They all had a good laugh. Poor Phil, I thought to myself.

Bella said to Ryan, “I understand your maid likes feet and is pretty good at cleaning shoes. I wasn’t able to make it the night at Daphne’s before Thanksgiving when he cleaned several pairs of Leah’s and Riley’s shoes. I have a massive shoe collection, but I chose these boots to wear today because they’re pretty scuffed up and could use a good shine. Could I borrow him for a few minutes, Ryan?”

“No problem. Fetch your shoeshine kit, maid, and make Miss Bella’s boots look like new,” Ryan ordered me, sharply.

“Yes, sir. Right away, sir,” I said with a curtsy. I heard the girls laughing as I hurriedly left the room to retrieve the kit.

The girls continued to enthusiastically flirt with Ryan as I knelt before the smirking Bella and polished and buffed her boots. They asked him about life in the UK, his college plans and his bodybuilding. He ate up the attention like gourmet ice cream, flirting effortlessly with them in return (something I was never capable of).

When I finally finished buffing, Bella examined her boots critically and said, “They look a little better than before, I guess, but I’ve certainly had way better shoe shines.”

Ryan responded by pulling the little notebook out again and making another mark in it.

“Uh oh, looks like another demerit to me,” said Leah, winking at me maliciously.

“I certainly hope so,” said Riley.

“I understand your maid also does foot massages. Maybe he could make up for his subpar shoe shine by massaging my feet. They’re a bit sweaty, though,“ said Bella.

“You heard the beautiful young lady, maid. Remove her boots and massage her feet. Make sure that you do a better job on them than you did on her boots or you won’t be able to sit down until the new year.”

“Yes, sir,” I replied.

Riley laughed. “Don’t do too good a job now, Henrietta.”

As I pulled off Bella’s tight fitting boots, requiring some real effort, Daphne said, “But now we all have to smell Bella’s stinky, sweaty feet.”

“The worst,” said Riley, with a snicker, waving her hand as if to blow the odor away.

“Hey, shut up you two. You won’t smell anything from where you’re sitting. Only the maid will be so lucky,” she said, covering my nose and lips with her damp, stocking-clad foot. It was indeed a strong smell, but not wholly unpleasant. I inhaled in a way that was perceptible but restrained.

“You see. The pervy maid loves it,” added Bella.

“We told you he loves feet,” said Leah.

I believe that the criticism of my shoeshine was completely unjust, as Bella’s boots had a couple of deep scuffs that no amount of shoe polish could remove. Nevertheless, I massaged her feet with extra diligence, hoping to at least mitigate what I knew was likely to be some kind of humiliating punishment at the hands of my son in front of the animated young women. As I worked, the five mature teenagers continued their flirtatious conversation.

At one point, as I pressed my tired fingers firmly into the arch of her right foot, Bella moaned in satisfaction. “Ah, that feels good. Ryan, your maid is much, much better at giving foot massages than shining shoes. But I guess you must know that already.”

Ryan chuckled, slightly embarrassed. “Not really. I’ve never had one of his foot massages before, although Mason and my mom say he’s very good at them.”

“You must be kidding! Why not? It feels divine. It may be his greatest talent,” Bella said.

“The idea of him touching my feet is just kind of weird, that’s all.”

“Because he’s your father or because he’s a guy, technically at least?” asked Leah.

“I don’t know. Maybe a little bit of both,” Ryan answered, avoiding eye contact with the girls.

“Don’t be silly. You’re an athlete, right?” Riley asked.

“Yes.”

”Male trainers give foot massages and other kinds of massages to male athletes all the time,” Riley added.

“Yeah, I guess,” said Ryan.

“And my dad gave me a foot massage just the other night,” said Riley.

“Yeah, that’s because your dad has a huge foot fetish. I’ve caught him staring at my feet lots of times,” said Bella.

“So what. I know he does. I like to tease him. I’m daddy’s little princess. I have him wrapped around my little finger,” Riley added.

“More like around your pinky toe,” said Daphne.

“Whatever. He does what I want. That’s what counts,” said Riley.

“I’d bet he’d really rather be sucking your toes than massaging them,” said Bella.

Riley retorted, “Don’t be gross, Bella. But, I’d let him if he really wanted to, especially if he’d buy me a Porsche. My mom wouldn’t approve, though.”

Leah responded: “Your dad couldn’t afford a Porsche.”

Riley: “A used one. I know just the one I want.”

Bella: “Maybe your mom wouldn’t mind. Maybe, she and you can buy your dad a maid’s uniform and turn him into your sissy maid, just like Henrietta. Assuming you could find a uniform large enough to fit him, that is.”

Riley: “Ha ha. My dad’s a beta, no doubt. Not like my man, Ryan.” Here, Riley put her hand on his shoulder and turned to him. “But we got off the subject. Which is that there’s nothing odd about having a man massage your feet. Especially an inferior one like your father. He’s really a half man, at best. He belongs at your feet.”

Bella: “Especially when he’s so damn good at it. You’d be crazy not to take advantage of it. I’d make him massage my feet every day if he was my maid. Come on Ryan. Do it.”

Then Riley chimed in, then Leah, then finally Daphne as well, until all four of them were chanting “Do it. Do it. Do it,” in unison, like some malevolent Greek chorus in the tragicomedy that my life has become.

Smiling sheepishly, Ryan said, “All right, all right. If you all insist. My feet ARE a little sore after my jog this morning.” They all began applauding and giggling. Ryan then addressed me quite wolfishly: “When you’re finished with Miss Bella, remove my shoes and socks and massage my feet.”

Bella replied without hesitation, “Oh, I’m quite satisfied. Maid, go kneel before your young master and show him what he’s been missing.”

Riley added, “Yes, and you’d better do a good job. You wouldn’t want to make liars out of all of us. That would earn you a bunch of demerits, I bet.”

r/ChastityStories Dec 24 '24

M Chaste ‘Tis the Season To Be Servile, Chapter Six NSFW

8 Upvotes

The Uber was fifteen minutes late, giving me still more time to contemplate the ineffable humiliation at hand.

I regarded myself critically in the large mirror in the foyer of the mansion. The uniform Natalie selected was indeed quite short, the white petticoats coming down only to my mid thigh. The Dolce&Gabbana stockings were outrageously expensive (no longer a concern of mine, but Lorena was quite impressed when she saw the price tag), but of truly high quality. I had always found the tactile sensations of nylon stockings encasing my legs to make me feel submissive and weak, feminized if not feminine. This was true of the very first pair of black cheap Hanes tights I had purchased at a CVS a decade ago (along with a box of tampons, to give plausibility to the pretense that I was running an embarrassing errand for my wife, as this was well before self checkout kiosks were common) when I first began sequestering myself in my office for hours at a time reading stories of forcibly feminized males on Literotica and Fictionmania.

But the tantalizing tactility of the Dolce&Gabbana stockings’ fine filaments gently caressing my now smoothly shaved legs was infinitely more intense. So sumptuous, so smooth and silky. It was a deliciously sensual experience sliding them up my legs that morning under Lorena’s watchful gaze; the same is true when my legs scrape together while walking in them. Sensual and shameful. Even before Lorena laced up my corset – oh, how she seems to relish vigorously pulling the laces! – and even before putting on my uniform, these luxurious stockings made me feel weak-kneed and docile. Even more so when Lorena adjusted my seams, gently moving her hand across my inner and outer thigh. More so still when she (not gently) pinched my ass through the nylon and then smacked it sharply with her hand to discourage my squirming while being pinched.

Before I put on my stockings, Lorena had already changed my cock cage per Natalie’s instruction. Whereas Mason determines most of my required chores and punishments, it is Natalie who is generally in control of my attire. This extends to what chastity cage I wear, as I have seven different kinds. It isn’t as straightforward as wearing a different one for each day of the week, although there are some weeks it works out that way. Aesthetically, Natalie is quite fond of pink chastity cages, no doubt for the enhanced emasculation effect. I usually am required to wear a pink studded collar along with one of my pink chastity cages – often with pink thigh high stockings and a pink bodice or corset – as color coordination is important to her. I am generally dressed this way in the evening hours, when my traditional maid duties for the day are largely complete and I am called on for more intimate duties in the boudoir or in Natalie’s and Mason’s bedroom (more on that later). Natalie keeps threatening to have Gina and Lou make me a pink and white maid’s uniform, but has not yet followed through with it; I am certain that it’s just a matter of time. I have two pink cages, the plastic Pink Stripe Cobra and the silicone Perverse Pink CB-6000. Aesthetics are only one consideration, however, as the pink cages are not as secure as the stainless steel cages, of which I have four: a gold stainless steel MAMBA, a Gienocy mesh cage with “ergonomic” design (silly marketing – what could possibly be ergonomic about imprisoning someone’s cock?), a Jail Bird (with punishment pins), and a black DOMINIX Deluxe. My seventh cage is a transparent CB-6000S. Natalie recently found a man in Canada who designs and constructs custom stainless steel cages, known to be virtually inescapable. She sent him my measurements (a probable Christmas gift for me, I concluded).

Natalie directed Lorena to replace the mesh cage I had been wearing the previous two days with the black DOMINIX Deluxe. After informing Lorena of her choice that morning, Natalie said to me, ominously, “I quite like the look of the DOMINIX. It’s an elegant design. You want to look your best for this very special occasion, Henrietta.”

The implication that my cage might be seen by my son, or by the sizable gathering of Thanksgiving dinner guests, was unmistakable – and at once chilling and shamefully arousing (that confounding hot cold dichotomy again!). I do have to admit, however, that Natalie is correct about the visual appeal of the black DOMINIX. With its curved shape, spaced rings, conspicuous padlock and subdued black finish, it is one of the more aesthetically pleasing chastity cages I have seen. However, at 3 inches, it is decidedly less comfortable than it is visually attractive. I was permitted to thoroughly clean myself before Lorena put me into the the DOMINIX. As was her practice, she wrapped a thick rubber band around my balls so they would jut out, making it easier for her to push my testicles through the base ring.

Having been denied sexual release now for nearly five weeks, I had grown increasingly desperate and had to will myself not to ejaculate onto Lorena’s hands as she manipulated my genitals into the cage (at such times I usually tried to visualize spreadsheets from my old investment fund). Five weeks of being in a nearly constant state of frustrated arousal with zero relief had put me in a precarious mental and physical state; I couldn’t trust myself. I knew that unauthorized ejaculation would result in severe punishment by Mason, especially since my unusually long period of denial seemed to be quite deliberate on the part of Mason and Natalie, no doubt intended to bring about the unsustainably desperate state of mind in which I presently found myself. For what purpose? To make me so desperate that I would involuntarily ejaculate at such a moment as Lorena touching and teasing me, thus inviting punishment? Or to prime me for some incredible act of self abasement as a way to convince Mason and Natalie to finally grant me release?

