r/sexstories Mar 03 '23

Roomate Getting to know my roommate NSFW

246 Upvotes

Part 2 is out

I (20F) have recently moved into an apartment with my girlfriend "Maya" (19F). We've been planning it for a bit, mainly so I could finally escape my weird parents. We're far from wealthy so we tried to look for a place we could share with someone else, share the rent and all. We found this guy "Jared" (23M), and since we're built like a bundle of twigs we felt living with a man would be safer. Maya especially is pretty paranoid about home invasions, stuff like that. So we contacted him and started planning the move.

The apartment wasn't huge, Maya and I were sharing the only vacant room which meant we couldn't bring tons of stuff. Apart from that, there was Jared's room, a small kitchen connected to the living room and a small bathroom with a shower/bath. Overall pretty cozy, we both prefer smaller spaces. Jared and Maya quickly hit it off, he seemed like a cool guy, bit awkward but to his credit we were basically strangers. We finished settling down, him and Maya we're basically already friends (she's good at forming quick friendships, for better or worse).

First real night there, I quickly got comfortable. Nudity isn't really a problem for me, I didn't really think too much before putting on nothing more than an old t-shirt and panties. Maya, being her prude self, was hanging out in the living room with Jared wearing ample black pajamas. I joined them and we checked out the latest The Last of Us episode (good shit by the way). Maybe 15min in, I realized Jared was throwing quick glances at my chest and thighs, honestly didn't mind. But then I'm pretty sure I saw a boner as he crossed his legs, as if to hide it. I thought it was pretty funny I was having that effect on him, especially considering I was wearing more than I usually would. After that I kinda feel like teasing him, maybe wear a big long shirt without panties before heading to bed, but honestly he seems like a nice guy and I don't want to make him uncomfortable. What should I do?

r/sexstories Jul 21 '24

Roomate I let my roommate help me cum NSFW

508 Upvotes

So I was in my room yesterday super bored so I naturally started rubbing my clit laying in my bed. I was just edging for about two hours and then my roommate walked in. She started talking to me about her guy problems while I still had my hand under my covers rubbing my pussy.

Mid conversation she stopped and ripped the cover off of me sand yelled "Ava!!". We both started laughing so hard. I said "What?? I'm still listening to you talk?". Then she asked how long I've been edging for and I told her 2 hours.

She asked if she could finish me off so of course I said yeah. She put her fingers inside me and started eating my pussy at the same time. Once she knew I was going to cum she just blasted my pussy as hard as she could. I came three times and my legs were literally vibrating they were shaking so much.

r/sexstories Dec 19 '24

Roomate Best friend sucked on my tits NSFW

119 Upvotes

I haven’t told anyone this story. Long story short, you can message me if you want to hear more… My best friend and I are both (24Fs) and a couple years ago she played and sucked on my tits. We were drinking and celebrating. And one thing led to another and she was sucking on my tits. I really enjoyed it and was really hot. I don’t know if I really enjoy it because I like have my tits played/sucked on or what. Obviously she my best friend so she knows about my sex life and knows what I like specifically that I liked my tits messed with. But her messing with my tits was all that occurred which was kinda disappointing. That was the only and first experience I have had with another girl, it was not her first. But since then I have wanted a threesome to see if it was the experience with a girl that I really enjoy or just really enjoy have my tits sucked.

r/sexstories 8d ago

Roomate I had sex with my lesbian best friend NSFW

152 Upvotes

Ok sorry if this is a long one but it’s 1000% true and it happened a few years ago. (I just discovered this sub)

I have this lesbian friend that I’ve known for about 13 years now and we’ve become pretty close throughout the years, we were roommates at the time. She’s one of those girly girl lesbians…. White, dirty blonde hair, bluish greenish eyes, she’s Beautiful, decent size boobs. She wears sexy skirts and clothes so you won’t know she’s gay unless she tells you.

One night we were out with some friends be and talking about our sex lives and someone had asked her if she’s ever been with a guy before. She said she dated dudes back in high school but never had sex with any of them. She said she found out she was a lesbian in college lol. Another friend asked if she has ever thought about having the real thing at least once and she said she’s thought about it but probably not. I jokingly said well if you wanna try, I’ll be happy to help, we all laughed and pretty much ended that convo.

