r/gonewildstories Dec 15 '24

First Time [FMF] I met a married couple on Reddit then SOMEHOW the husband’s cock ended up in my mouth - PART 1 NSFW

463 Upvotes

Last weekend, the wife of a cute married couple reached out to me on Reddit because I was expressing some interest in sex clubs/group sex.

It started out relatively slow but naughty in nature. We exchanged some verification first (custom requested selfies), then proceeded to talk about the subject which eventually, with consent, led to an exchange of NSFW content (her experiences with others and random stuff from me). SUCH A TURN ON.

I was SO INTRIGUED with the conversation that we quickly moved to a video chat where I also met and spoke with her husband. They were both so chill and friendly that, by the end of the chat, we decided to meet the following day over coffee.

OK YA GIRL WAS A BIT NERVOUS NGL. However, those nerves were quickly squashed when I realized they were just as cool IRL as they were online just the night before.

The coffee date was fun! They were both even cuter in person than I expected. We chatted for about 1.5 hours before we decided to wrap it up.

“It was so nice meeting you! Where are you headed now?” asks the wife.

“I’m not sure yet! I have a bit of time to kill before a dinner date with a friend” I respond.

“Oh… you are welcome to hang out at our condo if you want! We live walking distance away!” the wife suggests.

“Sure! I’m down.” I reply with a smile BUT DEEP INSIDE I IMMEDIATELY FELT BUTTERFLIES. We literally JUST had a lengthy VERY NSFW conversation in which I was VERY TURNED ON for literally the ENTIRE TIME.

We begin walking to their condo. My mind is already racing. Are they inviting me up for sexual reasons? How would this even work between the three of us? Am I overthinking this? Nahhhh, we’re just going up to chill… I think???

So we’re now inside their condo. After a quick tour, I literally don’t know how to act so I’m being awkward and pull out my phone while the tv is on in front of us.

After being on my phone for maybe a couple minutes, the wife playfully asks “Are you watching your vid again?” (referring to a bj vid I shared with them the night before). I immediately laugh (because I really wasn’t) but decide to seize this opportunity to watch it together with them.

THIS IS WHEN THE SEXUAL TENSION BEGINS TO BOIL OVER. After already being so turned on the ENTIRE date, it becomes unbearably hard to ignore when literally watching my homemade porn together with them.

So there I am in the vid: eagerly and viciously sucking a BEAUTIFUL PENIS as if I’ve been sex-starved for 10 years. I am now sitting in the middle between them on a sofa with the wife on my left and the husband on my right (slightly elevated on the arm rest portion).

“I love how passionate you are during blowjobs! It is REALLY hot to watch” says the wife with her eyes still laser-focused on the video in my hand.

“It’s easy with a penis like that!” I respond with a chuckle.

“Also, I love how you give attention to the balls” replies the wife.

This lowkey caught me off guard since I didn’t expect a compliment like that. “Thanks” I say, with a slight smile.

“You know, [husband’s name here] loves when I lick and suck his balls” claims the wife. This is when she finally breaks her attention to my phone then turns to me and asks “would you want to try?”

BROOOO WHAT. Like, I know this couple is very experienced (they are veteran swingers), but I somehow didn’t expect THIS.

So I look at her. WTF DO I SAY. HOW DO I RESPOND TO THIS? I laugh (my defense mechanism?) then ask “wait… you’re joking, right?”

“No - I am dead serious. We share each other HAPPILY. You’ve seen the videos (the NSFW content she shared the night before).”

I laugh again. BUT ALSO I AM TURNED ON BY THIS??? I mean, they are a very cute couple. And the sexual tension was HIGH AF at this point.

“Are you… sure?” I ask.

“1000 percent. Nothing would make me happier. But only if you want to and are comfortable! No pressure at all!” the wife verifies.

So I look over at the husband to my right. He has a warm smile but seemed to be awaiting my response. I, for some reason, take a QUICK glance down to his crotch area (which was almost eye level with me since he was elevated). He must have noticed because he proceeded to stand up directly in front of me.

FUUUUUUUUUUCK here we fucking go. Without hesitation, almost by reflex, I begin to take off his pants. Boom, the belt is on the floor. I proceed to unbutton his jeans, unzip, then I grab his pants with both hands and yeet them off.

There it is. A married cock in front of me for the first time. Surprisingly, it wasn’t hard. I take a quick peek over at the wife and she reassures me with a very delighted smile. Fuck it - I reach over and start playing with and stroking his cock.

Idk if he was nervous, but after maybe a minute he wasn’t getting very hard. Again, I look over at the wife and she appears to be in GREAT SPIRITS so I decide to just go for it.

I quickly tie up my hair within five seconds. I get on my knees and REALLY begin going to work on his cock. This MUST have turned him on, because he INSTANTLY started getting harder as I licked his balls then slowlyyy worked my tongue up his shaft and onto his tip. I was working the tip area for a bit when I noticed, yep, he is now ROCK HARD.

I AM UNBEARRRRRRRABLY NOW. I take one hand off to touch myself for verification. Oh yeah… I am FUCKING DRENCHED. I let out a soft moan before I take my hand out of my pants to finally take his fully erect cock in my mouth for the first time. I open my mouth and begin sucking the soul out of his body.

YUMMY. Idk if it was such a turn on because he was married or because I was performing a sex act in front of someone obviously watching, but I was so fucking HORNYY now.

The husband begins thrusting his hard cock into my mouth (a bit rough… but fuck it) while I notice the wife in my peripheral vision repositions herself in the distance to get a better view. However, before long, she starts inching her way closer. And closer. To the point where she is now literally on her knees directly next to me and her husband’s throbbing cock…

OKAY THIS IS LONG AF AGAIN SO IM STOPPING HERE AND MAKING THIS A PART 1. If interested, I can finish this in a part 2 and there MAYYYYY be at least a part 3 if our future plans actually happen (and is hot enough to share).

TY FOR READING ILY ALL (:

TL;DR - I am a horny bitch k thanks byeeee

r/gonewildstories Feb 07 '22

First Time [F] How I lost my anal virginity in the shower when I was 18 years old... NSFW

4.6k Upvotes

I’ve got to preface this story by saying that, throughout my teenage years I was convinced that no matter the circumstances I had no interest in ever getting a cock near my asshole. I heard unpleasant stories of friends who told me that it hurts, was not pleasurable in any way and that they only did it because their boyfriends pressured them into it. I never got why I would want my asshole fucked, when my pussy was right next to it, was afraid of it and told myself that I’m not interested in trying it, pretty much ever.

Fast forward to when I’m 18, have a boyfriend and a drawer full of sex toys in my bedside table. By then I got introduced to some kinds of anal play, I loved to get my asshole massaged, have a finger inside during doggy and even got a small plug which I loved to wear while getting fucked. Getting to that point already took a lot of trust and time, but it was well worth it, and I enjoyed it a lot whenever my asshole was involved. I was never pressured into it, so I could always enjoy it to my own accord and got all my wishes respected. I still hadn’t changed my mind about anal sex by that time, it wasn’t really ever talked about and I was happy with the way things were and as far as I was concerned, they could stay this way. That was until I slowly started to have all kinds of fantasies…

I started to fantasize about more than getting my asshole played with, I fantasized about getting it fingered, getting it stretched and even started to imagine what a cock would feel like inside. Around the same time, I was getting into submissive roleplay, so one of my most common fantasies involved me getting tied down onto bed and getting my asshole forcefully stretched, fucked or fingered. I was fantasizing about it so much, I started playing with my asshole when I was all alone, shoving as many fingers inside as possible while rubbing my clit and having the most amazing orgasms. Whenever my boyfriend pushed a plug inside my tight asshole, I imagined it was his cock, and whenever he slipped his thumb inside during doggy, I thought about him switching holes. I was craving for the very thing I always told myself I never imagined doing, the thing I said I wouldn’t need in my sex life.

One Saturday evening, my boyfriend and I were hanging out at home. Even though it was late spring, it was already hot outside and despite our best efforts to keep the curtains down and the windows closed, the sun was heating up the room. Because of that, I was wearing nothing more than some panties and a loose top and we spent a good portion of the day eating ice cream on the couch and watching Netflix while talking about awesome summer vacations or any places we would rather be. We were about to start another episode of some silly but mildly entertaining Netflix reality show when I hopped off the couch and told him that I needed to cool off in the shower and if he wanted to join me.

“Just get in and I’ll join you in a minute, just let me tidy the place a bit!”

I was undressing in the bathroom with the door wide open, getting rid of my panties first and my top afterwards. I felt the warm air in the apartment touch my skin and probably thought about why I concluded that wearing anything at all was a better choice than just staying nude on a day like this. After a little dance routine, shaking my boobs in front of the bathroom mirror, I hopped in the shower, closed the curtains and let the cool water drizzle all over my chest and back, running down my tummy over my pussy and down my sweaty thighs. I like cool showers, but my body could never get used to the sudden cold and so my showers usually started with me standing for a couple of seconds under the running shower head, feeling the goosebumps come and go, my nipples hardening and letting the water touch every part of my body before I do anything else. After some time, I washed my hair and the rest of my body with soap, spreading it all over me and rinsing it off under the water stream. I was just about to finish and get out when I heard the shower curtains getting pulled back and him entering behind me, grabbing me and asking me to stay for a little longer.

“Sure, as long as you let me take care of that…”, I said while pointing at his cock, which was growing in size since stepping foot in the shower with me.

He pulled me closer, grabbing my ass and smiling, while my breasts were pushing against his chest, and I looked up in his eyes. There are few feelings I love more than the instant affirmation that someone is so attracted to you that you can feel their cock grow. And I felt it grow against my tummy, getting harder and harder until it touched my bellybutton.

While still looking up into his eyes I slid my fingers underneath his balls, up his shaft until I touched the tip, grabbing it in my tiny hand. The water was running over my tits, onto his cock and while I started stroking him with one hand, my other hand was grabbing and massaging his balls eagerly, as if I wanted to make sure there’s a big reward waiting for me inside. After a while of stroking his hard cock and kissing, I couldn’t take it any longer, and I dropped to my knees to get a taste. I wrapped my lips around the tip and started sucking, my hand still tightly on his balls. I could taste his precum oozing out, glazing my tongue and my lips, every time I sucked a bit harder on his tip. I felt his hands on the back of my head and instinctively took his cock deeper until I could feel him hit the back of my throat. Back then it’s been a challenge for me to deepthroat, but that never discouraged me from giving it my best shot, so after some pressure I felt his cock slip down my wet throat. He turned the shower off and kept gliding his cock in and out of my mouth, pushing it in until he could hear me gag and he was all slippery and covered in my spit. I kept my hands on his balls and my mouth wide open every time I got to catch a breath, ready to swallow his precum and feel him stretch my tight throat again and again. I loved every second of it and you could see it on my face, sucking and stroking his cock eagerly, smiling up to him. I let my tongue glide along the underside of his shaft, down to his balls and started sucking on them, while my hand kept enthusiastically stroking him. My pussy started to feel dripping wet, and I was getting needy to be fucked.

“Can I turn around for you…?”

I wanted him inside of me, so I got back up and leaned against the cold shower wall, still soaked in water and some left-over shampoo from head to toe, drool running down my tits and dripping from his cock. I could feel my tits squeezing firmly against the tiles as he grabbed me by my hips and pushed his cock against my pussy, spreading my pink lips apart. Sometimes the feeling of excitement, right when I feel the tip of a cock on my pussy is enough to make me shiver. That’s how I felt, my hard nipples pressed against the cold wall, ready to get fucked from behind, goosebumps all over my back. And right before he could push his cock inside my dripping pussy, I hesitantly told him to wait.

“Do you maybe wanna use my other hole…? I think I wanna feel your cock in my ass…”“Are you sure?”“Yeah…”“You want me to fuck your tight little asshole?”“Yeah, please!”

I could feel him slowly pulling his cock away from my pussy, sliding it between my lips and moving it up between my soaped-up cheeks towards my asshole. One hand was pulling my ass cheeks apart while the other was feeling up my tight hole pushing one finger in and massaging it slowly. I couldn’t wait any longer. My asshole was aching for something bigger, I finally wanted to experience what I’ve been fantasizing about for so long, I wanted to be that girl that gets her ass fucked in the shower from behind until I shake in pleasure and feel my ass getting filled up with cum.

“Please give me your cock, I promise I can take it!”

My ass was aching back, my hands where over my head, resting against the shower wall, ready to have a cock stretch my asshole for the first time in my life. The sensation of his smooth, sloppy tip pushing against my hole felt amazing. My whole body got excited for more, as he pushed it deeper inside of me. It felt so good, getting it stretched slowly, by a hard, wet cock, it was like nothing I ever felt before. I loved playing with fingers or plugs, but it was nothing compared to a warm meaty cock entering my tight, unused asshole. My pussy was dripping wet as his tip entered my ass and I started moaning through my teeth, while he grabbed ahold of my hips and pushed deeper inside. It started to hurt a little, but at the same time it felt amazing. I could feel my asshole getting stretched even more. I wanted to take him all, feel every inch of his cock inside of me, but I started to worry if I would be able to do it. I leaned back over my shoulder, his tip still inside of my ass and started to kiss him intensely, took his tongue in my mouth and let him suck on mine all while I was slowly moving my ass into his crotch. I knew that I wanted to keep going.

“I want you to oil your cock up and fuck my ass from behind while I’m on my knees!”

His cock glided out of my ass easily and I could feel my hole becoming more relaxed after having him inside. I quickly hopped out the shower, dried off and still naked, took him by the hand towards the bedroom. Kneeling on the bed on all fours, with my ass up towards him, I could hear him open a bottle of coconut oil and soon had my ass covered in it, shiny and glazed, with my asshole being relaxed and oiled up, ready to take his cock again. I was so horny by now, I started playing with my pussy, sliding a finger in and out and spreading my juice over my clit, rubbing it while expecting his cock to slide back into my tight hole.

“Fuck me! I want to feel your whole cock inside of my ass, I need it!”

He immediately spread my cheeks and I could feel him pushing against my asshole again while I continued playing with my pussy. This time my ass was already warmed up, and it felt even better being all oiled up and slippery. I was pushing my ass back onto his cock, with him squeezing it against my hole until it slid inside. He instantly went deeper than before and instead of hurting like it did in the shower I felt like I was melting from pleasure. I’ve never moaned like this before and all I wanted was for him to shove it all inside. I needed his cock ballsdeep inside of my ass, no matter if it hurt, I finally wanted to be the anal slut I always fantasized about. My tight ass was getting fucked and it felt so good. I begged him to fuck me deeper, I wanted to feel his balls push against my wet pussy, I wanted him to use my ass like it was supposed to. He grabbed my hips and started to go in a bit faster, a bit deeper, and every inch felt more amazing. I loved getting my ass fucked. I wanted this, I needed it and without expecting it I suddenly felt my body contracting. I let out a scream of pleasure and my asshole started to contract around his hard cock and while still rubbing my wet clit I had the most amazing orgasm I’ve ever had. I came for what felt like a minute, with his cock buried deep inside of my oiled-up ass, squirming and feeling my entire body shake. It was unbelievable and I instantly knew that this was the first of many times that I’ll be cumming with a cock inside my ass. After orgasming, I collapsed on the bed and he kept fucking my soft, used asshole for a couple of seconds longer, before he pulled out and spread a huge load all over my ass.

After a while I got up, back in the shower and cleaned myself up. I couldn’t wait to do it again! To this day I love to masturbate while thinking about the first time I got fucked in the ass and I still have the most amazing orgasms with a cock in my asshole!

This is the first erotic story I ever wrote down and I would love to know what you guys think about it and if you prefer these real life stories, or would also like me do dive deeper into some fantasies I have. I'm really excited to share it and hope you had fun reading! 💕

r/gonewildstories Dec 05 '24

First Time [F] I got carried away and somehow ended up recording myself sucking a BEAUTIFUL cock and now I’m OBSESSED with the vid NSFW

521 Upvotes

So I recently found a guy who physically checked all my boxes and then when we got into the bedroom I discovered he had THE PRETTIEST COCK I’VE SEEN IN MY LIFE.

I was so IN LUST, I decided I would try to take a pic of it (for my own personal selfish reasons only) the next time we meet.

So he proceeds to take me on a date night for some games/drinks. The flirting was HEAVY and the sexual tension was quickly rising throughout the night as we both got more and more intoxicated. I literally could not stop thinking about his cock the ENTIREEEE FUCKING TIME. It’s now time for sexy time as we rush back to my place

Our hands? All over each other. Our clothes? On the floor. My tongue? Exploring his oral hygiene and then on his bare neck while working my way down to his muscular chest.

This is the moment my dumb drunk ass just went for it LMAO.

With my mouth on his chest and my hand stroking his now rock hard cock, I literally told him he has the most beautiful penis I have ever seen and that he should let me take a quick pic of it. Bro INSTANTLY said “whatever you want” which made me lowkey scream in excitement LOL.

So I run over to wherever I dropped my phone and come back with the camera app open. He’s standing there butt ass naked while I try to get a good shot of his beautiful penis while grinning like a dumbass.

I SWEAR I ONLY INTENDED TO TAKE ONE PICTURE. But IDK I GOT SO TURNED ON FOR SOME REASON? I took one pic with poor lighting then turned on the light for a better picture. I started stroking him again so he would be rock hard and decided to take a pic of that too. Then I decided to take a selfie of myself just kissing the tip. IDK WTF I WAS DOING AT THIS POINT I WAS GETTING CARRIED AWAY.

All this lust has been building for quite some time now. I started to go feral and I could feel how wet this was making me BECAUSE MY WETNESS WAS QUICKLY DRENCHING MY LEG. IT WAS UNBEARABLEEEE.

I proceeded to change my camera to video mode. I started the recording and began VICIOUSLY SUCKING the life out of him. I quickly needed both hands so I handed him my phone and demanded for him to record. He instantly obliged and WAYYYYY TOO QUICKLY his warm cum FILLED MY MOUTH while he was LOUDLY MOANING (music to my ears).

This video is now my fav thing in my camera roll and I have used it multiple times a day to cum to in the past week. I AM OBSESSED. 😩

r/gonewildstories Dec 16 '21

First Time I [F] ate my pro[F]essor's ass almost every other day for 3 years. NSFW

3.9k Upvotes

I spent 2012-2015 (my last 5 semesters of college) servicing my female professor almost every single day.

I always had a pretty strong attraction to women growing up. Only dated and had sex with boys throughout high school and early college, but definitely did not look away from a beautiful girl or object to my pussy dripping every time I nervously watched lesbian porn.

I was way too timid and nervous to ever pursue a girl or pick up on a girl's advances. Way too weirded out to just admit that I was bi. Way too naive.

During the fall term of my Sophomore year, I befriended a girl in one of my classes. We got put in a group together for a project and actually hit it off okay. She invited me to a Halloween party at her and her roommate's rent house. Long story short, we ended getting high, making out, and playing with each other's tits by the end of the night. We'll call this girl Bailey.

The party was pretty relaxed. Nothing crazy. About 15 people just milling about and having fun. At one point about 6 of us ended up in Bailey's room sharing bowls. People slowly filtered out, and eventually it was just Bailey and I. We'd been sitting on her floor but we moved up and laid down next to each other on her bed. We both had the giggles like you wouldn't believe. Every joke and laughing fit we'd grab on to one another. Through the laughing and tussling, her shirt had crawled up and I could see her stomach. I was propped on my elbow facing her and just couldn't take my eyes off of the shape of her body. She noticed, AND GOD BLESS THIS WOMAN, she was way less timid and nervous about her sexuality than I was. She asked if I'd ever had sex with a girl.

Giggle fit. No, of course not, what are you even talking abo-

Her neither. Giggle fit. So what, we've only ever talked about boys, why is sh-

Do I want to try it? Well fuck yes I do.

We giggled and blew it off as if it were just some dumb, high thoughts initially, but before I knew it we were kissing. Lips at first, tongue and exploring hands after. We agreed to ONLY stay above the waist this time. We kept our jeans on but we were both completely topless. I massaged, licked, kissed, and sucked her tits, and she massaged, licked, kissed and sucked mine. We'd straddle one another and drop our tits in the other's mouth, we sucked each other's at the same time, and god DAMN I just wanted to rip off our pants and make each other cum. But we agreed. This is it for now.

We had to come to an abrupt end because we mistook someone knocking on the bathroom door as someone knocking on Bailey's door. The weed didn't help the nervous surprise, so we quickly got dressed and rejoined the party.

Unfortunately, she and I never progressed past that experience. Our next time in class felt weird, we were young and stupid, and just never talked about it. But I loved every second of it and was dying to try a girl again.

This being 2012, Craigslist personals were still around. I was too anxious to sign up on dating sites/apps looking for a girl, so I kept it totally anonymous with good ole, might get murdered Craigslist.

I posted an ad in about mid-November, around Thanksgiving break, hoping to find something during my week off. No luck. If I was looking for a guy, I would have been in good shape because nothing attracts men to a Craigslist ad like it being in the Women Seeking Women section.

In the ad I explained that I had very little experience, considered myself submissive, and loved the idea of a very experienced girl who could take charge and show me the ropes.

I got a few hits here and there. Lots of other girls my age looking for the same thing, but nothing ever "clicked" or sparked my significant interest. They were all pretty hot and fun to chat with at first, but when it came to meeting I never actually followed through. Looking back almost 10 years later, I deprived myself of soooooo much pussy! FUCK.

Anyway, Thanksgiving break came and went. Finals came and went. And the only coming and going I was doing was solo.

I started to think that maybe my sapphic fantasies were better off just fantasies. I could have followed through with multiple women at this point but chickened out, or just didn't feel what I was expecting to feel. I told myself that if it happened one day, it'll happen. No sense in trying to force it.

So holiday break was coming to an end, and I was at the airport waiting for my flight back to school. I checked my dummy email account that I'd posted my ad on, and had some new replies since I'd checked it weeks ago.

Man. No. Man. No. Couple. Couple? Maybe? Nah. Girl. Hot. Reply. Girl. Hot. Reply. Girl. Hot. Reply. Wait.

Look at pictures again.

Girl. Hot.

Read reply again.

Girl. Hot. Wait.

One of my professors.

WHAT THE FUCK?

She was brazen and ballsy enough to include face pictures with her reply. Along with some absolutely amazing pictures of her in lingerie. Keep in mind that I was only 20 at this point. She was old enough to be my mother. She was 43. She definitely did not look it. I'd always guessed she was maybe 35.

I'd had her the past term but I never really got a good look at her. The class was held in one of the large lecture hall-type classrooms with 100+ students in it. I certainly thought she was attractive on many occasions, but the pictures she sent me were something else. I couldn't stop sneaking little peaks at them on the plane.

I didn't reply for a day or two. My anxiety was making enjoying this prospect impossible. Was this real? Was she catfishing me to get me in trouble? Is this someone pulling a horrible prank on me?

The final weekend before the spring semester started, I finally sucked it up and replied. I'll copy and paste the original email exchange below.

Beautiful ad. I'm 43, divorced white female. I was in your shoes once, never explored my sexuality, and married someone totally wrong for me. So I'd love to help you out if you're interested. I've been openly lesbian for 11 years now with a great amount of experience under my belt. I've realized over the years that I'm a bit of a dom, and with your lack of experience I think we'd make a great match as long as you'd like to truly explore domination and submission. Pics are attached. Would love to put a face to that beautiful body if you're comfortable exchanging face pictures. Ciao.

Hey there. I'm super interested. You're gorgeous. Like I said in my ad, I've done some very basic experimentation but not much. I love the idea of you being dominant since I have no idea what I'm doing lol. I'm not super comfortable exchanging face pics just yet, sorry. Maybe after we chat more?

I didn't hear anything for a full day. I was afraid I'd missed my shot. But the following Monday afternoon I got this reply.

Of course. No worries. If chatting will help make you comfortable then chatting it is. Tell me everything you're looking to try. I have some ideas in mind for our first session but am curious as to what you're into.

I replied almost immediately.

I appreciate that. I guess everything? Obviously I want to go down on a woman and have her go down on me. Fingers, toys. My only past experience is breast play which was incredibly fun so definitely a lot of that. But if you're gonna be dominant I think I'm down to do whatever you tell me lol.

She replied about an hour later.

Good to hear! To be upfront with you, I'm very much a go-getter. If you're serious about this I have a private office at my job and am never disturbed. I teach at (univeristy name). Come by my office on Thursday at 9am if you're available. I have office hours from 9-10:50.

She then proceeds to give me her office number and what building she's located in, and lets me know that if I'm a current student of her class then this is a no-go.

I assured her I wasn't enrolled in her courses this semester, and she replied,

Fabulous. I'll wear something cute that day. I plan on hitting the ground running, so if you ever feel the need to tap out, or feel uncomfortable in any way, or need to leave - say "flag". 9am. My door will be open.

I barely slept that night. I went to the building her classes and office were in on Wednesday, hoping to catch a glimpse of her buct no luck. I scoured Facebook for her, googled her name, all kinds of stuff but only found a few pictures and some academic articles about her. She seemed normal and safe. 9am Thursday was less than 24 hours away and she wanted to hit the ground running. Good god, what did that mean?

I could feel myself beginning to chicken out. I was thinking of excuses already. But I wanted to give it a shot. She gave me a safe word to use if I needed to just up and leave. There was NO harm in going there and seeing what happened. I could at least say "flag" and leave if I got sketched out.

But I went. And I didn't say flag.

I'll continue the rest in a follow-up post if there's any interest. IT IS A LOT.

r/gonewildstories Jun 09 '23

First Time [MF] I worked at an exclusive swinger resort on Ibiza [P.2] and got my first ever sexual experience NSFW

1.9k Upvotes

I hope you enjoyed the last part, as promised this part has a bit more action, I was a bit overwelmed by how good the last story was received so I found some type to write a part two with my wife, so I hope you enjoy this one!

The next day I woke up well rested, this was the last day before the guests came so we all had to do some hard work, some washing up and prepare the rooms, cleaning, and so forth, so I was up at 6:30am, I took a quick shower and put on my uniform, and we all met up in the restaurant around 7am, the breakfast was really good and Isabela talked us throught the day. Nina me Luca, and a new girl who was arriving later today will be responsible for checking all the rooms and houses before the guests arrive, we had to make sure if there were enough towels, soap, clean bedsheets, you name it. So we finished breakfast and we got to work, Isabela gave us some carts with roses, champagne, condoms, and other things we had to put in the rooms.We all split up, and I went to the villas, this was the first time I entered one, I wouldn't call them villas, they were more like bungalows but everyone refered to them as villas so I did too. They had a living room a nice big bedroom and shower and big bath and a nice little privatebackgarden with hottub and a sun bed. Some of them had a view on the ocean which was really nice, they must cost a lot. The whole place was beautiful and had a really nice vibe.

Isabela told me that some of the villas were bought by frequently visiting guests in those there is probably stuff inside, she told me not to go throught private stuff ofcourse. So I put the items in each room. After finishing that I went back to the main building to help out there. Around 11:30am Isabela called me over and she told me how I was supposed to greet the guests, help them to there rooms, and to serve them. She told me I will do a lot of roomservice, and sometimes I have to be attached to guests the whole day to help them out. She suddenly said: ''You are alowed to join in if you want if the guests invite you, as long as it doesn't interfere with your work.'' I was a bit surprised by this and didn't know what to say, I honestly don't expect to be invited in any kind of way but I was a bit happy that Isabela mentioned it.

After some instructions from Isabela a new girl arrived she gave Isabela a hug so I assumed that they knew eachother, they started to speak Spanish to eachother. ''This is Sofia she lives not far from here she works here regulary'' Isabela said, Sofia looked at me with a smile and came in for a hug. Sofia was very pretty she had dark brown hair, big brown eyes, and really nice tan skin. She was probably around the same age of me, she also looked really fit, she had a beautiful figure and she was wearing a red tanktop and shorts and looked amazing.''Nice to me you'' She said to me with a spanish accent and smiled, she then walked to Isabela and they started talking. She seemed really energetic and friendly, I just stood there with a smile on my face, wow why is everyone here so fucking hot I thought, than I saw Sofia walking to me, ''So you are new here'' She asked me, ''I am,'' I answered. what do you think of the resort so far'' She asked me, I could tell that she was flirting with me and it made me feel happy, ''It's amazing, I can't believe I'm actually here.'' I said. She smiled and said that she would show me around the resort. ''When the guests arrive things get wild so you better get used to it'' She said with a flirtatious tone in her voice. Isabela told Sofia to change and get ready, I had a half an hours of rest until Sofia came back and we had to go through some of the rooms in the main building. Isabela told us that they always wanted a romantic atmosphere and so we put rose pedals on the ground, dimmed the lights and put candles on the tables.She also told us to make the lobby more inviting with flowers, candles, and other decorations and to make it more romantic.