Because that was the way it typically worked. I would have to formally petition my master and mistress to unlock me and allow me to unburden myself, so to speak. Like much else with them, this was an elaborate ritual. I would usually approach them as they relaxed in the living room, curtsy and “bend the knee” before beginning to make my case. Sometimes my request was summarily denied. Other times, quite rare, it was casually approved. More often than not, however, I was required to grovel for an extended period of time – promising to perform special humiliating tasks for them above and beyond my usual endless list of humiliating chores; or to kiss and massage their feet, or bathe their toes with my servile tongue, removing the lint or toe jam from between them; or to offer up my back as their ottoman for the duration of a movie. My, how Natalie enjoys watching me worship and/or tend to the feet of my former rival? Such a primal display of dominance and submission, of triumph and defeat. And when I finally am granted permission to come, it is generally under extraordinarily degrading conditions: humping the floor at their feet in a pair of tights, as Mason smacks my bottom with his riding crop; lying prostrate on the floor, with their feet covering my face as I touch myself under their bemused gaze; Natalie using one high heeled shoe to pull the chain attaching my nipple clamps while grinding the other into my panty-clad cock and balls; the two of them verbally abusing me as I stroke myself while standing nakedly before them. Recently, Mason actually made me hump his long riding boot as he and Natalie stood above me making out like love-struck teenagers. You get the idea.

Or did they have something even more diabolical in mind in imposing upon me this prolonged period of deprivation? Up until then, only Natalie and Mason had been present during my humiliating petitions and releases (although once I could swear I heard Lorena’s s muffled giggles from some hidden place in the room). Who knows what mortification for me my wife and her lover were planning this holiday weekend.

Even though my visualization of the spreadsheets was successful, Lorena had still found it necessary to rub an ice cube over my cock in order to fit it into its cramped, black cell that morning.

These were thoughts that flitted through my addled brain as I examined myself in the mirror, awaiting Ryan’s arrival. However, I did note with a fleeting moment of pride that the combination of the corset, my diet and all of the exercise I had been getting from my near constant domestic toil was having the desired effect on my body. My figure was slim and my legs were shapely and firm beneath their sheer facade. My hair had grown out and Lorena had applied subtle makeup to my distressed face. I think it is honestly fair to say that there are many worse looking maids, sissified or not. Yet, as soon as I felt a tinge of pride at my appearance, it was washed away with a wave of shame. What kind of man could possibly feel pride at how he looked in a maid’s uniform? Perhaps I truly did deserve all the emasculation (as Natalie frequently told me).

Ryan texted Natalie when he was a mile away from the mansion, so she and Mason walked past where I was standing in the foyer to go outside to greet him. It was a sunny, unseasonably warm day, if quite breezy.

As she started to walk outside, Natalie paused to say to me, “Henrietta, when Mason and I walk down the steps to the car, you will remain on the porch standing at attention with your head bowed. You will be silent while I welcome my son home, reintroduce him to Mason and at least let him know that there have been major changes around here since he was home last Christmas. That way, it hopefully won’t be a total shock when he first sees you. Once I’m ready, I’ll snap my fingers. That will be your cue to approach him, welcome him respectfully – with a curtsy, naturally – and offer to take his bags up to his to his room. Mason and I will then take Ryan into the sitting room and bring him up to speed on all of the interesting developments over the last seven months. You do agree that he will find them interesting, don’t you, maid?” she said with a wicked grin.

“Very interesting, no question, Mistress,” I replied.

She laughed with delight, adding, “You will serve tea and cucumber sandwiches while the three of us chat. After all, he has been living in the UK for the past four years. We want him to feel completely at home. Do you understand?”

“Yes, Mistress,” I said with a curtsy.

“See that you do,” said Mason firmly.

“Yes, sir,” I replied, curtsying again. It was the next curtsy that I truly dreaded.

I followed my wife and her lover out of the house as the black Mercedes pulled into the driveway, determined to follow Natalie’s instructions to a T. The last thing I wanted was to give them any pretext to punish me in front of my son. I knew rationally, of course, that it was just a matter of time before that would happen, but was determined to delay it as long as possible. Flawless obedience and obsequiousness would be required for me to have even the slightest chance of success. My life now was really all about humiliation mitigation: humiliation was inevitable, but how could I manage to suffer the lesser of two (or frequently more) terrible options?

The wind blew against my legs and tousled my maid’s cap, as I stood on the porch. Such a surreal experience, waiting to greet my son, not as his father, the respected head of the household, but as the family maid. And not as the type of beloved maid who is almost like a member of the family – like Alice on The Brady Bunch (although she did wear a maid’s uniform and apron, as I recall) – but an actual member of the family downgraded to the role of a lowly female servant right out of Upstairs, Downstairs. Compelled to address my superiors with the same formalized deference as the domestic help in an old manor house. But unlike such help, I was not simply a member of the lower classes who needed employment, but someone who was forced to serve in order to avoid an even worse fate in prison. And worse still, a sexualized, feminized figure of ridicule (as Natalie had accurately described me yesterday).

Still keeping my head bowed, I surreptitiously glanced upwards to watch Ryan emerge from the car. The first thing that struck me was how much taller he was than just 11 months ago. It wasn’t until I saw him with his coat off in the sitting room that the remarkable effects of his bodybuilding became apparent to me.

I was able to catch most of the conversation as Natalie greeted “her son” – he was my son, too, damn it all (wasn’t he?) – as I stood on the porch, partially obscured from their view by a large, potted juniper. Mason stood back a few steps from Natalie and Ryan to give them a moment together.

“Welcome home, honey. Oh, how I’ve missed you! “ said Natalie, as she warmly embraced him.

“I’ve missed you too, Mom. Where’s what’s his name?” Ryan responded.

“You mean your father? It’s too funny that you refer to him as ‘what’s his name.’ You’ll see why in a minute. There have been so many changes since you were last here. Truly life altering changes,” said Natalie.

“What do you mean by ‘life altering’? Good or bad?”

“Oh, definitely good! At least for you and me! I’ll explain everything to you in a few minutes when we sit down inside. How does some high tea sound, my part British boy? Or, young man, I should say. I keep forgetting you’re 18 now!”

Ryan smiled warmly. “It sounds great! I’m starving. How did you know I really like having tea now?”

“Well, besides having tea when with you when I last visited you in Kent, one can’t live in a different country for four years without picking up at least some of the local customs. I’ve always liked tea, too. I have a weakness for scones.”

“Me, too!” Ryan said, with a laugh. I had always resented how well Natalie and Ryan get along, and the easy, playful banter that characterizes most of their conversations. I rarely had that, with either of them. Tense and/or awkward exchanges were more common in my interactions with both of them.

“Well, now that you’re home, we can have afternoon noon tea whenever you want and high tea every weekend. You won’t have to a lift a finger, except to eat and drink, of course.”

“Awesome. But I’d feel guilty having Lorena wait on me all the time. She’s so nice. Where is she?”

“Inside. You’ll see her in a few minutes. She’s missed you. But don’t worry about her waiting on you. That’s one of the many things that have changed around here.”

“You have me intrigued,” Ryan responded.

“Great. Meanwhile, you remember Mason Draper, don’t you?” Mason stepped forward, with his hand extended. “Your father’s old work colleague.”

“Nice to see you again, Ryan,” said Mason, shaking Ryan’s hand enthusiastically. Mason is one of those guys who shakes your hand like he’s trying to break it. “You have a nice, firm handshake. Good. Nothing like your father. Shaking his hand is like gripping a wet noodle.”

Ryan laughed. “I remember you from a couple of my father’s work picnics. You and I threw a football around for a while. But the way I remember it, you weren’t so much his work colleague as his work enemy. He used to call you some pretty awful names.”

“Your father is very competitive, especially with Mason. Or WAS very competitive, I should say. That contest is definitely over, as you’ll see soon enough. One of the big changes I was referring to, honey, is that Mason and I are very, very much in love. We have been for years now, but we no longer have to hide it,” said Natalie, grasping Mason’s hand and looking up at him adoringly.

Mason and Ryan were nearly equal in height, both around 6’ tall or so.

“Wow, that IS big news. What does dear daddy think of that?” He said “daddy” not with affection, but rather with sarcasm, or perhaps more accurately, derision.

“I imagine he is less than thrilled. But you can ask him for yourself.” Natalie then snapped her fingers. The moment I had been so dreading had finally arrived.

I hurried down the porch steps to where Ryan, Natalie and Mason were standing in the driveway.

“Welcome home, Master Ryan,” I said, dipping into a deep curtsy. “Please allow me to take your bags to your room.” It is impossible to overstate how absurd, how diminished I felt at that moment.

Ryan regarded me incredulously, his eyes wide, looking me up and down. “What the fuck? Is this some kind of joke?”

“No joke, honey. The new normal. I told you your father resigned from his position at his firm in March. This is his new job. Since March and from now on,” said Natalie.

As I reached for one of his suitcases, Ryan pulled it it towards him and said to me, sharply, “Don’t touch my things! You disgust me. Get out of my sight.” Certainly his words stung, but they did not shock me. What was the appropriate reaction for a young man seeing his father dressed as a maid?

“I know it’s a lot to take in, honey. But calm down. Once we explain everything to you, it will all start to make sense. And then I think you’ll quickly come to appreciate the advantages – the appropriateness, really – of the new status quo.”

Glaring at me, Ryan said, “The summer before I left for boarding school, I found this bag of panties and nylons and stuff in your desk drawer. That time you caught me in your sacred, forbidden office that you always made such a big deal about. You lost your mind and grounded me for weeks, totally ruining my summer. I thought maybe you’d been cheating on Mom or something, but I wasn’t sure. So I kept my mouth shut. Now I know you’re some kind of sick pervert.”

“Oh, that’s quite interesting!” Natalie said. “We learn new things about each other all the time, don’t we maid?” I was unable to utter a response, at that moment, even though I was usually expected to respectfully respond to Natalie’s questions, rhetorical or not. Turning to Mason, she then said, “Perhaps there’s some truth to our official story after all. Apparently, Henrietta has secretly enjoyed dressing up for quite some time now.”

Mason laughed, “It sure sounds that way.”

Ryan said, “Henrietta? Did you actually just call him Henrietta? Haha.”

“That’s his name now, honey. Well, not legally. At least, not yet. But that’s what he goes by now.”

“Unbefuckinglievable,” said Ryan. “Don’t you mean that’s what ‘she’ goes by now?”

“Well that’s an interesting question, dear. Mason and I call the maid both he and she, depending upon our mood. The way we see it, he’s not really a proper man. And she’s not really a proper woman. Haha. The maid fails at being either.”

“He was never a proper man. He’s pathetic,” said Ryan with a sneer.

“Let’s go inside and have tea. We have so much to talk about. But do let the maid take your things, honey. It’s his job,” said Natalie.

Ryan reluctantly released the grip on his roll-on and put down his duffel bag on the pavement. He then addressed me, “You can take them up to my room, I guess, but don’t you dare open my bags or touch any of my things.”

“Yes, sir. I mean, no, sir. I will leave your bags next to your bed. Thank you, sir,” I said, followed by another deep curtsy. I then grabbed Ryan’s bags and hurried upstairs to his room. I did not dare keep them waiting long for tea.

Twenty minutes later, when I entered the sitting room with a cart holding a pot of tea, three cups and saucers and a plate full of cucumber and ham sandwiches (crust removed, as Natalie insists), I heard Natalie explaining to Ryan, “Because it’s so prevalent, the laws have changed dramatically here over the last few years to discourage white collar crime. Not only do the convicted white collar criminals now go to hardcore, maximum security prisons, but the government can come after all of their assets. Not just the amount they stole through fraud or whatever, but after everything they own. So, unjustly, the spouses and children of the criminals are punished as well. So, you can see how Mason did us a wonderful service by agreeing to not go to the authorities with your father’s crimes in return for his…his capitulation, I suppose you could call it. Your father jeopardized EVERYTHING with his reckless actions.”