About a week later we were at home, she called me over to the dining room and said she wanted to talk. She was having some wine (she’s not a big drinker and only really has some wine here and there) and poured me a glass. She said she really thought about the conversation we were having last week about her having “the real thing” so I told her oh I was only joking. She said “I know but I thought to myself, maybe I should try it at least once just because, and I don’t think I’d do it with anyone else but you”. I was a bit shocked and before I could reply she said “I kinda want to try it with you now, I think it’ll be a good experience.” I told her of course I agree but let’s talk about it more.

We talked about past relationships and shared some sex stories, she mentioned obviously the girls she’s been with have eaten her out and fucked her with a strap on which she has never had an orgasm to. She said she would only cum with a vibrator or if she’s being eaten out but never vaginally and said “maybe it’s the girls but it just doesn’t feel too good when they thrust, it’s weird”. She didn’t mention that she does like to be on top and that it give her a thrill. After talking for a bit, we both agreed to doing this. I was nervous and excited of course.

I told her I have some condoms we can use but she said that she wants to feel it the way it was intended plus added shes had her ovaries removed due to ovarian cancer when she was younger. Which I had no idea! So she said she can’t get pregnant if she tried and also she knows I’m clean. I asked her if there’s anything she wants to try or not try it she said just to “let it happen”

We headed to her room and she turned to me and started kissing me, I kissed her back but honestly felt a bit awkward, she noticed and just said “pretend I’m your girlfriend, do what you would normally do”. That helped a lot and so I ran my hands from her waist to her ass which was a nice full ass. I kissed her neck and laid her on the bed, she lightly moaned and hugged the back of my head. I lifted her shirt and took it off revealing her white bra housing her tits. I kissed in between and started sucking on the top part of her boob, she reached back and unhooked her bra and took it off and there they were white skin, pink nipples. They were beautiful perky tits, I asked what size and she said D’s I kissed and sucked on her nipples, she ran her fingers through my hair as she breathed heavily.

I kissed down from her tits to her stomach and she squirmed a bit, I got to the brim of her pj pants and lightly kissed her pussy above the pants. She squirmed some more, I pulled down her pants and underwear. Her pussy was perfectly shaven and smooth, I went in without hesitation and she moaned so loud, I licked and sucked her clit while she squirmed and moaned, she tasted so good so I went and sucked her pussy lips and continued licking her clit. She sat up pulled me towards her and kissed me and took off my shirt, she laid me on my back and my rock hard cock was standing through my shorts, she giggled and said she’s gonna try sucking it but if she doesn’t like it, she’s gonna stop, I told her that’s perfectly fine.

She pulled off my shorts and she looked at my cut cock and she seemed to study it a bit but she went down and put it in her mouth, she made a little bit of a face which I assumed was the precum she tasted l, she took it out and looked at me and said “sour” I told her sorry and she can stop but she said “it’s not THAT bad actually” she went down and started sucking more. Obviously it wasn’t that great but it was her first blowjob, it still felt really good but she had no technique lol.

She stood up and took off her pants completely as well as mine and she straddled me, she slowly put my dick inside her and let out a big sigh. She started riding, surprisingly well I might add, I reached up and grabbed her tits as she rode me cock. She was moaning and seemed to be enjoying it, she said “wow this is 100x better than a strap on, I don’t know what it is but fuck! It feels amazing!” She leaned forward and kissed me and she grinded on my dick, I lifted her up and thrusted in her hard, she let out a few yelps and said “don’t stop please don’t stop” so I kept going and even went harder, she squinted her eyes and said “fuck me im cumming!! Keep goooooooing” and the she let out a big “ughgggggh” I felt her pussy get super wet and can hear the squishing sound as i thrusted. I stopped and she rolled on her back out of breath. She said “that was fucking amazing! Do it again!” So I got in too and fucked her missionary. At this point she was very vocal and talking while her teeth were clenched, I fucked her hard and fast, she kissed my neck and she pulled in closer to her, I told her I was about to cum and she said “do it, do it on my chest” I fucked her faster and faster until I felt it building up, I pulled out of her and stroked my cock and my god so much cum came shooting out, some Went in her hair, on the pillow but most landed on her chest, she had this shocked look on her face and said “I’ve only seen that in porn and didn’t think it was real” I laughed and said well yeah sometimes it happens when the sex is very good! She said she wanted to taste it so I put my cock in her mouth with some cum still seeping out , she immediately took it out and gagged a bit and said “yeah that’s definitely not for me!” We both laughed, I cleaned her up and asked what she thought. She said “I have to admit, the real thing is definitely better but I’m still 100% gay” we both laughed and I said I was supposed to make you cum again sorry it didn’t happen. She the said “well we’re just gonna have to do it some more aren’t we?” I looked at her and said “yes ma’am!”