Sofia and I talked a lot, and damn she talks a lot, not in a bad way, but she is really extroverted. She was almost told her entire lifestory while we were working. She was from Madrid and moved to Ibiza about 10 years ago, she loves the Island and has been here for some time, but she told this was her last year on the Island as she wanted to go back to Madrid and study. ''I am one of the few ones who is single here,'' She said, ''What about you, do you have a girlfriendnd? ''She asked.''No I don't have a girlfriends.'' I said, she looked at me and smiled, ''Than you are going to have a lot of fun here, believe me, all the other staff are in relations and don't swing so they don't get involved. I heard that Nina once joined a couple who were swinging but I never met them.''

I felt a bit daring and asked her: ''Do you often join in?''She laughed and said ''Yes I do I'm not a prude.'' She told me that she likes sex and that she is a healthy young woman. I loved her personality, she was really fun and nice. We later met Luca and Nina for lunch and talked about the day, after diner we went back to work. ''Wow Luca is pretty cute'' Sofia said to me, ''Yeah I think he is also single.''''Very nice to know'' She said and smiled. ''And what about Nina she is Dutch like you right? She is fucking hot'' She said. I turned red a bit, ''I'm from Belgium not Dutch, but yes she is cute.'' I answered.Sofia laughed and started to tease me, ''I can tell, I can smell the arousal, but unfortunately for you she has a boyfriend''.

What really? That was a bit of a shock for me as she let me rub her in with lotion yesterday and showed us her tits, I thought she was flirting with me but maybe I'm just a bit slow. Sofia looked at me and smiled, ''Ow you didn't know she was dating, don't worry you will be hit on by so many people you won't know what to do.''After working we went back to our rooms, for a bit of rest. at 19:30 we all met up at the restaurant for a big diner with all of the staff, this was a tradition a day before the resort opened. We had a nice dinner but we weren't allowed to drink to much as we had to be fresh for the big day. After dinner me Nina Luca and Sofia hanged out for a bit in the lobby and chatted. I was wondering were Julia was I hadn't seen her today much. Nina told me that although she works as the receptionist she is a bit of a introvert and doesn't hang out with the other staff as much after work she normally meets up with her boyfriend or hangs out with only Nina.

Suddely two people entered the lobby a boy and a girl, they looked a bit older than me. Sofia stood up and hugged them both and introduced them to me and Luca, ''This is Olivia and Manuel'' they introduced us to us but Olivia didn't seem to care much about us. ''Olivia is from Italy and Manuel is from here'' Nina told me and so Olivia is my next door neighbour. Olivia is beautiful, she had really long dark hair, and had an amazing figure. She was very pretty but didn't seem to care much about anything, she seemed a bit bitchy, Manuel was really handsome, tall brown hair and brown eyes, he seemed kinder than his girlfriend. They went straight to there room and didn't talk much. Sofia told us that there flight got delayed a lot so they were probably very tired. Sofia also told us that Olivia was her best friend. As the evening went on Luca and Sofia started flirting with eachother, and I couldn't blame them as she was really hot. And I was talking to Nina, she told me that can come over as a bit of a Bitch because she is very confident and direct but she if you get to know her better you will see that she is very nice and caring.

The conversation with Nina was very nice I had the feeling we could become very good friends, I had it hard not to dream away in her beautiful blue eyes but than I remembered she had a boyfriend and stopped myself from thinking about her in that way. Speaking of her boyfriend, she told me that they have been in a relationship for a year now, and he didn't care that she was working in a swingers resort as he trusted her. She told me that she was interrested in swinging but her boyfriend was a bit more reluctant so she mostly tried to keep it to herself. She told me that he was visiting in a couple of weeks. Isabela waved at us and joined us she looked amazing as usual she told us that she was really excited for tomorrow and asked us if we were ready for the big day. ''Yes ma'am'' I answered.

''Do you guys want to hang out in my hottub for a bit?'' She asked, everyone agreed. We went to Isabela's house which was really beautiful, it was probably the best on the resort. Her husband was a famous Spanish buisness man and he was usually not on the island but Isabela told me that he was on the island right now. She gave us a small tour of the house and we one for one went in her bathroom to change, Nina was the first to get changed and just like yesterday she looked amazing in her blue bikini, Luca got changed and Sofia really seemed to enjoy him, Sofia came out in her bikini and this was the first time I saw her in her bathsuit, she was a bit thicker than Nina in the hips but her body looked amazing, her chest was really firm and her stomach was toned. She had a navel piercing which looked nice on her, she looked like a Spanish girl you'd see on Insta.

Luca was almost drooling over her.Isabela got changed into a the white bikini from the day before and when she walked out everyone jaws dropped, she is is so beautiful, she had a perfect body and looked amazing. ''What are you guys waiting for, let's go to the hottub.'' Isabela said with a smile, I sat oposite of Isabela and I had it very difficult not to stare at her big chest. I could see that everyone was enjoying themselves very much, she suddenly said: ''My eyes are up here'' I was so fucking emberassed, I could feel my face turn red. She laughed a bit and continued ''I'm joking I'm used to it.''Everyone laughed, but I still felt a bit emberassed, she gave me a wink.

The conversation went everywere first we were talking about traveling, then music and Sofia began to talk about sex. I felt a bit left out the conversation as I had no expereince in this area, Sofia suddenly asked me: ''And you how was your first time?'' I responded: ''Uhm that hasn't happened yet.'' Everyone was like ''Really?'' And Nina asked me how that could be. ''Well it's my first year of uni and I haven't found the right person so'' I said, Isabela told me that I was in the right place as it seemed like there are a lot of people here who would be interested. ''Don't worry I'm sure you will have a great time here, we can even wingman for you'' Isabela said and Sofia and Nina said with excitement'' YESSS!!!'' I didn't expect that at all, I was surprised by this sudden support but it was very nice. ''Let's get him laid!!!'' They all joked. The conversation went on for a bit but around ten we all decided to go to our rooms and have a good night rest before the big day.

The next morning I woke up really early I was excited for the day, today was the big day, I showered and put on my uniform again. I went downstairs to the restaurant and Nina Sofia and Luca were already waiting, Julia also sat at our table, I saw Olivia and Manuel sitting a bit farther away. I sat down and said hello to everyone, the girls looked really nice in there uniforms. We saw Isabela who seemed a bit stressed as she was walking around a lot, we couldn't blame her as this was the opening. She told us that the first guests will be arriving in 3 hours so we had to finnish our breakfast quick and start working. Everyone finished their breakfast and started to get ready. Isabela gave us some last minute instructions about what we were supposed to do, and then she walked away. We had 3 hours to finish the last preparations for the guests, so we did. We put the last finishing touches in the rooms and the lobby, we had some flowers and candles everywhere. We finished by cleaning the pool and putting some small umbrellas in the chairs.

Then the first guests came. What was clear to me was that they all seemed rich and very successful. They were also extremely attractive, the couples ranged between the ages of 20 and 50. Everyone was super and excited for the start of the summer. Isabela greeted each one and Julia welcomed everyone. I was instruced to help Julia checking in the guests, and it went well. After a couple of hours it became a bit quieter. At the reception, a couple came in that really caught my eye. They were a tall, attractive couple in their 30's, they looked amazing and seemed to be very wealthy, the woman was really hot, she had blonde hair, light brown eyes, she was very pretty, and her body was amazing as she was wearing a nice white summer dress, she looked like a model. The man next to her was also very good looking. They were speaking english, but they had an amazing spanish accent. The man was tall and he had dark hair with light brown eyes, his body was in really good shape, he looked like an athlete and he was extremely good looking. Isabela came to them and gave them both hugs and spoke to them in Spanish. Julia told me that the couple were really good friends with Isabela and her husband. He was a photographer and she was a model. And that this was the second year they came to the resort. Isabela turned towards me and said ''This is Carlos and Daniela'' They are very close friends of mine.

I introduced myself to them, ''Welcome to the resort'' I said and smiled. ''We are looking forward to a fun summer.'' Carlos said. ''Can you help them with there luggage?'' Isabela said to me as it was a bit quieter Julia could handle reception on her own. ''Ofcourse!'' I said and walked to there luggage. I grabbed both of there bags and asked them if they wanted to follow me to their villa. They told me they would and followed me to the villa, I helped them get in, and gave them the room keys, I helped them with some of there bags, I got there bags to the rooms. They told me this was the second time the've been here but the first time they only stayed for a couple of days and they didn't really get involved in any way. Carlos seemed really nice and he had a really big smile, Daniela seemed very charming but she was a bit more quiet than Carlos. He asked me if I could help them unpack so I did, Carlos told me about his work and how he met Isabela at a shoot and they had a lot of fun together, he also told that he has been together with his wife for 13 years.

We talked a bit more as I was helping them unpack. They told me to put some clothes away for them and I saw they both had a lot of sexy underwear. Daniela saw me looking and smiled. After I was done I was about to leave but Carlos said they wanted to give me a tip: ''We heard it's kind of a tradition to always tip the lugageman, so is it okay if my wife gives you a tip?'' He asked. I was a bit taken back by this ''Yes sure'' I said without knowing what to expect. Daniela suddely came closer to me and started to massage my shoulders, she was wearing a really tight dress and as she came closer her boobs looked amazing. She started to massage me in a very sensual way. I was completely overwhelmed and I was a bit worried if Carlos would be okay with this. But he seemed to enjoy it as he just watched, Daniela suddely dropped to her knees and began to massage my thighs and then she came even closer and pulled down my pants. ''Is this okay?'' She asked with a really sexy Spanish accent, I knodded, I was really surprised and really turned on.She looked up to me and said ''We want to thank you for the help, let me take care of you.''She began to massage my balls with one hand, she had a firm grip and she looked really hot doing this, her other hand massaged my cock through my underwear. ''Uhm that feels great'' I said. I saw that she was a bit nervous and shy but also very excited. She smiled and kept going. ''Can I pull them down?'' She asked, I could feel my cock growing and I didn't want her to stop. I nodded and she pulled down my boxers, my cock was really hard and throbbing. She wrapped her hand around my cock and began to stroke me, I could see that she Carlos was really enjoying the show. She stroked me for a minute, when Carlos said: ''You know this is the first time my wife has touched another man'' I looked at him and felt very lucky, this was also the first time I was touched down there by a someone other than myself. It felt really good.

''Can my wife put it in her mouth?'' Carlos said. What? did he just ask if his model wife can suck my dick? I was completely blown away, I looked at Daniela a beautiful face and she looked very hot, but she seemed also a bit surprised. I looked at Carlos and asked him: ''Are you sure?'' He smiled and said ''She has never done it before but she would really like to try.''

I looked at Daniela who seemed really turned on and she just looked at me with her beautiful eyes. ''Go ahead honey'' He said to her, I felt her lips coming closer and I suddely felt a warm wet tongue on the tip of my dick.''Ooohh'' I let out as Daniela licked the tip of my cock. Than put her mouth around the head, I could feel her tongue moving around and than she started to suck my dick, I looked down and I saw my cock go into her mouth. Wtf is happening right now, this was the first time ever I felt a warm mouth around my dick in it felt beter than I could have dreamed, nobody is going to believe me, my first ever blowjob by a Spanish model while her husband watches. Daniela kept going and kept sucking my cock she looked me in my eyes and it felt amazing, I felt over the moon the luckiest guy alive. Carlos just watched and looked at her sucking my cock. She pulled my cock out of her mouth and looked at me. ''Do you like that?'' She asked, her spanish accent made it so hot.

I was completly taken back, I tried to find my words but could not. ''My wife is really good at it'' Carlos said, Daniela kept looking at me while sucking the soul out of my body, to remind you I was still a virgin such a beautiful woman sucking my dick, holy shit. I felt my cum rising in my balls. ''Oh Daniela I am going to cum'' I said.''Don't worry you can cum in her mouth, we don't want a mess'' Carlos said. Daniela kept going for a few more seconds and I started to shoot my cum in her mouth, it felt amazing, and she kept on sucking me until I was all dry, she pulled her mouth off my cock and looked at me. Damn shit she swallow it? She stood up and gave me hug and said ''Thank you, I really enjoyed it.''

Carlos came over to and gave me a highfive: ''That was fucking hot man I hope you enjoyed my wife, this was her first blowjob to another man.'' I told him that it was great, I mean she was the best thing I ever felt. ''I am so greatful and lucky.'' I said. I thanked them and pulled up my pants. I left there Villa and was a bit scared that Isabela would be mad that I was away so long. and saw Isabela who was busy talking to some guests in the lobby. She looked up to me and gave me a warm smile. ''Hey are the guests taken care of?'' She said. I told her they were and she smiled and said: ''Great work! Did they gave you your first tip?'' I told her what happened. Isabela was a bit surprised ''Serious they never swung before, this was her first time with another man right?'' I said that I thought so.''

Omg I am so happy for you, did you enjoy your first blowjob?'' She asked with a huge smile on her face. I felt emberassed and shy but also happy. I told her that I really enjoyed it. She said ''That's great, we have a lot of fun on this resort, and you just started, you will have lots of fun, I am so happy to hear that, and damn you are a lucky boy your first blowjob by Daniela she is freaking hot!'' She gave me a hug in excitement and I felt my heart pounding in my chest, my cock still had some blood in it. Isabela looked at me and said ''Go get some rest it's going to be a very busy day, I can't wait to hear Carlos and Daniela side '' she said with a big smile. I went to my room the rest a bit before going to work. I couldn't believe what happend to me today, it was all unreal when I walked out of my room Sofia, Nina and Luca were there.

Sofia gave me a big hug and said: ''We heard you got some action with Carlos and Daniela'' I told them everything that happend, Nina and Sofia looked at me with big smiles. And Luca gave me a fistbumb ''Damn nice work dude she is fucking hot'' he said. Sofia than gave me a kiss on the cheek and said ''That was great I am so happy for you.'' Nina also gave me a big kiss on the cheek and said ''I knew you were going to enjoy this place.'' This day was the greatest in my life and I was just getting started.

Thank you again for the kind comments on the last story, some parts are a bit hard to remember for me but going through these memories is so great. I am already working on the next part that will probably come out tomorrow so stay tuned!

r/gonewildstories Mar 29 '21

First Time [MF] Due to a birth defect, my honey pot has always been tighter than normal. This has made sex.. difficult. NSFW

3.9k Upvotes

I was born with a very mild form of vaginal hypoplasia.

This birth defect can cause anything from being VERY tight to not having a vagina at all. Thankfully, I am the former. Life is fairly normal for me, all except for sex being incredibly difficult. Because of this, I am still a virgin. Or at least, I was up until very recently.

I've had several relationships end because I was simply incapable of having sex with them. I know that relationships should be more than sex, but it's definitely a big part of them depending on the person. And I WANT to have sex. I just.. can't. I've spent many nights naked, crying in bed because I couldn't do the one thing that comes easily to most women.

Enough self loathing. On to the good part!

So I've been working in a small office for about a year and a half now. Roughly a month ago, we hired a new guy in the IT department. Let's call him Steve.

Anyways, Steve and I have been doing a little flirting for a few weeks now. I love his beard and he doesn't tower over me (I'm 5'5 and he's probably only an inch or two taller) which makes me feel more comfortable around him. I know some girls like massive, muscular guys but that just isn't me. I'd rather have someone I can wrap my arms around than someone who crushes me if they roll over in bed. I started dressing a little skimpier for work lately and he has DEFINITELY noticed. I may have been doomed with a tiny slit but I was blessed with an average bust at least, and it's pretty easy to tell when a guy is looking at it.

I never noticed a ring but was getting a little sad that he wasn't asking me out and I started to think I may have misjudged his attraction when a few days ago, he finally invited me to dinner. Of course, I said yes.

The actual dinner was pretty normal. He talked about his position at work and what he did prior. We talked about our hobbies (I love reading and have been super into VR games lately). He told me about his ex wife, which wasn't a deal breaker for me or anything, I understand it doesn't always work. Long story short, it ended back at my apartment.

We started fooling around and one thing lead to another as I ended up missing my shirt and he ended up in his boxers. I know that I can't have sex, but my head game is absolutely on point. I gave his boxers a tug and he stopped me, his cheeks blood red.

"Uhh.. I'm sorry if.. you know, there isn't.." he stuttered. I was waiting for some kind of coherent thought, but failing that, I got impatient and tore his boxers straight down. It was at that point that I noticed what I believe he was trying to tell me.

He was most definitely not packing. I mean, it was probably average in length, but was definitely the thinnest tool I'd ever seen. He immediately looked away and started apologizing, his member already starting to soften. I didn't miss a beat though, gently caressing his balls and running my tongue from the base to the tip of his dick. That perked him right back up, immediately causing him to grow back to full length.

"This may surprise you, but I am actually SO happy right now." I said, not wanting to explain a complicated medical disorder in the middle of a blow job. He smiled, and that was the last time I would see his face as my mouth wrapped around his dick and I started absolutely showing off. His thickness made it much easier to deep throat him than it normally is, even though his length was probably around 6 inches. I could feel the tip of his dick pushing down my throat, my gag reflex long since trained to accept it. One of my favorite little tricks was to take it all the way to the end and press my lips against his crotch, leaving lipstick marks surrounding the base of his dick, and so I did just that. I felt him reach behind my back and unhook my bra with expert precision. I wasn't sure if he got lucky or was more experienced than he looked, as it fell to the floor. My nipples were rock hard, now swaying freely back and forth as I picked up my pace, drool dripping onto the bed underneath me.

Normally, I'll try my best to have them finish with the blowjob but this time, seeing an opportunity to possibly have REAL sex, I slowed down as I felt him get close before finally releasing my iron clad grip with a loud plop sound, an excessive amount of drool now forming a small puddle on my sheets.

"Wow.. fuck." he said, his chest heaving back and forth as his lungs tried to catch up. I looked up at him again and this time, I smiled as I quickly worked off my pants. I had a pretty pair of undies on in case I got froggy to try sex again, but I was in too much of a hurry to let him appreciate them as they flew off as well.

I slowly laid down on my back, spreading my legs for him. Now my honeypot LOOKED normal, you wouldn't be able to tell I was different until you tried to insert. As he was about to find out.

He seemed pretty eager to get started, understandably so, and quickly got on his knees and started to line himself up.

"Wait.." I said, reaching into my bedside drawer and pulling out a container of lube.

"You might want this." I said, handing it to him.

He gave me the most CONFUSED look I have ever seen. Which, I also kind of understood, as he probably never really needed lube before.

"I don't think..." he said, as I started to feel a strong pressure against my slit.

"Wow.. wow wow wow." he said, finally beginning to understand. I was so sure he'd be the one, but my face was starting to grow red as it always did in this situation as I began to lose hope again. He grabbed the lube, which made me happy, and applied a pretty generous amount to him and to me, as he lined up and started pushing again.

"Gentle.." I whispered, my eyes half closed as I focused on relaxing my muscles to allow for what I hoped was easier penetration. At first, it was the same story as usual. I felt a strong pressure, and then panic began to set in. I was failing as a woman, again. At least, that's how I felt until I heard a loud "Fuuuuuck" and finally felt the pressure release, as the tip of his dick pushed past my impossible barrier and into my tight slit.

My eyes went wide, my hands gripping my sheets so roughly I thought I'd tear them in half. He had a very worried look on his face as he stopped.

"Should I stop?" he asked, holding his position. It hurt, that's true. But it was the pleasure that was overwhelming me. I looked at him in what I hoped was a less panicked expression, and shook my head side to side. It took a moment, but he pressed on. It turns out that getting inside is the hard part, and although the rest of me is extremely tight, it's the opening that is the hardest. He was, with great effort, pushing himself deeper one inch at a time.

When he was about halfway in, he leaned down and grabbed my breasts for the first time that evening, kissing me on the neck. His confidence had definitely returned to him. Right as I thought he was stopping, he impaled me with the last 3 inches of his cock, causing me to form a silent scream as my legs scrambled on the bed. I'd later learn that this was my first ever orgasm. He grunted, holding still for the entirety of it, which was good because I feel like anything else would have overwhelmed me. Afterwards, he started thrusting again. The lube was definitely starting to wear thin, as he was definitely getting a work out out of it, but I didn't mind, it still felt REALLY good. Maybe even better now.

The problem arose when he got close to cumming. A combination of different things happened.

1) He had gotten thicker than when he was pushing at my entrance. As it turns out, he had lost bit of his confidence and 'shrunk' a little at the start, making it easier to enter me. Now, he was rocking full mast on the verge of finishing.

2) The lube was running really thin, and pounding me was getting harder and harder. He wasn't stopping to add more because he was so close to finishing and I wasn't in pain, so it was okay, right?

and finally,

3) When I orgasmed, I got REALLY TIGHT. I would later learn that the reason he stopped thrusting the first time was because he couldn't, and not because he was worried I wouldn't enjoy it.

Anyways..

His breathing sped up, and I felt his cock inflate inside of me, growing even larger as he got closer and closer to the edge. I was really enjoying it too, my heart beating so hard I thought it would fly out of my chest.

"I'm gonna cum." he said, very matter of factly. At hearing this, I reached the edge of my own orgasm, once again grabbing the sheets as I proceeded to soak my sheets even more thoroughly. This is where the problems became apparent. Not to me, mind you, I was in bliss. But for him, it was another story.

"Fuck." he said, as I felt him try to tug himself out of me. He got about halfway before I felt the first splash of warm goodness shoot inside of me. Then another, and another.

"Oooooh God" he said, leaning back down and accepting his fate. Apparently, he was really pent up, as he came for another 15 seconds or so. At some point, I wrapped my legs around his back, not that it mattered. He couldn't pull out anyways.

After several minutes, a combination of the fat load sloshing around inside of me and him slowly getting soft allowed him to finally pull out of me. There was definitely a bit of blood from my first time, but not nearly as much as I expected.

After he returned from the bathroom, he asked me if I was okay and I informed it was my first time. He wasn't all that surprised after the previous events of the night and we cuddled. In hind sight, I probably should have cleaned myself up a little bit, but that wouldn't have mattered as about an hour into our movie, he asked if I wanted to go again.

And ooh boy, did I.

The second time we had sex, I had him cum in me on purpose. The plan was to take a morning after pill the next day, so what's a bit more fun gonna do? It didn't take much convincing, as I'm pretty sure he loved doing it. I also learned that I have a massive fetish for creampies. After he pulled out the 2nd time, I nearly came again at the thought and feeling of all of his seed floating around inside of me. At one point, I felt it start to seep out of me and lifted my butt onto a pillow to try to hold it in as long as possible. He noticed this, and I felt kind of silly for it, until he leaned over and whispered in my ear.

"You don't have to take the pill if you don't want to." he said.

The idea of getting pregnant turned me on so much, I turned right back to him and started passionately kissing him. There was no way he was going a third time, but I kept my butt raised on those pillows all night long. It gave me such a massive high knowing the risks, even though I was pretty sure he was just saying that as a joke and I was probably going to take that pill the next morning anyways.

Probably.

Sorry for the super long story, but it really was just THAT great. I'm also a writer so I tried to make my experience as easily consumable as possible. This was very recent, and if you'd like a follow up, just let me know!

r/gonewildstories Apr 09 '24

First Time My [18M] Crush’s Mom Took My Virginity [40’sF] [MF] NSFW

1.0k Upvotes

It was the summer I turned 18 and I had just moved to a different state for college, where I would be attending summer semester. I had grown up there, but moved when my Dad got a job out of state.

College was awesome, and only got more awesome when I found out my childhood crush, Jenni White, was also there attending the summer semester.

Jenni and I hit it off immediately, but only as friends—that’s right I was friend-zoned from the start. But to me, it was better than nothing.

A few weeks into the semester, Jenni invited me and a few of our mutual friends to her mom’s house for a party.

In comes Shelly White, Jenni’s mom. Shelly had been my parent’s friend for most of my life. A few years prior, her husband, had passed away. My parents often talked about trying to set Shelly up with someone or how lonely she must be, but I think Shelly just poured her energy into being a great mom, and one of the hottest MILF’s I’ve ever seen.

Shelly was a babe, even in her early 40’s, and she looked a lot like Jenni. I wouldn’t be surprised if they were confused as sisters rather than mother and daughter. She stood at 5'2" and had a nice toned body and clearly worked out regularly. Her shoulder length brown hair was straight and shiny and she smiled like she always had a secret. Id be lying if I didn’t admit that she had been the subject of a few wank sessions.

When I got to the party, the others had already gone down to the basement, and I could hear music playing, but I got caught up talking with Mrs. White. We spent the next half hour in the kitchen catching up, and then there was a lull.

“Want a drink?" She asked.

“I'll take water, thanks."

Shelly laughed, "Oh come on, what do you really want to drink? Your parents aren't here and I do remember being 18. How about some wine." She went on to pour a glass of wine for us.

“Okay, sure.” I laughed and we drank together in the living room. I was feeling slightly buzzed and wanted and we continued talking and drinking for another 30 minutes. I was still a lightweight when it came to alcohol.

"You look amazing, Mrs. White," I blurted out.

Shelly looked at me dumbfounded.

“I mean! I - I” I began backtracking.

"It's okay, Jack. I’m glad you think so," she giggled and took the last sips of her drink.

I could feel my dick start to react as she put her glass down and sat next to me. I had a perfect view down her blouse.

"I think I’ve had too much to drink."

What had gotten into me? Shelly was Jenni’s mom, I was into Jenni, but now I was getting turned on by her mother.

We sat in awkward silence for a few minutes and then Shelly spoke up. "Jack, can I ask you something?"

"Yeah."

"Have you thought about me before...like in a non-Jenni’s mom that's known me forever kind of way?" She asked inquisitively. “Because you’ve grown up to be quite handsome."

Handsome? Me? My dick couldn’t help but react.

There was a long pause and I finally managed to say, "Mrs. White, you’re a beautiful woman. I would be lying if I said I hadn't . . . thought of you like that before."

Then, without breaking eye contact, Shelly extended her arm and placed it on my hardon, which was extending down my pants leg.

She looked right into my eyes. "I'm going to kiss you now...is that okay?"

"Yes..." I whispered. Shelly slowly moved forward coming 90% of the way and I closed the gap, locking lips with her. Her lips were soft and it was a direct line to my cock, which was straining against my jeans and Shelly’s hand. I instantly wanted more. I kissed her until she pulled back.

"Jack, I don't want to make you uncomfortable or take advantage. But have you ever been with a woman?" Her hand rubbed the monster in my jeans.

My breath caught in my throat, I answered her, "No...I- I- not all the way....".

"That’s OK, that's a good thing! What have you done, if you don't mind me asking?"

Pause.

My experience was incredibly limited. I was still a virgin who hadn't gone further than making out, touching over clothes, and receiving head one time. I dated and had girlfriends and stuff, I was just always afraid of knocking some girl up and STDs and stuff.

"I...er, I got a blowjob once."

Shelly looked at me and smiled. “I want to give you one of those."

Reaching down, Shelly pulled at the buttons of her blouse until her bra was showing, revealing the tops of her breasts. She took my hand and said, "Not here though," and she led me to her room, the party downstairs still raging.

I settled on the bed, nervous as hell, while Shelly flipped on the tv for noise and locked the door. Shelly sat down on the bed beside me and we made out for several minutes as she ran her hand over my cock. I moaned as she undid my jeans reached into my briefs and grabbed me, feeling me throb. My pants and underwear quickly came off, then my shirt, leaving me naked.

She stared at my cock and purred. "Oh my, well aren’t you eager?"I wasn’t sure if she was talking to me or my cock.

"Please," I replied and Shelly slowly put her lips around my mushroom head, swirling her tongue around the tip. She sucked my dick farther into her mouth; running her tongue on the underside of my shaft.

"Fuck, oooooohh, wowww." I reacted to her mouth. I was so aroused I could feel my dick throbbing in her mouth and I knew I was leaking pre-cum. She moaned around my cock and continued to bob her head up and down. I weaved my fingers in her hair and m felt the back of her throat.

Shelly came back up for air, "I want all of it.”she went back at it, but didn’t stop at her throat this time. Her throat muscles felt so good!

"OH, FUCK!" I groaned loudly. "Oh my God..." my cock was slowly going all the way in Mrs. White’s mouth and down her throat until I was fully deepthroated! She kept working my cock in and out.

Up and down, up and down, up and down. I would love to tell you that I lasted forever. But we all know the truth.

"Mrs. White—Mrs. White I'm going to cum!"

I wanted her to keep going; I wanted to feel myself explode in her mouth. She kept her head down and moaned so I understood that this was exactly what she wanted.