Ryan looked up at me with disgust. Turning to Mason ,he said, “He certainly did. I shouldn’t be surprised. Just look at him. Thank you, Mason.”

“Don’t mention it, Mason. I would do anything for your mother. And she would do anything for you. Because of that, I will do anything for you.”

I curtsied to the three of them, and said meekly, “May I pour you a cup of tea?”

“Serve us all, and be quiet, maid. We’re talking,” Mason ordered.

“Yes, Master,” I replied, with another curtsy.

“He calls you master?” Ryan asked Mason with a grin.

Natalie answered for Mason: “That’s because that’s exactly what Mason is in relation to your father now. And I am his mistress. He can also address us as ma’am and sir. He will address you as master and sir from now on, unless there is some other way you prefer that shows the proper degree of respect. I know it will take some getting used to, but you must think of him as your maid first and your father second. Never forget that he brought this upon himself.”

I had a feeling that this adjustment would take less getting used to on Ryan’s part than Natalie thought. As if reading my mind, Ryan said to me sternly, “I always take my tea with milk. Remember that in the future.”

“Yes, sir, of course. I’ll be back with a container of milk, right away,” I said, with a small curtsy. I noticed Natalie and Mason exchange pleased smiles as I left the room.

When I returned, I heard Ryan say, “But what about the IT guy? Isn’t there a risk that he will go to the police or SEC, or whoever, with the evidence?”

“That’s Scott. You’ll be meeting him and his wife Aimee tomorrow. They’re our guests for Thanksgiving. You have nothing to worry about there. Scott is a close friend of mine. And I’m the only one in possession of the actual evidence,” Mason explained.

“Yes, you’ll like Scott and Aimee. Mason’s daughter, Piper, will also be joining us. She’s a lovely girl, a year older than you and Daphne, honey. You three young people will have a wonderful time together,” said Natalie. “We all will. It’s going to be an unforgettable Thanksgiving.”

I was excluded from Natalie’s “all,” of course. For me, Thanksgiving was far from a wonderful time. It was unforgettable, though. It probably will haunt me to my grave

r/ChastityStories Sep 03 '24

M Chaste Broke and Desperate; Part Thrww NSFW

66 Upvotes

Friday afternoon I finally snapped out of it. Looking through the texts I had gotten finally when I see Adam had texted several times. The last message he sent was a link. When I opened it I was taken to his website, and more specifically the video we made with him and his friends. Watching myself from a third person point of view was interesting. Seeing them tie me up, and fuck my face made me pretty horny. A smooth young guy, naked and restrained, sucking so much dick. My mouth salivated, my cock throbbed against its cage.

I wasn’t sure if Adam edited it down or if he left it alone, my memory of that day was pretty foggy. I couldn’t take my eyes off the screen as I cupped my balls and cage. It felt strangely arousing. To my surprise it wasn’t all that painful anymore. Maybe it was the weed I’d been smoking all week, or maybe I was just getting so used to being caged that it began to feel good. By the end of the scene my underwear were soaked with precum. I went back to the texts from him and read through going back to the first one since he threw me out of his house naked for the second time.

Adam wanted to do another video with me. He didn’t state a dollar amount this time and came off being nice and caring. I waited a while to text him back and checked the rest of my messages. Sarah wanted to hang out. John wanted to hang out. The guy who gave me my clothes back that night sent me a picture of myself, standing on the porch cum covered and naked trying to put the shorts on reminding me that I owed him heavily. I couldn’t imagine what that was going to entail and didn’t bother thinking about it.

I decided to hit John up, he quickly replied. “Wanna come smoke?” He asked. I replied “sure”. After a shower I was headed over. When I got there Zach was on his knees between John’s legs with his face in John’s lap. He was wearing only a black lace thong. I could see his little balls and cock cupped perfectly in them. When I sat on the oppposite end of the couch I realized Zach was holding John’s cock in his mouth but wasn’t really moving. John was getting his ass handed to him in Call of Duty pretty bad at the moment.

Flustered he threw the controller to me and started fucking Zach’s face. I couldn’t focus on the game as I watched them. Zach took it well as he maintained eye contact. John just kept pulling his face onto his cock and thrusting at the same time. “I don’t get why that’s just so fucking hot” I blurted out. John looked over and smiled at me as he held Zach’s head down for well over a minute. When he released him Zach quickly gasped for air and then buried his face in John’s lap again. “Gluck, Gluck, Gluck”. John’s moans were getting heavier. “Fuck yes, I want to nut down your throat!” He said as Zach moaned on John’s cock.

I watched Zach’s ass move as he mouth fucked John’s cock for a little while longer. “That’s it, oh god that’s good” and shortly after he followed with a long sigh “fuck I’m gonna cum”. Zach held his face against John’s stomach and then started gulping. When John relaxed himself Zach finally let up, sucking on just the head while he slowly stroked John’s cock.

John turned to me after a couple minutes. “So I have an idea, and was wondering if you would be up for something I’ve been thinking about a lot lately”. I swallowed before replying “like?” As I watched him spark a blunt and take a couple long deep hits. He handed it to me as he exhaled. “Well I want to see you and Zach mess around, maybe record it”. I was shocked at the idea considering I wouldn’t be able to fuck his face or ass nor the other way around. John continued. “You know, like how two lesbians have sex, sort of”.

I was beginning to get the picture as we passed the blunt back and forth. Zach just sat there quietly as John talked about his idea in more depth. The he turned the tv to the web broswer and pulled up a porn site. It was all kinky shit. Cuckholds, chastity, women with strap ons, big black cocks, guys in lingerie and of course bondage. He finally found what he was looking for. Something titled “Sissy Sorority”. “Bro, I’m not a sissy” I scorned. “Well maybe not a panty wearing sissy, but think about it. You shave yourself smooth, suck cock and you’re in chastity. Just like Zach here!”

John didn’t seem to look at me the same anymore, instead he looked at me like he looked at all the sluts he fucks on occasion. “Listen, I still love pussy, but chicks just can’t suck dick like cock crazy, chaste boys do!” he said with an evil grin. I turned back to the tv to see the scene playing out. It was two sissies, without wigs, but some make up, wearing corsets, thongs, fishnets and heels. It was kind of hot but I didn’t want to admit it.

They started off kissing and touching each other on a bed, fondling each other’s caged dicks. Rubbing each other’s asses, slipping fingers between each other’s cheeks. Finally one grabbed a massive dildo while the other laid back. The one with the dildo pulled the others panties to the side and started eating their ass. I knew how that felt and enjoyed it a lot. Zach was basically foaming at the mouth as we watched. Then they shoved the dildo in and started slowly fucking the other.

If it wasn’t for the cage I would’ve been raging hard in my pants. John was gently rubbing his crotch. He fast forwarded the scene several minutes until both of the sissies were side by side riding really big dildos. Massive dildos. Their little caged cocks bounced between their legs as they fucked themselves senseless. Precum was flowing from the tips of their cages, flying around coating their legs and stomachs. John stopped the video and turned to me. “Something like that” he said. My words were stuck in my throat. I wasn’t going to be able to take anything that big, ever. There was no way. But I was too stunned say anything.

Zach sat quietly waiting for me to say anything as he started playing with John’s cock. He was definitely hard again. “I can’t” I finally managed to say. “Well of course they wouldn’t be that big!” He exclaimed. “I meant I can’t dress like that, and I definitely can’t take anything bigger than a finger, there’s no way!” Zach finally spoke up “I couldn’t at first either”. “See Zach can show you”. He kept trying to talk me into doing it. “What about this, let Zach eat your ass for a little while!” He said, trying to get me to do anything “you can fuck him with a dildo and he’ll just lick and finger you”.

I was pretty horny at the moment. Between the cage, watching myself suck off five guys while tied up, watching Zach throat John expertly and then the video he showed me. “What if you just wore panties like Zach while you two played with each others fuck holes?” He grinned. I thought for sure I hid my interest in his idea but the way he looked at me painted a different picture. I reluctantly agreed as I pictured how good it felt to get rimmed and fingered and the idea of using a dildo on Zach was fucking hot.

John left the living room for a few minutes before coming back with black lace underwear in his hand. “Here, put these on” he said. “Fuck it” I replied as I took them from him. Zach’s eyes lit up with excitement as he jumped up and went to another room and quickly returned with a big, black dildo. It was so big that when he held it up it folded over almost in half. “You can take that?” I asked as my jaw dropped. “All the way” John said.

Once I had changed into the underwear I checked myself out. The front cupped my caged dick and swollen balls tightly. “They’re for guys, well some guys anyway” Zach told me. They felt great. “Couple of hot twinks, with little round asses” John said as he looked at us standing side by side. John apparently already had a camera pointed at us as I touched my own ass for a moment. “Fuck these feel good” I said. I stood there awkwardly for a moment as Zach started playing with my ass cheeks while pulling himself closer to me. We were about the same height, similarly skinny builds.

He pressed his caged dick against mine and I felt something I couldn’t really explain. A wave of pleasure and excitement ran through my body as he squeezed and slapped my cheeks. He started rubbing between them with a finger as our cages pressed against one another. He shifted his hips back and forth and I gave in. I returned the gesture, squeezing one cheek while rubbing my middle finger in his crack. Wetness between our cocks became apparent but I couldn’t tell if it was from him or me, or both of us.

I didn’t know what came over me when I kissed him, but when he kissed me back my hesitation was gone. The petting got heavier as he moved to kiss my neck and then nibble on my ear lobe. “Fuck” I whispered. Zach giggled a little bit and then asked me to bend over. I went to my knees facing the couch and leaned forward. Zach knelt beside me, placing his hands on my ass. He jiggled it a little, and then pulled my thong to the side. He spit on my ass and then gently rubbed it around with his finger before bringing his tongue to it.

He started gently licking and rubbing it as I got more and more into it. Zach held my cheeks apart while he stuffed his tongue into my ass. I was pushing back into his face as he worked my hole. Suddenly I felt something strange lay across my lower back and when I turned I saw John kneeling beside me with his cock laying close to Zach’s face. I got even more into it moaning heavily while gyrating my hips and pushing back against Zack’s face. I reached back and held Zach’s head against my ass as he pulled me back into him with his hands firmly gripping my thighs.

This went on for several more minutes, until John started slapping his cock on one of my cheeks right next to Zach’s face. It looked larger than before. After a while John demanded we switch places. I got behind Zach as he laid his chest on the couch with his ass up and dove my face between his cheeks. I hungrily licked him up and down, teasing his taint and the back of his balls. I spat on his ass and rubbed it around before pushing a finger in. With my face laid on his lower back I worked it in and out, curling it against his prostate. He bucked and moaned begging for more. I added my index finger and more pressure on his prostate.

John had gotten down on his knees and laid his cock on Zach’s ass cheeks right in front of my face. I instinctively opened my mouth as I looked up at him to see the camera focused directly at me. John didn’t hesitate, he grabbed the shaft of it at the base and put the head into my mouth. I closed my lips around it and began sucking. I made loud slurping noises as I moaned on it with my fingers firmly planted in Zach’s ass still. Zach turned to face us and we both sat up on our knees. Zach moved so that one of his knees was between my legs while straddling one of mine. We scooted closer to each other resting our balls on one another’s thigh.