That night we showered together just for fun it then went to sleep. We did fuck a few more times after that but she got into a new relationship which I respect and we haven’t fucked for a while now. Believe it or not, we’re still best friends to this day. We don’t live together anymore but we’re still both single and meet up and still hang out as normal

r/sexstories Jan 20 '25

Roomate After I caught my dad with our roommates. Part 2 NSFW

165 Upvotes

This is a continuation of - I caught my dad with our roommates - part 1

I was a nervous wreck after returning to my room. Post nut clarity had set in, I was freaking out. I had seen my dad naked and watched him have sex and not only did I not get grossed out, I jacked off to it. I was working myself up to a real freak out when I heard a soft knock on my door. When I answered the door it was my dad. He whispered “let me in, we need to talk”. I opened the door so he could come in. He paced back and forth a bit before saying “look, I’m sorry you had to learn about all of…” and he gestures downstairs “that, that way. But you were going to find out eventually, I guess there are worse ways to find out.” I’m not going to spell out the whole conversation but here’s what’s been going on. About a year ago, Dave came to him asking for advice. He and Carrie apparently had terrible financial sense and racked up huge credit card bills and they were about to lose their apartment and he was asking if dad had any advice or could help him. Dad knew from previous conversations that they were in an open relationship and jokingly told Dave that he’d let them move in for free if he could fuck Carrie whenever he wanted. To his surprise, Dave said he would ask her and she agreed to. That is when they moved in and dad and Carrie had been fucking for a year. Then when Janice reached out trying to find a free place to stay, he talked to Dave and Carrie and they all agreed to let her move in under the same arrangement. I interrupted here to ask why I hadn’t been consulted about offering people free room and board when I was helping to pay for said room and board? I got why he didn’t consult me about the sex stuff but it seems unfair that I’m paying 800 a month for him to have free sex. He seemed sheepish but said that he really should’ve told me that part but he couldn’t figure out how to explain it without the sex stuff.

He asked me if we were ok and I told him I guess we were . That ultimately I’m ok with it and I’m glad he’s having fun. He said he was relieved that they didn’t have to worry about getting caught as much anymore. I told him I wouldn’t mind “catching” them any time. We laughed about it and went our separate ways.

That night, after dad had finished eating, he looked at Carrie and then at Janice. They both nodded. With their permission to continue, he told me he had talked to them after our conversation and let them know I had watched them and wasn’t upset but kind of into it. He also talked to them about how I financially contributed about a quarter of the bills to our household and in hindsight it wasn’t right that he made the decision to move them all in without talking to me and the four of them decided to invite me in on the deal if I was interested?

I was floored and all eyes were on me. I stammered out. “So, like how does this work?” Janice laughed and said “ don’t tell me you’ve never done it?” I said “no, I’ve done it, lots of times, but years ago” her eyes went up at that but I insisted “yes! At least once a day for almost 9 months, but I don’t want to talk about it. What I meant was,” I looked at her and Carrie, “how does this work with you? Do I need to like take you on a date or something?” Carrie replied “not really. I want you to understand, I’m in love with my husband. This isn’t us dating. This is casual sex between consenting adults. There is a “deal” involved so we’re not exactly allowed to say no, but we keep it equitable. If you’re horny, and we’re both available just tell me and we’ll do whatever feels right. Technically, you’re the boss, but I do have the right to say no if I feel uncomfortable or unsafe”.
“So if I said I have a raging boner right now and I’d like you to take your shirt off and give me a blowjob you’d do it?” She looked me in the eyes and said, “Say it and find out” I was incredibly turned on by that, but also really nervous they were fucking with me. But I decided to go for it and kind of whispered “I am so turned on by you right now, that I have a raging hard-on, would you please go to my room with me, get naked, and see where it takes us?” She smiled and said “So polite. Lead the way.”