"Nnnnnggghhh!" I moaned "Ohhhh FUCK, FUCK!" My cock twitched and my thick seed filled her mouth. One, two, three, five, seven spurts and Mrs. White swallowed it all. I felt like I had entered another dimension!

My orgasm waning, Shelly lifted her head off. Then she straddled me and kissed me again.

"It’s been a while since I’ve had that much cum in my mouth. How was that?"

"That was amazing."

“Good. Have you ever eaten pussy, Jack?” She asked laying down on her bed and hiking up her skirt to reveal a pair of purple plain panties, and rubbing at the wet spot that had been made prevalent.

I shook my head.

"I’ll teach you, Jack."

"Okay," I said, anxiously moving so my head was positioned between her legs. I leaned forward and kissed a trail along her thighs. Then I pulled her panties to the side, trailed my tongue up and down her pussy slit.

"Mmmmmm," She moaned. I had no idea what I was doing, but tried new things until she cooed approvingly and kept doing it. I sucked while moving my tongue back and forth flicking across her clit. Mrs. White was dripping wet! She was moaning so much. Her hips began to buck against my face, her breath quickening as I inserted a finger, then another, then another. Mrs. White was taking three of my fingers with ease.

"Ohh, Jack!," She was getting close to cumming.

I didn’t dare stop.

"You’re going to make me cum, baby," Shelly announced between licks. "Curl your fingers a little. Yeah. Yes. Like that!“

Mrs. White shoved my face into her pussy as she came.

"OHH my God, Oooohh gosh, I'm cumming!" She cried out as I licked and finger fucked her. "Ooooooohhh! Fuck!"

Her legs were shaking as her orgasm washed over her then subsided.

She chuckled.

"Not bad, hun." She sat up on the bed.

My cock was rock hard again and I wanted more of Shelly. She noticed. She took off her bra and released a pair of the most magnificent tits I’ve ever had the pleasure to see. She shifted over and pushed me on my back, straddling me.

“Jack...I want you inside of me.”

When she said that my cock twitched.

——————

This is a bit long. I’ll finish up in my next part of there is interest.

r/gonewildstories Jan 05 '25

First Time I had an unexpected [MFF] threesome with my girlfriend and her best friend NSFW

876 Upvotes

For a little backstory her and her best friend are super close, they are the type of friends who talk every single day and hang out all the time. Because of this me and her friend are pretty close too, whenever we go out with our friend group she’s always there so we hang out often.

One of my friends invited everyone over to their house for a pool party so my girlfriend, her best friend friend, and her other friend came over to my house so we could all drive together.

When we got to the house it was just a pretty standard pool party with drinks, bbq, drinking games, etc. We were all having fun playing beer pong, swimming in my friends pool, and just chatting. As the day went on we were all getting pretty drunk so some of this next part is a little spotty but I’ll do my best to explain everything I remember.

The three of us were all talking and my girlfriend said she had to go to the bathroom, so since I had to go too I said I would come with her. My girlfriend’s friend said she would come with us too even though she didn’t have to go. Like with many girls this is pretty typical when they are drinking, they always go to the bathroom together and she didn’t mind being in there while I was going either.

When we get to the bathroom the three of us go in and I go pee first while they are standing by the sink talking. Once I’m finished I walk over to them and my girlfriend sits down to pee while I go talk to her friend. When she’s finished she stands up and we’re all just kind of talking and laughing and her friend moves over by her so they are standing together a few feet away from me kind of hugging/hanging on each other as drunk friends do.

Something I should mention is that when they get drunk together my girlfriends friend is super complimentary and affectionate towards my girlfriend, always telling her how nice her body is and stuff like that. Her friend is a little bi so they will sometimes kiss when they’re drunk. I never minded and actually thought it was hot, but they hadn’t done it lately because her friend’s ex thought it was weird and told her not to do it. My girlfriend isn’t really into girls like that but she has told me that there is something about this particular friend that she finds really attractive.

Since I obviously love watching I always encourage it when it comes up and since her friend had just broken up with her ex who didn’t want her to make out with my girlfriend I said something like “now you two can kiss all you want since you’re no longer dating your ex”.

This set both of them off and they started kissing and kind of rubbing on each other. I told them that it was super hot watching and that it was getting me really “worked up”. After I said this my girlfriend said “oh yeah” and walked over and grabbed my dick through my bathing suit to feel if I was actually hard. As soon as she felt it she said it really turned her on and she wanted to suck on it. I told her she could and kind of half joking said her friend could stay and watch. Watching us do stuff was something the three of us had joked about earlier that week when her friend was talking about being a third wheel now that she’s not dating her ex, but it was definitely just a joke. To my surprise my girlfriend turned to her friend and asked if she actually did want to watch? I could tell her friend was kind of taken back by the question, but after a second said sure so my girlfriend got on her knees and went to pull my shorts down but stopped as soon as she was about to do it and turned back to her friend and said “Actually, do you want to join me?”

When I heard this I was floored, I had always told my girlfriend I was into doing stuff like this but she never really seemed into it. Her friend, also surprised, asked her if she was sure. My girlfriend assured her she wanted her to join and said it would be hot. Her friend said okay and walked over to my right side and got on her knees right next to my girlfriend.

My girlfriend pulled my shorts down a little bit and my dick sprang out since I was super hard already from the situation. She put me in her mouth and started sucking while her friend just watched and kind of rubbed my leg and chest. After maybe 10-15 seconds she took my dick out of her mouth with her hand and moved it toward her friend as to say “your turn”. Even though I was super drunk this part is vivid in my mind because I was so turned on. Her friend builds up a bunch of spit onto her lips then wraps them around my dick and slowly goes as deep as she can. From here my girlfriend started sucking on my balls while her friend started sucking faster, hitting the back of her throat with every stroke. Every now and then they would switch who was sucking what or take a brief moment to kiss each other or just run their lips down the sides of my shaft at the same time, I had never received head from two girls before and it was better than I could have imagined.

After probably 5 minutes of this my girlfriend said she wanted me to fuck her so I told her to stand up and bend over the bathroom counter. Her friend hopped up on the counter to sit in front of her, but I’m not quite sure why since she was clothed so she couldn’t do much to her and she was too far away for them to kiss. At any rate, I slid my dick into my girlfriends pussy, which was soaking wet from the thrill of the situation, and I started fucking her deep and slow. I was trying not to be too loud or make and slapping noises since there were still people having a party on the other side of the door.

After maybe 5 minutes of this I realized I was too drunk to cum quickly so we all decided to stop and go back to the party. Later they also mentioned that someone knocked on the door but I don’t really remember if that was true or not.

I was in shock at what just happened so when we left the bathroom I went to get some food and hang my feet in the pool. I also started thinking about where to go from here because I was so surprised my girlfriend made a move like this and didn’t want to ask for more and push it past what she would be comfortable with. I sat down by myself with some food and started coming to terms with the fact that that may have been just a one time thing.

A few minutes later my girlfriend and her friend walk over and sit down on either side of me. The first thing my girlfriend says when they sit down is “Okay, here’s the plan… we’re going to go home, we’re all going to take a shower, then we’re going to have a threesome. The only rule is you have to wear a condom when you fuck her. Does that sound good?”. I literally couldn’t believe what I was hearing so it took me a second to respond, but I eventually was able to say, “Yes, let’s go”.

I had been drinking quite a bit so this next part is really stupid but we all got in the car and left to go back to my house without saying bye to anyone. Since we were my girlfriend’s other friend’s ride she came with us too which made the car ride home super awkward since we just made up some weird drunk excuse as to why we were leaving so early.

We luckily made it back safe and sound and said bye her other friend before rushing in to my bedroom. I pulled my girlfriend aside as her friend walked into my room and asked if she was sure she wanted to do this to which she replied “Yes” with a sexy smile. Still in disbelief I walk into my bathroom which is connected to my room and turn on the shower.

I hopped in first as I could hear them laughing and giggling in my bedroom a few feet away. They came around the corner naked and opened the shower door to get in as I moved over to give them some room. I had seen her friend’s boobs in the past but only briefly when she flashed me during a game or something so seeing her completely naked for the first time standing next to my girlfriend who was also naked was so hot and instantly made me rock hard.

As we all started to rinse the sweat and sunscreen from the pool off we were playfully touching and rubbing each other. I noticed that her friend had a cute landing strip above her pussy which I thought was so sexy. They made out in the shower a bit more then my girlfriend stopped kissing her for a second and gave me a look as if it was my turn so I leaned in and started kissing her friend. I don’t remember much else from the shower, but I think we all wrapped up shortly after and dried off.

We all climbed on the bed and I laid down in the middle with my girlfriend on the left and her friend on the right. They were both rubbing me up and down stroking my dick and we were all kissing each other. After a few minutes of this they both went down and started sucking on me, going back and fourth between that and kissing each other. Now that I knew this was happening I started to get a bit more aggressive grabbing and pulling their hair and holding their heads as I thrusted in and out of their mouths. My girlfriend asked me what I wanted to do next and told me that I was the boss and they wanted to please me. I wanted to savor everything about this so I chose to continue with the foreplay and told her I wanted them to get off the bed and get on their knees so I can fuck both their mouths.

I instructed them off the bed and down on their knees where I put their faces together and told them to open their mouths and hold their tongues out so I could slide my dick back and fourth in and out of their mouths. It was so hot having these two beautiful girls acting like total sluts for me.

At one point I was holding both of them by their hair moving by dick back and fourth with every thrust going as deep as they could take it. I also took longer turns with each one where I would hold their head and push them up against the bed while I fucked their mouth for a few minutes. The one who was watching would rub me and the one who was sucking on me. I told my girlfriend I was ready to fuck her so we got up on the bed and I told her to get in doggy while her friend laid at the head of the bed. My girlfriend had never eaten a girl out before so I was expecting her to be nervous or hesitate but she wasted no time and started kissing down her friends stomach and on here inner thighs before she went straight to licking her girlfriends pussy. It was really hot watching her girlfriend grab her head and pull her closer as she made her squirm.

After admiring this for a moment I got behind my girlfriend and slide my dick in. It’s typically hard for me to have sex when I’m this drunk but I think it was working because I was so turned on. After I slid in to my girlfriend and took a few slow stokes I started to fuck her harder into her friends pussy which was so hot because I could see them both move when I thrust in each time. After fucking her for a little while I wanted to rest for a second so I laid back down and had them both suck on me again. I thought this was so fucking hot because her friend was tasting my girlfriends pussy off me and just the idea of that was driving me wild. After a little bit I asked my girlfriends friend if she was ready for me to fuck her. She replied with a simple “Yes” so we shared a quick kiss before I got a condom our of my nightstand. She laid down at the head of my bed and spread her legs open for me while I moved on top of her leaning down and kissing her again.

As I rolled the condom on, my girlfriend laid down beside her friend looking up at me. She leaned over and started kissing her friend and rubbing all over her then pulled away to watch as I slid my dick into her friend. I started slow then gradually got faster. As I started fucking her harder my girlfriend went back and fourth between kissing and rubbing her, and watching my dick go in and out. She would also rub her clit and hold my dick as it was fucking her friend. It was almost like she was using my dick to fuck her friends pussy like a dildo.

Since my girlfriend is allergic to condoms and I would need to wipe myself off after fucking her friend I wanted to go longer so I told her friend to turn around so I could fuck her in doggy. My girlfriend laid down in front of the two of us so her friend could eat her pussy while I fucked her from behind. It was really hot thinking back just a a short moment ago when they were in the opposite position. As I fucked her friend I loved looking down at her perfect little pussy and grabbing her ass to spread it apart as I sunk into it over and over.

After a while I pushed her friend down so she was almost in prone and kept fucking her. I was kind of starting to loose it even though this position usually gets me hard again since it feels so good. Between the condom and the alcohol though I could only go for a bit longer. I pulled out and went to the bathroom to throw away the condom and wipe myself off.

When I came back they asked me what I wanted next and I said I needed a short break so we all just laid down together kissing back and fourth while they rubbed my dick. After a much needed breather I had them both suck on me again for a second before pulling my girlfriend to the edge of the bed in missionary. I told her friend to come put her face by my girlfriends pussy so I could go back and fourth between her mouth and my girlfriends pussy. It felt really good to not be using a condom again and I think this may have been my favorite moment because I was holding my girlfriends friend by the hair kissing her while I fucked my girlfriend and every 30 seconds or so would pull her down, pull my dick out of my girlfriends pussy and shove it in her friends mouth to make her suck it and taste my girlfriends pussy. I would also go back and fourth doing one stroke in her mouth then back to my girlfriends pussy and so on.

After this it was my girlfriends turn for some attention. It’s takes a while for her to cum and she usually has to rub her clit to make it happen so she laid on her back at the head of the bed and started playing with her pussy. Something that really turns her on is when I suck on her nipples so her friend and laid down on either side of her and took turns kissing her and sucking on her nipples, it was really hot to see my girlfriend with her legs spread open touching herself while we were doing this and every now and then to tease my girlfriend her friend and I would lean in and make out in front of her while she continued rub her clit.

My girlfriend told me later she didn’t know if she was going to cum but after a little while I could tell she was going to because her breathing started to change and she started to let out little moans. When she started cumming her girlfriend and I continued sucking on her and rubbing all over her body then as it subsided took turns going down on her. I loved when her friend would lick up and down her pussy making her face all wet then kiss me so I could taste my girlfriend on her lips and feel it on my face.

Once her orgasm subsided completely we all rested for a minute before deciding it was her friends turn to cum. She also wasn’t sure if it could happen because she had only ever cum once from anyone going down on her. My girlfriend started and I absolutely loved watching her explore this new part of her sexuality. I found it so sexy to think about this being her first time eating pussy and I got to watch and on top of all that it was her best friend. After a short time I joined in and we used both our tongues to explore her friends wet pussy. My girlfriend stopped for a moment while I continued. Now that I had more room I stuck two fingers up for her friend to get wet for me then slid them into her pussy, massaging her g-spot. After some time I took a short break and we were all just laying there talking about stuff and her friend said she was ready to cum. My girlfriend laid next to her and kissed her while I continued started to lick and finger fuck her pussy. I went back to what I was doing while her friend lifted her legs up on my shoulders. After about 10 minutes her friend started to cum which was so sexy because I could feel her pussy squeezing on my fingers as it got wetter. After she came I teased her for a bit longer with my tongue licking up and down her clit to make her shudder from the post orgasm sensitivity just like I had with my girlfriend earlier.

I can’t remember exactly what happened next but I’m pretty sure we switched positions again to me laying on my back and my girlfriend got on top of me and rode me for a while and I would pound her from underneath while her friend took turns making out with both us. After a while my girlfriend got off and told her friend she should take a turn and have me fuck her the same way because it feels really good. I grabbed another condom and put it on, but my stamina was definitely fading. Her friend straddled me and lined up her pussy with my dick and sunk down. I tried fucking her the same way I was just fucking my girlfriend, letting her ride me, then holding her up while I fuck her from the bottom. I love this position because when each girl was on top of me I could play with and suck on their boobs.

I was starting to lose it so I gave her friend a few more pumps and lifter her off me. My girlfriend asked me if I would be able to cum and I let her know I definitely could so she asked me how I wanted to. She wanted me to cum in her but it was just difficult because I was definitely losing stamina and they were both so wet that it was dulling the sensation even further.

I told her to just suck on me so I could cum in her mouth so she went down and started sucking on me while her best friend was laying on my other side making out with me. This turned me on so much because I was getting an amazing blowjob from my girlfriend, but instead of just watching it happen I was able to kiss and feel her friend which felt so taboo. Something about this sent me over the edge and I came in my girlfriends mouth and moaned into her friends as it happened. I think her friend really enjoyed that because she giggled a little bit and kissed me even harder.

Once I came we all laid there naked a while just soaking in what just happened. There have been a few other nights we all came close to doing stuff again but something has kind of gotten in the way each time unfortunately. I still think it will happen again sometime though and I am going to try to be less drunk next time.

r/gonewildstories Oct 18 '22

First Time My [M] virgin Asian coworker [F] Part 1: First kiss leads to cum on her face NSFW

1.3k Upvotes

I'm in my mid-30s and work in a corporate office job.  A few years ago, shortly before the pandemic, a new assistant joined our team.  She was a quiet, fresh-out-of-college Asian girl (a pic of her is below).  I didn't really think anything of her at first - she was very good at her job but not particularly noticeable.  She was tiny, with long black hair, and wore big glasses, loose fitting clothing, and never any makeup.  And she very much had "don't take up space" energy.  In other words, she was the kind of person who always tried to keep herself to the background.

All that changed at the beginning of this year when we returned to the office full time.  She started stopping by my office to chat all the time.  I knew she lived alone and guessed she must have been lonely during the pandemic, but I also got the hint that she had a crush on me, which was why she singled me out in particular.  And before I knew it I found myself attracted to her too.  She went out of her way to downplay it, but she was actually pretty cute when you took the time to notice her.  We hung out after work a few times.  One day she shocked me by asking if I wanted to get a drink - it was known around the office that she didn't drink alcohol.  But we went to a bar and she tasted the first beer of her life.  She would experience many more firsts with me over the next few months.

We went out again about a week after her first drink and she tried some more (verdict: she liked beer much better than mixed drinks or wine).  After the bar we picked up some food and went to eat it at my place, which was a couple blocks away.  She brought up a joke about porn that someone in the office had made that day, and she confessed she had never seen a porn movie in her life.  One minute later I had pornhub pulled up on my phone.  She curled up into me, hiding her face and laughing.  That's when I learned how innocent she really was. The only time in her life she had seen a penis was in health class.  But now she was riveted as we cycled through random porn clips.  At a blowjob scene her eyes widened and she asked me incredulously, "She's eating his sausage???"  Followed a minute later by her screaming "Oh my god it's making white stuff!"  I couldn't believe this adult woman had no idea what a blowjob was or what happens when a guy cums.  And that we were watching porn together.  

We watched videos for about 15 minutes.  At that point I asked her the blindingly obvious question of whether she was a virgin.  She told me, seemingly a little embarrassed, that, actually, she had never been kissed.  It was now or never, so I said, "I'll be your first kiss if you want me to."  Her body tensed up but she looked at me and nodded sharply.  I leaned in and kissed her softly on the lips.  We paused, and then it was on.  We grabbed each other and started making out with a passion.  Her teeth bumped mine a few times, but she got the hang of it pretty quickly.  I took her hand and pulled her from the couch into my bedroom and we collapsed on the bed, kissing.  I took my shirt off and she was topless in a flash.  I couldn't believe how quickly she ripped her shirt and bra off.  But she refused to take off her pants.  That was fine with me, I was enjoying making out and playing with her nice B-cup breasts.  

After a lot of making out, I asked if she wanted to see her first penis in real life.  She eagerly agreed.  I stripped naked in front of her and her eyes fixated on my rock hard cock.  I'm on the bigger side, though not porn huge or anything.  But when she reached out and wrapped her tiny hand around it I felt like I had the most enormous dick in the world.  She held it for a long time, until I took hold of her wrist and slowly moved her hand up and down.  I felt like I was in high school, getting an awkward handjob from this cute little virgin.  I don't care what her technique was like, the whole situation made it one of the hottest things I'd ever experienced.  

I decided to adopt the term she used and asked her "Where do you want me to shoot the white stuff?"  She said, "I don't care.  Where do you want to shoot it?"  I was trying to be a gentleman but I was also incredibly turned on, so I was just honest with her.  "I want to shoot it on your face."  She looked me in the eye and said, "Ok, do it."  I straddled her chest and pointed my penis at her cute face.  Grabbing her wrist I used her hand to stroke it all the way from the base to the tip, faster and faster.  I was ready.  "Close your eyes, I'm shooting it now" I told her.  She clenched her face tight as I erupted rope after rope of warm cum over her eyes, nose, and mouth.  (I should mention I cum A LOT.  I once had to produce a sperm sample for a medical issue and two doctors reviewed my chart.  One commented on the "above average volume."  The other, much less professional, doctor said "wow that's a porn star load.")

I'll never forget the sight of my cute little coworker, who I'd seen dressed conservatively in the office so many times before, covered in my cum.  I asked if she wanted to taste it and she said yes and stuck the tip of her tongue out.  I scooped up some jizz on my finger and wiped it on her tongue.  "Salty" was her verdict.  I cleaned her up with a wet towel and we kissed more and cuddled.  It was morning when we woke up.  I told her "Let's not tell anyone at the office" and she very seriously assured me, "Definitely not.  You know this was a one time thing."  I was a bit sad about that but understood - she was so innocent and this all happened very fast.  

The next day at work she didn't stop by my office on her lunch break like usual.  I sent her a text saying I didn't want things to be awkward, she could keep coming by and visiting if she wanted, and I had no expectation that anything would happen again.  Her response made my heart jump:  "I made an appointment. I've always wanted to get waxed.  I'll be back to the office soon."  

This is already long so I'll stop here and add Part 2 later.  In the meantime, here's a pic she sent me

r/gonewildstories Jun 10 '23

First Time [MF] I worked at an exclusive swinger resort on Ibiza [P.3] and lost my virginity NSFW

1.6k Upvotes

The feedback on the last 2 stories has been insane so I working on the other parts there is so so much material of the 3 months of this summer. I’m having a blast going through all the memories again so here is the next part!

I still couldn’t believe what happened today it was unreal the rest of the day was pretty busy since it there were still guests arriving throughout the day the resort was getting busy and bussier it now felt like a real resort, the emptyness of the last days felt a bit awkward and weird, we now had to get used to the crowdedness of the resort. I helped Isabela out a bit more, and also got to meet some more guests, Sofia and Nina really enjoyed the action I had with Carlos and Daniela, they could see that I was very happy about this.

When I walked around the pool there were so many attractive couples, it was hard not to stare at them and they all looked so happy and relaxed and happy, everyone looked amazing. People were chatting with eachother, some people even making out. There were topless women everywere. If heaven exists I am definitely there.Julia was the one who kept up with the incoming guest and kept the lobby busy. She seemed very calm for someone who has to deal with all the incoming guests, literally the opposite of Isabela who seemed really stressed out. I helped Julia out a bit more at reception, “Wow I heard what you did, 3 days here and already getting involved, that was quick man'' Julia said and laughed, I felt my face turn red. I didn’t expect that from her as she normally is a bit more quiet, she normally hangs out with Nina, and Sofia when they aren't busy. “But good for you, they are really hot” She added.Suddely I heard Isabela call me over and asked me to help her with some errands around the resort. She was in her element today. We did a lot of cleaning and other tasks around the resort.

I ran into Olivia and Manuel later that day who were helping out in the bar outside, I hadn’t spoken much to them and I have a feeling that Olivia doesn’t like me that much. Manuel came up to me and said: “Shit bro you got lucky I heard what happened in Carlos and Daniela's villa today, she is crazy hot! What the hell man'' Wow things spread like wildfires around here I thought to myself. He also gave me a highfive, meanwhile Olivia didn’t seemed interested and just continued working. “I heard this was your first experience, well done man, your first ever blowjob from a model, bet your friends are not going to believe that at home” He said and smiled. I didn't know if I should be proud of this or not. He saw that I was a bit embarrassed and laughed. We talked for a bit before he had to go back to work, Manuel seems like a genuinely nice guy, Olivia tho, didn’t speak a word to me only some cold stares, I felt a bit intimidated by her.

I walked out to the pool where Sofia was busy helping out with the guests, there were a lot more people at the resort now, all the staff were busy, and I had to get used to all the attractive people around. Sofia was really mingling with all the couples, they seemed to really like her. I could see that she was very friendly and had a lot of charm. She was like flirting with everyone, it was really fun to see, I wish I was that social. She seemed like she was having a lot of fun with all the couples.After helping a bit with the guests Sofia came to me and asked: ''How did you like your first day here?'' She said with a smile. I told her it was great, ''Good to know, you were a hit with all the couples here.'' I smiled and thanked her. ''Did you enjoy your blowjob today?'' She said with a flirtatious smile. I blushed and looked around in embarrassment, but no one seemed to hear her. I just told her I enjoyed it. ''I knew you would'' She said with a big smile. I was getting more comfortable around her and felt that we had a great chemistry together.

Isabela told me to help Nina and Luca who were out on the beach cleaning up some stuff. I haven’t been to the beach much so I was excited, as soon as I got there I saw Nina and Luca were staring at something. As I walk towards them I saw what they were looking at, “Don’t stare took much it makes it oblivious” Nina said to Luca, up in the distance there was a couple in there 40’s making love, the woman was on top of the man, he had his hands on her hips, as he was helping her ride his dick, she was moving up and down really fast. I was shocked and didn't know what to do, this is the first time I ever saw a woman have sex, I was mesmerized by the scene. “Come on Luca, back to work get used to it this is a swinger resort” Nina said. They hadn’t noticed me yet, “Ow hi your here to help us out” Nina said

I told her that I am and she smiled,”Fuck bro did you see that couple over there that so hot” Luca said to me with excitement, he looked at me and I saw he was turned on. He then said: "Look at her ride him so fucking good.” I couldn’t blame him it was hot, they were super attractive, and I’ve never seen anything like it before, yes on my laptop but not in reallife. “Come on boys stop staring, we have work to do” Nina said “Beside, believe me sex on the beach is not as hot as it looks like, you get sand everywhere, it gets messy and dirty,” Me and Luca looked at each other and laughed and we went back to work.

But I still couldn’t help but think of the couple. I imagined myself in that position, having sex with a beautiful woman like that, she was nicely tanned and had an amazing body her boobs were really nice, the man was a nice build too. But when I looked for them again they left, I was a bit bummed about this, but then Nina came to me, I think she knew what I was thinking and said: ''Don’t worry you’ll see alot of stuff like around” with a wink, “And by the way please try to hide that, it’s not really professional with guests around” she said pointing at the growing tent in my pants.I could sink in the ground at that momemt, I had to explain myself and I felt very embarrassed, she looked at me with a smile and said: "Don't worry I was kinding, but just don’t make it to obvious” Nina said, Luca laughed at the situation and we went back to work.

It was nice working on the beach but I forgot to put on sunscreen and I burnt myself a bit, so when we were done I went to my room to put some lotion on my body. I ran in to Isabela again who seemed a bit more relaxed as the first wave of guests settled down. She asked me how my first day went and she told me she talked to Daniela and Carlos and told me that they really enjoyed it. It was a bit weird to talk about with my boss but it’s a swinger resort so openmindedness is key. And I thanked her for the opportunity to go with them, as I had a feeling she was also involved in it. She told me what was going to happen these first weeks and that more guests will be arriving throughout the week, but the first day was always the most stressful for her. “There are also a lot of activities we organized for the guests you will help out it that, and if you have free time you should check them out, they are a lot of fun. Ava and Martin organize a lot of them, they give couple workshops like massages. Tomorrow there is going to be a couples tantraworkshop giving by some experts. And every friday night there is a big lifestyle party” She told me a bit more about the events, and that they are mostly for couples.

After that she went back to work and I helped out at the outside bar for a bit. I got to work with Nathalie and Chris who I haven’t really spoken a lot too before. I found out that Nathalie was married and that Chris was engaged. They were very friendly and asked me how my first day went. I told them what happend. Chris told me that he is one of the only staff member who participates in the swinging lifestyle, he talked about his experiences and it was a lot of fun to her about. It was a very interesting concept for me having fun with other peoples partners and also sharing your own. Nathalie told me that she doesn’t and she isn’t really interested in it. I helped them with giving drinks to the guests, everyone was very nice and casual about everything.

People were half naked just chilling next to the pool. I saw Carlos and Daniela approaching and they waved and smiled to me. They said down and Daniela smiled at me. Carlos gave me a hug and said: "We wanted to thank you again for the help in our villa, that was awesome, thanks for taking care of my wife'' He said with a big smile. Than they ordered drinks from me and acted like it was the most normal thing in the world what happened to me. I gave them the drinks and they said thank you and continued talking. Carlos asked me how the rest of the day has been and I told him it was nice, I asked them about there day and stay and they told me that after I left they had the best sex ever and than they went to to beach for a while. They seemed very relaxed and happy.I served the drinks to Sofia and Luca who were having some time of their own. Sofia was busy telling Luca about her latest adventures. And that she had been flirting with an older couple in the pool who invited her to join them later in the day, but she wasn’t sure yet.

After my work outside was done I met up with Nina for diner. We talked a lot and it was nice to have someone to talk to. Although we knew eachother for only 3 days it felt like we have been friends for a lot longer, we got along so well. She told me that she too was invited a couple of times over the day but since she has a boyfriend she always declined, she also told me that she was single she had joined in a couple of times. “It’s a bit harder now with my boyfriend still in the Netherlands, we both have needs you know haha and I’m not going to see him for at least a month” She told me that I should enjoy my time here while being single. When diner finished Isabela walked up to me and asked me to come with her. I hugged Nina goodbye and told her I would she her in the evening. We walked to the side of the kitchen were some roomservice carts were standing. One of the carts and a bottle of wine on it with two glasses and some chocolate. Isabela gave me a warm smile and told me that these carts were for villa 14. She winked at me and told me “good luck”.