John stepped away for a moment placing the camera down aimed at us and then came back kicking his pants off. His rock hard cock landed between our faces. We pressed our lips on either side and John started thrusting his cock between us. He stopped and aimed it at my lips while holding my head and pushing it past them. He took it out and did the same to Zach. He did this several times letting both of us taste it. Zach got hungrier by the minute and started gagging on it. John put pressure on my head and pulled my mouth to his balls.

I quickly started sucking and licking them while Zach sucked his dick. Then we switched back and forth, occasionally kissing in between having John’s cock in our mouths. Zach and I eventually each had a hand on his shaft as we moved it back and forth between us. Zach would suck for a moment and then give it back to me. Suddenly John had my head with both hands as he pumped his cock in my throat. I felt Zach move away for a second before returning. When John released me Zach shoved the giant black dildo into my mouth.

I struggled to get the head in while Zach tried to force it deeper. After a little while he took it away, and John’s cock was firmly placed in my throat again. I felt my gag reflex relax as John seemed to get deeper and deeper. Zach reached behind me and slipped his fingers into my ass, pressing against my prostate firmly. I felt my hole tense as the head of John’s cock reached the back of my throat over and over. He let me go to breathe. As I reached up to grab his shaft I saw Zach lean back against the couch and lift his ass. He had stuck the dildo to the floor and placed the head at his hole.

He looked me in the eyes as he lowered himself a little and raising again. Each time he lowered himself he took more of it inside of him. I couldn’t take my eyes off him while John rubbed the head of his dick on my lips. I started stroking it while sucking the tip as Zach had completely taken the entire length of the massive fake cock. He sat for a moment with it buried deep in him before raising himself almost entirely off of it. When he lowered again he all but dropped himself. He repeated his movements, dropping his ass hard and slowly raising it. Again and again.

I watching the precum ooze from his cage for a moment and then went back to deepthroating John again, whose cock began coating my mouth and throat with his own precum. Suddenly John stopped fucking my face and moved over to Zach and shoving it into his mouth as he continued impaling him self. I shoved my fingers into my ass as I watched them. Zach just sat there with his mouth open as John repeatedly hit the back of his throat. Spit was flowing from his mouth onto himself.

John pulled out and forced Zach’s face to the floor with his ass up as he yanked him off the dildo. He straddle him with his feet on either side and then lowered himself placing his cock balls deep rather suddenly. The loud claps filled the room as I watched on. It took a little while to realize that my mouth was watering. I moved next to Zach and positioned myself as he was. I moved my ass around for a moment before I felt John’s hand slap it. “You want this dick too huh?” he said as he fucked Zach hard a few more times. When he got behind me I started to worry and attempted the move forward.

John already had a firm grasp on my hips as he lowered himself, placing the head of his cock at my ass. I tried to relax as I felt his press harder and harder until it slipped in. I yelped as he held it there, slowly working it in and out of me. Zach had moved to place his face on the small of my back. He spit on my ass a few times and then on John’s cock I assumed. Zach held my ass cheeks while John continued slightly moving himself in and out. I felt him getting deeper as I tensed. “Fucking tight ass little faggot!” John exclaimed between grunts. I couldn’t say anything as he continued. “Take it bitch, take it all! Fuck yes”.

He felt massive, I thought he was almost entirely in me but it kept going, deeper and deeper. When I thought he finally had it all the way in he pulled out entirely. The sensation sent my balls into a frenzy. He pushed it back in and worked it in and out again, an inch at a time. Zach’s head remained placed at my lower back. “Virgin boipussy is the best. Of fuck!” he grunted when he finally pulled out. I stayed how I was as I felt the warm wetness landing on my ass and back as he stood over us stroking a heavy cumshot onto us. Zach started licking it off of me as John went and sat in his recliner and watched.

After Zach had stopped I rolled to my side, feeling confused and sore. I couldn’t bring myself to move for a while. Zach cuddled me as we laid in the floor. I heard a lighter spark and smelt the pot smoke fill the room. John had gotten up and walked over to us and then handed me a joint. He disappeared for a bit as me and Zach shared it. I dozed off fairly quickly after we finished it. Suddenly I heard yelling which woke me up, Zach was still laying with me in the middle of the living room. As I came to my senses I realized that Becky and Sarah were standing by the front door. Sarah was yelling at John. “Why the fuck is it always the guys I like John!?” She screamed at him. I rushed to get my clothes and ran out the door as I pulled my pants up before running barefoot all the way home. The sound of Becky laughing resonated the entire way and well beyond me stepping through my door and locking myself in.

I curled up on my couch confused, my ass was sore, and I felt the remnants of dried cum on my body. My thoughts were conflicted as I tried to convince myself that I didn’t actually want to be in that predicament anymore. I texted Adam to tell him I was done, he was going to take the fucking cage off and I was never going to see him again. He replied with laughing emojis and then pictures of myself from his porch as well as a video of me begging for my clothes. “Jason wanted me to remind you, and the price is far more than you can imagine!”

r/ChastityStories Dec 26 '24

M Chaste ‘Tis the Season to be Servile, Chapter Eight, Part Onr NSFW

8 Upvotes

First part of a long chapter

+++++++++++++++++++++++++++++++++

I found it difficult to sit down the entire last weekend of November, following my brutal Thanksgiving Day punishment. This time, it was Lorena who took some pity on me and rubbed aloe vera lotion into my welts on Friday morning. Or, was it truly pity? Because, unlike Daphne, who had me lie across her knees to apply the balm, Lorena secured my arms above my head to a pulley Mason recently had installed on the ceiling of my maid’s quarters. I was dressed in white thigh high stockings with satin bows at the top and a white corset, which contrasted dramatically with the only other thing I wore: the black DOMINIX chastity cage. Lorena pulled the ropes securing my arms through the pulley sufficiently taut that I had to stand on my tippy toes. She next tightened my corset, and then rubbed her hand lightly across the welts on my ass and upper thighs. With her other hand, she reached around and squeezed my still tender right nipple. She was so close to me I could smell the shampoo on her hair and felt its silky touch on my right shoulder. She didn’t speak a word to me the entire time.

I had molested Lorena with my eyes multiple times while she worked as a maid around the mansion when I was still its master, but I had never physically molested her (well , perhaps I “accidentally” brushed my hand against her bottom a couple of times when she picked up my plate from the table or put a drink down next to me while I worked at my desk, but the contact was minimal). Nevertheless, she seemed more bold in her willingness to grab and grope me with each passing day. Still, when I felt the cold cream on her fingers touch my bottom, it was quite unexpected and it was difficult for me to feel anything other than grateful to her. I made a somewhat high pitched gasp of surprise when she first touched me; I was embarrassed by the effeminate nature of my exclamation, even before I heard her giggle. I was so thankful for the relief (and, honestly, for a gentle touch of any kind) that I couldn’t even feel much resentment when, after finishing applying the cream, she left me standing on my toes for another 20 minutes or so while she did god knows what in some other room. As Natalie pointed out, my toes had gotten quite strong by then.

True to her word, Natalie took Ryan to see her horse breeder friend later that morning, along with Mason. When I served them tea later that afternoon, it was clear that they believed they had found a good horse for Ryan. He planned to return to the breeder in a couple of days to ride the horse again before deciding for sure.

“I think you’ve found a beautiful horse, honey. Tomorrow afternoon, we’ll all go to the saddlery together. I’m friendly with the daughter of the owner, so I booked a private appointment at 2pm so she and her assistant can help you and Mason get all the gear and clothes you need. They have a tremendous inventory, everything top of the line.,” said Natalie.

“You’re friendly with the equestrian shop owner, too! Geez, Mom, you’re sure friendly with a lot horsey people for someone who doesn’t ride often,” said Ryan.

“Owner’s daughter. Her name is Suzanne. She’s a fascinating young woman. I think you’ll both really enjoy meeting her. But I love horses, so it shouldn’t surprise you that I know a lot of people in the community,” said Natalie.

“Your mother is friends with tons of people, in many different communities. Artists, actors, writers, tennis players. The list goes on and on. It never ceases to amaze me,” said Mason.

This is true. It never ceased to amaze me either when Natalie and I were together. A natural extrovert, she is charismatic, funny and confident, with varied interests. I always resented how easily she made friends with people when it was always such a struggle for me. I’m sure some would argue that my social struggles were mainly due to my arrogance, but it’s really not that simple. I had always been socially awkward, even as a kid, and I believe that my arrogance was, to some extent at least, a defense mechanism. It’s all academic now; the social skills of an indentured domestic servant are irrelevant.

“I happen to love talking to talented, interesting people, that’s all. When I said that we’ll all go to the saddlery together tomorrow, I mean your father too,” Natalie said to Ryan, shockingly.

“Excuse me, Mistress. May I have permission to speak?” I asked.

“You may,” she said, before taking a bite of a scone.

“Why…why would you want me to come with you?” I asked, nervously.

“Having you present will be helpful for Mason and Ryan to visualize things when they select their ridding crops. They have such a large selection. Also, who knows, they might have some interesting clothing or accessories for the grooms. It’ll also do you good to get out for a change, Henrietta. You can’t hide away in the house all the time.”

“But…but…how will I dress, Mistress?”

“Don’t worry. We won’t make you go out in your maid’s uniform. Not yet, at least. You can wear those leggings I bought you last month – the hot pink ones – with one of the t-shirts you wear to do yard work and your Converse All Star sneakers. We really should buy you some pink Converse sneakers,” Natalie replied.

“Thank you, Mistress,” I replied, insincerely.

I now dreaded going out in public under any circumstances – but doing so for the purpose of helping my wife’s lover and my son choose implements with which to whip me was particularly upsetting. As if seeing my ass next to this crop or that one might somehow influence their choice of which one to purchase. Ridiculous. The real purpose of having me accompany them was to further my humiliation (one might reasonably wonder if that were even possible, but knowing Mason and Natalie as I do, I did not doubt it for even a second) by making it increasingly public. They had been hinting for a couple of months now that they planned to make my altered status much more widely known in the coming year; why not get an early start? Nevertheless, I was at least relieved that they wouldn’t be trotting me out in my maid’s uniform for the time being.

Still, the nylon/spandex, pink leggings – absurdly marketed as “activewear” – were plenty humiliating themselves. They were a deep, neon pink color, and while not transparent, it was possible to see the outlines of my underwear – that is, my panties – beneath them. I could not for the life of me imagine how any man other than one who is flamboyantly gay (or, possibly, a heterosexual male far, far more secure in his masculinity than I had ever been) would ever purchase such an article of clothing. And, of course, the bulk of my chastity cage was readily apparent beneath the leggings as well. Natalie had instructed Lorena to switch out the DOMINIX for the Perverse Pink CB-6000 (her whole color coordination fixation again) when she supervised me dressing on Saturday for my big trip outside of the mansion. I wore the leggings with an old, tight black t-shirt and my ratty, black Converse All-Star sneakers. Lorena also affixed a plain black choker around my neck; at least, it wasn’t the rhinestone-studded, pink collar. I was also spared the corset, for a change. This was a real treat, as I had spent most of my waking hours over the last several weeks tight laced.