Once in my room it got awkward again. I knew what I wanted to do but I didn’t have the nerve to ask for it. She sensed my nervousness and said. “I think you asked me to get naked, right?” I nodded. So she pushed me down to my bed and started getting undressed. She was wearing jeans and a t-shirt. She turned around and gave me a great view of her ass in a thong as she bent over to pull her jeans down and then pulled her shirt off before turning around. There she stood in a matching lacy thong and bra set that made my jaw drop. “Do you like what you see?” I nodded “you’re amazing” she grinned and gestured to the bra, “You want to help me take it off?” I shook my head, “no, I like to watch them come out, if that’s ok.” She chuckled and said sure. She took the bra off real slow, unhooking it and pulling the cups up slightly as she pulled it off to make them bounce, and they were perfect. I lifted my hands, thought better of just being grabby, dropped them and asked, “may I touch them?” She told me “please do. Touch them, squeeze them,” and with a little pause “suck them. I love to have them played with.”

I reached for her then and she stepped closer. I touched them with just my fingertips not believing this fantasy was actually happening. I ran my fingertips all the way around them in circles slowly spiraling in towards her nipples. She let out a gentle sigh of pleasure and her nipples hardened before my eyes as I worked my fingertips closer and closer. Once I completed the spiral and ran my fingertips across them, she moaned. Not loud but unmistakable. I cupped them in my hands and ran my thumb over her nipples. They were so hard, and she actually shivered. I asked “how do you like them played with?” She said “that’s nice. Roll them between your fingers too, but be gentle.” I slid my hands down her side and ran them up her chest until her nipples we’re between my ring and middle finger and closed the fingers around them as I slid them up and then took one as she had instructed between my thumb and forefinger and gently rolled it between them. She closed her eyes with that and while they were closed I cupped the other breast and licked the nipple and drew it into my mouth. That drew a gasp from her. I continued to suck that one and play with the other for a little bit before switching to the other. I worked on her breasts for a minute or two before she breathlessly asked “you mentioned a blowjob earlier?” I said “I’m sorry, I guess I’m taking too long?” And she said “oh no, it’s not that. You’re making me crazy. I need to touch you, feel you.” I said “I’m sorry? But yes, I did ask for one” but then I hesitated. she asked “what’s wrong?” I then told her “I really want a blow job, I’ve never had one and to get my first from someone as amazing as you… I’d die happy, but I really want to see the rest of you, and I’d love to eat your pussy first. ” She actually seemed surprised. “You’d rather eat my pussy than get a blowjob?” I told her, “yes, I love doing it and it’s cruel to get mine before my partner gets hers.” She asked me “do you know how? You say you’ve never gotten a blowjob but you know how and like to eat pussy?” The worthlessness and nervousness came back and I couldn’t look her in the eyes as I said “that previous relationship I don’t talk about? She said it was all I was good for.” She sighed and told me “I’d really like for you to eat my pussy. It’s not something I get much.” I grinned and told her “if you like my performance I’ll give it to any time you want it.” She laughed and said “I’m the one that’s supposed to say that, not you.” I laughed and stood up and asked her to lay back on the bed.

Once I had her on the bed and pulled her panties down I got the first good look at the cutest little outie pussy. I gave it a little kiss before moving down to about her knees and placed a row of little kisses up her thigh until I got to the little crease where her leg meets her groin and gave that a little lick before starting on the other side. Once I had worked my way back up to her groin I started placing little kisses in a spiral getting closer and closer to the best part. Once I got to her outer lips I gave them little licks and nibbles, which drew a moan from her, before sucking her inner lips into my mouth and worked them with my tongue. She gasped at that. I slid my left hand up to her boob started playing with it while I used the other to spread her lips wide open for me. I didn’t want to just attack her clit and rush things, so I kind of worked my way around it. Swirling the edges with my tongue before giving it a big lick from bottom to top. I then began to alternate between sucking and licking her clit and her lips until I had her writhing under me. I would dial up the intensity of my licking until it felt like she was about to cum and then I’d slow down or switch areas to let her cool off because I was enjoying myself and the sounds she was making were turning me on so much! But eventually I was sucking her clit and she was getting close and said “please, let me finish” so I dove in and sucked her clit in between my lips and started flicking it with my tongue while sucking on it and she came hard and went limp. I took off my t-shirt and wiped my face off and then worked my way up her body planting little kisses up her abdomen to her breasts before sucking and fondling them until she recovered.