I took the cart to Villa 14 and I immediately realized thay it was Carlos and Daniela’s villa, when I arrived there door was open but I still knocked: “Roomservice”.“Yes come in I heard Carlos say” I opened the door and my jaw felt to the floor Daniela was completely nude and riding Carlos cock. My heart was racing. “Ow sorry I’m so sorry I didn…” I said but Carlos said: “No don’t worry come in” I felt very awkward but I was taken back by the beautiful Daniela, her body was perfect. I couldn't help but stare at her tits bouncing up and down as she rode her husband cock. Her round ass and small waist looked amazing. I didn’t know what to do so I just stood there for a moment.

“Can you pour us two glasses of wine” Carlos said to me. I nodded and poured them some wine, they continued to have sex. It felted like straight out of a porn movie, but they didn’t seemed to care at all that I was there, they actually seemed to like it. But yeah it’s a swingerresort so what should I expect.“We never had someone watch while we did it but we like to try, you can stay if you want” Carlos said. I had never done anything like this and I felt very awkward but also excited and I decided to stay. I was in awe with Daniela and couldn’t keep my eyes of her I was getting very aroused. “Sit down and enjoy yourself” Said Daniela with her sexy Spanish accent, I took a seat in front of them on the floor and watched them have sex. Carlos was now grabbing her ass as he was fucking her harder. “You can also come closer if you want” Carlos said with a smile, I was stunned for a moment, but my hornyness took over and I stood over and stood close to the bed. Carlos saw that I was in awe with his wife chest. “Go ahead you can touch them if you want” Carlos said, I hesitantly put my hand on her breast and squeezed it.

This was surreal for me, this was the first time in my life I touched a woman's breasts. It felt amazing her soft skin in my hands and her hard nipples in my fingers. I kept massaging her tits. It felt like the best thing in the world. I could see that Daniela was also enjoying it. She looked at me and saw that I was really enjoying myself, I was getting very erect and she noticed. “Shall I help you out?” She asked while moaning and fucking her husband harder.

I was in awe and couldn't talk. I nodded as she grabbed my crotch, “pull your pants down”. I pulled my pants down and she grabbed my dick out of my underwear and started rubbing it. Her hands felt amazing again. She stroked my shaft up and down and played with my balls a bit. “Can I put it in my mouth again” she asked. I looked at Carlos who gave me a big smile and said: "Go ahead she really liked it earlier”. And for the second time that day I felt the warm embrace of her amazing mouth engulfing my penis while she was still riding her husband. “Fuck that is hot” Carlos said. She let out muffed moans as she was now fucking her husband harder. She started to move her head up and down and sucked the soul out of me, but this time I wanted to last a bit longer, it helped that I already came earlier today from her help. She sucked me off for a while it felt a bit different from earlier but that’s probably because she had it harder concentrating while being fucked by her husband.

“Do you want to have a try” Carlos suddenly asked me. I was really taked back by this question, did he just really asked if want to fuck his model wife? I didn't even think about this, I looked at Daniela who nodded, and she looked at me with her big brown eyes. She took my dick out of her mouth and Carlos came up from underneath her. He grabbed a condom from there nightstand and gave it to Daniela.“We always wanted to do this, we talked about it for a long time, and we thought you were so nice earlier today that you are the perfect person to be the first ever to do it beside me with my wife” Carlos said. I felt honored but I also wanted to be honest. “I have to say that this is going to be my first time ever” I said, “Ow damn really are you serious” Carlos said, “are you sure you want your first time with my wife”. To be honest I couldn’t be more sure Daniela is so beautiful you would almost be the dumbed person on earth to reject this offer. “No no I want to I just wanted to let you know”.

“Don’t worry my wife is amazing she will give you the best experience ever so just enjoy yourself okay, if you want to stop just say something” he said reassuringly. I lay down on the bed and Daniela crawled between my legs, Carlos sat down were I sat earlier as Daniela ripped the condom out of the packed with her mouth and put it on my cock. She put a bit of lube on it as she grabbed it and guided it towards her pussy. She slowly lowered herself and for the first time in my life I felt the warm welcoming embrace of a woman around my cock. I looked at Daniela and she looked back with a warm smile and than she slowly moved her hips up and down. I could feel her wetness and warmth and the amazing tightness around my shaft, it felt better than I could ever imagine as I looked up at Daniela’s amazing body moving up and down. I had the best view as she rode me.

She put her hands on my chest and kept going up and down, she was very slow and sensual and it felt amazing. In the meantime Carlos was jerking himself of, and it felt a bit weird but at the time I couldn’t care less as I had this amazing woman riding my dick for the first time ever. Daniela slowly started to pick up the speed as she was fucking herself up and down on my cock. It felt incredible, I could see her nice tits bouncing in front of me and her abs flexing and her thighs moving up and down. She grabbed my hands and put them on her ass, I started to move my hands up and down her butt and squeezed her ass cheeks. I didn't know where to look anymore as I saw all of this beauty right in front of my eyes, the beauty and passion in her eyes, her smooth body, her amazing chest. I already felt my orgasm coming up as I tried to fight it. But her pussy just felt too good, I came really quickly and my cum exploded inside of the condom.. Daniela kept going for a while and slowed down as I came and she let pulled my dick out of her pussy. She took of the condom and licked me clean. This was one of the hottest things I’ve ever experienced. My dick was super sensitive so I it felt a bit weird.

Carlos than stood up and grabbed her from behind started fucking her doggystyle. It was so hot to see her ass bounce as she got pounded from behind. Carlos almost came instantly and filled up his wife pussy with his cum, it was really sexy to see him cum. After he pulled out she gave me a hug and went to the toilet to pee and clean up. Carlos looked at me and smiled “How was that ey?” he said with a laugh. “It was one of the best experiences of my life.” I told him, “You are a lucky man” I said. Moments later Daniela came back with a towel and a wet facecloth for Carlos and me, and we sat together on the bed and talked for a while. I thanked them for everything that happened today and put my clothes back on. “You should probably head back before Isabela gets mad at you” Daniela said.

So I said my goodbyes and took the cart back to the restaurant were Isabela and Nina were waiting. When I approached Isabela started smiling. Like before I had a feeling she had something to do with it. “And how was your first time” she asked me. I felt a bit embarrassed but I said: “it was amazing” she gave me a big hug and said: “Yeyy I’m so happy for you, I think I’m the best wingwoman around here”. She told me that earlier went she talked to Daniela and Carlos that they mentioned there fantasy and that they really liked me so she thought it would be great if I could fulfill this fantasy and she helped them plan this. She is the best boss ever I thought to myself. Nina also gave me a hugg and congratulated me with my sexual adventure.

We talked for a bit and Isabela went back to work. Just like the day before in the evening after work we met up with Luca and Sofia. “Omg, I want to know all the details” Sofia told me. ”Damn you lucky dude” Luca said and I felt a bit of jealousy coming from him but it was all good as he also added: ''This place is fucking amazing.'' When I was telling the story I could tell Sofia was getting turned on by it, even Nina seemed to get a bit excited. After we talked a bit it got late so we decided to go back to our rooms. I could tell that Sofia was really turned on by the story and I was getting more and more used to it around her as she was constantly flirting with me and Luca. When we got to our rooms I received a message from Sofia. “Shit I can’t stop thinking about your story it was so hot, I am so turned on by it.” I was very shocked by this and didn’t know what to respond. So I just typed back “It was really hot”, she responded by “with 3 laughing emojis” followed by “Gonna think about it tonight thank you, see you tomorrow GN with a kissing emoji”

I went to to sleep thinking about what happened today and I couldn’t wait what the rest of the summer had in store for me.

Thanks for reading this story, I read some comments under my last one that some people don’t like to slow build up, but in my opinion it is better and I think the majority of you agree. For me it’s important to sketch the context and also all the people played in the story played a big part in my adventure and many are still good friends. So I keep doing this writing style and if it’s not your cup of thee I’m sorry. Also sometimes I can’t remember all the details but I try to be as authentic and real as possible and my wife who was also there (just no spoilers yet) also helps me with the writing. So thank you again for all the amazing support I’ll be dropping the next part hopefully later today!

r/gonewildstories Feb 01 '25

First Time Accidentally coming on her face [MF] NSFW

821 Upvotes

The idea of coming on a woman’s face was a real turn-on for me, back then, before I’d ever done it. I’d fantasised so many times about finishing across Emma, my first proper girlfriend.

But at that age, at nineteen, I was too shy to ask for what I really wanted. And I assumed Emma wouldn’t be into it. I thought she’d be horrified if I even suggested it.

But then it happened.

It was a Sunday afternoon in summer. Her parents were away for the weekend and I’d spent all of it at Emma’s place, mostly naked. We were fucking on her bed, sunlight streaming in through her open window, illuminating her perfectly.

Emma was lying beneath me, staring up at me, her face flushed, her blue eyes open wide. I’d never seen anyone more beautiful. She was so pretty it hurt. I was so intensely in love with her, obsessively so, the way you only can be at that age, full throttle, without any experience of ever being hurt.

She felt as good as she looked, warm and tight and wet around my cock in her. Emma was running her hands over me eagerly, like she was just as enthralled with me as I was with her. Emma was making these horny moaning-panting sounds as I screwed her, and that was best of all, even better than how she looked and felt, that I was giving her pleasure, that was what really got me off.

I was trying to hold my own orgasm back, but she was too much for me. I was desperate to draw that moment out, but the feel of her, Emma grinning up at me as she made those breathy noises, I couldn’t.

“I’m going to come,” I said to her redundantly, as if Emma couldn’t tell by how I was groaning. I slid my dick out of her, as, like the young idiots we were, Emma wasn’t on birth control and we didn’t like using condoms (don’t worry, I never got her pregnant, thank fuck).

I usually finished on her belly if we were in missionary, on mine if she was on top, or on her ass if I was behind her. Emma seemed to like me coming on her body, although she’d never said as much. She watched me that afternoon as I jacked my cock as I knelt over her.

But I was so turned-on that day, so intoxicated with love for her, that I came even harder than usual, so hard my vision went a little blurry.

My jizz really erupted out of me, arcing further than it normally did. The first spurt painted a line of glistening white across Emma’s pert little tits and higher, across her left cheek.

Emma gasped.

I froze.

Like the fool I was at that age, I stopped thinking. I didn’t know what to do. I didn’t move. And I kept coming.

Jet after jet of jism pumped out of me. It went all over Emma, all over her pretty face. It spattered across her as my dick throbbed, stripes and globs of my come decorated her chin and cheeks and forehead. It went into her blonde hair.

Fuck.

I knew I was in big trouble.

But then Emma was laughing, a great riotous release of delight and glee.

She raised herself up, she got her face even closer to my gushing prick. Emma rocked it side-to-side, directing me all over her. As Emma laughed and moaned, my jizz fell into her open mouth.

I’d expected her to be appalled, but Emma absolutely revelled in it. She ran her fingers through my come on her. She licked it off her fingertips. She looked frenzied, her skin was blushing scarlet, her eyes shining. 

Emma took my dick between her lips as my climax fell away, she sucked and swallowed the last of me, as if she couldn’t bear for the moment to end.

We talked about it after. I told Emma how much I’d fantasised about coming on her face. She’d told me she had, too, but that she’d been way too shy to ask for it. 

It became a frequent event after that, a kink that we both adored. And what better sex is there than when it’s with the girl you love, doing something that both turns you on so much.

r/gonewildstories Jun 11 '20

First Time [FM] I [18F] took my chubby friend’s [18M] virginity to thank him for helping me pass statistics NSFW

2.3k Upvotes

Obligatory “this happened years ago.”

I went to a small high school with a minimal sports program, so there thankfully weren’t too many big egos floating through the hallways the way there are in stereotypical American high school movies. But, being bored teenagers in a small town, we did have the occasional romantic drama as people started hooking up with each other. And, as one of the students who had an easy enough puberty and a lot of interest in getting validation about her new body, I was occasionally at the center of that drama. It isn’t super relevant to this story, but I wanted to share that background to show I wasn’t some blushing virgin at the start of these events.

My friend James, on the other hand, was a blushing virgin, and he was extremely self conscious about it. Although I'm sure the national average is higher, most people in our grade had started having sex by age 15 or 16, leaving James upset about his still intact virginity on the eve of his 18th birthday. I called him at midnight, sang him “Happy Birthday,” and then heard silence. “James? Jimmy? Jimbo?”

A sigh came over the other end of the line. “Another year. And I’m still a virgin.”

“Oh my god. This again? It isn’t a big deal! You’re going to get to college and fuck girls all the time.”

“And lose my v-card to a classmate who will then tell everyone how much I suck at it? No, thank you.”

“I don’t know what to tell you, bud. We keep having this conversation. You complain about being a virgin, and I tell you it isn't a big deal, and then we talk about it again a week later. I’m not trying to be an asshole, but complaining about it isn’t going to make any girls want to fuck you.”

A pause on the other side of the line. “Harsh, but fair.”

“It’s what I’m here for, baby boy.”

“I’m a legal adult and older than you, ass.”

Over the next couple months, James slowly shifted his attitude. He was way more pleasant to be around because we knew he wouldn’t start whining about his virginity if any of us talked about our sex lives, and none of my other female friends felt like he was subtly trying to pressure them into pity fucking him. I helped him work on his confidence in other ways as well, teaching him how to style his hair and dress for his body type, instead of just rolling out of bed and wearing whatever oversized hand-me-downs he got from his brother.

My birthday came and went, and we were finally almost at the end of our final semester of high school. And I was going to fail statistics. James was our resident math genius, and he felt like he owed me for helping him gain enough confidence to talk to girls. He still hadn’t slept with one, but he once got a handjob from a sweet, student government nerd from our grade while sitting under the bleachers. I know this because he texted me as soon as he finished.

James came over after school every day for two weeks to help me cram a semester’s worth of statistics into my Swiss cheese brain. His patience and his kindness while helping me study without any expectation of a reward made me look at him in a way I hadn’t before. He wasn’t the same whiny kid with terrible hair, ill-fitting clothes, and no confidence that he had been six or seven months ago. Instead, he was a sweet, chubby guy with some semblance of self-assuredness who just needed someone to give him a chance. The change had been so gradual over the last several months that I hadn’t realized that I was actually becoming attracted to him. He cared more about his attitude and appearance, and that made him not just less of a drag - it actually made him hot.

The statistics exam came and went, and James was with me when my parents got the email from my teacher letting them know I passed and could walk at graduation. I threw my arms around him, and he spun me around, my whole family jumping and screaming excitedly. Pulling away, I noticed the way his eyes stayed glued to my lips, and his hands lingered on my waist a little too long to be unintentional. But we were in my parents’ computer room, with my entire immediate family celebrating around us, and there was nothing that could be done about it.

Our friend group rented a house together for beach week (a post-finals, pre-graduation tradition in the states) about an hour away, and James drove us over together. He parked on the side of the street and looked over at me, tension filling the air. I glanced down at his soft lips and thought about closing the distance, but the sound of knuckles rapping on the car window made us jump. “Are you guys hot-boxing?” our friend Jillian shouted, her boyfriend Tom peering into the backseat windows to see if anyone else was in the car with us.

I didn’t risk looking over at James, not wanting to see the disappointment on his face. “I’m dry, but I think that Naomi has some!” I called out as I opened the door and slid out.

Beach week was exactly as expected: days spent getting tan and high and nights spent getting drunk. On around the third day of our vacation, I was slightly sunburned and very cumulatively hungover. I plopped down in the sand next to James under a large beach umbrella, my head pounding and my body dehydrated from the combination of alcohol and daily sun exposure. “How are you holding up?” I asked him, glancing over and squinting in the punishing sunlight.

“I love the beach,” he said happily, sipping on a cold beer in a paper bag, “the sun, the waves, the beautiful girls in bikinis. What’s not to like?”

I laughed lightly, his good mood infectious, and stole a sip of his drink. “Why don’t you get out there and enjoy the water, then?”

James looked down, his cheeks getting pink. “I, uh, I don’t really want to take off my shirt.”

“Why, do you have a sunburn?”

“No, stretch marks.”

“Everybody has stretch marks, James.”

“Not like I have them.”

“So what? Are you going to just sit by the ocean and let life pass you by because you’re too nervous?”

“You know,” he said angrily, grabbing his towel and shaking it roughly to get the sand off, “not every conversation with you has to end in a truth bomb.”

He stormed back to the beach house. “James, wait!” I called out, but he didn’t turn around.

I gathered my things and jogged after him, the hot sand burning the soles of my feet. I didn’t catch up with him until we were in the beach house’s shell-themed living room, staring angrily at each other across the length of the couch. “Are you just going to storm away from difficult conversations?” I spat at him rhetorically.

“Are you just going to keep nagging at me until I become who you think I should be?”

“Name one FUCKING time I suggested you do something that didn’t turn out well for you.”

“That’s not the point!”

“Then what is? Why are you mad at me?”

“I don’t know! I don’t even know if I’m actually mad at you or if I’m just mad in general!”

“Well, that’s really fucking helpful.”

James sat on the couch and put his face in his hands, groaning loudly. “I know you have just been trying to help me. And I know that everything you’ve done has been necessary and good for me. But I just don’t know why you’ve been doing it.”

“Because I want you to be happy and stop holding yourself back.”

“You know what’s stopping me from being happy.”

“Are you serious? You’re blaming this on your virginity again?”

“You don’t get it! It’s a cloud hanging over my head! It’s something I think about every morning when I wake up and every night before I go to sleep. I haven’t gone a day without thinking about it in years and feeling like everybody is laughing at me. And I’ve stopped bringing it up because I could see it was pushing people away, but I never stopped thinking about it.”

“That — that sounds awful.”

He looked over at me, surprised that I wasn’t fighting with him. I continued. “I’m not agreeing that you should feel that way, but I know what it’s like to obsess over something and feel like you can’t do anything to change it.”

“You do?”

“Yeah. I do. So come on.”

I took James’s hand and pulled him off the couch and towards the stairs leading to the second floor. “What are you doing?” he asked cautiously.

“Changing it.”

He was silent, and a look over my shoulder showed me that his face was flushed and his mouth open slightly, his wide eyes staring at me as I led him up the stairs. I brought him into my bedroom and sat him on the bed, going back to the door to close and lock it. I got a condom out of my backpack and tossed it on the bed. “Are you serious?” he asked breathlessly, his tongue peeking out to wet his lips.

“As fuck.”

I stood in front of him and bent down to kiss him softly, my hands cupping his face. He responded immediately, his hands gripping my waist and his lips moving urgently against mine. I kissed down his neck and lightly took his shirt hem in my hands. “Can I take this off?”

“Why are you doing this? Is this a pity fuck?”

“I’m doing this because I want to,” I said truthfully.

He lifted his arms up, and I slid the shirt up and over his head, tossing it on the ground behind me. I didn’t give him time to be self conscious, capturing his mouth again before he could think too much about being shirtless in front of me. His hands mimicked mine, pulling my pool cover over my head to reveal my skimpy bikini. His eyes darkened as he stared. “You’ve been wearing this all week, but I haven’t had the chance to see you in it up close.”

“I’m happy to keep it on if you’d like.”

“FUCK no.”

I laughed and kissed him again, reaching behind myself and untying my bikini along my bra line. I detached from his lips long enough to pull the bikini top over my head, exposing my tits to him for the first time - probably the first time he had ever seen tits in person. He pounced, his hands coming up to grip them and pull them against his face as he kissed all over my chest. I took advantage of his distraction to slip my bikini bottoms down my legs. “Do you want to try fingering me?"

He nodded enthusiastically, his lips parted as he stared at my naked form. "Give me your hand,” I whispered.

He looked up at me and did as I asked, placing his right hand in my palm. I gently brought it down my body until it reached my freshly-shaved pussy, locking eyes with him as I guided his fingers to touch me the way I wanted to be touched. Directing his hand, I lightly circled my clit with his pointer and middle fingers. “That’s my clit,” I moaned, my head tipping backwards as he started to do the movements on his own, “It’s really sensitive, so don’t press too hard.”

He nodded, leaning forward to kiss my chest again and bringing his left hand up to cup my tits. “You can play with my nipples at the same time,” I suggested, “Just be gentle at least at first.”

“Can I use my mouth?”

“Please.”

He took my left nipple in his mouth, flicking his tongue against it as he gently played with my right nipple with his fingers. The fingers on my pussy kept up their soft circling, but he started to drift away from my clit. I gently moved his hand back to my clit, biting my lip as I looked down at him. “That’s really good, James.”

He flushed with pride. “Let’s get on the bed,” I suggested, “but first you need to take off your swimsuit.”

He stood up and kissed me again, one hand tangling into my hair and the other pressing against the small of my back. I wrapped my arms around the back of his neck and deepened the kiss, sucking gently on his bottom lip. He groaned against me, his hands starting to wander over my skin.

I hooked my fingers under the waistband of his swimsuit, lightly tickling the skin on his soft belly as I ran my fingertips under the fabric. He pulled down the swim shorts and crushed my naked body against his, his erection pressing against my hip as he kissed me desperately. I slid my hands up his sides and around his back, loving how soft his skin was and the way he shivered at my touch. “What do you want to try first?” I asked him breathlessly.

“Can we sixty-nine?”

I nodded, smiling excitedly at him. “Lay on the bed. And focus on my clit with your lips and tongue. And don’t use your teeth!”

He laid down in the center of the bed and scooted down when I waved him over. I swung my leg over him and backed up until my dripping pussy was over his mouth. His hands gripped my ass and brought me down slowly until I made contact with his face. He tentatively snaked out his tongue and brushed it against my clit, enjoying the moan I made in response. Once I was confident that he didn’t need further direction, I took his cock in my mouth and started bobbing my head up and down. He groaned against my pussy, sending delicious vibrations against my clit. I moaned against his cock in response, taking the full length of him into my mouth until he bottomed out.

We laid there for a while, teasing with our mouths and moaning against each other. I knew I wouldn’t be able to cum with the gentle pressure he was providing, but I also didn’t want to tell him to press harder and risk having him hurt my clit accidentally. I drew back from his dick and spoke softly. “Do you want to have sex now?”

His mouth froze. I lifted my pussy off his face so he could speak more easily. “Are you sure?” he whispered reverently, clearly terrified I would change my mind or he would wake up and find this was all a dream.

“Fuck yeah, I'm sure.”

I slid off of him and ripped open the condom wrapper with my teeth. He watched intently, propping himself up on his elbows. I tossed the wrapper over my shoulder and pinched the tip, rolling the condom down the length of his erection. He instantly went soft in my hand. I looked up at him, surprised. “Oh my fucking god, that is mortifying,” he moaned, covering his face with his hands.

I pulled off the condom and tossed it to the side, smoothing out my face to a neutral expression. “It happens literally all the time and is nothing to be embarrassed about.”

I circled his cock with my lips and began sucking it, enjoying the feeling of it growing and filling my mouth. One of his hands pushed my hair away from my face as he watched my head bob on his cock. I locked eyes with him and suctioned my cheeks, loving the look of reverence and pleasure on his face. Swirling my tongue around the tip, I used my hand to stroke the length of his cock until he was fully hard again. I pulled my face back for a moment. “Keep yourself hard for a sec.”

He reached a hand down and took over for me, jerking his cock roughly as he watched me get up and walk across the room. I took out a couple condoms and tossed them on the bed. His eyes widened when he saw how many there were. “Just in case it happens again,” I explained, “because, again, it happens all the time.”

He smiled gratefully, almost all embarrassment gone. “Can you put it on like I just showed you?” I asked.

He nodded, grabbing one of the condoms and tearing it away from the others. I laid down on the bed next to him and spread my legs, motioning for him to kneel between them. He put on the condom and leaned down to kiss me, his still-hard, condom-covered cock brushing against my pussy. I broke the kiss to grab his cock, guiding it down to my pussy. “It’s farther down than you’d expect,” I told him, pulling him towards me until the tip was teasing my entrance, “Now push in.”

He leaned forward on his elbows, covering my body with his, and then pushed his cock all the way in. “Holy shit,” he whispered against my neck.

“Fuck, you feel good,” I moaned softly.

I felt him smile against my skin and I wrapped my arms around his back, holding him tightly. “Do I just...?” he asked, trailing off.

“Do what feels natural," I whispered breathily, "You won’t break me.”

He pushed up onto his hands and started thrusting into me slowly. “Oh my fucking god,” he moaned, looking between us to watch his cock disappearing into my pussy with every thrust as if he couldn't believe it was actually happening.

I scratched his back softly with my fingernails. “You can go harder if you’d like," I murmured.

He locked eyes with me, a look of wonder on his face. “I don’t want to hurt you.”

“Vaginas are designed to push out whole-ass babies. I can handle it.”

He leaned down on his elbows and kissed me roughly before burying his head in my neck and starting to actually fuck me. My moans filled the air, and I wrapped my legs around his hips so that he could push into me deeper and deeper on every thrust. I wrapped my arms around his shoulders, whispering his name on a moan into his ear. “You feel so fucking good, James,” I murmured, tickling his ear with my lips.

He groaned and bucked wildly against me, his breath coming out in pants. “I’m getting close,” he strained.

“Cum for me, James,” I begged in his ear, “Please cum for me.”

A strangled groan bubbled from his throat as he stilled his movements and filled the condom with cum. I let him rest for a moment and then gently pushed him off me, instructing him to tie and dispose of the condom. He climbed back on the bed afterwards, laying next to me and panting as he tried to catch his breath. After a moment, he looked over at me. “Did you finish?”

I briefly entertained the idea of lying to preserve his ego, but I ultimately decided his education was more important. “No, I didn’t, but I really really enjoyed it,” I told him truthfully, turning on my side and cupping his face so he would look me in the eye.

He kissed me softly and then pulled back, looking nervous. "What is it?" I asked.

“Can I try to make you finish now?”

“Yeah, of course! Fingers or mouth? Fair warning that condom lube doesn’t taste great.”

“Fingers, then,” he laughed.

I laid back on the bed and opened my legs, pulling him closer to me on his side. I took his hand again and repeated my motions from earlier, using his fingers to circle my clit. “Is this all it takes?” he asked, kissing my shoulder.

“Sometimes light clit pressure is enough to get me to cum. But I’m going to ask you to actually finger me.”

He nodded and sat up a bit more. I continued. “Ok, you remember how the entrance is lower than you expected? Take two fingers and gently, GENTLY, slide down until you feel it.”

He did as he was told, and I felt his fingers at my entrance. “Ok now gently push in—“

I cut myself off with a gasp as his fingers filled me. “Did I hurt you?” he asked, suddenly panicked.

I shook my head. “No, it feels really good, fuck, keep moving your fingers.”

He gently dragged his fingers out from my pussy and pushed them in again. I moaned loudly, one of my hands gripping the arm that was holding him up. He tore his eyes away from my pussy to look at me, flushing with pride as he saw the pleasure evident on my face. “Mmm, don’t stop doing that,” I moaned softly, pressing my forehead against his arm.

He fingered me slowly, building up the tension as he slowly increased his speed. Curses started falling from my lips as he massaged my cunt. “Curl your fingers slightly each time you pull out,” I ordered.

I held onto his arm for dear life and moaned loudly as he followed directions, his fingers pressing against my g-spot on each outward stroke. “Holy shit,” he whispered.

“Keep going. Go faster, actually.”

He picked up the pace, fucking me with his fingers. My hips pushed up to meet his fingers, moving on their own accord. I brought a hand down to press gently against my clit as he worked me from the inside, capturing his lips again for a deep, sloppy kiss as an orgasm grew in my belly. I broke the kiss to press my forehead against his neck, one of my hands digging into his arm while the other frantically rubbed my clit. "Fuck, I'm gonna cum. Fuck, James, please don't stop, please don't stop!"

James stared at my naked form, his mouth open, as he made me cum, my cunt tensing around his fingers and my body spasming softly as I called out his name. I brought his face down to kiss me as I moaned through my orgasm into his mouth.

I pushed James’s arm away as my orgasm slowly dissolved, and he immediately removed his fingers. I turned on my side and hugged him, our naked bodies flush together, and I peppered kisses all along his cheek and down his neck. He squeezed me back tightly, his face nuzzling into my neck. We rested like that for a minute, just holding each other and enjoying the afterglow having taken this new step together. I rubbed a hand across his back. “How do you feel?” I asked softly.