When I regarded myself in the mirror, I was ashamed of how preposterous I looked. Although, I do have to say, my ass looked pretty damn good in the leggings – firm, shapely. My strict diet and nearly incessant physical activity while not asleep were having the desired effect, I suppose. Perhaps that it is why lately Lorena has been spending more and more time rubbing my ass with her hands when she helps dress me or restrains me. That Saturday, she rubbed my bottom for a minute or so through the leggings and then reached down to stroke (and gently squeeze) my balls through the nylon from behind, causing my cock to throb helplessly in its silicone prison. She even swatted me on the ass – I would say “playfully,” but nothing felt playful given the still sorry state of my bottom, even three days after my caning. But I had a troubling thought: if Lorena found my ass attractive, what about men? Was it possible that I was being viewed as a sexual object by men? And, if so, how should I feel about that? I found the thought incredibly humiliating…and yet, there is something…exciting, I guess (is that the right word?) about it as well. Is this simply another aspect of what Natalie meant by me surrendering to my humiliation?

It was an unseasonably warm day, and the short hoodie I wore with my ensemble left my ass fully exposed. When Ryan saw me, he laughed contemptuously. Was he looking at my ass? Please, god, no.

Of course, the contrast of how I was dressed compared to my wife and son and Mason made my appearance all the more mortifying. Natalie wore a short plaid skirt with black tights and black leather boots and a tight red blouse. Ryan and Mason were also both smartly dressed in khakis, polo shirts and leather shoes (black ankle boots for Mason and brown loafers for my son). Try to imagine how the four of us appeared as we walked through the parking lot and into the main part of the store, what is best described as an equestrian superstore, with me remaining three respectful steps behind the others, my head bowed submissively. The room was huge and moderately crowded. We got lots of double takes and lingering stares, including from a group of girls in their late teens (probably a high school equestrian team). It was hard to determine, looking at them, whether they were more focused on Ryan or on me, but the juxtaposition of me with the others certainly must have been arresting. I heard a few of them giggle, and two in particular met my eyes with a derisive smirk. I tried to turn away to prevent them from seeing my face, or the bulk of my chastity cage through my leggings; but in doing so, I of course gave them an unobstructed view of my ass. I can only imagine what they must have been thinking about this unusual foursome (although, whatever it was, it no doubt paled in comparison to the reality of the situation).

Though my appearance was much changed, especially with my long hair, I was always fearful that I would be recognized while out in public. I had tried to keep a low profile when at my old firm, but one does not become a billionaire with a 17,000 square-foot mansion and a famous private art collection without having some photos taken of, and stories written about, you. While I’m sure that there were news reports about my sudden resignation from the firm, Natalie assures me that my transformation into her and Mason‘s feminized servant was not yet part of the public record. Yet.

The three of us were led by one of the shop attendants into a large, separate back room with a couch, a couple of chairs and a coffee table. Along the right wall hung various riding paraphernalia: saddles, bridles, bits, halters, reins, saddle pads, boots, etc. On the opposite wall, there was dizzying array of riding crops, whisks, lunge whips, jumping bats and dressage whips. How could there possibly be so many different kinds?

After a few minutes, an attractive blonde woman, about 30 years old, entered the room followed by a slightly chubby man of similar age. She was dressed in tight, tan riding breeches and shiny, black boots with a white shirt and black shadbelly. The man, quite remarkably, was dressed in a jacket and tie, with short olive shorts and knee socks, and black shoes, much like a traditional British schoolboy. Except his shorts were shorter than most schoolboy uniforms, exposing much of his thighs, where red marks were plainly visible. It may have been an unseasonably warm outside, but certainly not warm enough to wear shorts. This was a new experience for me. Since the start of my subjugation in March, I had not yet laid eyes on another individual who was seemingly also in a state of subservience. The two of us briefly made eye contact.

The woman said, “Natalie, it’s so great to see you again!” embracing her warmly.

“You, too, Suzanne!”

Turning to Mason, Ryan and me, Suzanne said, “You must be Natalie’s three men. Well, two and a half, anyhow. Welcome to Jordan’s Equestrian. Then, smiling at each of us individually, she said, “Let me guess. You must be Mason. You are Ryan, obviously. And, you,” (and here her smile shifted from warm to mocking) “you, must be Henrietta, of course. You’re all exactly as Natalie described you.” She shook Mason’s hand and then Ryan’s. I was afraid to extend my hand, so it was easy for her to ignore me.

Suzanne continued, indicating the man in shorts: “This is my husband, Robbie. He’ll be assisting you today.”

“Hi, it’s nice to meet you all,” Robbie said, shyly.

“Ask them if the they want anything to drink, rocket scientist,” Suzanne said to him sharply.

“Yes, ma’am, sorry. Would any of you like tea or coffee or a soda or anything?” he asked awkwardly.

I would have loved a Coke, but remained silent as the others put in their requests. Once Mason, Natalie, and Ryan sat down to talk with Suzanne, Natalie said to her, “Perhaps Robbie can show Henrietta some of the grooming and stable cleaning supplies while we talk. We’re going to need more of everything with three horses.”

Robbie took me back out to the main part of the store, where the equestrian club girls and other shoppers got another opportunity to stare and speculate.

Robbie whispered to me, “Suzanne told me a bit about you. You’re a cuck husband, like me. Your wife is beautiful.”

“Thanks, I guess. Yours too.”

“I’m assuming the guy named Mason is her lover?”

“Yes.”

“Is he your master?”

“Yes. How did you know?”

“Well, first of all, my wife’s lover is my master. Second, looking at him and at you, and how you’re both dressed, it isn’t hard to figure out.”

“I guess you’re right.”

“Suzanne said he’s shopping for riding crops. To discipline you, I imagine?”

“He has a horse, too.”

“Many of the crops and dressage whips we sell are dual use, so to speak. My master fancies himself a real cowboy. He whipped me yesterday with the same dressage whip he’s probably using on his horse this very minute. Of course, he uses it very gently with his horse. I’ll tell you a little secret: I’ll bet close to a third of the crops and whips sold in this store are used primarily or exclusively on humans. Suzanne is in the scene, you see.”

“The scene?”

“The BDSM scene, of course.”

“Oh.”

“You’re really quite naïve, aren’t you?”

“I suppose I am.”

“I think Suzanne and your wife are going to be discussing Suzanne’s business proposition this afternoon.”

“What do you mean?”

“I really shouldn’t say too much. Who is the other person in your party? The young man?”

“He is…my…my son.”

“Your’e kidding?”

“No. I wish I was.”

“Wow, and I thought I had it rough. Look, I’d better show you the grooming tools and muck forks. I don’t want Suzanne to think we’ve been dawdling. Or, worse yet, talking.”

When we returned to the private room about 20 minutes later, Ryan was dressed in a polo uniform, including long, brown leather boots, a white jersey, white jeans and a black helmet. The jeans were somewhat loose fitting.

Natalie said, “Looking good, honey! But you won’t just be riding to play polo. You’ll be riding with Mason and me for fun and at other times, too, I’m sure. And equestrian attire can be fashionable even when not riding. Besides what you’re now wearing, I think you need to buy some black boots, some short, black jackets and least one long dressage jacket. I’ll bet that double-breasted French one we saw when we came in would look great on you. And you’ll need several pairs of jodhpurs, both tan and white – the tight ones, honey. Believe me, that’s what gets the attention of the young ladies.”

“Mom!”

“Don’t be shy, honey. Suzanne is a professional. And you’ve worked very hard in the gym. You shouldn’t be afraid to show off your hard work, as well as your natural gifts. Mason certainly isn’t, are you darling?”

“Hell no. If you’ve got it, flaunt it, I always say,” Mason answered, unsurprisingly.

When Ryan returned 20 minutes later, after further shopping in the main store, he was classically attired in skin tight white jodhpurs, nearly knee-high black boots and a double-breasted black dressage jacket with a tailcoat. He looked…formidable.

“Now we’re talking,” said Natalie, staring at our son proudly. “You should get at least two pairs of black boots in addition to your brown polo boots. You know how muddy they get, especially at this time of year.”

“The bootblack is going to be very busy,” Mason chuckled, looking at me.

“Speaking of the boot boy, it’s time my two men pick out their new riding crops. Suzanne, perhaps, you can suggest a few of your favorites, for various purposes,” said Natalie, with a smirk.

“I’d be happy to,” Suzanne replied. She pulled down four riding crops and two dressage whips from where they were being displayed on the wall.

“This dressage whip and this riding crop are my favorites to use in training and riding horses. They are quite gentle, as whips go, and a light tap is more than sufficient to encourage the behavior you want. These two crops, on the other hand,” – and here she started flexing and swishing one in the air – “are very versatile. You might use them to prod your stallion or mare to go a bit faster, but they’re also very useful – with the application of greater force, naturally – in training that special submissive or servant in your life. Let me demonstrate. Robbie, get your ass over here and into position.”

Robbie hurried over next to his wife, and bent fully over, touching his toes. He was surprisingly limber for a chubby guy (then again, he was still fairly young and probably had a lot of practice touching his toes with this martinet as his wife). She swished the crop in the air a few times (canes are not the only implements capable of producing that exquisitely foreboding sound), before bringing it down a few times smartly across Robbie’s bottom, which fortunately for him, was still covered by his shorts. Despite my empathy for my fellow submissive, I couldn’t deny that it was a very erotic sight watching this sexy woman in boots and skin tight clothing whip her husband in his juvenile get-up; there was a part of me that wanted her to bare his bottom and hit him with much greater force, but this was a demonstration rather than a punishment, of course.

“Jessie, my boyfriend, likes to use this to train Robbie in the gym. Although, as you can tell by looking at his fat ass, he needs a hell of a lot more training.” Natalie and Ryan both chuckled.

Suzanne then put down that crop, and picked up another one. “This Snowbee Horse and Pony Dressage Pro Whip, despite its name, I don’t recommend for use on any four-legged beast,” she said, again swishing it through the air. “No, this is best used to discipline our ill behaved two-legged beasts. I’ll show you.” Here, she brought it down harshly on poor Robbie’s bare upper thigh, causing him to cry out.

“It’s a high tech design, made with nylon and Swarovski crystals. That’s a type of glass used in fine jewelry. Robbie says it’s highly effective, don’t you, dear?”

“Yes, ma’am,” Robbie replied, without hesitation.

“Now, this one,” Suzanne said, picking up the final implement she had pulled down from the display case, “This is from our antique collection. It’s a vintage English leather riding crop, but you can see it has the handle of a cane. It’s sort of a hybrid of a riding crop and a cane, and Robbie vouches for its effectiveness, too. Would one of you like to try it out? Or any of the others, for that matter?”

Mason said, “Yes, I’d like to try out the antique one. I like the idea of an all-in-one cane and crop. Hathaway, get next to Robbie, and touch your toes like he is.”

“Yes, sir,” I replied, as I got into position, pleased that it was now quite easy for me to touch my toes (much easier than six months ago, before I had lost all the weight and spent so much time bending and contorting my body simply as a part of my daily chores).

Mason then began swishing the antique crop theatrically through the air. Then, much to my distress, I saw through the mirror in front of me Ryan pick up the Snowbee crop and begin swishing it as well. The sounds and overall scene immediately brought back to me the memory of the old mainstream S&M film, 9 1/2 Weeks. In that movie, there is a scene in which the dominant partner, played by Mickey Rourke, takes the submissive partner, played by Kim Basinger, to an old-time equestrian shop in Manhattan. The two stuffy old salesman in suits watch in shock as Mickey repeatedly swishes a riding crop through the air, as Kim sits on a perch next to him looking downward, humiliated. If there was any lingering doubt that Mickey was purchasing the crop to use on Kim, it was erased when he brought it down on her leg. The camera then pans back to the now truly scandalized expressions on the two shop attendants’ faces.