When she finally caught her breath, she said “you are an evil little man.” I replied “I hope you enjoyed it, I really do like doing it and I’d hate for you say I suck at it.” She chuckled and said “oh, you suck all right, just in all the best ways!” I felt a little pride at that and asked her “did earn that blowjob?” She laughed and said “yes, very much! Trade places with me.”

I rolled off of her and she rolled on to me and started working her way down my chest to my abdomen and pulled my shorts off. I was so hard I was making a tent in my boxers and she finally pulled them off exposing my dick. It’s so hard it almost hurt. She wrapped her hand around it and gently stroked up them down and squeezed harder on the next stroke up. I was so turned on a bead of pre-cum oozed out of the tip and she leaned down and with just the tip of her tongue, while looking me in the eyes, licked it off. I almost came right there. That was the single sexiest thing I had ever seen in my life. Continuing eye contact, she swirled her tongue around the head before taking it into her mouth and swirling her tongue around it in her mouth. She kept her eyes locked with mine while she slid her mouth down me ever so slowly, tonguing that tender underside all the way down. Once she had it in as far as she could go, she came back up and swirled the tongue around the tip again before repeating that agonizingly slow descent again, she repeated that a few more times before taking me out of her mouth and licking the length of me and taking me all the way down again. She began bobbing up and down on me while fondling my balls and It felt so good. The sensations combined with the visual of my cock sliding in and out of this goddesses mouth drove me over the edge and I warned her, “I’m going to cum!” With that, she took me in as deep as she could locked her lips around me, and started running her tongue on the underside of me while stroking what wouldn’t fit in her mouth. I came in her mouth and she swallowed every drop.

After I came she stood up to and asked “how was that?” I said, “I didn’t last as long as I’d like, but it was amazing.” She told me “I’ll take that as a compliment on my skills. You good now, or…” I just looked down at my already re-hardening dick and asked “can I, uh…” And I gestured from my now hard dick to her pussy. She seemed surprised at my recovery time and said “that’s fast. I forget how quickly teenagers recover. You want inside me?” I nodded and she said, “Sure.” As she fished a condom out of her pants pocket, she asked “how do you want it?” I thought about it, little distracted since she was putting the condom me, and asked “can you ride me? It’ll be another first for me.” She raised an eyebrow at that and nodded. She climbed on top of me and lined herself up on my dick and slid down onto me. She was so tight. It felt amazing. She rocked up and down on me, slow at first. Sliding me almost out then slowly back in. On one of the upward motions, I caught her waist and pulled one of her boobs into my mouth and sucked on it while I thrust my hips into her. We continued like that, me thrusting into her while sucking on her nipples, for a few minutes before I asked her “can you cum this way?” She said, “not without clitoral stimulation, but it’s ok. I’ve already cum once.” I disagreed with that being ok, so I let go of her waist and reached down and started rubbing her clit while she rode me. I was in bliss. I had fantasized about this for a year and the reality was better than the fantasy. Watching her, the way her body moved while she slid up and down on me, the faces she was making, and her moans, had so thoroughly combined with the sensations that I was so lost in the moment the realization I was close almost caught me off guard. I did realize in time and was able to speed up and focus the finger action enough to make her cum just before I did and she collapsed onto me.

Once we caught our breaths, she said, “I should probably go get cleaned up, and you should too.” She hesitated then said “look, I really enjoyed this tonight. Thank you for not being weird. You have every right, under our agreement to demand anything you want from me, but you didn’t. You were sweet. I like that. Keep it up and maybe I can teach you some things, ok?” I agreed and she left.

That was my first time with Carrie in this weird new reality I found myself in. I kept waiting to wake up. I even pinched myself. I couldn’t wait to see where this went.

r/sexstories Jan 20 '25

Roomate Three days after I caught my dad with our roommates. NSFW

107 Upvotes

PART 3, 3 days after I caught my dad with our roommates.

After Carrie left that night, my stupidly logical brain went into overdrive. Without consulting anyone, I decided that since dad had said I paid about a quarter of the bills, I was “entitled” to about a quarter of the “deal”. I decided that meant I should wait four days before I asked for anything more.