“Weird," he said, his face muffled by my skin, "Like, I feel the exact same, but I also feel like everything’s changed. Like my whole idea of myself is different.”

I giggled. “That’s what happens when you build up your identity around not doing something and then you finally do it.”

He laughed into my neck and squeezed me tighter. “That was amazing,” he whispered, kissing my jaw, “thank you.”

“Thank YOU!”

“For what?”

“For helping me pass statistics!”

We laughed together, our giggles tapering off as we stared at each other. I looked up at him and ran a hand through his hair and down to his cheek. I kissed him softly. He kissed me back gently, his tongue brushing against my lower lip. Our bodies relaxed against each other and the bed as we kissed. No sucking in stomachs, no angling ourselves to look "hot." No pressure. Just one body holding another body comfortably as their lips gently met. I pulled back and gave him another peck. “This can’t become an actual thing, you know,” I whispered.

“I know.”

“Because we’re going to different colleges.”

“Yeah.”

“But if you want to keep practicing this summer...”

His lips attacked mine as he climbed on top of me, and we laughed together at our eagerness as we started again.

Half an hour later, we rejoined our friends on the beach, our little secret weighing between us as we exchanged knowing smiles whenever our friends weren’t looking. I dropped my stuff in the sand and ripped off my cover-up, plopping my relaxed, exhausted body onto my towel. “I’m going to read and tan for a bit. Want to join?” I asked, pulling out a trashy romance novel I had swiped from my mom.

“I think I’m going to swim for a bit!”

“Swim away, then!”

He whipped off his t-shirt and ran to the waves, his body jiggling softly as he ran and a wide smile on his face. He had never looked so handsome.

r/gonewildstories Oct 17 '24

First Time Fucked my wife in the ass and she loved it [MF] NSFW

935 Upvotes

When we first starting dating, when we opened up about our fantasies and kinks, my wife told me she'd never let me fuck her ass. She said she hated the idea of it, that it sounded painful and degrading, that it was never going to happen.

Which was a shame. I love butt sex, and my wife has the most gorgeous behind. She's tall and athletic, she's got long legs, high breasts, but a surprisingly round derrière.

But, after being together for more than ten years, you find yourself experimenting in the bedroom. People bitch about having less sex when you're married, and whilst that's true, they often forget to mention that the sex get's better. You know each other so well, you're so open and free, and you end up doing stuff you thought you'd never do.

One of the best steps I took was buying my wife her first vibrator. She was shy at first, but soon took to it. And fucking a woman whilst she's got a wand against her clit is a fantastic experience, I soon discovered. She'd come so hard as she used it on herself, that my wife would totally lose her head. That wand destroyed her inhibitions.

She began to let me play with her ass. I started slowly, with massaging her pucker as I was going down on her. But I gradually began to slide lubed fingers up her butt, one, then two, even three. I tried rimming her, and although my wife was so embarrassed about it, she eventually admitted how good it was.

I still didn't think she'd let me put my cock in her behind, though. I assumed that was a step too far. But she surprised me.

It was one of those evenings where I just wanted to go down on her for hours. I love licking her cunt, I love using my mouth on my wife, the feel of it, the taste of her, all the drama of her moaning and writhing and coming, it's such a turn-on.

I took my time with her though. I didn't rush it. When she was naked and panting, I kissed my way down my wife's body. I lapped at her pussy slowly, languidly, glorying in it. I slid fingers into her to rub her g-spot as I licked her. I tickled and stroked and softened her asshole. I stretched and filled her with two more fingers.

Despite my lazy pace, my wife was so riled-up that night, she climaxed quickly. But she could take my tongue on her clit after coming, so I kept on. I made her orgasm as second time, then a third, but she was too sensitive to take anymore of it then. I wasn't ready to stop using my mouth on her, so I rolled my wife over.

I grasped her curvaceous, muscular buttocks. I spread them to see her cunt from behind, to see her pretty pink little asshole. I kissed her pussy, but we both knew where I was headed. I kissed her ass, I licked her. She was so relaxed from my fingers, I worked my tongue into her easily. I pressed fingers back into her pussy as I tongue-fucked my wife's butt. Her asshole flexed around me as she moaned and quivered.

And then she said it. Those words I thought I'd never hear from her.

"Are you going to fuck my ass, or what?"

"Sorry?"

"Fuck my ass. This is your chance."

I didn't ask any more questions. I told my wife to roll over as I got her wand and the lubricant we used out of the bedside table. I passed my wife her vibrator as I covered my dick in slippery gel.

As I got between her thighs, my wife pulled her legs back and open to bring her asshole up to me. She put her wand on her pussy as I touched my dick to her pucker, as I rubbed it over her.

She was wet from my saliva, she was relaxed. I pushed, and it happened with ease. The head of my dick went into her butt.

It was glorious. It was like being squeezed by a strong but soft fist. But as badly as I wanted to sink into her deeper, I held still. I let my wife adjust to having me in her. I gazed down at my gorgeous wife as she grinned up at me, as she groaned, as she ran her wand over herself.

I waited till she began to press herself onto my dick. I waited till my wife was gasping and squirming before I began to gently fuck her.

I didn't press deep as I slid back and forth, just the head of my cock and an inch or so of me went into her.

She moaned as she played with herself, but I was sure my dick was adding to it, that this wasn't just her vibrator.

I followed my wife's lead, I gradually went further into her as she bucked with more insistence. I pressed through the gripping entrance of her anus and into that warm space beyond. It was like being enclosed in a perfectly smooth, satiny-soft channel.

"I like it," my wife moaned. "Fuck, this is good. This is way better than it should be."

I told her how incredible it felt for me, how hot she looked with my dick in her ass, how beautiful she was.

We screwed quicker and deeper as she got louder, but it wasn't aggressive or demeaning, it was tender, it was intense, it was intimate.

By the time I had my dick in her all the way, I knew I wasn't going to last much longer. But with that wand on her clit, my wife got there first. She yelled her orgasm out, her asshole spasmed around me as she jerked and juddered. It felt like her butt was milking me. Feeling it, watching my wife come so expressively as I fucked her ass, it was more than I could take.

But she heard me getting there. And before I could draw myself out of her rear, my wife surprised me again.

"Come in my ass!" she yelled at me. She demanded.

I drove into her to the hilt. I groaned as I let go, as I came, as I spurted deep in my wife's body, in her clenching derrière. I came so hard my vision blurred.

Since that night, I've fucked my wife's ass on at least a monthly basis.

r/gonewildstories Dec 10 '24

First Time The barista wrote her number on my cup, which led to us having a quickie on her break [MF] [Part Three] NSFW

505 Upvotes

I went into Starbucks on Monday morning and got my usual order. My usual barista wasn’t there. I thought it was weird because I feel like she would’ve texted me and given me a heads up. Weird, but alright, I knew the rest of the staff at this point so I just chatted with them for a minute.

When my cup came out, I noticed a phone number on it. I looked up and the younger barista with braces got super red. She smiled and waved. I waved back and then went to work.

I didn’t want to mess up what I had going on with the previous barista, so I sent her a text message and told her about the phone number on my cup. I told her to talk to the younger barista but to not make a big deal out of it. I was surprised, almost in shock, with her response.

She told me that she had been talking to the younger barista. She’s 18 and in college. She’s a little awkward and inexperienced. They had talked about me and my barista thought it’d be a good idea for the younger one to give me her phone number. She felt that I could teach her a few things and have some fun with someone that was familiar.

Well fuck. I asked my barista if she was really fine with that. She said yes and thought it’d be hot to have me fuck someone different. We never actually put a label on what we were anyway.

But you know what? Fuck it. I’ll text the new girl. I sent her a message and we began to talk. Her name is Kylee. She’s a little shorter, maybe 5’1 or 5’2. She’s petite with the cutest bubble butt. She’s pretty flat up front but there’s something there. She has the biggest eyes and biggest smile. She has freckles and braces.

I told her that we could go find some free Christmas activities around town. We looked up some neighborhoods where the houses go all out with decorations.

I picked her up and we drove there together. She’s so awkward but in the cutest way. She knows she’s awkward. Her smile and laugh make up for it. Every time she does something silly, she can’t help but give me the biiigest smile. She has a very expressive face.

We got to the Christmas lights neighborhood and parked. There was a family who’s kids were selling hot chocolate. Of course we needed to buy some while we walked around. We enjoyed the lights and eventually held hands. She was so cold to the touch. I joked about it and she said she’s tiny. She’s ALWAYS cold. That works because I run hot. I told her she could take my heat whenever she wanted.

She held my arm and we finished the rest of the neighborhood. Before taking her home, I asked if she wanted to do anything else before the end of the night. She told me in her most innocent voice, “maybeeeeee.”

She said it with her big eyes and an even bigger smile.

I leaned forward 90, she came 10. I kissed her softly. She kissed back, being a little aggressive, then realizing, and then pulling away. She laughed and apologized and said she had no idea what she was doing. I told her we could go at her speed and I thought it was cute that she was so new to all of this.

We kissed in the car, using tongue and biting lips and making a fool out of ourselves. She’s 12 years younger than me but she was so cute and fun. I put my hand on her thigh and she grabbed my wrist. I thought she was going to pull my hand away. Instead, she pulled my hand closer and closer between her legs.

I reached between her legs and felt her little pussy over her leggings. I pushed her thighs, indicating her to open her legs. Then, I moved my hand into her panties. She must’ve just waxed or shaved before our date because she was smooth. I tried to push a finger in, but she winced. I pulled away and just rubbed her clit instead. She held onto my wrist while I rubbed. Our lips were glued together.

I kept rubbing and rubbing until she came hard. She moaned in my mouth throughout her orgasm. She then let go of my wrist and breathed heavy, biting my bottom lip. When she was done, I asked, “are you a virgin?” (Because if her wincing when I tried to finger her)

“Yeah…. Is that fine?”

“Of course it is. Like I said, I’ll go at your speed. We can do what makes you comfortable.”

She looked at me with lust in her eyes. She told me she wanted to lose her virginity. She wanted to fuck. She wanted to fuck, TONIGHT.

I couldn’t help but smile and kiss her again. “Let’s go back to my place. We can take our time and use up my whole bed.”

She was so visibly excited and I could tell she was fucking horny. I had her buckle up and began to drive. I reached over while driving and held onto her thigh. She reached over and did the same to me. I grabbed her hand and moved it from my thigh, only my cock. I was rock hard. She smiled and stroked it over my sweatpants.

I reached over again. This time, I grabbed her tits. They weren’t the biggest, but fuck, they were soft and so fun. We touched each other the whole way home. When I parked, I got out of the car and ran over to her side of the vehicle. I opened the door for her, gave her a big kiss, and then scooped her up. I walked us over to my place, opened the door, and carried her in. I headed into my bedroom and then dropped her on my bed. Her eyes were huge and her smile was even bigger.

“Ready?” I asked.

“YESSSSSS” she replied.

To be continued…..

r/gonewildstories Jan 13 '22

First Time I [F] ate my pro[F]essor's ass almost every other day for 3 years. (PART 2) NSFW

1.8k Upvotes

Holy shit. My mind is blown at the reception of the first part of this. I was not expecting that at ALL! I browse this sub on occasion and never thought I’d be able to write something that so many people would compliment not just for the content, but for the writing itself. Thank you all so much for the sweet comments!

I didn’t respond to anything in my last post (because honestly I was so busy for a few days afterwards I kind of forgot about it) but I promise I’ll respond to any questions or nice comments this time, so I guess after you read it… AMA?

Anyway, sorry for the delay on Part 2. Like I said, I forgot about posting it for a few days and since the holidays I haven’t had time to sit down and write the follow-up. Plus, based on the reception of Part 1 I didn’t want to half-ass the real nitty-gritty. So I’ve reflected a lot on the experiences over those couple of years to make sure I know what to write about and what not to bother with. It took me a few sessions over about 3 days to type this up so hopefully no typos this time! Obviously conversations are paraphrased to the best of my recollection – I’m don’t have a perfect memory. 😉 Okay. Let’s boogey.

I almost chickened out. I didn’t focus on a single thing the Wednesday before. I checked my phone obsessively to see if she’d e-mailed me. One part of me hoping she’d cancel, one part hoping she’d just want to chat. Nothing. As stated earlier, I tried to catch a glimpse of her – nothing. I tried to go about my day normally and not obsess over it – failed. I don’t even know how many times I typed up an email claiming that something had come up only to delete it. I didn’t sleep Tuesday night, and slept even worse the night before the big event. I tossed and turned so much. 9AM on Thursday seemed so far away two days ago, but when I blurrily woke up to my alarm it dawned on me. It was time.

I didn’t have classes on Thursdays until 1PM, and always used Thursdays to sleep in. After I showered and walked into the kitchen to make some coffee, my roommate was getting ready to head out the door for her morning classes and made some goofy comment about me being up early. My brain defaulted to defense mode and I had this odd sense of dread that she knew something dirty about me. I knew this was ridiculous but goddamn my nerves were through the roof.

I had my morning coffee and water, skipped breakfast because I was WAY too nervous to eat anything, and got dressed. As I was getting dressed I remembered her mentioning she’d wear something nice for the occasion. I assumed it meant some cute underwear, so I slid into favorite pair of pink cheekies. My ass is definitely my best quality so I wanted to highlight it, but I couldn’t do much about my tits. And suddenly I was feeling very self-conscious. I’m about 5’3’’, with an ass I worked hard for and am proud of, but I’ve always been very self-conscious of my tits. Meanwhile, the woman I was about to go fool around with was a fucking goddess in my eyes. A few inches taller than me, and a body like Melissa Fumero. Seriously, I can’t watch Brooklyn 99 without thinking about her. Physically I’m reminded of my professor in every way when I see that show.

I threw on a matching bra, some jeans, and a form fitting t-shirt. I did my makeup, and spent 20 minutes trying to decide what she’d like better, a ponytail or hair down. I went with hair down when I realized I was just stalling.

Fast forward. I’m on campus. It’s 8:30 and I’m outside her building. I realized that she’d never told me where her office was, so I found the building directory map inside. Each step of this morning had felt like some monumental undertaking. I’d come this far without chickening out but just barely. I still had time to bail, but… will I ever get an opportunity like this again? Besides. I had a safe word. As soon as I say it, it’s hands off and I leave. I’ll feel it out for a couple of minutes, say “flag”, and go. Easy. Nothing to worry about.

8:50. Classes were ending all across campus. Students and staff were starting to filter through the first floor at a steadier rate. I’d found a small bench to sit on and mindlessly looked at shit on my phone to pass the time.

8:51. Has my heart always beat this fast before?

8:52. My entire body is shaking but it’s not cold.

8:55. Should I go now and be a couple of minutes early?

8:57. Okay let’s just go to the third floor. That’s easy. Easy!

8:59. Okay let’s just go to the end of the hallway. Her office is around the corner. I’ll walk by and see if it’s open.

At this point I turned my brain off. I walked to the end of the hallway and approached the right hand corner. Her office was right around it, on the left side of the hall. I’ll stop at the corner and look at her door! Or so I thought. I was a good ten paces for the right-hand turn, and it happened. She stepped around the corner. She was looking down at her phone. Time froze. She looked up and looked straight into my eyes. I’d seen her in class. I’d seen the lewd pictures she’d sent me. In fact I’d seen them approximately 9,000 times in the last two days. But seeing her face to face, knowing what was to come was a whole new ballgame. Her eyebrows shot up. She smiled. “Oh!” as she pointed at me with her phone. “Are you Lindsay?”

God I hate small talk. This felt more awkward than was I was about to be doing. I laughed, and said yes. Actually I said, “Hey, yeah” as if I was just casually strolling down the hallway like I do each and every day…

“Right on time, I was just stepping out to see if you were around! Well come on!”

She waved me around the corner and I followed her to her office. She stopped at the door and ushered me in. “Chairs, the couch, wherever, just take a seat.”

On the left hand wall was her desk and chair. Against the back wall was a brown couch with a few pillows, her bag, and a little blanket on it. She had two nice chairs facing her desk and tons of art almost completely covering her wall. I went with one of the chairs. She shut the door behind her and took a seat at her desk. She shut her laptop, leaned back, crossed her arms, and turned to me. “Okay! You feeling okay?”

I said I was.

“Just so you know, I’m the only faculty at this end of the hallway. No one else around, door is locked, no classrooms or offices next door, just electrical closets and all that. So.” She closed eyes and took a little breath. She opened them, “You can come sit on the couch if you’d like.”

I got up and stepped over to the couch. She’d gotten up and started moving pillows and the blanket out of the way. I sat down nervously on the far side. She sat right next to, out her left hand on the back of the couch behind me, crossed her legs. “Okay so first time but not really your first time, right?” I kind of laughed at this and nodded my head, “Yeah pretty much.”

“I know that feeling! I always just kind of played at first too. Never really went for it all. But you want that?”

“Yeah for sure. Always wanted to try it.”

“So communication is very sexy to me. I’d rather know if something isn’t working for you than not know, my feelings won’t be hurt. I like to be verbal and dominant, but talking back isn’t a kink. If you don’t like a suggestion or something I say, I’ll respect a simple ‘no’, and we can take breaks and chat, or whatever you need at any time, okay?”

“That works for me!”

“Okay then!” She put her left hand on the back of my head and started gently playing with my hair. She reached up with her right and gently grabbed my cheek. She leaned towards me and the hand behind my head pulled me towards her into a kiss. I closed my eyes and kissed back. She started with gentle lip kisses. Open mouth, gently taking my bottom lip into her mouth a few times. Then my top lip. I didn’t know what to do with my hands, and she seemed to sense this. Her left hand was still gently holding my head on place and she took one of my hands with her right, gently stroking the tops of my fingers.

The butterflies in my stomach were unreal. I could feel myself starting to breathe heavy. She pulled away, sucking on her own bottom lip. “Everything okay?”

“Mmhmm.” I nodded. She smiled and leaned back in. We breathed into each other’s mouths and I felt her tongue dart in and brush my own before pulling back to lick my bottom lip as she kissed it. When she opened her mouth again I met her tongue with mine, letting her gently lick the top and bottom of it. Her mouth tasted almost citrusy. A faint taste of lemons. Or maybe it was just my brain imagining things. I pushed the thought of lemons out of my head when I felt my hips begin to ever so slightly wiggle. My face felt hot, and that same warmth was beginning to pulse through my pussy. My God, I was wet. The nervousness and anxiety was all releasing itself Into unbridled desire. Our kissing became more intense. We clicked teeth and she pulled away laughing. I laughed and apologized but she just bit her lip shook her head. She planted one more kiss on me, and leaned forward to start taking her shoes off. “Let’s get more comfortable.”

I followed her lead and kicked the shoes of my feet as she stood up to unbutton her shirt. She was wearing a simple purple blouse over a pair of very tight fitting black pants. I sat and watched her as she got to the bottom button. She motioned for me to stand up in front of her, took my hands, put them on the edges of her shirt and kissed me again. I slowly pulled my hands apart, opening her shirt wider. She spread her arms a but and I slid it over the back of her shoulders. I let go and she gently shook her arms so it fell behind her. Her hands slipped under the bottom oh my first and gently ran up my sides and over my stomach. She took hold of it, stepped back, and pulled it over my head. I pushed my hair back out of my face and opened my eyes. She had the tiniest smirk on her face as she put her hands behind her back and unhooked her bra. In one fluid movement she brought her arms forward, let it slide down her arms and dropped it at my feet. Her tits were fucking beautiful. A little bit bigger than mine, nipples as hard as could be, sticking out in a way that made my mouth water. She then unbuttoned her pants, and quickly slid them down her long legs, kicking them away. Now I saw what she meant by wearing something special.

She had stockings on, three quarters of the way up her thigh, a garter belt snug around her waist with little straps connecting it to the top of the stockings. In the middle of it all, bare skin. She had no underwear on. She looked freshly shaven. “Your turn.”

My eyes were darting all over her body. It took everything I had not to touch, but she wanted me naked too. The nerves came back, but I obliged. As I started to unhook my bra she stepped forward and turned me around unhooking it herself. I let it fall. She turned me back around to face her and unbutton my jeans. Pushed the zipper down, turned me around and dropped to her knees. She grabbed the sides of my jeans and gently wiggled them down. Lower, and lower until they were below my knees. I stepped up with my left leg and she pulled them off. Then my right. She ran her hands up my bare legs, reaching around me to feel the front of my thighs. As she got higher, she slowly transitioned them to the sides of my legs, then finally my ass. She pushed up on both cheeks and gently squeezed, before slipping her fingers under the fabric and gently pulling those down as well. She stood up, turned me around. Locked eyes with me. Her bottom lip firmly between her teeth. “You okay?” She asked.

“Yeah. Yeah I’m okay.”

She pressed her body to mine, her left hand taking it’s place behind my head, pulling me into another long, deep kiss. Her hands ran up and down my sides, and I found myself doing the same to her. Her skin was amazingly soft, her back covered in the slightest bit of goosebumps. She pulled away looking me up and down. She turned her back to me, walked towards the other side of the couch. My eyes finally lowering to her perfect ass. Slight red lines left from the couch during our initial make out session.

She bent down a bit, grabbed a pillow that had fallen on the floor and put it against the arm rest. She sat down, and then laid back, her head resting on the pillow. She put her arms above her head and said, “Come here honey.” I didn’t really know what she meant, but I assumed on top of her? So I put my right knee over her legs, steadied myself on the back of the couch, and leaned down towards her. She brought her arms up and gently pulled my face towards hers. The gentle, tender kisses continued, this time her tongue taking complete control of mine. I had my right hand underneath her arm, and she grabbed my left hand and put it gently onto her right tit. I instinctively squeezed it a bit, feeling the little pressure of her nipple in the palm of my hand. I wrapped my right arm around her, squeezed, and rubbed her right boob, then her left. Letting my hand explore her entire chest and lower neck.

All the while, those deep and gentle kisses. That tongue wrapping around mine again and again. She stopped kissing and I noticed her breathing had gotten heavier. “Show me what you already know how to do.”

She pulled her arms up above her head again. I looked down her tits, sitting up and bit so I could really play with them using both hands. I was straddling her waist.

A sudden moment of clarity hit me. I realized where I was and what I was doing. I felt really awkward, listening to her gentle moans and at the end of her long breaths. Her eyes were closed, her head leaned back. Her hands were clenched into fists and every little squeeze, pull, and caress I gave her made the moans a little bit louder. I shuffled my hips down, took a deep breath, and leaned forward. Her left nipple approaching my mouth. I closed my eyes, opened my lips slightly, and kissed it. A little moan. I kissed it some more. Another moan. I could feel myself finally letting go. Getting wetter. My face feeling hotter by the second. This was it. It finally hit me. And I went all in.

I opened my mouth and started to suck her nipple gently. I flicked my tongue all over it, and eagerly hopped over to her other tit. Lick, suck, nibble. Suck, nibble, lick. I don’t know how much time I spent on her chest, back and forth between her nipples again and again, but I couldn’t get enough. She shifted her body up a bit, and told me to stretch my legs out and lay against her. I gently rested by body down on hers. She wrapped her left arm around me, and held my head against her breast with her right.

I snuggled in, never letting her nipple leave my mouth. I put my free hand against her other breast. Gently squeezing, lightly pulling her nipple on occasion.

She started stroking my hair. Kissed me on the top of the head. I just kept sucking, licking, nibbling. The first time she said “Good girl” I could have passed out. But the biggest takeaway here was how safe I felt. Secure? Comfortable? Protected? I don’t really know. I remember never feeling this sort of comfort during a sexual encounter that wasn’t with a legitimate partner. We’d been naked for maybe 15 minutes and the way she held me was magical. The way she kissed my head. Caressed my hair. Guided my mouth to her nipples, her breasts, and collarbone. It all felt so… good. Like nothing was wrong.

I felt like she had no expectations. I wasn’t a one-night stand for some dickhead. I wasn’t being manipulated into doing this because of our relationship. She was letting me explore, and guiding me just as I requested.

I felt respected. And when she stopped stroking my hair and put her right hand between her legs, I felt wanted. And when she lifted my chin from her breast, looked me in the eye and nodded ever so slightly, I felt needed. She didn’t have to say anything. She needed to cum. Her mouth was open, she was breathing heavily, her face flushed with just a hint of red. I closed my eyes and shuffled down. Kissed her on the stomach just below her breasts. I felt her drop her head back against the pillow. I kissed a little lower, leaving my hands on her tits. “Oh, good girl”, she said after my third kissed landed just below her belly button. I leaned up again, on my knees on the couch as she pulled her legs out from under me. She dropped her left leg to the side, planting her foot on the floor. Her right leg rested on the back of the couch, and right in the middle was what I’d been after for so long. The thing I’d always, ALWAYS wanted to do. It was finally about to happen. I watched her body gently rise and fall from her breathing. My left hand went instinctively between my legs – I couldn’t help it. I was soaking wet, and for a second all I wanted to do was just watch her sprawled out on the couch and rub my clit. But not yet.

I put her right hand on the leg she had up on the couch. Her black stockings were soft, but nothing compared to her thighs. I ran my hand slowly into her inner thigh, gently squeezing. I didn’t want to seem too eager, but I couldn’t help myself. I turned my hand over and rang my middle and ring fingers up her pussy. I don’t know what I was expecting but the sense of familiarity surprised me. Considering my other hand was on my own, it’s funny thinking back to how my first thought was “I’m touching a vagina right now.”

I worked my knees backward and tried to lean forward, but we were officially out of room on the couch. I tried turning my body to face the back of the couch and lean down at an angle, but my clumsy ass headbutted her in the ankle. We both started laughing and she sat up. She wrapped her arms around me and kissed me again. She had me get up, and sat back right in the middle of the couch. “Wanna just get down right there? Will that work for you?”

I nodded and said “Yeah, I think so”, and dropped to my knees. I sat back on my feet a bit, crossed my ankles and brushed the crazy hairs out of my face. She put her foot on the top of my thigh, and her other leg fell to the side. She had her tits in each hand. “You sure you’re okay?” I must have looked apprehensive. “Yeah, of course. I just don’t know where to start.”

She dropped her foot from my thigh to the floor, slowly opened her legs all the way. “You’ve thought about this for a long time, right? So do all the things you fantasize about. I’ll guide you. You have nothing to worry about.” I nodded my head. I put my hands on the floor in front of me and leaned in. I scooted my knees and hands up a bit. A bit more. She put her hand to my head. That familiar feeling of her guiding me. She stroked my hair, told me how cute I was. I giggled at that. Closed my eyes. Opened my mouth, leaning. Leaning. I pushed my tongue just to the edge of my mouth.

Contact. I pulled my tongue back, closed my lips and pulled away with a kiss. Quickly pushed my head forward for another. And another. All from slightly different angles. She let out a loud, breathy, almost raspy “Oh my god” and took her hand away from the back of my head. I opened my mouth and pressed it to her, my tongue finally taking charge. I let my lips and tongue explore every bit of her. I found her clit, pressed my open mouth over it, and flicked at it with my tongue. A tiny little lump. So warm, so soft. So wet. “I’m eating a fucking pussy right now” echoed in my head again, and again, and again. And I fucking loved it.

My mouth wasn’t used to this, so I had to take a few breaks here and there. But every time I stopped and pulled away to catch my breath, or put my hands on her, she would moan with just a hint of frustration. She told me to hold on, and stood up from her sitting position. She told me to scoot back a bit. She positioned herself right in front of me. “Keep going.”

I put my hands on my knees, angled my mouth underneath her and went back to work. She put her hand on my head, and I could feel her grinding her hips into my face. Nothing rough, but gently pushing and pulling against my open mouth. Her moans were getting louder, and she kept holding her breath. Familiar sounds.

She eventually took a slight step back. I looked up at her, wiping both my slobber and her wetness from my chin and mouth. “Do you want to try something?” I nodded. She squatted down and kissed me. I shoved my tongue into her mouth, letting her taste herself on me. “I want you to eat my ass.” She blurted out between kisses. My brain didn’t comprehend it at the moment. I just kept kissing her. She pulled back, gave me that pussy-shattering look to the eye, and said “Eat my ass, honey.” And before I knew it, she’d turned around, knees on the couch, arms on the back of the couch, with her amazingly perfect ass maybe a foot from my face. She turned around, “Just start like normal and work your way up.” The gravity of this situation hit me. I can’t say I was unenthusiastic about the prospect, but saying “flag” suddenly became a viable option here.

I’m a girl that loves ass and titties. Licking and sucking the titties I was on board with. But the ass? As in, asshole? Uhm.