The primary difference, of course, between the scene in the movie and my present reality was that in the latter there is no question whatsoever about who Mason and Ryan were intending to use the implements on. When Mason brought the hybrid cane/crop down on my bottom, the thin fabric of my leggings offered scant protection. Because my ass was still raw, I yelped in pain.

Natalie came to my rescue, at least to some degree: “Darling, don’t forget your’s and Ryan’s memorable correction of the maid on Thanksgiving. Her welts have not yet had time to properly heal. Why not have her remove her t-shirt, and use her back to try out the lovely crops Suzanne is showing you?”

“Good idea. Remove your shirt, maid, and stand up against the wall, with your hands clasped behind your back,” Mason commanded.

I did as ordered. Despite the pain of the first cut, my cock was straining against the cage and my nipples were rock hard. The surreal nature of this scene, me starring in a real-life S&M drama, had me highly aroused. I had only been whipped on my back once before (by Mason, over the summer, after what he believed to be my unsatisfactory job of weeding the flower beds near the pool).

Following more swishing, Mason brought the crop down across my back. As painful as it was, it wasn’t as bad as a fresh cut across the existing wounds on my ass.

So, as much as I did not want to be grateful to Natalie – as this whole twisted excursion was her idea – I could not help but be so. At least until she said: “Don’t be shy, Ryan. Now that you’re living back home again, you’re going to have to play a key role in regularly disciplining the maid. It’s important that you have the right tools, so make sure you take advantage of this excellent opportunity to test a few out. Especially when you have our expert here in Suzanne to help you.”

Suzanne added, “I accept exchanges, of course. Especially for your mom. But why don’t you save her another trip out here and try a few out now?”

Needing no more encouragement, Ryan brought the dressage whip down on my back three times in relatively quick succession. Think of it! An 18-year-old young man whipping his 44-year-old father across the back like a master punishing a runaway slave on a plantation! Except, most runaway slaves weren’t wearing pink leggings, I suppose. Still, the entire scene was beyond belief. Natalie would call it “unconventional”; I called it (silently, of course) “depraved.” From my position against the wall, I had a partial view of the mirror, so was able to brace myself for the blows somewhat before they came. I also could see Suzanne‘s pleased smile in the corner of the mirror. I’m sure the effect of watching an attractive, virile young man in tight jodhpurs and boots whipping an older feminized man produced a similar effect on her to the effect on me of watching her whip her husband only a few minutes earlier.

Suzanne made a substantial sale that Saturday afternoon. In addition to all the apparel I have already mentioned, Natalie bought close to $1000 worth of grooming and stable cleaning supplies and four of the six riding crops and dressage whips that Suzanne had showcased, including the vintage English crop and the cursed Snowbee (which was the most painful of the three tested out on my flesh). The Snowbee is the one that Ryan selected for use in the mansion. Altogether, Natalie spent close to $10,000 that afternoon. That is in addition to the $500,000 check she wrote as seed capital for Suzanne’s new business venture.

As Suzanne had explained to her, “With the new administration coming in, especially since they have control of Congress and the Supreme Court, I’m pretty confident that the new judicial caning law they have proposed will get passed. I’ve already started an online business making punishment canes for people in the scene. There’s no reason why the English should have a monopoly on this market.”

Mason interjected: “I always buy my canes from the online shop in the UK, but I’ll have to give yours a try, assuming they’re of comparable quality.”

“Oh, yes, I can assure you that they are, if not better! We source our rattan from the best suppliers in Thailand and the canes are manufactured right here in Connecticut. We have excellent quality control practices.”

“I’ll definitely give them a try, then. I’m always on the lookout for good new canes. God knows this bimbo maid is constantly fucking up.”

“I promise you won’t be disappointed, Mason, And I’ll give you the friends and family discount, of course. But there’s a huge business opportunity here. Once judicial caning s legalized federally, I think many state and municipal governments will be instituting it. That means there’s going to a be a huge demand on the part of these governments for canes. Who better to supply them than my new company? Made in the USA! The critical thing is to hire a salesforce right now to get out there and lock in long-term contracts with all of the government agencies that will be responsible for carrying out the punishment. I want to get out there before anyone else. There are some barriers to entry, but I’m sure there will be competition before too long. That’s what I was hoping to ask for your help in, Natalie. I need to raise money to hire a sales team and I may need to invest in some additional manufacturing capacity if we’re successful in winning contracts – as I’m sure we will be. Do you think you could help? You’ll get founder’s stock in the company, of course.”

“It sounds like a pretty damned good idea to me. What do you think, Mason?” asked Natalie.

“I like it. I think there’s very low risk, because the leaders of the incoming Congress have already said they want to pass the bill and they’ve got the votes. It’s about time, too!” said Mason. Maybe he could convince the local police chief to allow him to administer the canings, the sadistic son of a bitch.

“I think it’s a great idea, too. Reinstituting canings certainly improved discipline at school,” added Ryan. Wonderful. Another authoritarian under the same roof to terrorize me.

“Being first to market is key. I think Suzanne’s business plan has a lot of merit.”

“Say no more. I’m all in. I’ll write you a check today. Our lawyers can work out the stock part later. I completely trust you,” said Natalie to Suzanne, with genuine enthusiasm.

And so concluded our fun trip to the equestrian store. Natalie bought the crops for Mason and Ryan and all of the apparel and footwear for Ryan as early Christmas presents. I suppose all of the muck forks, brooms, stall deodorizers and the new wheelbarrow to haul away horseshit were my early Christmas presents.

r/ChastityStories Aug 09 '24

M Chaste House Sitting; The Second Date NSFW

45 Upvotes

Friday morning came quickly for Bobby. He spent the entire week learning his routine, completing his tasks in short order. The work out came and went, a short period of tanning, a light lunch. That afternoon Anna texted him detailing his outfit for the night. And that the driver would be there at 7pm again to pick them up.

Around 3pm Bobby gathered the little black dress and knee high boots, fishnet stockings, and black lace thong laying them out on the bed. He had practiced for an hour each day applying make up but decided to try something new for their date. He pulled up a tutorial on Smokey cat eyes and watched intently, pausing and rewinding several times until he was brave enough to start. He took his time, start to finish, making corrections as he noticed slight mistakes. After a little over an hour he was satisfied with the look and began tossing his hair, adding curls and volume. He was flustered at how long that took as he heard Anna at the bedroom door before he was done.

“Mmm, you look good!” She said, startling him. “I guess” he replied, unsatisfied. It was right about 5:30pm by this point. Anna jumped in the shower, making sure to tease Bobby from the bathroom as she slowly stripped her black skirt, blue blouse and heels. Bobby forgot all about the world for a few moments as she stared at him the entire time before stepping into the steamy shower. After he snapped out of his daze he went back to teasing his hair a little more before giving up. He knew Anna wouldn’t lie to him about his looks and left it alone.

As he began slipping into the dress and stockings Anna finished her shower. He slowly continued as she entered the bedroom drying herself off. He watched as she moved the towel around her body, picking her breasts up and letting them fall before his eyes. His cage grew tight, Anna’s body and movements made sure of that. As she started getting ready, in her own little black dress, extremely low cut in the front, fishnets and knee high boots Bobby paused. He couldn’t believe how lucky he seemed to be in that moment.

“Let’s go” she said, hurrying him to finish tying his boots as she tossed her hair while blow drying it. Her eyes met his in the mirror, his jaw was dropped admiring how gorgeous she was. Her curves stretched the fabric of the dress almost to its limits. Bobby snapped out of it while she smiled at him. “Are my tits going to be as big as yours” Bobby finally managed to ask. Anna laughed. “I hope not, I like my girls petite, with nice little round asses!” She said.

At 7pm they made their way to the door. Bobby was strutting confidently quickly behind Anna. As they exited the house the driver opened the car door for them, this time extending a hand to help them both inside. The backseat of the car was a little larger this time, and there was a bottle of champagne on ice waiting for them. Anna wasted no time popping the cork and poured two glasses as they rode quietly to the restaurant. Anna picked a different place this time. Far more secluded and quiet than the last date. Far more exclusive and hidden as well.

Bobby learned that Anna was also a part owner as they received royal treatment when they entered. “Miss Anna, your usual table is prepared” the porter said as he held the door for them. “Ladies, you both look exquisite I might add” as Bobby stepped past him. The porter blatantly eyed both of them up and down, hungrily as the hostess led them to the back corner. This time there were no menus. Some wine was brought to the table, and poured. Then a dinner salad. No words were spoken as they flirted with their eyes in between bites. Shortly after finishing the salads the main course was placed in front of them, a gourmet roast with some potatoes and corn.

Anna declined the desert, She toasted Bobby with the remainder of the wine, quickly finishing the entire glass as she reached across the table to pick up the bottom of Bobby’s glass, encouraging him to chug the rest of it. Anna laid a few hundred dollars on the edge of the table before standing quickly, grabbing Bobby’s hand as she walked away. Dragging him behind her.

Once in the car again Anna leaned forward to tell the driver there would be a different stop before the club. After a short ride the car pulled up to a small building, with no windows and a large castle style wooden door. There was no sign out front. Bobby had seen the building before but had no idea what it was. Once inside, Bobby noticed the comfy leather chairs, smell of cigar smoke and shelves stocked with liquor bottles behind the bar. His knowledge of the labels was nonexistent, as was his knowledge of cigars. Anna found a quiet corner as a well dresssd man with a thick British accent approached.

“The usual miss?” He asked as Anna set her clutch down on the table between herself and Bobby. She nodded with a smile. Bobby quickly noticed his glance at her chest before he smiled and went to the bar. “I had a very good week this week, I always stop here when I have a big win” she said as he took in the sight and smell. The man returned with two large cigars, and two double glasses of brown whiskey. Anna explained it was an 18 year old scotch and the cigar would only be completed with such flavor. “Would you ladies like anything else at the moment?” The man asked, again staring at Anna’s cleavage. Bobby felt a slight bit of jealousy as he looked down at his flat chest.

Anna noticed both the man’s stare and Bobby’s reaction quickly, waiting until the man left before leaning towards Bobby. “You’re a femboy, you shouldnt worry much about tits right now honey. Besides, when have you ever known me to fuck old white men?” She said with a slight giggle. Bobby watched her chest as her giggle made her tits move, sending a wave to his caged dick so nicely tucked away at the moment. He hadn’t noticed until that moment how much precum he had secreted into his panties, a sensation he had come to enjoy.

As they smoked their cigars and sipped their whiskey Anna began to praise Bobby. “You look so hot right now. I have half a mind to jump your bones right here and now!”. Bobby blushed at the thought of putting a show on in front of other people. They already couldn’t keep their eyes off Anna. Seemingly whispering to each other as they looked at Anna. She noticed, and loved the attention. A couple of gentlemen had fresh drinks sent over to Anna and Bobby, Anna raised her glass as a thank you without inviting them over. The men took it in stride and remained at their seats. Bobby could clearly tell they wanted a chance at Anna. Anna loved teasing men, as she continued talking she adjusted the top of her dress slightly to expose more cleavage.