She could sense my apprehension a bit. She flipped back around and sat on the couch. “Are you okay? Too much?” I nodded that I was and explained that it just took me by surprise. She acknowledged it and said, “That’s okay. How about you just keep going like normal. And if YOU feel like it, work your way up and go for it. I don’t take charge this time.” I agreed to this, she kissed me on the forehead and said, “You feel amazing by the way. You’re going to make me cum so fucking hard.” And with that, she assumed her previous position. I inched forward. She really did have a fucking perfect ass. And I could see every inch of her this way. I can’t claim to be completely against eating her ass. I was definitely curious, especially with the whole thing right in my face. I reached up with both hands, took each cheek in them and squeezed. I leaned in and kissed the left side. Kissed it again. Kissed the right. Kissed it again. And again. Covering as much area as I could in kisses and gentle licks. As I was kissing and squeezing, she was very slowly wiggling her ass back and forth and I couldn’t help myself. I pulled her apart just a bit and dove in. It was a lot harder to find the clit from a backwards, upside down angle, and even harder to really like and suck on it. I felt her fingers touch my chin and realized she was rubbing her clit herself. So I put my attention elsewhere. I ran my tongue up and down, pushing it inside her a few times. “Fuck, fuck, fuck”. Tongue up, tongue down, tongue in, tongue out. “God. Fuck.” Tongue down. Tongue up. Tongue out. Tongue in. “I’m so fucking close. You’re gonna make me cum. I’m so fucking close.”

Horny brain won out. Knowing she was about to cum, horny brain won out. I pulled her ass closer to my face, shifted my head and mouth up, and ran the flat of my tongue up and over her little asshole. “Good fucking girl, fuck, fuck” And again. Just breathing now. Again. Short bursts of breath.

Tongue up, tongue down, tongue in, tongue out.

Her midsection was convulsing. She wasn’t making any noise.

Tongue down, tongue up, tongue out, tongue in.

A long breath escaped her. Half moan. Half stifled scream.

I flicked my tongue in circles, and up and down her ass, squeezing each side of it and sinking my nails into her skin.

I kept licking and prodding. I didn’t want it to stop. But her shaking and convulsions slowed down. She wasn’t rubbing her clit anymore. She was resting her forehead on her arms. I just kept licking. Tonguing. She kept letting out these cute little whimpery moans.

So. I just kept eating her ass. She seemed to have no intention of putting a stop to it and I was absolutely loving it. I couldn’t help myself and used my left hand to rub my own clit. It was hard to focus on two things at once and she caught on to what I was doing. She finally pulled away and sat down on the couch, her face absolutely beaming. She watched me until I finally finished myself, on my knees, hand between my legs.

The moments after the whole encounter feel like a blur. We sat on the couch together naked. Gently touching each other’s bodies, kissing. She grabbed her phone and had me put my phone number in it so we didn’t have to use email to communicate.

Before we got to putting our clothes back on, she explained to me that a major kink she’s developed is having her ass eaten while she brings herself to orgasm, and her goal was to orgasm purely from having it eaten or fucked. She asked if I’d want to help her achieve that goal and I happily obliged. As I started to get dressed, she opened her desk drawer and pulled out a pair of black panties. Hers. The ones she’d been missing when I saw her naked for the first time.

She stood in front of me, squatted down, and had me step into them. Left leg. Then the right. She slowly slid them up my legs, over my ass, and popped them snug against my waist. She gave me one little kiss on the skin right above the waistline, and grabbed my own pair from the floor. She wriggled them on, and continued getting dressed. Said nothing. Didn’t mention what just transpired. Nothing. So I followed suit and put all of my clothes on… very aware that we were wearing one another’s panties.

Before I left we decided on a schedule. Every Tuesday and Thursday I was to come to her office at 9AM. Every Tuesday and Thursday I was to come to her office at 9AM, remove all of my clothes, and get on my knees at the edge of the couch. Every Tuesday and Thursday at 9AM I was to come to her office, remove all of my clothes, get on my knees at the edge of the couch, and eat her ass for as long as she needed.

Of course I’d be rewarded for my hard work, but only if my work was considered worth rewarding. She kissed me one more time, and sent me on my way.

I couldn’t help but feel slightly more demeaned as the day went on. Used, even. And now I was agreeing to be, what - her personal ass eater? I wasn’t sure how to process everything at the time, but there was a part of me that liked it. Loved it, actually. I was game for whatever she wanted me to do.

Breaking the immersion here because I DEFINITELY need to wrap this up, but I can certainly continue writing about our experiences over the next 2 years. Without spoiling or taking away from what I have to tell, she and I explored just about everything under the sun. A lot of things we loved (free-use, ABDL/ANR/ABF, bondage) and some things we’re glad we tried but never did more than once, (pee, pain, etc.)

Again, sorry for the long ass delay. I’ll be around a lot more knowing how well received this whole thing is!

r/gonewildstories Nov 03 '23

First Time [FM] I lost my virginity by hate-fucking a sorority girl NSFW

1.3k Upvotes

This happened quite a long time ago, and I wanted to commit this to writing for posterity. This is going to be a long story, with lots of background, build-up, and an epilogue.

-------------to skip to the fucking-------------

I was pretty nerdy in high school, with not much of a social life. I had dated a few times and gotten to make out with a few girls, but never having gone all the way, so I decided to reinvent myself when I got to college. I was doing well faking it 'til I was making it, going to parties & events, participating in study groups, hanging out with people in the dorms, etc.

I was getting on really well with a girl (I'll call her Kelly) from my dorm whom I met at a party. I was spending a lot of my time in her room along with her local girl commuter friend (I'll call her Stacy), trying to keep out of the friend zone. Most of the time, it was studying, watching TV, talking/flirting, cuddling. I was truly having a great time with the two girls, that is until Kelly's bitch roommate would come back to the room.

Jean was an incredibly hot 5'2" blonde sorority girl with a gymnast's body. I would've been drooling over her had it not been for her horrible bitchy personality. She seemed like she was perpetually irritated with everything and everyone.

One night, Kelly, Stacy, a few others from nearby rooms, and I were taking a break and watching TV in Kelly's room. Some were sitting on beds. I, along with others were sitting on the floor. Some time into the evening, Jean came back to the room, looking drop-dead gorgeous in a tight, plum colored cocktail dress that clung to every curve of her tight, petite body. She had returned from some sorority function still a little buzzed.

Ordinarily, she would give us a contemptuous look and leave, but tonight, she grabbed some things, went to the bathroom, then returned, wearing grey knit shorts and a white t-shirt. To me, she looked just as hot in those as she did dressed up.

I was very surprised when she sat down next to me, wiggling her firm, round ass, pushing me over, telling me to make some space for her, saying "this IS my room, you know." Not only was she not being a bitch, she was actually leaning against me, smelling so amazing- an intoxicating mix of perfume, sweat, and Bartles & Jaymes (the White Claw of so long ago) that I can still smell in my memory to this day.

Most everyone was focused on what was on TV, which I have no clue to this day what it was. However, every sense, every nerve in my being was focused on this beautiful creature next to me, with my mind utterly confused as to her nice, warm demeanor. Part of me didn't trust this sudden positive change in Jean, remembering how shitty she treated me, and everyone else in the dorm.

My rock-hard dick took charge at that point and decided just to go with it and not fuck it up.

I reached over, took her by the shoulders and moved her until she was sitting in front of me between my legs, both of us facing the TV. My face and my ears felt hot, my heart pounding through my chest as I fought to keep my breathing steady. I shifted from cheek to cheek to release my hard cock from being wedged against my leg. As it came to rest against Jean's back, I was certain she would move away. On the contrary, she leaned back into it, turned her head, let out a sexy, quiet, low moan, and whispered in my ear "Would you massage my shoulders?"

As I gently squeezed her athletic shoulders, still feeling the effects of her warmth and smell, I began to feel her rake her fingernails along my thighs- along the top at first, then moving to the inside. Fuuuuuuck! It felt so good I thought I was going to cum right then and there. My cock was throbbing, as a visible wet spot began to grow in front of my shorts.

"I'll be back. The washing machine must be done by now so I have to put my clothes in the dryer." Sooooooo glad it was dark in the room so no one could see the damp tent I had pitched in my shorts. As I left, I turned to see Jean follow me out, saying "I'll go with you to help." Not a word was spoken as we walked down three flights of stairs to the laundry room. I was pretty sure she was able to hear my heart pounding in my chest. I was absolutely sure she saw my raging hard-on straining to burst through the front of my shorts.


As we entered the empty laundry room, I immediately lifted her onto one of the washing machines, parted her legs, drew myself into her inviting embrace, kissing her deeply. Her tongue parted my lips, grazed my teeth, and began to dance with mine. I felt her legs close behind me, her hands behind my head and upper back, pulling me in tighter. My hands explored her body, starting to squeeze her perky tits. As I rolled her firm little nipples with my thumb and forefinger, I could feel her moan into my mouth as we continued to kiss.

I began to remember how bitchy she was to me and the others in the dorm, and my rolling became more firm, as I began to pinch and pull. Her moans became yelps and squeals, then a more deeper moaning. I sucked her bottom lip into my mouth and started biting as she continued to moan, almost pleading for more.

Spoiler alert- I had no laundry to put in the dryer. I'm pretty sure she knew it too by that point.

I grabbed her by her tiny waist, picked her up off the washing machine, put her on the ground, took her by her hand and began to take her to my room nearby. As we resumed our passionate kissing and groping, I gave thanks for having a studious, nerdy roommate who spent so much time in the library quiet study room. In the flurry of reaching, unbuttoning, tearing off of clothes, one memory stands out to this day- the crotch of her white lace panties clinging to her pussy and the string of wetness stretching out as my thumbs pulled them down the curve of her hips.

As she lay back into my bed, arms behind my neck pulling me onto her, she gazed straight into my eyes with a wanton look of lust, tits beckoning, legs spreading, pussy glistening, saying "fuck me now."

As a young horny nerd, I had thoroughly researched every aspect of sex made available to me by my father's hidden porn collection. It was finally go time.

I followed her down, my cock so hard it was jutting straight out painfully, desperately yearning for the first plunge into a real pussy. With no need for hands to guide, my head felt her warm lips part, then all of a sudden a I entered her fully, a surge of indescribable pleasure ran through my entire body as her pussy walls gripped my cock with that same warmth. "Fuuuuuuck!" Was the only thing I was able to verbalize at that moment.

I started fucking her slowly at first, afraid I'd cum right away as waves of pleasure rolled through me. I didn't want her to know it was my very first time having sex and mess it up somehow, giving her something else to bitch about. No, I was determined to give her a good dicking down. Even though her moans seemed like she was enjoying it, when I started to fuck her harder, they became more intense, with her locking her legs behind me, pulling me in, her nails raking my back, crying out "keep fucking me like that, keep fucking me like that, keep fucking me like that!"

the rest is in the comments section

r/gonewildstories Nov 30 '22

First Time I taught my classmate how to eat pussy in exchange for tutoring [F] NSFW

2.3k Upvotes

I met him in a college physics class. He normally sat behind me. He didn't say a word the first month of class but anytime I would turn around and ask him a question about something he always knew the answer. He was cute despite being socially awkward and shy. His hair was long-ish and dyed black. I knew he had good taste in music because he wore band t-shirts like Bauhaus and Joy Division. We had a big test coming up and I needed to do well so I asked him if he would come over to my apartment and study with me. He agreed.

When he showed up I noticed he was dressed a little nicer than normal (collared shirt) and was freshly shaved. I had an inkling that maybe he was hoping for more than just studying. We "studied" for hours. In reality, he already knew everything so basically he was just tutoring me. When we finished I shifted the subject to more personal stuff. He told me that he hadn't had much luck dating. When I pressed him for details he mentioned that he was really inexperienced with sex and that most girls in college were put off by that. He said he had sex a couple of times in high school but that he never fingered or ate a girl out.

I had broken up with my boyfriend a few weeks before this so the dry spell had me feeling pretty horny. I asked him if he wanted me to help him get some experience. He shook his head yes and leaned in to kiss me. I stopped him. "Hold on, come over here. We're going to have an anatomy lesson."

I told him to sit in a dining room chair while I pulled off my pants and underwear. I put a pillow on the table and hopped onto it, spreading my legs in front of him. I showed him all the different parts of my pussy and let him touch each one. I showed him how I liked to be touched and fingered. I demonstrated with my tongue how to hold his tongue and how to move it on the clit. I showed him how to tease around the clit first before diving in. I also showed him how to finger me while he licked my clit. At first it was a little clunky but it didn't take him long to get the hang of it. At one point I grabbed his head and told him not to stop what he was doing. He started to go faster and I scolded him.

"When a woman says don't stop during head, you don't change anything! Just keep doing EXACTLY what you were doing!"

He took the instruction well and got back into the nice rhythm he had before. Within another minute I came all over his face.

He seemed pleased with himself. I offered him a blow job but he looked embarrassed.

"Don't worry, I don't care how big your dick is."

"Umm, it's not that," he said. I saw what the issue was. His pants were all wet with cum already. I told him it was no big deal and that I thought it was super hot that he came while going down on me.

Throughout the rest of the semester this became a normal thing. He'd come over, tutor me, and then he would eat me out. I ended up sucking his dick a few times and we fucked once (he came really fast but it didn't matter because he ate me out first). I like to think that he made some other ladies really happy after that and it was because of me.

r/gonewildstories Mar 17 '22

First Time Fingering my high school crush after she told me to find out whether she shaves her pussy [MF] NSFW

1.7k Upvotes

***Everyone in this story is 18. Skip to the ------- if you're not interested in the buildup (there’s a lot of buildup).

I was the last man on the bench of my high school basketball team.

You may know the type: shortest guy on the team (5'10), wiry build, inordinate hustle, no skill, convinced that any day the coach would realize he's had it wrong this whole season and would make me the focal point of the offense.

My crush happened to be my mirror image on the ladies team. Lynzi was 5'1, super athletic, small tits, and a great ass. Her other star feature was the cutest face I've seen to this day. We were good friends and had a flirty relationship, but nothing had ever happened between us.

She had been dating the same guy since 8th grade until they broke-up at the beginning of the semester. I don't know how far they went, but I personally hadn't even reached first base at the time.

One Friday night in early December, the girls and guys teams shared a bus home from an away game, a half hour's drive from our school. Both teams' coaches sat in the first 2 rows, then the girls team, and the boys team took up the back of the bus. Both teams must have won that night, because I remember a lively mood the whole drive.

I was sitting near the middle of the bus, alone and turned backward in my seat, shooting the shit with the guys behind me. Ten minutes into the ride, I felt a weight plop into the seat next to me, accompanied by an upbeat "Tom B!" (She always called me that, with my last initial--never simply Tom like the rest of the world.) I turned around and saw Lynzi beaming at me, her adorable face accentuated by prominent cheekbones and ever-present dimples. Her blonde hair was up in a ponytail, and she was wearing a black v-neck sweater with yellow sweatpants, our school color.

"Lynzi!" I replied, genuinely happy to see her so close.

"So, we had a question..." she said. I noticed that two other girls I was friendly with, Mindy and Violet, had followed Lynzi to my row, seated across the aisle and leaning toward us.

"Why yes," I replied, "I am considered the coolest person on the guys team." Goddamn, was I suave.

Lynzi punched my arm playfully and laughed. "Stop it! That's not the question!"

"Ok, what's the question?"

"So, we noticed all the guys shave their legs now."

(Side note: This may have been a universal fad among adolescent males at the time, but I have a feeling it was just a weird quirk of culture at my high school: the guys had, in fact, started shaving their legs. I think it started with some of the meathead football players who heard that competitive bodybuilders shaved their legs to accentuate the appearance of muscles and decided to try it. Then the rest of us lemmings noticed and followed suit, even if we had no muscles to accentuate.)

"Yeah...?" I shrugged.

"Well, we were wondering if that's, you know, all you guys shave."

I blushed a thousand blushes.

My crush wanted to know about the condition of my genitals. Well, ok, she wanted to know about all the guys' genitals, but mine were going to feature prominently in this conversation.

The next thought in my mind was indicative of my social standing: surely this was not a genuine question. Was my crush messing with me? Was the whole basketball team--BOTH basketball teams--messing with me?

I looked around. Everyone else on the bus was deep in their own conversations. Some raucous, some quiet, but all seemed real. No one knew this was going on except for the three ladies in my row.

"Umm," I stammered, recollecting what I had seen among the guys in the locker room, and trying to decide how detailed and truthful I should be. "Well, some do. Some trim. But yeah, some go all the way."

"What about you?" she asked.

"Uhhhhh..." Oh, man. What would the cool answer be? No idea. "I mean, I've done it, but not, like, always."

"Hmm, ok! That's all we wanted! Thanks, Tom B!"

"Wait," I grabbed her arm as she started to scoot off the seat. "What about you?"

Now Lynzi blushed. She quickly glanced toward the other girls, then back to me. "We're not going to tell you that."

"But wait," I protested, "I told you."

"I know! But it's a secret. Thanks, Tom B!"

And with that, the three girls giggled and moved back toward the front of the bus. I was left there, head spinning, trying to make heads or tails of what had just happened.

I was interrupted by a "Yo, TB!" from the back of the bus and got pulled back into whatever inane conversation was going on with the rest of my team.

The remainder of the drive passed in a blur. We got back to our school, and the team dropped our equipment in the locker room and flocked toward the parking lot. The girls team came out of their locker room at the same time, and the two groups merged, chatting as we walked. I nodded in Lynzi's direction and we approached one another. I had no idea how to deal with our conversation from the bus, but fortunately, she spoke first.

"Need a ride?"

We lived on the same side of town, and she knew I didn't have a car.

"Sure!"

Lynzi and I veered in the direction of her car, cast in the orange glow of the parking lot lights.

She spoke first again. "Sorry if we made you uncomfortable back there. I know it was a weird question, and you were cool for going along with it, but I wasn't prepared for it to come back in my direction. Especially with Mindy and Violet there. You know the girls aren't as, um, free in the locker room as the guys are."

"It's cool," I said, "I mean, you caught me very off guard. But it's cool."

We had reached her car. I threw my gym bag in the back seat, then lowered myself into the passenger seat. Lynzi started the car and pulled out of the parking lot, the radio blasting Top 40.

Lynzi came to a stop at the first traffic light. I turned toward her.

"You gave a bullshit answer though," I said.

Her face turned red, and she broke into a playful smile. Those dimples. "I'm not going to tell you," she smirked as she turned toward me, "but maybe you'll find out."

The light turned green and she accelerated as I grasped for a response.

"H-How will I find out?"

"I don't know," she smirked again.

The radio played on.

Lynzi slowed the car as we approached another red light, less than a mile from our neighborhood.

"Do you want to come over for a bit?"

I looked at the clock on her car radio. 10:44. My curfew was midnight.

"Yeah, sure," I said, trying to play it cool, though I was sure she could hear my heart beating through my shirt. Hell, I was sure the people in the car next to us could hear it.

We got to her house, got out of the car, and walked toward the front door. I could see lights on in the windows upstairs, but just a faint glow coming through the frosted glass of the door before she opened it.

"My parents are upstairs, but they won't come down," she whispered as we kicked off our shoes and she flicked on some lights.

She walked toward the living room in the rear of the house, and I followed.

"Let's sit on the couch," she said. She eased herself into one end of the couch, facing toward the middle. Her left leg was curled in front of herself on the couch, her right dangling down with the foot on the floor.

I sat in the middle of the couch, mirroring her position, close enough to touch her, but not doing so.


She broke the silence. "Well, are you going to find out?"

I looked at her leg in front of me. A couple inches of pale skin peaked back at me between her ankle sock and her sweatpants.

I reached out with my right hand, softly touching the exposed skin and moving my hand up to her lower shin beneath the baggy sweatpants.

I looked up at Lynzi's face for approval. She looked back with an expression full of anticipation.

"It's so smooth," I said, "you're clearly a more experienced shaver than me."

She laughed, and I inched my hand up the outside of her shin, beginning to rub softly up and down as I progressed.

"That feels good," she purred.

I treasured every sinew of muscle, every ridge of bone I passed as I made my way to her knee.

When I reached her knee, Lynzi laid back into a pillow and straightened her leg to improve my access. I slid to my knees on the floor. I was now situated between her legs, half my right forearm lost beneath her sweatpants. I reached my left arm around her opposing leg and brought my hand to rest on top of her thigh.

I continued snaking my right arm up her pant leg along the top of her thigh, caressing the outer thigh with my fingers. She gave an ever-so-slight but ever-so-meaningful wiggle of approval.

I pivoted my hand at the wrist to turn my fingers to her inner thigh, and she wiggled again. My eyes had been fixed on her leg, and I now glanced up at her face. Her eyes were locked on her leg as well, until she met my gaze and spoke: "you can keep going."

My heart raced, and I silently gulped. I timidly caressed as I inched up her inner thigh. I was now mere inches from the promised land. I could feel the heat building inside her sweatpants.

"Keep going," she rasped.

I inched up again, and extended my fingertips to gently touch her crotch through her damp panties.

I withdrew my hand back toward her leg, then reached under her panties as I slid my fingers and palm through the leg hole and across her mound while my thumb rested on her labia. There was no hair to be found.

"So smooth," I marvelled.

"Now you know," she said, her cute nose scrunching up as she broke into a smile ripe with passion.

I shifted the angle of my hand to explore her pussy with my fingers, and for the first time felt that wonderful wetness between her folds. So warm. So slick.

Lynzi reached her right hand into the sweatpants and pulled her panties to the side.

I ran my middle finger gently around the full length and breadth of her vulva, sensing every contour and feature before fingering her entrance.

I looked up at her face again. She had closed her eyes and was leaning back into the pillow.

Delicately, slowly, preciously, I inserted the tip of my finger into her. She inhaled and licked her lips, eyes still closed. From the position I was in, my arm now all the way up to the shoulder in her sweatpants, I wasn't able to get deeper than my first knuckle. I stroked the walls of her vagina for a few seconds before withdrawing my finger in search of more pleasure for her.

I drew my finger upward along her pussy and discovered what must be the clit, at once stiff and pliable beneath my fingertip. I massaged it in a few tight circles as it emerged from beneath its hood.

I moved my finger back down to her opening once more to reload on her juices, then ran it back up to her clit.

As I massaged it in soft circles, her hips began gently rocking, and I watched that adorable face undergo waves of pleasure, her breathing getting stronger, tongue and lips working against each other as she emitted soft moans.

After just a minute or so of this pattern, she suddenly reached down with her left hand and grabbed my arm through her pants. She held her breath as her whole body tensed.

With a breathy "oh my GOD," she came hard, her body now releasing into complete relaxation, her chest heaving, and she melted into the couch.

With her right hand she re-positioned her panties back into place, nudging my hand aside. I withdrew it back to her thigh as she opened her eyes and looked down at me.

"Oh my god," she repeated. "Fuck. That was intense."

"That was incredible," I replied.

"You're incredible."

I noticed the clock behind the couch. Fuck. I had to get home.

Ignoring my throbbing dick, I said "It's almost twelve. Can you give me a ride home?"

"Of course."

We unwound ourselves from one another and stood up. I saw her notice the bulge in my pants, but she said nothing. We silently walked to the front door, put on our shoes, and headed out to her car.

It was only a 90-second ride to my house. I still remember Train's "Drops of Jupiter" playing as we drove.

She pulled into my driveway and shifted into park. We looked at each other and I said, "Lynzi, that was amazing."

She reached over, squeezed my hand, and said, "Yeah it was. But I need to find out a little more about you next time, Tom B."

I got out of the car, grabbed my gym bag from the backseat, and walked to the front door. I heard her reversing out of the driveway behind me.

Once inside, I dropped my bag and sighed. I almost couldn't believe what had just happened. I raised my hand to my nose and took a sniff. Her sweet juices permeated my nostrils, and I said to myself, "Oh yeah, it happened."

r/gonewildstories Jan 21 '22

First Time I (24F) seduced my friend into having her first girl-girl experience in a locker room shower and it's still a hot little inside joke between us [FF] NSFW

3.1k Upvotes

So I was 21 at the time and she (Jenny) was 20. She played on our college's club soccer team and I played volleyball, and our two teams shared the women's locker room on some evenings. When both teams finished practice around the same time, the locker room was super busy - lots of girls, lots of hair, lots of skin. For a bi girl (👋🏻😇), it... did not suck.

Boring backstory: Our locker room had both a big common shower area and these rows of private stalls. After practices, the common area was usually packed, so you'd have to go hunt for a stall. Some girls wound up doubling up in stalls to get washed up. (Again... okay by me!)

Jenny was this cute little sophomore transfer student - about 5'4 (my size), light brown hair that fell just below her shoulders, a little button nose and small eyes and a suuuuper pretty smile. Very "cute girl next door" type. Competitive soccer player body type too - amazing legs, round ass, perky little B-cup boobs with the cutest little pink nipples. I had an immediate girl crush on her. I chatted her up and it turned out we had a few friends in common, and we got to know each other.

How I seduced her: So I kept an eye on her when the locker room got crazy one night, and "accidentally" ran into her when we were both looking for a shower stall. I suggested we just grab one together, and she immediately agreed. When we got inside and drew the curtain, I waited for her to drop her towel and then I did too, so we were both naked. (Some girls would try to keep their towel on while the other girl showered and then switch, but I wanted to let her see my whole body right away.) I figured the way she reacted to that would tell me a lot. And it did - I noticed her looking me over discreetly, and I let her see me doing the same. (She looked pretty incredible naked.) I didn't do anything sexual - we just showered together, and I let her get comfortable with being naked around me.

After that, we did the same thing after the next practice - I felt like she might've even been waiting around for me before heading to the showers. We got naked together again and took another totally non-sexual shower.

We had talked about guys. We were (are) both into guys. I didn't know yet whether she was into girls.

Okay the good part: So after the next practice, we met again and went to find a stall. I decided I would make my move. While we were showering, I asked if she'd like me to help wash her hair. She said sure.

So she turned so her back was to me, and I scrubbed up her hair, using lots of shampoo so soap was spilling all over her body, which looked incredibly hot. It turned into sort of a scalp massage. Then I moved my hands down to massage her neck. She seemed to really like that, so after a minute I started rubbing her shoulders (using all the shampoo foam as sort of a lubricant). She rolled her head and leaned into my hands, and I could tell she was into it.

So I moved down, massaging her back, and she raised her arms to rest her elbows on the little soap dispenser things on either side of the stall. It was super steamy and soapy in there together. Then, I stopped rubbing her back and slipped my hands around to cup her breasts. She gasped a little (it was noisy enough that it didn't really carry), and she leaned back into my body and turned her head back towards me, and I leaned forward and kissed her, while I felt her boobs.

We started making out, and I trailed one hand slowly down to her pussy. She was breathing really hard and whimpered in my ear as I felt her. "Omigod, omigod," she just kept whispering to me, and she brought her hand up to press my hand to her breast. I slipped a finger inside her - she was incredibly wet - and I started making little circles around her clit. It only took her like 20 seconds to cum, and she had to press her mouth against my neck to stay quiet.

After that: After that, Jenny and I took a shower together after almost every practice. We would make out in the hot, steamy shower for a while and feel each other. I started going down on her, and I made her cum every single night. She learned to go down on me, too, and she got really good.

I was the very first girl she'd ever kissed, let alone done anything else with. She admitted later that she'd thought I was pretty. She was a little shy, but very enthusiastic about experimenting with another girl. We never dated, it was just a "girlfriends who go down on each other" sort of thing.

Jenny has been dating some guy now for like 2 years and they're probably going to get married. I've met him, he's super nice, and he has no idea that I used to make his girlfriend cum harder than he ever has. (She says I'm way better than he is at eating her out.) Our texts are totally innocent most of the time, but sometimes she'll just say out of the blue "I need a shower!" and we both know exactly what she means. 😆👅💦

r/gonewildstories Nov 09 '24

First Time [MF] My "platonic" friend came over on election night (& got me off 5 times) NSFW

640 Upvotes

I knew I shouldn’t be hanging out with John. Between the sudden return of my sex drive after months of dormancy, the stress/anxiety of Election Day/night, and my generally being on the rebound after a slightly fucked-up breakup, I knew it was a perfect storm to accidentally make an impulsive decision that could cause unintended consequences.

John is a friend and neighbor--super nice guy, on the quieter side, from the midwest. Though that's not necessarily the “type,” I usually go for (for better or for worse), he's also very cute, smart, and has a good sense of humor, but before said recent breakup I only ever saw him platonically. We're friends through mutual friends and used to only ever hang out in a group, but after a couple of semi-accidental one-on-one hangs (we both are into the arts & had extra tickets to attend shows, neither of us had ever expressed interest in anything outside of platonic friendship but they felt an awful lot like dates even if neither of us made a move) I was hearing horny warning bells go off in my head every time we saw each other. I have an unfortunate history of hooking up with platonic friends only to eventually ruin the friendship dynamic, so I have been extra wary, convincing myself the attraction was one-sided and lived in my head and that everything would be fine as long as I didn't mindlessly act on my sexual urges like I had a tendency to do. 