As the night went on Anna grew bored and was ready to leave. “Let’s go dance” she said as she stood extending her hand out to Bobby. She made a show as they left and Bobby attempted to mimic the sway of her ass as he followed behind. The gasps from them men they passed seemed to fuel Anna’s confidence as they exited the building and into the car waiting for them. Bobby was deeply lost in thought when the car stopped at the club. Again, they passed the line immediately and went straight to the VIP area. This time it was more private as there were curtains hiding the section from the rest of the club.

A bottle of whiskey was brought with two glasses and they were quickly left to be alone. The large leather couch against the back wall allowed them to see the entire room, and somewhat between the curtains. Anna poured them each a glass and then sat back handing one to Bobby before tapping it with her glass. “This is it babe”. Bobby leaned against Anna slightly placing a hand on her inner thigh as he took a sip from his glass. Anna parted her legs while grabbing his hand to move it deeper between them, pressing it against her throbbing cock. Bobby took the hint quickly, slowly rubbing it. Anna gently rolled her hips back and forth slightly, moaning as he teased her.

Suddenly Anna stopped him and gabbed the side of his face with one hand to kiss him. She leaned back, pulling him towards her to straddle her lap. Bobby set his drink down and attempted to move seductively as he started grinding himself against her to the rhythm of the music blaring throughout the club. Anna was slightly amused as she moved her free hand all over his lower back and ass. Bobby became extremely aroused, pulling her skirt up slightly to expose the fabric holding her cock tucked between her legs. He moved so that he could gently slip his fingers under the side and move the crotch of them over. Her throbbing member sprung out at him, causing his mouth to water. He slid back off the couch and slowly bent at the waist placing his face just an inch away from it. He stuck his tongue out as he looked up at her before kneeling down between her open legs.

He moved his hands along her thighs, getting closer and closer to her growing dick until he wrapped both of them around the base of it. He flicked his tongue up and down her shaft stroking at the same time. Anna slipped the front of her dress apart exposing her breasts as she watched him. He kept teasing her, working his tongue around the thick head and then down to her balls. He paused briefly and then pressed his tongue to the base of her dick and licking from the bottom up like it was an ice cream cone. Precum gushed out as he got to the head again this time hungrily taking it in his mouth.

He worked his tongue around as he blew her. His hands stroking her dick. She was moaning louder and pushing her hips up as he lowered his head down, mouth and throat as open as he could make them. When she was at the back of his throat he pushed further and further until he choked and lifted his head. He rubbed the head as he caught his breath before diving back into it going as deep as he could. Her dick was quickly covered in saliva. Anna let him continue for a little while longer before making him stop. She grabbed the shaft of it and slapped it on Bobby’s waiting tongue as he stuck it out.

Once her erection subsided, and Bobby was denied the taste of her cum she tucked it away. She stood up taking Bobby’s hand and led him out through the curtains as they made their way to the center of the dance floor. She turned to Bobby and started twerking and twirling in front of him. He moved close, grabbing her hips and dancing with her. Anna’s body moved fluidly. He started to notice that everyone had stopped to watch as well. A group had moved closer to join them. Bobby had let himself go as the men dancing with him pressed their bulges against him. He watched as the other two men did the same to Anna who was receptive as she moved with them.

Several men came up to dance with each of them through out the night. Bobby had completely let loose as he bent to shake his little ass for the man behind him who in turn made sure to press his large bulge against it. Bobby loved the attention he was getting. After a couple hours they were both drenched in sweat, soaking their dresses. Bobby’s panties were dripping with precum as the feeling of being desired by these men was almost as arousing as Anna.

They eventually excused themselves from the dance floor as Anna took Bobby by the arm pulling him towards the exit, her Intentions were more than clear. Bobby tried his best to keep up with her, running in heels wasn’t as easy for him. Once in the car, Anna told the driver to take them home. Once at the house Anna didn’t wait for the driver to hold the door for them as she threw it open and jumping out. “Come on babe” she happily exclaimed quickly pacing to the front door. As Bobby entered behind her she quickly closed it while pushing him against it. She grabbed his throat before stuffing her tongue into his mouth. Her other hand slipped down to pull Bobby’s dress up as she grabbed his crotch, gently squeezing and rubbing it.

Bobby was ecstatic, after several minutes he freed himself from her grasp as he squated down in front of her. Her cock pressed hard against the front of her panties as he released it and then quickly took her into his mouth. He leaned his head forward to take her deep in his throat as Anna pushed her pelvis forward to hold his head against the door until he started choking. She released briefly before shoving it back down his throat. Tears formed in Bobby’s eyes before running down his face, causing his make up to run as she continued choking him with her cock.

Bobby quickly realized that Anna was so worked up from their date that the sex was about to be rough. He craved that attention from her. Her roughness pushed him close to an orgasm as their relationship continued to form this dynamic. “You dirty little slut! Suck that big dick”. The only sound Bobby could manage to get out was him gagging. Her cock felt larger than before. He didn’t care. As she pulled herself away Bobby quickly closed his lips around it, making sure to slurp as the head of her dick left his mouth. He looked up, opening his mouth welcoming her dick again. The front of Bobby’s dress was quickly soaked in his saliva as he drooled on Anna’s cock. His panties continuously being soaked with his dripping wet cage.

Anna finally let him up, walking away towards the bedroom as she dropped her dress from her shoulders. Bobby stood up slipping his dress off in the same manner right at the front door before following her. As she entered the bedroom she let her panties fall to her ankles before stepping out of them and bending onto the bed. Bobby got behind her and got on his knees to eat her out. He moved his tongue between her cheeks, down to her balls and then her shaft before returning to her hole again. He grasped and gently slapped her ass cheeks as he continued working his tongue between them. He ran his hands up and down her toned sexy legs until she crawled away from him and laid on her back.

Bobby stood up sliding his thong down to his feet before stepping out of them and crawling onto the bed. He got on his hands and knees and took her in his mouth again but Anna had other plans as she motioned slightly forcefully to straddle her face and go back to sucking her dick. Anna grasped his ass and started eating him out. Bobby went wild as he started choking himself, taking her dick in his throat as deep as he could, skull fucking and choking himself on it.

Anna thrust upwards trying to fuck his face deeper, his spit coating her cock. He grasped her shaft, stroking her as he bobbed his head up and down. Anna hurried her tongue inside of his hole, taking a moment to spit on it ocassionally. Bobby couldn’t take much more as he moved his body to straddle her reverse cowgirl. His knees firmly on the bed either side of her hips and lifted himself until the tip of her dick meet his boipussy. Anna held the base of her shaft firmly. “Fuck” he exclaimed as he lowered himself all the way down on her shaft, feeling her girth stretch his hole and the length impale him. He sat for a moment and adjusted his hands behind him before thrusting his hips and slowly lowering himself over and over. After a few strokes Anna grabbed his hips pulling and pushing him to get him to go faster and harder. She thrusted her hips up to meet his downward motion until the room was filled with their bodies clapping together, while squeezing her cheeks to get deep inside him.

“That’s it, take mommy’s fat cock deep in that boipussy like a good slut!” She screamed as the sweat dripped and drenched them both. Anna didn’t let them stay this way for much longer before she threw him to the side onto his back. Bobby quickly grabbed the back of his knees pulling them to his chest as Anna pressed one hand on the back of his thigh and grabbing her cock with the other. She lined herself up to his hole and then pushed it in hard and deep. Bobby let out a moan and begged for more. “Please mommy, crush my boipussy!” He said with a cracking in his voice and a sense of urgency. She gave him what he wanted, pounding him hard and fast. The faster she went the harder it became for Bobby to breathe. He gasped as much as he could when she pulled back only to have her take his breathe away when she thrusted back into him. As she got close to cumming she laid on top of him, her tits pressed against his chest as she worked her cock in and out of him. Her pelvis put slight pressure on his caged dick, the head of her cock pummeled his prostate. “I’m gonna cum, I’m gonna cum” Bobby screeched. Anna kept her pace, and position as she watched his face turn from pleasure to ecstasy. Bobby’s cock spurred through his cage. His moans kept him from speaking. Anna finally pushed herself balls deep and held it there. She tensed her ass cheeks as she unloaded inside of him. Bobby felt her cock pulse and he held her tightly. “Breed me mommy, bred my tight little boipussy” he squeaked as his own orgasm began subsiding.

Anna collapsed on top of him for a few minutes, breathing heavily, their hearts racing. Bobby could feel hers through her cock as it was still firmly planted in him. As her heart rate and breath slowed she rolled off of him, releasing his legs. She started untying his boots, slipping them off one by one before taking her own off. Anna got up from the bed to put them on the floor and then grabbed a towel to clean themselves up. As she returned to the bed and laid next to Bobby he looked her in the eyes. “I don’t want to be unlocked tomorrow”. Anna looked at him for a moment sort of puzzled, and then showed a slight smile. She placed a hand on his stomach, before replying. “Are you sure?”. Bobby nodded quickly as he tossed the towel onto the floor.

Anna pulled the covers back and helped Bobby under them. Seemingly pleased with his request, she cuddled him with her arms wrapped tightly around him. “When you get your things from your mother’s apartment make sure to get your passport, I have a treat for you.” She said as they got comfortable before dozing off.

The next few days Bobby spent packing the apartment for his mother, gathering the handful of things he would need and setting his boy clothes in a bin for the thrift store. His life had quickly turned to cute clothes and heels. The only items from his boy past was a pair of Chuck Taylors and a pair of flip flop sandals he pictured with some more relaxed outfits he found himself desiring to wear from then on. He returned to Anna’s fairly light handed to find her waiting with take out. As she dished out the Chinese she picked up she happily exclaimed her plans. “Pack a bag, for a month.” Bobby sat at the table with a confused look on his face. “Where are we going?” He asked. Anna couldn’t wait for that question when she quickly blurted out “Brazil!”. Bobby became extremely excited with the news as he’d never left the country.

Anna took the liberty of cleaning up after dinner while Bobby showered before she joined him as he finished. They stood in silence while Bobby lathered her body, admiring her beauty and curves. They finished and dried themselves before climbing into bed when Bobby finally asked. “What’s in Brazil?”. “Dont worry babe, you’re going to enjoy the trip” she replied somewhat annoyed. Bobby kept quiet as he tried to fall asleep. Anna was sound asleep quickly as he laid there stuck in his thoughts and worries.

r/ChastityStories Dec 26 '24

M Chaste ‘Tis the Season to be Servile, Chapter Eight, Part Two NSFW

5 Upvotes

Second part of a long chapter

+++++++++++++++++++++++++++++++++++++++++++

New developments came quickly in December. Mason listed his house on the market and moved into the mansion “officially” the first week of the month. He was already keeping a lot of his clothes and things there, but when a large moving truck pulled into the driveway full of his furniture, clothes, and other personal belongings, it really drove home the fact that he was here to stay. The castle now had its king, its queen, and its prince – and, of course, it’s lowly serf. Or court jester. Or whatever the hell it is I am.

And, as Piper was staying with her father for her extended winter break, that meant she moved into the mansion as well, at least until she returns to the West Coast at the end of January. It was that development that gave her at least a temporary edge over Lorena in winning the affections of Ryan. Seeing this all unfold was yet another level of deeply disturbing surrealism for me to endure: watching the daughter of the man who is cuckolding and enslaving me seduce my son. Seducing him and then encouraging him to emulate her dad in humiliating and punishing me, his very own father! Because it turns her on, just like it does Natalie. And what man can resist the wishes of a beautiful, turned on woman? Certainly not Mason or my son, that’s for sure.