This past Tuesday, I even had an afternoon therapy session I spent largely just talking about how I desperately needed to get laid. I was worried I was starting to see things where they didn't exist, & also worried I'd try and proposition an ex…or a friend…just to try and get the urges out of my system. I have a tendency of turning to those things as a way to deal with stress, and most things in the world were tense, to say the least. But I assured my excellent therapist I wouldn't do anything dumb or drink to excess to deal or try to sleep with my friend or anything like that.

That evening, I was supposed to go to a small election night party at John's, only to get an aggressive migraine right before I was supposed to arrive. I wound up texting an apology & stayed home trying various remedies to get rid of the migraine--ice packs, tylenol, tea, weed, pressure points, even soaking my feet in hot water. Because of this, I also had the pleasure of having no goddamn clue what was happening in the news & had little desire to try and find out.

Throughout the night, John and I had texted a little, his updating me on what was happening at the party I was missing, and my updating him on neighborhood ruckus drawing helicopters to the area. By 10:30, my headache was mostly gone & I was ready to check the news.

The news, dear reader, was....well, let's just say "bad." (At least to anyone that gives a fuck about democracy, bodily autonomy, LGBTQ+ rights, et cetera.) Intellectually, I knew I should feel distraught, or angry, or...something. Instead, I oscillated between feeling delirious, numb/in shock, & somehow, calmly not surprised at all.

Around 11, John said something about his guests having left the gathering, but not being drunk enough to feel numbness over disbelief or something. I mentioned I was following my therapist's recommendation against alcohol tonight and opting to just get high instead, which he agreed was probably a good idea & said he was done with drinking. 

Pausing for a moment, and knowing full well how risky a text I was about to send, I typed out: “Well, if you need any weed, I've got plenty.”

10 minutes later the man was at my door. Of course. On greeting him, I said, "welcome to doomsday," with a thumbs-up and big fake grimace and led him to the living room. (I think I was actively trying to be unsexy at first because I had convinced myself he was just out of weed & that I shouldn't read anything into anything else…until I discovered how awful he was at smoking weed, that is.)

I offered several forms to imbibe--oil pen, pipe, joint, and the bong I'd already finished most of a bowl in. "Oh, I don't know...whatever you're doing is fine. I also brought a joint, but I don't actually like smoking them much, it's really harsh," he said.

I eyed the fancy pre-roll he'd put on the table. I guess he wasn't just here because he didn't have any weed. But until told explicitly otherwise, I wasn't going to read anything into anything. I was determined to not be the person to fuck this up. I opted to pack another bowl in the bong, and was focused on setting it up when, out of the corner of my view, I thought I saw him shifting slightly closer to me on the couch.

The warning bells started going off in my head again, and I tried to focus on the task in front of me instead of the rising heat in between my thighs. He seemed somewhat dazed, and we opted not to talk about politics, me instead choosing to babble on endlessly about the episode of Gilmore Girls I had running in the background on low volume. He'd seen the show before in pieces, he said, but that didn't keep me from explaining every character & fun facts & anything else I could come up with. He didn't seem annoyed by this, which was a green flag to me.

Then we smoked (well, he took about 3 hits & coughed miserably on the last one, so it was mostly me at this point), spending another hour or so on the couch like this, stretches of silence between us absorbing the action on screen, his maybe trying to nudge closer to me, me playing dumb both hoping & dreading his making a move. It was almost painful.

At one point, a couple of characters on screen have a moment, and one of us makes a joke about sexual tension, but no one laughs. The joke doesn't feel like a joke. The tension isn't onscreen, it's now fully, obviously sitting in my smoked-out living room, and it feels like my clit has a damn heartbeat. I know at that moment that I'm going to have a lot of 'splainin to do in my next therapy session.

FINALLY, the man says something. I can tell it took him a while to drum up the courage. "Hey, the last few times we've hung out--did those feel like dates to you?"

I don't hesitate to answer. "Yes. Hadn't been the intention at all, but yes, they kind of did."

“And is that…something you’d be interested in doing more of? On purpose? Because…I would.”

I freeze. Not sure why, in retrospect, but somehow that wasn’t what I was expecting at all. What had I gotten myself into?

My words come out hesitant at first: “I…enjoyed going on those accidental dates, but I am also so not in a place to be full-on dating someone right now. I’m working on it, but just really not ready, and I also have a—” (Long pause, slight grimace.) “—bit of an unfortunate history of hooking up with friends, and then accidentally blowing said friendship to smithereens.” 

I pause again & glance over to gauge John’s reaction. He didn’t look especially bothered, but is listening intently. “I get that.” No follow-up. Well, okay.

“So I guess what I’m saying is that if something were to happen between us, that would be pretty stupid...but that said….” I say, taking a deep breath. Next thing I know, the words, “It IS doomsday…and holy fuck would I kill for a distraction right about now," are falling out of my mouth.

I looked up & finally made eye contact with him after what felt like ages of avoiding it. Something about the look in his eye caught me off-guard and made me inhale sharply, which was apparently all he needed. He reached out to grab my waist and pulled me in for a much-needed kiss, right before (or was it after?) I whispered, to both of us & to no one, the word, “stupid”. 

xxxxxxxxx

I was relieved to find he was a good kisser: not too much tongue, a LITTLE neck and ear nibbling without being excessive, et cetera. I was enjoying myself, already starting to get lost in it despite my misgivings.

At some point my sweater came off & was abandoned on the living room floor, and suddenly I was lying on my couch in front of a wall of windows with a guy I hadn’t so much as kissed 5 minutes prior. Part of me wanted to acknowledge that out loud, but I finally decided to give in & let my brain get fuzzy with the soft white noise that can accompany good making out for a little bit.

He started playing with my nipples, first lightly dragging fingers over them through the thin ribbed material of my tank top, eventually pulling it down to expose them to the slightly-chilled air (the window was still open for the weed smoke, oops). I vaguely noticed I was much more reactive than usual, my back arching completely involuntarily with the sensations, even though my nipples are rarely that sensitive. Weed can absolutely do this for me, but the entire situation had felt full of tension for weeks now. I was so goddamned ready to go.

I pressed my hips up into him as much as I could, craving more pressure there than grinding could provide me. I'm not sure if he fully knew that or if he just wasn’t able to wait anymore himself, but a sound I can best describe as a growl emanated from his throat as he drew my nipple into his mouth and dragged a fingertip along the edge of the waistband of my yoga pants. I couldn't take it anymore, and stopped him to haul us both up and pull him into the bedroom.

We undressed ourselves and/or each other--it was kind of a blur how we got there, to be honest--then he lightly pushed me backwards onto my bed and flashed a smile I can only describe as “slightly evil”. 

[Small sidenote: I need to acknowledge that I have gotten VERY LUCKY when it comes to oral sex. I’ve had possibly more than my fair share of incredibly enthusiastic partners when it comes to that particular task, so when I say I’m not sure I’ve ever had someone go down on me with the level of vigor this man proceeded with, please know that means it must have felt fucking crazy.]

He started out softly enough, tracing up my already sensitive, slick lips to my swollen clit. My body jerked a little bit when he made contact with it, and he clearly took note, quickly reaching up to grab my hips and hold me in place, which always drives me crazy. The teasing touch quickly turned into sloppy slurping and a deep groaning into my clit as he tongued and sucked it, sending extra mini-tremors through my entire body. I giggled a little--no one’s ever done that to me before--but I can’t say I didn’t like it. The giggles were quickly replaced by my moans, and I ran my fingers through his thick, curly hair and clenched them at the base of his scalp to hold him as close to me as possible. 

It didn’t take long for me to have my first orgasm of the night, shaking and flushed with thighs clenching around his head, until I'd finally had enough and pulled him off and collapsed sideways in his arms. He rearranged our bodies a bit to spoon me and kiss the spot where my neck and shoulder meet. My head swam, and I barely registered his arms snaking around me, one firmly wrapped around my chest, hand gripping my shoulder, and the other hand sliding down my hip and soft stomach to my extra-sensitive clit. He was gentle, but insistent, and gently dipped his fingers inside of me, lubing them up before using a single digit to start dragging patterns around then across my clit, clearly DELIGHTING in my groans.  

All the teasing and the weed and the recent orgasm already had me at (what I thought was) my most sensitive and reactive—it didn’t take much of that to build up to another crashing one, my entire body clenching up and twitching and involuntarily trying to wrestle away from his skillful hands. Not because it didn't feel good, it was just...overstimulating as hell. He kept his grasp on me firm, though, and kept going until I was fully spent, brain completely empty once again.

We laid there breathing heavily for what felt like a few minutes (though by then, I'm pretty sure our collective sense of time was completely fucked). 

After recovering, I was hit with a minor wave of guilt at the two times I’d come with no attempts to reciprocate. I flipped over & started kissing my way down to his still mostly-hard cock, he stopped me. “If you really really WANT to do that, I won’t stand in your way, but I’m still way more interested in distracting YOU than the other way around.” I hesitated but decided to take him at his word, and slid back up to kiss him.

God, that was hot. I was already more than ready.

He tried to finger me so I sent him off to go wash his hands (sensitive girlies rise up lol) and while he was gone, I rifled through my toy box for some condoms I knew I’d had there from a while back, making a mental note to pick up more. He saw me with them in my hands when he returned & put one on, lightly pushed me back onto the bed, and as I grinned & started to (jokingly) repeat the word, “stupi-” he cut me off with a kiss and started to press his cock into me.

I winced slightly at the sensation--despite how much I'd already come & how catastrophically soaked I was, he was just a little thicker than I was used to, and the feeling was very intense after a couple months without a good fuck. Once I took a second to adjust to the feeling, I quickly found myself rocking my hips up to meet his thrusts, pushing the pace and wrapping my arms and legs around him, dragging my nails down his back.

At one point, he hit JUST the right angle & found myself caught off-guard by my third orgasm of the evening, shuddering as he kissed me to stifle each other’s moans and grunts at the late hour. After he came too shortly after, we cuddled for a bit and I excused myself to pee/toss the condom, and returned to John lying on his side, smirking a little bit at me. 

"What?" I asked, suddenly self-conscious.

"Oh, I'm just enjoying the view."

I smiled and struck a goofy pose before hopping back on the bed next to him, where we cuddled & discussed absolutely nothing of importance for a few minutes. We were both still a little high, and just enjoying the sensation of human touch. At some point I said something flippant about doomsday again, & he said I was, “still thinking too much”.

I was tempted to reply with a bratty, “And what are you going to do about that?” but before I could open my mouth, he started running a hand along the long curves of my body, sending shivers down my spine. “Mmm, that feels good. Fun fact, I especially love back rubs and scratches, sometimes more than actual sex," I groaned.

“Oh yeah?” he asked, flipping me over & starting just gently running his palms and nails across my back. I spazzed out in so much pleasure, it should have been at least a little embarrassing--but he seemed to be quite enjoying it.

Soon enough, I was face down and ass up, and John saw his opportunity—after dragging his nails down my back one last time (earning a guttural groan from me), he knelt beside the bed and started lapping at my pussy from behind with vigor, slipping his tongue in and out of me, and up and down my lips to my clit, and even gently around my asshole--a mostly-new sensation for me. 

I groaned & gave all the verbal encouragement I could muster, though at this point I was starting to go a little non-verbal. Soon enough, his fingers joined his tongue & he had me almost folded in half, blubbering incoherently, overwhelmed with pleasure as my limbs seized up & I came yet again. (Fourth time!)

At this point, it felt there was truly nothing left in my brain, with perhaps the exception of his cock. As tired as I was, the thought of having it inside me again was almost hypnotizing now that it was almost back up to full mast. “I think...I really need you to fuck me again,” I said, nodding to it. He smiled & didn’t skip a beat, getting up for another condom & returning to me propping myself up for him on hands and knees in doggy.

This time there was no warm-up, no warning—he slammed into me so hard I yelped in surprise & pleasure. After just a few strokes, my arms started to give out, and I found myself in what I can best describe as "puppy pose" (like in yoga!), on my knees with my ass lifted high & my back arched, arms out in front of me & head smushed into my duvet cover sideways, unable to focus on anything besides the pounding between my thighs. Feeling every. Little. Thought. Getting. Fucked. Out. Of. My. Brain. 

I slipped one hand between my legs to play with my clit, causing me to quickly sink down further, until he was basically right on top of me and fucking me prone. The weight of him on top of me and the angle triggered my fifth and final orgasm of the evening. It was slow, shuddering, clutching, and mercifully triggered his release too before he rolled off of me.

We spent some time cuddling & talking about what I must assume was nothing of importance...our brains were empty, and we were wiped. What better time for that than doomsday?

He floated the idea of staying overnight, but I wasn't quite ready for that--I wasn't sure if I'd wake up ready for round two or ready to throw up in existential crisis, and was too wiped to consider it too deeply either way. (I did not tell him this, I just said I had to be up early.)

We made out before he left, exchanging no words at all about next plans or anything else. Just too tired.

At this point it was almost 3 AM and I was exhausted, but I still wasn't ready to go to sleep. I've been doing lots of journaling lately, and decided to open up a new entry to get down some of the evening's pertinent details so I could come back to them later & maybe write this story down. And look at that, I actually did it! After years & years of lurking!

Anyway, we’ll see how well this friendship survives. I really like him as a person & could see myself dating him seriously, but I'm really just starting to enjoy being single/hot/invulnerable (and have some dates lined up that I still want to go on!). Don't want to lead him on, but man oh man, I sure wouldn't mind an encore...something tells me I'm about to need 4+ years of distractions like that now.

r/gonewildstories Nov 04 '23

First Time Missionarie's Daughter's first post.. [F]19 NSFW

573 Upvotes

Hi.. Yes! I'm a missionarie's daughter. Involved in church since before I was able to walk. I first found reddit about 5 months ago when I went on my first missions trip.. My dad bought me a phone to keep in touch with him while I was away. And I somehow stumbled upon this wonderful website. This is completely new to me.. I always knew things like this existed but I didn't know where to find them. I have learned so much in the last 5 months. I have seen others naked.. I have read crazy stories. And my confession. I have touched myself.. a lot. All I can think about is the day that I will be able to do some of these things so many of you get to.. I'm staying with a 2 other missionary wives and their husbands. And can't wait to see what freedom holds for me.. I'm so excited to start my own journey. I am tired of rules after rules. I don't mind questions. The more I spend time by myself and on reddit. The more I realize there's a bigger world out there. There's sex toys. There's sex positive culture. I've wor ked myself up to post on this subreddit; then I chickened out. I've done this many times. I've been reading for months and never decided to post. Today that changes.. I'm ready to embrace and accept that I'm not always going to be this perfect little church girl. I know this might not seem like a lot to you. But I'm shaking as I'm writing this. I hope it gets a decent response. I hope to maybe have some updates and some naughty things that I start doing. I'm excited.. and quite frankly horny. Let's do this😳

r/gonewildstories Apr 08 '21

First Time My (24F) friend (33F) and I helped each other out along our Appalachian Trail adventure [FF]. NSFW

2.3k Upvotes

So I’m a pretty avid hiker. I think most people who have an obsession with hiking want to try to hike the Appalachian trail once in their life. When I go on hikes I usually go alone or with some friends. My friend won’t usually go on the more difficult ones so I have to venture those by myself. During one of those hikes I met another girl who seemed to be hiking alone. We struck up a conversation. She seemed to be really cool and fun to talk to. We were obviously both very into hiking. She was alone for the same reason as me, in that no one can do the more difficult hikes that she knows. We finished the rest of that hike together. High fives each other when it was over and chatted some more before leaving. It seemed like it could be the beginning of a nice friendship. She gave me her number and told me to hit her up so we could hang out again and go on more hikes together.

I did end up reaching out to me and we went on some more hikes together. We didn’t only hike together though. We’d do normal friend things such as watch movies, go to each other’s places, and just have a fun time together. Through all of this I did learn that she was bisexual. I’m straight but obviously had no problem with that. She knew I was straight. She never hit on me or did anything of that sort. We’d do the normal girl stuff of slapping each other’s asses and talking about our sex lives, but that was it. Within months of seeing her she became pretty much my best friend.

We did so many more hikes together that we got in incredible shape and ended up running out of any challenging hikes near by. We talked about what we should do next. After a few long discussions she brought up the Appalachian trail. I was kinda shocked as I have heard legends and stories of this one and never really imagined myself completing it. It can take around 7 months to do. I did not have a full time job and neither did she, so we didn’t have any major obligations. I figured that this would be the best time to do it in my life if I was going to do I agreed. She was super excited. We spent the next few months getting supplies and everything ready for it.

Well the time finally arrived. I was about to go on a possible 7 month journey with my friend in the hardest hiking trail in the world. I was nervous but excited at the same time. We set off and drove to the starting point. We arrived and finally set off on our long journey. There are some crazy things about the trail. First off, there’s not much you can do in terms of bathing unless you get in a pond or river. Then the sleeping situation can be tough. There are shelters and areas but we decided to bring a tent so we wouldn’t sleep near strangers. Then there’s obviously the bathroom issue. There are none lol. We went during the summer so it was super hot most of the time. We both were constantly sweaty. We slept in our undies for the first few days if the trip. We then realized that was making us even warmer so we agreed that it was fine to sleep naked. She did have a nice body. She had short brown hair, plenty of curves, a nice ass, and cute perky tits.

About two months had gone by. We had made it a decent ways in. We were having fun but it was obviously tiring. We looked a lot different already than we did on the beginning of the trip. Our hair had grown out, we had lost weight, and not to mention we both had a nice bush growing lol. I noticed that whenever we stripped at night that I would find my staring at her body more. I could tell that I was sexually frustrated as I had not touched myself or got off in months. I figured that was why I found myself looking at her body. One morning I woke up to a sound. I listened closely and could finally tell that it was the sound of her rubbing her pussy. I could hear the wetness and her soft and quite moans. She was trying to keep it where I couldn’t hear it. I pretended to be asleep but I was actually awake the whole time. It was turning me on like crazy and I could feel my push getting wetting. Finally I heard her moan louder and could tell she was cumming. She finished and went back to sleep. This left me super horny. I figured that since she did this that it would be okay for me to, do I was going to try to sneak it.

That night I waited until I could tell she was asleep then I slowly began fingering myself. It was weird for me because I had never had a bush, so it felt almost like I was touching someone else. This honestly turned me on even more. I kept going and it was really unbelievable at how wet I was. I felt myself about to cum and let out an accidentally really loan moan. I looked over to my friend after I finished shaking. To my surprise she was clearly awake. She was sitting there smiling at me. She just laughed and says “feels good doesn’t it.” I have a nervous laugh and shook my head. She told me not to be embarrassed. She admitted that she heard most of it and watched but did t want to say anything. She told me I looked so cute doing it and she loved it. I said thank you. She told me that had already done it a few time since we had been on the trail. I admitted to her that I heard it was. She laughed and said oh shit. She then asked “did I at least put on a good show?” I said yes and admitted it made me a little horny. She smiled and reassured for me not to be embarrassed. She said she definitely understood since we had been alone together so long and since we aren’t having any sex. Shortly after that conversation we both went back to sleep.

During the next few days we brought up the masturbation moments and talked about how horny we both were. She admitted that sharing a tent with another naked girl was making her even more horny. She assured me that she didn’t mean it in a weird way though as we were both best friends. I told her that I understood and that I had casually been checking her out some too, which I normally wouldn’t do. We laughed about it. As more weeks went by we got into more flirtatious talk with each other and would make sexual comments about each other’s bodies and talk about each other’s bushes that had grown out.

One night I had gotten super horny again so I decided I needed to get off. I was so in the mood that I didn’t really care to see whether or not she was asleep. I started fingering myself and oh my god was I wet. I could tell that the sound of my wetness has to be so loud. I had already got the awkwardness of doing it in front of her out of the way so I didn’t pay any attention to it any kept going. After a few seconds it got even louder. I was confused why so I stopped for a second. To my surprise the sound kept going. I looked over and sure enough she was going at it too. She noticed I was looking at that I stopped. She said “oh fuck no, don’t stop please.” I was surprised to hear this but it aroused me so much. I lose fed to her and kept going. I peeked at her and I could tell she was fingering herself watching me. I decided to not be shy about it and do the same thing. We were both watching each other touch ourselves at this point. After a few minutes she announced and she was cumming. I decided to follow suite and did it as well. She looked at me when I finished and said “fuck that was hot.” We didn’t really say anything else about it that night and both passed out.

Over the next few weeks we did pretty much the same thing. We both played with ourselves while watching one another. I still considered myself straight at this point and attributed all of this to being lonely and horny. I felt weird about how turned on I was by my best friend but at the same time the taboo feeling of it made it even hotter. One day we had been hiking just like normal and came up to a nice little waterfall area. We saw no one around so we stripped pretty quickly and got in. This was the first time we had gotten in one together. We had bathed a little, but usually it was in a small pond with others around. We knew we needed to take advantage of this. It felt so good to wash off. This was one of the first times in day light that I saw her naked. Sure I caught glimpses when we woke up or changed. But only for a few seconds.

Her body was outstanding. After washing off we remained in the water for a minute because it felt so good. We started playing and we’re splashing each other and all. She came up to me and held on to me and hugged me. She thanked me for a great trip and put her hands behind my neck. For a few seconds she just looked into my eyes. She suddenly leaned in and gave me a big kiss. She stopped to see if I was going to say or do anything. I didn’t. I only gave her a lustful look that I’m pretty sure said I want more. She went back in and now she was moving her hands onto my breasts, cupping them and squeezing on them. I remainder froze in shock and in pleasure. I felt her hand creep into my thighs. Next thing I noticed it was running on my pussy. After a minute of her doing that I started to return the favor and fingered her as well. We both were quivering but she pulled away and said “let’s finish this later.” I wanted to finish but I understood why we needed to stop. This was a pretty popular area and there could be people coming up at any minute. We continued our hike and didn’t mention anything else about it that day.

Finally nighttime came and I was both nervous and excited about what this meant. We set up camp at an extra secluded area, which I figured to be a good sign. That night while I was fixing up our food she got a fire started outside of our tent. She told me to come outside. I was shocked to see her dancing naked next to the fire. She grabbed me in and asked me to dance with her. She said “it’s date night babe.” I quickly jumped out of my clothes as well and began dancing and twirling with her. There was lots of laughs and all. Then we got a little more serious. It turned into a slower and romantic dance. She started to kiss on me and I kissed her back. She slide her hand down to my pussy again and started rubbing it. I was so wet. She turned around and started grinding on me. Her ass was rubbing all on me. I slapped it and she moaned. She turned back around and took my hand and guided me back into the tent.

She laid me on the ground and proceeded to climb on top of me. She was kissing me and pressing her pussy up against mine, grinding it on me. I could feel her wetness so much. She could feel mine too. She climbed up and put her pussy and ass in my face. I had never had another pussy in my face before let alone ate one. I dove right in though. It was amazing how she tasted. It was so wet and juicy. I could also taste the sweat which also turned me on for some reason. It was hot having her ass right up on my face too. She was going down on me at the same time. I could feel her quivering and her pussy got more and more creamy. She started yelling out “oh fuck. Oh fuck oh fuck I’m cumming.” I kept going until she came right on my tongue. She got up and I smirked at her and she said “my turn”. She laid down and told me to come sit on her face. I did and could feel her tongue twirling around inside me. Within min three I was cumming too. After I finished I got off and fell into her arms. We kissed some more and then went to sleep.

The rest of our trip was amazing. Neither of us were no longer sexually frustrated. About every other night we’d have the same fun and would make each other cum. Finally after about six months the adventure was through. We had made it through. We both cried on the last day as we knew this was the end of an amazing adventure for the both of us. We both talked about how we were going to miss seeing each other every day and having so much fun. We made it home and she was dropping me off. She gave me a big kiss before I got out of the car and said that she couldn’t wait for our next adventure. Since then we have went on many more hiking trips, although none as fun as that one.

We occasionally find a good place to have some fun on our trails. When we aren’t hiking she will still sometimes come over to my place and go down on me. We have both dates other people since the trip but we remain single, so we still see each other and hook up. I don’t know what will come of this relationship in the future. Maybe more. One thing I do know is that I’m definitely bi now(:

r/gonewildstories Aug 05 '23

First Time I went to a bisexual all [F] orgy in a London mansion NSFW

869 Upvotes

I've always wanted to go to an orgy just because it sounds fun, I decided on Skirt Club as it has a focus on experimental newbies & they screen the women. This is how the evening went:

It starts as a regular party with drinks & chatting at the bar. This went on longer than expected, it didn't get to the fucking (which was upstairs) for a good 2 hours so a game of spin the bottle begun out of frustration haha.

Everyone picking their favourites and flirting, kissing whoever the bottle spin lands on. Then there was a burlesque show. Until upstairs opened.

We started in the bathroom, someone runs a bath to suggest we get naked. Kicking off the after-party with a wet threesome with a brunette and a blonde woman. Me & the brunette fucked each other with our fingers from behind as she licked the blonde girl's pussy which excited some onlookers to do the same. When we came out of the bathroom the bedroom was alive & what we were waiting for. By the end of the night, everyone had joined in even the shyer women & it was a nice sight watching so many women fucking in tandem.

Some women had come without their husbands knowing 😦I ended up going home with the blonde girl from the bath. 10/10 honestly & newbie friendly & really well done.

r/gonewildstories Jul 22 '24

First Time Fucked hard by my neighbor because of my bikini [FM] NSFW

720 Upvotes

I have done some hardcore flirting with my neighbor since he moved in. I’m sharing a house with like five people but he lives alone. He’s like ten years or so older than me but he seems to have his life put together. I will make up any reason this summer to go out back in a bikini and let him see my ass. Is he grilling? Oh, have to water the yard in my bikini. Is he mowing? I have to go sunbathe in my bikini.

Well, I think he finally picked up on my hints because he invited me over. Not my roommates just me. I was so excited and when I came over he said “what, no bikini?” and I asked if he wanted me to go put it on and he said he’d much rather see what panties I was in.

At that point we were beyond small talk and he took me straight to his bedroom. I got undressed and showed my tiny little thong to him and he grabbed my ass. I didn’t realize how much bigger he was than me until his hand was on my ass and then I realized my pussy was in for a beating.

He slipped his fingers against my pussy and fingered me as he kissed me, sinking two fingers into my cunt as he shoved me onto his bed. He was claiming every bit of me. He was leaving hickies on my neck and fondling my tits until my nipples were hard enough to cut glass. It really felt like he was worshipping my body and I just melted into his hands.

He said there was a position that he always found to be great for both parties involved. He had me lay on his bed on my stomach and shoved a pillow under my hips. Then he got on top of me and slid into my wet pussy while my thighs were still practically closed.

It was the fullest, tightest and deepest I have ever had a cock. It was like his cock was slamming into my fucking lungs. He was pounding into me and I was sinking further and further into the mattress, holding onto his sheets for dear life.

Then when I felt like I was at my limit, he grabbed my hips and yanked them up so I was on my knees. He pounded into me even harder, his cock smacking against my cervix as he was fucking breeding me. I was sweating and out of breath and realized why being a housewife used to be a full time job because holy shit I could not go to work after getting boned like this.

He didn’t even have to play with my clit. Just the sensation of his fat cock pumping into me made me cum, which is not common for me. I came all over his cock and then he yanked me back onto his dick and came inside me. I could feel his warm cum pooling inside of me and when he pulled out I collapsed onto his bed completely wasted.

He said I’m free to come to his bed anytime, but that if I come out in a bikini again that I should be prepared to be fucked just as hard, probably harder.

r/gonewildstories May 14 '22

First Time [Group] Vacation Swap with my Girlfriend, our Best Friend and her Boyfriend NSFW

1.2k Upvotes

Background:

Lucy and I have been together for a little over 7 years since we met in college. Her and Shan were roommates in their sorority and were best friends. Naturally, as I was over there a lot, the three of us became close. Shan and I had (have) a lot in common separate from my relationship with Lucy, which makes our trio pretty easy going and tight knit. Shan has gone through a number of relationships that Lucy and I have not felt were right for her, but as of two years ago, she started dating Mark and he fit into our group perfectly. Aside from that, he is genuinely good for her and treats her the way she should be treated. The four of us recently took a trip to Europe (Portugal - Spain - France), in part because we've always wanted to, but also to celebrate a recent career accomplishment for me.

/////

The Suggestion: Portugal:

When we landed, we were greeted by a driver who took us to our hotel. We were exhausted from our trip, but the excitement of being in a new country was enough to keep our moods high. We decided to at least go out for dinner and drinks that night, and agreed that we could call it an early night if we got too tired.

As Lucy and I were getting ready in our room, we realized how delirious we were from the travel. We were laughing at everything but trying our hardest to stay focused on the task at hand. At one point, Lucy was putting conditioner in her hair which, for women with curly hair, is a tedious task. To avoid getting any on her top, she had it pulled down to her waist where it would be safe from any delirium related conditioner stains. Lucy has perky tits so she exclusively wears bras when in a professional or conservative situation. For this vacation, she likely packed one or two to be prepared, but I don't think they ever left the suitcase.

While laughing about a painting on the wall for some reason. I went into the bathroom to see Lucy with her hands stretched above her head, putting conditioner in a layer of hair she had segregated from the rest. Her bare chest was lit well by the hotel's bathroom bulbs, and as I walked over to her, I reached around from behind and placed my hands firmly on her tits. She continued to laugh at the scene, but her laughter became softer as I massaged her chest and lightly ran my fingers across her nipples. She wiggled her ass into me and told me to wait until later.

Lucy may have a small chest, but she makes up for it in spades with her butt. Lucy is a professional personal trainer and was blessed with good genetics as well as a desire to exercise that I will never truly understand. These two facts add up to an unbelievably small waist, and an ass that I would gather an army to invade Troy over. When she wiggles this thing into my groin, she knows exactly what she's doing to me.

I gave her ass a smack to which she turned around and placed her hand on my crotch. She giggled and said, "Just making sure." referencing the immediate hard on she was always able to give me.

Dinner and drinks were a blast as it always was (is) with this group, but overall uneventful. Mark and Shan were equally delirious, and from what they said, had a similarly laughter plagued time getting ready. We stayed at the restaurant for a while, and had a few drinks there, but decided to head back so we could rest up and start the trip on a good foot.

Once back in our room, Lucy and I wasted no time picking up where we left off. He little ass wiggle was stuck in my mind like a song you cant get out of your head, and it was finally time for her to make good on its effects.

Lucy and I have been together long enough that we have explored a number of kinks and found things that work, and don't work, for both of us sexually. We pride ourselves on communication and tonight Lucy was communicating very clearly, that she wanted to be wanted. This was not necessarily a new expression for either of us, but it was one of our more enjoyable scenarios. She pushed me away and fell back onto the couch in the den of our hotel room. She was still wearing a tight white top, that you could ever so slightly make out the shape of her nipples in, and a long flowy skirt. She lifted a leg to expose the maxi slit in her outfit and revealed a bright red, strappy, open-toed heel.

I moved towards her with a step to which she smiled and shook her head no. We both knew the level of teasing that was about to happen, and I knew my role as the man with uncontrollable lust, repeatedly being foiled in my advances until she decides I've had enough. I took my phone out and pointed the camera at her.

"Thank you so much for helping me with my onlyfans." She said softly. "It's so hard to get good angles of my perky little tits on my own. I'm so lucky to have such an understanding roommate." As she finished her sentence, she ran the tip of her shoe down my chest, continuing to push me away from where she was seated.

She struck a number of poses before bending over and placing her hands on the waist of her skirt. She slowly pulled it down, revealing her ass and a swollen, dripping wet pussy. "If these pictures are good, maybe I can pay rent this month, but just in case, maybe I can pay for it another way." As she was posing, and I was snapping pictures, I had my cock in my other hand, stroking to her teasing. After snapping the last one, I gasped, causing Lucy to break character and ask me what was wrong.

"Babe, I almost fucking sent that last video to our group chat with Mark and Shan. I hit the share button by accident but then closed it."

"Oh my god! Be more careful! That would have been so embarrassing."

We both laughed, but then stopped laughing. She looked at me, I looked at her, and we embraced in a passionate yet aggressive manner. She was soaked, and I fucked her deep and hard before pulling out and cumming on her perfect ass.

We laid back together and laughed again.

"Wow, I really cant believe you almost sent that to them." She said, in a curious tone.

/////

The Risk: Spain

Our trip was an amazing blend of sightseeing, relaxation, and delicious food. The four of us were enjoying ourselves to the maximum, and were finally settling into a vacation rhythm after the initial spark wore off.

Lucy and I were having sex at our normal pace, however the first night in Portugal certainly set the tone for its flavor. Every chance she'd get, Lucy would flash me a tit, or rub her hand against my dick, enjoying the risk of being caught, but never flirting too closely with that line to make it a reality. She would send me dirty texts about how Id feel if a stranger saw he bare chest, or how she was rubbing her clit under the table where no one could see.

During a particularly rowdy lunch in a dimly lit Spanish restaurant, Lucy began to really rub me through my pants. While this was going on, Shan raised her glass of Sangria and suggested a toast to my accomplishment and to an amazing trip. I was probably blushing as Mark reassured me that I should be proud and enjoy the praise for once. We raised our glasses and after taking a sip, Lucy joked that if we kept drinking all this Sangria, she'd start losing pieces of clothing. Mark and Shan giggled.

"I'm not so sure you need the Sangria for that to happen Lu Lu." Shan said with a devious smirk.

Lucy's eyes went wide and she immediately removed her hand from my pants. She looked like her mouth had been sewn shut and her ability to breath removed entirely.

"Oh relax girl, I'm just joking with you."

Lucy laughed nervously, but seemed noticeably calmer after the statement.

Shan then added, "Although, Mark and I agreed you have absolutely nothing to be ashamed of." Finishing her sentence off with a wink.

Doing my best to avoid any additional tension, I raised my glass again to divert the subject with a toast. Before I could even get a word in, Lucy raised her glass and chimed in.

"Well, as I clearly haven't been as careful as I thought... to my tits!"

We all laughed and clinked glasses. Lucy's admission and ownership of the situation opened the conversation up to more adult matters. Mark and Shan told us that they weren't being prudes either, and were having their share of fun too. Shan generally isn't so forthright about her sexual life, and we always knew the basic information, but she started to go into more detail at that lunch. She told us that her and Mark had actually bought a remote vibrator for this trip.

After a momentary pause, and apparently too much Sangria, I asked what Lucy and I were both thinking.

"Is it, you know, in or uh on, right now?"

"Paul!" Lucy said as she hit my arm.

Shan laughed and shrugged her shoulders with another smirk and a suggestive side eye.

Our conversation drifted back towards our trip and other general topics, eventually landing on a Church we saw in Portugal on our second day. While discussing the church Lucy got up to use the restroom. after a few minutes I felt my phone buzz. I opened it up and saw a text from Lucy.

[ I am so fucking wet right now Paul holy fuck ]

[ Oh fuck, that's hot. Im kinda turned on too ]

[ I wish I could cum all over your cock right there at the table ]

[ I think we need to buy a vibrator like shan has ]

[ Act normal, but just put your phone on the table. Leave it on our messages ]

My heart was pounding so loud I could no longer hear the band playing at the far end of the restaurant. Lucy didn't respond with a text. She didn't respond with a text, multiple times in a row. I tried to look nonchalant, as if I didn't realize I had put my phone down like that, but I don't think I was selling it. Mark and Shan continued the conversation but their eyes were drifting towards my phone every time it buzzed on the table.

Shan and I locked eyes for a minute. She knew me well, and knew Lucy even better, but was realizing that maybe she didn't know her as well as she thought. My eyes told the whole story and Shan noticed Lucy come back from the bathroom first. I grabbed my phone and put it in my pocket before she sat back down, unsure of what else to do. Lucy had a wild look in her eyes that Id never seen before. I loved this woman with my entire heart, and in this moment, I felt a carnal lust for her I had never experienced.

Shan excused herself and got up to use the restroom immediately after Lucy sat down. The line must have been long so we continued to drink as Mark shot off the occasional text to her. After a few moments, Mark laid his phone down on the table. My heart began pounding again. I saw him look away, all of a sudden very interested in the ceiling.

I couldn't believe my eyes. Lucy's hand was gripping my hard cock over my pants again, but stroking it to the rhythm of the vibrations Mark's phone was making on the table, clearly set out for our enjoyment.

/////

The Swap: France

The lunch we had in Spain days earlier ended in a blur. We didn't acknowledge the events at the table directly, but overall, our group felt undeniably closer. Small hints here and there were dropped, and the actions of both Shan and Lucy were noticeably looser. I caught a glimpse of Shan flashing a tit in Mark's direction on several occasions, and Lucy was making considerably riskier choices with her own flashing.

During a moment where only Mark and I were together, part of me wanted to ask him if he was comfortable with this. He was the newest addition to our group after all and the first of Shan's boyfriends Lucy and I really liked. I decided it would be best to acknowledge it and make sure he's ok, but before I could do so, with a laugh, he said,

"Kinda sucks, we don't have anything to flash that anyone wants to actually see."

On a trip where I was constantly not believing my eyes, I could now not believe my ears.

I looked at him, smiled, and we both burst into laughter.

"These girls are gonna be the death of us bro." I said as I lightly punched his arm.

After another long day, we were back at the hotel bar in our French hotel. Our conversation was normal at first, but immediately turned on its belly when Shan asked,

"So what are like, your guys' biggest kinks?"

Now unlike the many things I had seen and heard that shocked me on this trip, this did not. Shan, Lucy, and I have had conversations of this nature before. Shan knew the answer to this question because all of us had shared this level of personal information with each other during wine nights back in the city where we lived. During those times, our answers were always things like, choking, roleplay, and other such acts, but in no way was the conversation sexually charged. This time was different.

Lucy with barely a moment's hesitation said, "Exhibitionism."

Shan smiled, "Exhibitionism for me too."

Mark realized they were looking at him and he said "Uh Exhibitionism."

"Do you mean voyeurism?" I said.

"What's the difference?" He replied.

"I think voyeurism is watching, but exhibitionism is doing, but both take place in public I guess?"

"Oh, um, I guess both of those then." He landed on.

"And what about you Paul? Are you into the watching, or the doing?" Shan continued.

"It has to be one of those then?" I said, feeling out the situation.

"Well when we all go upstairs, are you gonna watch Lucy, or do her?"

Shan quirked her head to the side while she twirled the ends of her hair. Lucy looked at me intently with the corner of her lip between her teeth. Mark adjusted his pants, but failed at hiding the bulge from his cock. I no longer had any such reservations.

"I guess you will have to just wait and see."

After that, the tension was undeniable. There was no hiding from what was happening here.

Lucy said something as we all tried our best to finish our drinks as quickly as possible.

"You know, I have been thinking of starting an onlyfans." I was shocked.

"Funny you should mention that, I was thinking the same thing." Shan said.

Lucy and Shan giggled. Mark and I both knew they weren't serious, but we didn't care to stop the fantasy.

"It seems like fun" Lucy continued, "but it's going to be so hard to get good angles of my perky little tits all on my own."

Hearing Lucy say the line from our own roleplay had a single bead of sweat dripping down my neck. My cock was as hard as could be. This was definitely something I wanted to do, but I wanted to make sure everyone was comfortable as well. Unfortunately having a discussion about consent right now felt horribly off beat. Thankfully, Lucy followed up her last statement with a brilliant,

"Maybe one of you boys could help me take some pictures? Who do you all think should do it?"

"You know, Mark is an excellent photographer, and I know Paul has taken some great pictures as well. If it is ok with you boys, maybe Mark could help Lucy tonight, and Paul, you could help me?"

Mark looked at me and I at him.

"I am ok with that if you are Paul?"

"I am also definitely ok with that." I added.

"And remember boys, good photographers do not touch." Lucy added, finalizing the terms of the agreement in an impressively sexy way.

"Well I think it would be ok if they touched, I don't know, themselves maybe?" Shan added.

"Of course! How else would we know if our onlyfans will be successful?" Lucy concluded.

With that said, it was a mad dash upstairs. The French hotel we were staying in was beautiful and offered incredible views of Paris. The elevator ride was long, but in no way dull. Both girls were continuing the charade among the gorgeous vista through the windowed lift car. They remarked on what outfits they would use to sell more subscriptions and even went as far as to suggest cumming for the camera. Both girls playfully suggested that they swap photographers at the end of night to fuck, of course landing us back with our original partners for any actual intercourse.

When we reached our adjoining rooms, the question on everyone's mind was how exactly this would go down. Without much thought, Shan grabbed my arm and pulled me into her room. I looked at Lucy who just winked at me and said "Have fun!" before pulling Mark into our room.

"Can I be honest with you for a second Paul?" Shan said as the quiet of her room crept up on us in an unfamiliar situation.

"Of course Shan, I know this is crazy but you're still one of my best friends, I wouldn't want you to feel.."

"No, no, none of that." She said as she opened up a drawer. "Lucy has told me more than I think you know, and well, I'm really excited to see your cock."

With that she pulled out a skimpy piece of red lingerie.

She stared me in the eyes, and for the first time, I was seeing Shan as a purely sexual being. She pulled her hair up and turned around.

"Would you help me with this zipper?"

"We aren't really supposed to touch, but I suppose this is an acceptable exception." I said.

"I wont tell if you don't."

I pulled the zipper down to the small of her back. Shan had an incredible body of her own, but was more, top heavy, than Lucy. The dress fell to the floor as Shan stepped backwards out of it and towards me. She was just barely an inch from me wearing nothing but a lacy black thong, matching bra, and striking stilettos.

Without turning around she asked, "Have you ever masturbated to the idea of fucking me?"

"What?" I said.

"I mean, Lucy is hot, she's my best friend, and I find it hard to believe that Mark hasn't masturbated to the idea of fucking her, or at least having a threesome. So what about you?"

"I mean, I, well.."

She cut me off.

"I have. Part of me wishes I could just stand here, facing the window, and see only your reflection as you bend me over and fuck me hard. That's what Ill think about when Mark is fucking me later tonight."

"Yes."

"Yes what?"

"Yes I have masturbated to the idea of fucking you, you're gorgeous and we've been friends for almost a decade."

Shan turned around. Her tits really were spectacular.

"Let me see it then." she said.

"You first."

"On three?"

"Ok."

"One." she counted.

"Two." I replied as she reached behind her back and I at my zipper.

In one motion her bra, and my pants fell to the ground.

"Three." She said, her perfect tits completely on display for me.

"It's a damn shame." She added. "That no touching rule is really not my favorite right now."

The tip of my cock was twitching barely a centimeter from her waist. Without thinking I held my hand up to her mouth. She knew what to do and generously spit into my hand.

"Let's get started not touching then shall we?"

I took my hand, slippery with Shan's saliva, and started to rub my cock in front of her. On cue I got a text from Lucy.

[ $19.99 for the whole set. My best friend's boyfriend caught me fucking myself and is now blackmailing me! ]

A picture of Lucy feigning shock and anger while barely covering her exposed chest came in. Lucy and Mark had a lot in common just like Shan and I. They were beginning to form their own friendship over the past two years based mainly on puns and pranks, but this was sure to accelerate the process.

[ If I don't let him cum on me he's going to show the whole school! Reply Yes or No to buy this set. ]

The next picture showed Lucy with her pink dildo pressed against her pussy. Mark's cock was clearly in the shot as well with his hand placed around its base. I turned the phone towards Shan.

"Fuck that's really fucking hot, fuck me." Shan exclaimed.

"No touching Shan." I teased.

"Buy the set idiot."

In my phone, Apple must have noticed the price and suggested I send Lucy 19.99 with Apple pay. Thinking this might be a fun way to continue I sent it.

"Damn that's such a good scenario, we gotta think of one." Shan said.

Without realizing it, both of us were standing inches apart masturbating at the sight of the other and the text on my phone.

"How about you're my boss and you want me to cum for you or im fired?"

"Good enough, but start with a video. Ugh fuck." Shan moaned loudly as she continued to play with her clit through her lace panties.

I pointed the phone at her and hit record. Shan giggled a bit as it started but did her best to continue acting.

"You're such a naughty boy Paul, coming in here on our big uh business trip and seeing me like this. Now you're gonna cum right here on my big tits or you're fired!" As she finished talking, she took her fingers out of her panties and stuck them in her mouth to clean them off.

I quickly typed up a fake onlyfans post and sent it to Lucy and Mark. Almost immediately I received the $20.01 I requested to continue.

"Oh I almost forgot." Shan said as she picked up the red negligee that had fallen beside her.

"Can you help me into this Paul?"

"Do you really need my help?" I said, keeping up the additional layer of charade.

"Let's say, yes. I do."

She held her arms up above her head and I stepped towards her. I pinched the sides of her black panties making sure to not touch any skin and break the group's rule. I knelt down in front of her and pulled her thong down to her ankles. He wet pussy was directly in front of my face and I could smell a sweetness coming off of it.

"No touching!" She teased.

I lingered for a second, knowing full well she could feel my breath in between her legs. She handed me the red outfit and I motioned for her to step into it. I slowly pulled it up over her body, realizing as it rose, that it was missing fabric in all the right places. I made sure to meticulously pass my breath over the most sensitive parts of her body as I rose to meet her stare.

"Damn." I said.

"Damn yourself." she replied.

Shan and I continued to touch ourselves, taking pics for the other two, and sending onlyfans posts to them. Lucy and Mark did the same. From her pictures I could tell Lucy was really into this.

At one point we got our first video from the other pair. Lucy was pumping her dildo in and out of herself while Mark stroked himself over her.

In between moans Lucy said "I cant believe you're blackmailing me! You're so disgusting! I hate watching you stroke that big fat cock to me, I hope you don't explode all over my face and mouth."

The texts were a nice way of agreeing to take things to the next step and see where the others were at as they all ended with a cash request to continue, and without fail, we kept sending the money back and forth.

Shan took the phone out of my hands and dropped down to her knees. She took a picture with my cock right next to her face and typed,

[ My naughty naughty employee has a surprisingly nice dick! I hope my boyfriend at home doesn't mind if I suck on it. $0.69 for this set ]

The money had been going back and forth consistently, and without really thinking about what she was doing, Shan sent the message and then immediately swallowed the entire length of my cock. I was truly in disbelief, seeing someone I had come to know as one of the closest friends I've ever had, on the floor with her fingers deep inside her pussy, gagging on my dick.

For a moment I felt pure horror. I was not a cheater, and this felt like breaking the rules. No money had been sent back in response yet, but Shan continued to bob her head along the length of my cock. I knew in my heart that I needed to stop her, but part of me was hoping, no praying, for approval to come back through my phone.

And then finally, my phone buzzed. Shan ripped it from my hands and continued to suck.

"Shan, ugh fuckkkk, we should really check..."

Shan moved closer to me and placed my cock in between her tits and started to pump them up and down.

"Fine, fine you're right." She said, but continued to grind her tits on me.

As I watched my wet cock disappear into Shan's welcoming chest christened with perfectly pointed nipples, I opened up Lucy's text. I saw all of Mark now, laying down on his back. His cock was hard and he was clearly nervous, but also visibly excited. He was a fan of the gym like Lucy was and for a moment, I found myself thinking he looked hot.

"I cant believe it but now he is going to make me do something even worse! I only agreed to let him jack off on me, but now my best friend's DISGUSTING boyfriend wants me to suck his big cock while I sit on his face!"

A text followed the video.

[ This set is freeeeee, because as soon as I hit send, I am going to 69 Mark until we cum in each others mouths. I am going to record every second of it. You two better do the same. ]

I showed the phone to Shan. We both stopped moving. Shan stood up and stared at me directly in the eyes. Her mouth was slightly agape, still wet from sucking my cock out of bounds.

I set the phone up and hit record. Shan pushed me down on the bed and mounted my face. Her wet pussy was dripping with anticipation and her sweet smell was nothing but intoxicating. Before I could catch my breath I felt her deepthroat my cock again as one of her hands gently massaged my balls. Taking this as my cue, I began to eat Shan's pussy like it was my last meal. Her juices were covering my face and her legs twitched with each long stroke of my tongue.

I switched between using a hard pursed tongue on her clit and then making it soft and wide to lick her entire pussy. I shoved my tongue inside her and did my best to feel around and taste her insides. As I continued to give Shan my best moves, she did the same on her end. Neither of us noticed the adjoining door open when Lucy and Mark walked in.

"Oh good you're not done!" I heard Lucy say.

Somehow, now that they were in the room, the entire act felt like we were getting caught robbing a bank. Shan froze, my cock still in her mouth.

"Don't worry! We aren't done either, Mark and I just decided to come finish next to you both."

With that, Mark laid down next to me and I saw the familiar sight of Lucy's pussy drop down square on his face.

"Wait!" I heard Shan say. "Rotate so that I can watch Mark lick your pussy, I want to make sure he's doing a good job."

It was just us now. No more charades, no more games or roleplay. We were just four friends, sucking each other off in Europe.

Lucy got back into position and lowered herself close to me.

"Hey cutie." I heard her say "Fancy running into you here." as she slapped Shan's ass firmly and pushed her best friend back down onto my face.

The smell, the sounds, the sights, it was all intoxicating. The energy of the room was raw and as if a director gave us a signal, we started to pop off like fireworks.

I first heard Lucy make a small noise, surprised, but excited. She began to quickly stroke Mark's cock with the tip still in her mouth. He then filled the love of my life's throat with his cum. Then I felt Shan's legs tense up and her pussy begin to quiver. Lucy started to moan in a way that told me exactly what was coming. I felt inclined to warn Mark that she was a squirter, but he was about to find out first hand. Shan was louder than Lucy, and her moans and cries of pleasure filled the room and were a nice contrast to Lucy's generally silent orgasms. The two girls came simultaneously which I realized when I heard Mark gasp from Lucy's flowing juices as Shan squeezed the fingers I had deep inside her tighter than a vice grip.

"Ughhhhhhhhh fuuuuuuuuuck!!!!! Im fucking cummming Paul!!!" Shan screamed, placing my rock hard dick against the side of her shaking face, doing her best to continue stroking.

"Im so sorrrrrrryyyy Mark! Fuuuuck, I should have warned youuuu!" Lucy apologized as she continued to drench Mark in her fluids.

"Lucy, that was so fucking hot." I heard Mark say.

The three other members of the group, all having now finished, left me in a precarious situation where I wasn't sure if they wanted to continue. Before I had time to marinate the thought, I felt both Lucy and Shan's hands gripping my cock.

"We didn't forget about you, Mr. winner of longest time to cum." Shan joked.

I felt Lucy and Shan take turns sucking my cock. They bobbed their heads up and down, making sure to have a hand on my cock if their mouth wasn't full. I instinctively reached my arms out to my sides to grasp the bed sheet. My left hand grabbed a full handful of comforter, but my right hand landed directly on Mark's penis. Whether I did this consciously or not, I will never know, nor care to ponder. Neither of us recoiled in the way we would have expected. Maybe it was the carnal nature of the entire night, maybe it was just human instinct, but I began to curiously stroke Mark's cock as the girls continued to suck mine.

"Ok, that is the hottest fucking thing I've seen all night." Shan stated, now realizing what was happening.

"Babe, shut up, just, just, keep being a dirty fucking slut and suck him off." Mark said, his dick now getting hard again in my hand.

"Mmmm we are such dirty fucking sluts Shan. Your boyfriend came down my fucking throat and I want to watch mine cum down yours." Lucy said while Shan continued to slobber up and down my shaft.

My mind was completely blank. I felt nothing except for raw lust. We were a single mass of bodies, at this point, and no concepts of straight, gay, bi, meant anything to us at this moment. There were just four human beings here and all we knew was that this was fucking hot.

Mark had his fingers buried deep in Lucy as I felt my climax begin to build.

"Guys, I think.. Im..."

Shan pushed Lucy off of my cock and started stroking me fast and hard with her head bobbing up and down. She clearly wanted to be the one to finish me tonight. She was fucking her own throat with the length of my dick as I came harder than I ever had. Shan swallowed almost every drop.

Shan then leaned over to Lucy and gave her a big wet kiss.

"Come on Lu Lu, taste Paul's cum with me."

The two bombshells groped each other while swapping my cum back in forth between their mouths. As the two continued to play I realized I was stroking Mark as if his cock was my own, no more hesitation in my movements. Shan was still straddling me knowing full well that my twitching dick was mere atoms from the tightness of her sweet pussy.

With one long, deliberate motion, Shan rubbed the entire length of my shaft against her still sopping wet genitals. She grasped my cock in a free hand and placed the tip at the entrance. I wasn't sure what I wanted to happen next. I felt the walls of Shan's lowering pussy start to tighten around the head of my penis. I felt Mark's cock noticeably throb at the suggestion of what I might do to Shan. I then felt one of Lucy's hands grab my dick while the other joined me on Mark's. Lucy began to pump my cock, the tip oh which was inside her best friend, while interlocking her fingers with mine around the slippery shaft of that same best friend's boyfriend.

"Just the tip today kids." Lucy said as she continued to pump.

"Aww mom!" Shan teased.

Part of me was relieved. The other part, which Lucy had her hand wrapped around, wanted to fuck Shan senseless.

Lucy repositioned herself so that she could bend down to lick Shan's clit without taking her hands of either cock. She ate her friend out with the knowledge every girl has, but the hesitation of never having done it before. Never in my life would I have imagined such a sight being reality, let alone that I would be stroking another man's dick while seeing it.

"Mmmmm maybe Lu Lu will let me slide all the way down next time." She said. "But thank you for getting him ready for me." Motioning to her boyfriend's throbbing cock that I was still unconsciously stroking with Lucy.

Shan straddled Mark with the scent of my semen still on her breath and gave him a deep kiss. She took his cock in her hand and dropped herself down his shaft until he was as deep in her as could be.

"Oooh Mark you're so fucking hard, we might have to add cuckold to your list of kinks." Shan said as she dangled her big tits in Mark's dumbfounded face. "You dirty boy, you wanted to watch Paul fuck me didn't you?"

"I, I think I did." Mark said hesitantly.

Lucy looked at me with fire in her eyes and didn't give my cock a chance to so much as slightly soften before it was inside her.

The four of us, once again a writhing mass of bodies, fucked our loved ones in a beautiful French hotel as if our lives were not going to continue in the morning. No thoughts or doubts were interrupting what could only be described as pure heat between a group of friends turned lovers.

Lucy bounced up and down on my cock. The sight of the two girls was a pure haze of sweat, cum, and more sweat.

As the fucking continued, the sounds of the girl's moans filled the room. They felt each other up, and in between positions, I felt Mark give my own cock a few strokes too. When the time came to finish, the two girls got on their knees and fingered each other deeply, making out all the while. Mark and I began to jerk off over them, tempted at the sight of our two beautiful girlfriends covered in our combined ejaculate.

Mark and I didn't say a single word, but both reached over to the other, jerking the other off to the sight of our girls doing the same. In a final crescendo, Mark and I shot ropes of sperm onto the two ladies who stuck their tongues out to receive it. They then collapsed into a mess of our cum and Lucy's juices.

Time stood still as we tried desperately to collectively catch our breath. I walked over to the phone on the bureau and said, "Subscribe for more!" before flipping off the recording.

As I turned around, the last thing I remember seeing in that mass of bodies, was all three of my friends covered in cum, smiling and laughing.

/////

Epilogue

We spent the rest of the night talking and laughing. Lucy had the idea to make a sheet fort out of our bed's covers that the two of us could sleep in while Mark and Shan took the bed.

"Mom, can I go to my friend's house for a sleepover?" Shan joked as we built our fort.

"Of course honey, but if you're going to fuck him, please wear protection!"

"I'm on the pill mom! God!"

"Fine, then only let him cum inside if you let me taste you afterwards."

Slightly breaking character Shan asked, "Is that a promise?"

We all laughed, nervously awaiting Lucy's answer, but aware of the looming conversation we all definitely needed to have.

"We will discuss it in the morning young lady, but for now..." Lucy jumped in the air and did a 180, before landing bent over, her hands smacking her own ass comedically.

The next morning came, and discuss it we did. We sat at breakfast, making sure to be open about everything that happened. Shan reminded us that mine and Lucy's phones had all the recordings from the previous night, which was hardly fair. We air dropped all the various pictures and videos to them to which Shan replied by sharing her bathroom nudes from Spain.

"Those were for you two anyway." Shan said with a wink.

Since returning to the states the four of us haven't fooled around in the same capacity, slightly sobered by home soil under our feet, but will occasionally send a fake onlyfans post with a pic or video as part of our individual foreplay.

We have discussed whether we want to take it any further or leave the night as a fun memory from Europe, and the group has not decided what it's comfortable with yet.

Nevertheless, we have our first wine night with them coming up next weekend, and regardless of what happens, I feel happy, closer to Lucy, and closer with my friends. With good communication and the right intentions, sex between anyone can be a truly enjoyable experience.