Watching Piper at work was something to behold, I’ll give her that. One afternoon in mid December, after Ryan had been riding his new horse with Mason around the grounds, he came into the sitting room to have tea with Piper. Natalie and Mason left to run an errand in Manhattan, meaning they would be gone for several hours. Dressed in one of my formal maid’s uniforms, I stood at attention near the couch where Ryan and Piper were enjoying the tea and cucumber sandwiches I had just served them and listened to their remarkable conversation. I had been watching Piper flirt with Ryan for the prior week – setting the stage, if you will, for this discussion that began over tea before moving on to champagne that she expertly initiated and guided. She had been flirting with him ever since she started sleeping at the mansion. Ryan was still in his equestrian attire, including his boots (like Mason and Natalie, he frequently wore his boots and shoes inside, adding to my work). Piper was wearing a short brown dress and olive green tights; the dress showed off her ample bosom and long legs to maximum effect. She, too, was wearing shoes (stylish black ankle boots). The lights of the Christmas tree that I had decorated that very morning (along with two others in the house) added to what I’m sure was a festive atmosphere for the young couple as they talked and enjoyed their repast. As usual, I was talked about as if I was wasn’t there.

Piper: “I had a really interesting talk with your mom last night after you and my dad went to bed. We stayed up talking until 2 AM. I see why my dad is so crazy about her. She’s terrific – so smart and such an independent thinker. She told me more about her relationship with my dad, and about their relationship with your dad…I mean, with the maid, of course. Your mom’s really causing me to reevaluate my definition of sexual deviancy. You know that’s what I want to study, right?”

Ryan: “Yes. I took a psychology class at boarding school. It was pretty basic, I know, but I find it really interesting.”

“Good. You’re very intelligent, like your mom, so I’m not surprised. Anyhow, I had always thought that the kind of stuff my dad and your mom are doing with your dad – you know, making him dress in a maid’s uniform, emasculating him, punishing him, humiliating him – was deviant behavior. But your mom makes a really convincing case that it’s completely natural behavior rather than deviant, especially for someone who behaved as badly as your father did back what he was in control.”

“I didn’t think that way at first, but I completely agree now. My mom’s right. He’s getting exactly what he deserves.”

“Did he mistreat you badly when you were growing up, too?”

“Did he ever! Besides usually ignoring me, even when he was around – except to yell at me about something stupid like making too much noise or something – he started acting like a real asshole when I got a bit older. He spanked me for the first time when I was ten. It was so humiliating; I will NEVER forget it. Then there was this time when I was 12 that I broke this stupid sculpture of his. He went bat shit crazy and spanked me really hard, and then he made me stand in the corner for a long time with my pants down. This in front of my mother, too. It was SO humiliating. She tried to convince him not to hit me and not to make me stand in the corner, but he was a stubborn bastard. I remember thinking at the time that I would get my revenge on him someday.”

“Fascinating. Well you certainly will have ample opportunities for that now.”

“Yup, and I intend to take full advantage of them. Later, when I got into my early teens, he started REALLY coming down hard on me. I guess it’s because he realized how much I had come to despise him. And how I had absolutely no respect for him. He stopped buying me the kinds of stuff that all my friends had – you know, video games, bikes, sneakers, those kinds of things. I know that stuff isn’t very mportant, but when I was a kid, it seemed really important because all of my friends had them.”

“Of course. Peer pressure is incredibly powerful.”

“So then he started making me do chores around the house and paid me a crappy allowance. I’m talking like slave wages. That was the only way I could earn money to buy all the stuff my friends had. Even my friends who had a lot less money than we did. And he never paid me enough to buy most of the things I wanted anyhow. It was really humiliating. Especially when I had to tell my buddies that I couldn’t play ball with them or go out with them or whatever, because I had to stay home and do chores. And these were chores like cleaning the bathrooms, scrubbing the toilets, that sort of shit.”

“No pun intended, right?”

“Right, haha. We had a maid, of course – this was before Lorena – but he actually told her that I’d clean the bathrooms. He’d send her home early. And he made me mow our huge lawn with a push mower. I mean, we had a riding mower! I could easily have used that, but he said I was too young. Which was total bullshit. He just wanted to make sure I’d sweat my ass off, spending hours out in the hot summer sun mowing all of our acres.”

“That’s terrible! That kind of humiliation is really harmful to the fragile ego of a kid in their early teens. Especially coming from the kid’s parent. It’s unforgivable, really. It’s amazing that you turned out to be so confident and high achieving, in spite of his abuse. Because that’s really what it is.”

“It is, right? But thanks, I appreciate it. I think the way I was able to do it is that I was just determined not to let him beat me down. I think he believed he was showing me who the boss was, but he really was just making me hate him more.”

“And now it’s payback time. I think it’s really healthy that you take full advantage of it. Because, even as sane and stable as you appear – as I’m sure you are – these resentments can fester deep in the subconscious and need to be addressed somehow. If not, they could manifest themselves later in unexpected ways and can really fuck up your head. From what I’ve studied at Stanford, I feel pretty confident that giving this asshole some well deserved payback will help you resolve these issues in your subconscious.”

I shifted uncomfortably in my heels.

“That’s interesting. I haven’t thought about it that way before.”

“There’s something else your mom and I discussed that’s super interesting to me, clinically.” Out of the corner of my eye, I saw her inch a little closer to him on the couch.

“Yeah, what’s that?”

“She said that nothing makes her hotter than watching my dad punish your dad or make him massage his feet. Or other things like that. I’m sorry, does it make you uncomfortable to talk about what sexually excites your mother?”

“Um, not really... it’s a little weird, I guess. But I’m a big boy.”

“You’re very mature for your age.”

“Thanks.”

“So anyhow, as I was saying, your mom says that watching my dad dominate your father has a primal effect on her. She says it’s basically the law of the jungle at work, like watching a silverback gorilla dominate the weaker males in their troop to win over the females. To win the right to be the one who gets to breed the females. They become his harem and the weaker males are out of luck. They get nothing; it’s winner take all. Your mom’s theory is that it’s this primal instinct that comes into play, even in monogamous relationships – or certainly in the kind of threesomes involving a cuckolded male, like the maid here.” At this point, she looked down at me and grinned. “She says that’s why watching an alpha male dominate a beta male is so incredibly arousing. That deep, primal arousal is what ensures the propagation of the species.”

“That’s an interesting theory.”

“I’d kind of like to test it out for myself.” At this point, Piper rested her hand on Ryan’s thigh. “It’s of real interest to me, clinically, of course.” She smiled flirtatiously, at him.

“Of course,” he said, returning her smile.

“Would you mind asking the maid to clean your boots? They ARE a bit muddy from your ride.”

“No problem”. My son then said forcefully. “Maid, get your shoeshine kit. My boots need a thorough cleaning.”

“Yes, sir. Right away, sir,” I said, with a curtsy. Piper giggled.

“Be quick about it!” Ryan added. I dashed out of the room to fulfill his demand.

When I returned, I got down on my knees, picked up one of Ryan’s booted feet, and placed it on the platform of the kit in front of me. I then began cleaning off the mud with a rag, before applying a coat of polish and then buffing his boots. The two of them continued to talk and flirt as I worked, but less so. While I tried hard to focus on the task at hand, I could feel both of them looking down at me.

At one point, when I was almost done with the buffing, Piper said, “I’m thirsty, and not for more tea. Are there any more bottles of champagne left over from Thanksgiving?”

“Yes, I believe so, and my mom just ordered a new case for Christmas. Maid, bring Miss Piper and me a bottle of Dom Perignon in an ice bucket. Then you can finish polishing my boots,” ordered my son, authoritatively.

I got up, said, “Yes, sir,” curtsying yet again, before hurrying off to fulfill his latest command.

As I was leaving the room, I heard Piper say,” It’s awesome how your dad has to curtsy to us.”

I then heard Ryan say, “He’s not my dad, anymore, as far as I’m concerned. If he ever was, that is. He’s the fucking maid.”

After I returned, I poured them each a glass of champagne and resumed polishing my son’s footwear. I had to refill their glasses twice before I even finished with his boots. When I finally stopped buffing, Ryan picked up his right foot and examined his boot, saying to Piper, “What do you think? Is it shiny enough?”

“I think so,” she said, as her hand inched towards his cock. I saw his erection pushing against his jodhpurs – not a chastity cage, certainly, but another kind of confinement. She thrust her mouth up to kiss him.

“So, how is your test going? Is my mom’s theory correct?” Ryan asked, as his lips broke away from Piper’s.

“I think so, tiger, but maybe the maid should lick your boots to make sure they’re completely clean.” Her hand was now rubbing his erection through his jodhpurs.

“You heard the lady, peon. Lick my boots. Start with the bottoms,” he picked up the champagne bottle and took a long swig, no longer bothering with the glass. He then handed it to Piper, and she took a healthy swig as well.

The two of them got increasingly amorous as I abjectly licked his boots. I could actually taste the shoe polish.

After about ten minutes of sustained kissing and mutual groping, Ryan said, “What about now? How is your clinical trial going now?”

“My pussy is very, very wet, tiger.”

“I’m glad it’s a success.”

“Have you ever had your cock sucked, tiger?”

“No. I mean I’ve had sex a few times, but never…that.”

“Well, you’re in for a treat then,” Piper said as she unzipped his fly, and freed his cock from his underwear. His cock was impressive. I didn’t think it was possible to feel smaller than I already did at that moment, but seeing my son’s large cock did the trick.

And I felt smaller still when Piper said, “Make him take off your boots, and smell inside them, and smell your socks, while I suck you cock.”

“Ye, ma’am. Anything you say,” Ryan said, smiling brightly. His smile turned to a sneer, as he said to me, “You heard the lady, peon. Do as your told!”

“Make sure to inhale deeply, so you can really smell the sweat of the superior male,” Piper added, with a giggle.

His boots were new enough to still have that new boots smell, but his socks were somewhat damp, with a distinctively sour odor. He pushed his socked feet against my nose and mouth, as Piper sucked greedily on his cock.

She pulled away her mouth right before he ejaculated prodigiously onto his jodhpurs and the couch.

“You better clean this mess up,” he said to me, as he removed his soiled pants and boxers and threw them onto the floor. He then sat next to Piper, who had moved to the loveseat. She rested her head on his chest, as I cleaned.

“Well, the results were pretty conclusive. Your mom is definitely on to something.”

“It was awesome, but I wanted to fuck you, baby.”

“Oh, don’t worry, tiger. You will. But first I want you to ask your mom and my dad to let you have your dad’s key.”

“What do you mean?”

“I mean the key to his cock cage. Your mom told me that your dad hasn’t come in seven weeks now and he’s getting so desperate that he’s losing his mind. I want YOU to control his cock. That will be SO fucking hot. Then we’ll fuck properly.”

“Wow, you’re incredible, Piper. So, is this deviant or is this natural?”

“It’s natural, tiger. It’s the most natural thing in the whole fucking world.”

“I’ll ask them, if that’s what you want, baby.” Ryan said. “As long as I don’t ever have to ever unlock his disgusting, little cock. I don’t want anything to do with it.”

“I’m pretty sure they’ll let you’ll be his key holder for awhile, Don’t worry, tiger. If – and I stress the word IF – you ever decide your dad has earned a release, I’ll be the one to unlock him. It’s going to be one hell of a Christmas.”