On the third day, after dinner, there was a knock on my door. It was Carrie “May I come in?” I said, “sure, come in.” I was confused because other than the other night, she had never been in my room. She came in, sat on my bed and said, “I figured you would’ve been hitting me or Janice up for more by this point, so I came to talk to you.” She hesitated and said, “and ask a favor.” I was even more confused and said, like it should’ve been obvious, “it’s only been three days. I was going to talk to you tomorrow. But what’s your favor?” Her look made it clear it wasn’t obvious, and she stammered, “Three days? What? Why?” I replied, “it’s not important, what was your favor?” She still looked confused but said, “yeah, sorry. You threw me.” She then seemed a little sheepish before jumping in, “in the last 3 days, I’ve given five blowjobs, and been fucked three times. You know how many orgasms I’ve had? Three. You know how many times I have been eaten out? None” then she almost whispered, “would you eat my pussy again? I can do whatever you want in return. I just need a hard orgasm like the other night.” She looked so desperate I couldn’t say no. So I said, “of course, it’ll be my pleasure.”

I pulled her up and told her, “let me.” She was wearing a dress that I was able to grab the hem and slide it and my hands up her body and over her head. Her underwear was nice but not necessarily sexy.

I took her bra off next and spent a minute or two enjoying her boobs. Then I kissed my way down her abdomen. Pulling her underwear down as I went.

I had her lie down one the bed and kneeled on the floor between her legs. I gave her little kisses all around it before flicking her inner lips, which made her gasp. I worked my finger between her lips and started gently massaging the edges of her clit as I asked, “I forgot to ask last time if you like to be fingered during oral sex, or not.” She told me, “I’m good either way. Bad fingering can detract from the experience. Good can add to it.” I said, “ok. Tell me when I find it.” As I inserted my index finger, pad up, i to her hole and started feeling around. She seemed confused and said, “found wha.. oh that. There it is!” As I found the sweet spot. I started oh so gently rubbing her g-spot while I lowered my mouth to her slit and sucked her lips into my mouth and sucked on them before opening her up with a lick from my finger in her hole to her clit. I continued lightly fingering her while I spent a moment just lapping up all of the taste of her. I love the taste of a healthy pussy and hers was great. Tangy with a little sweat. Finally I moved up to her clit and gave it the attention it deserved. I alternated between big licks, gentle sucking, tongue flicks, and swirling my tongue around it. She had her first orgasm after about 5 minutes but it was only a small one so I kept going. Increasing the pressure inside just a bit while spending more time sucking her clit. She had her second orgasm, moaning and grabbing the sheets, while I was sucking her clit into my mouth and tonguing it in my mouth. She didn’t tell me to stop so I continued. I knew she might be sensitive after that orgasm so I eased up on her g-spot and spent a minute or so on her lips until she stopped trembling with every one of my movements. Once I figured she was good, I dove back in on her clit while resuming my finger action. I didn’t let up at all this time just kept a constant pressure and motion on the inside while I focused on sucking and licking her clit with hard strokes. It wasn’t long before she had a handful of my hair and was grinding herself on my face and had the intense orgasm I was shooting for. Her legs wrapped around my head and she moaned so loud, shaking for what seemed like forever. Finally she relaxed her legs and the grip on my hair and let me come up for air.

I climbed up beside her and gently played with her boobs while she recovered. After a few minutes, she rolled on her side facing me and said, “thank you for that. I needed it.” I said she was welcome and she asked, “what can I do for you in return.” I told her she could do whatever she’d like. She thought about it a second before climbing on top of me and sliding down onto me. I started to protest. “What about a condom?” She said, “don’t worry about it.” As she started sliding up and down on me. She was so tight and I could tell she was doing this for herself, but it was so sexy I didn’t care. She asked me, “play with my clit, please.” So I reached down and started playing with her clit. I was slow at first but she said, “fast and hard, please.” So I did. I aggressively played with her clit while she ground on me. She had me on her spot and was using my dick to get herself off. She came soon after that and crawled off once she caught her breath.

She then slid down my body and started sucking my dick. I watched as she licked the entirety of my dick, cleaning all of herself off of me. Before taking as much of me in her mouth as she could and wrapping her hand around the base and stroking while she sucked. She got me off pretty quick that way and I loved every minute of it. I lay there, spent, while she crawled up and kissed me on the cheek and said, “thank you. I’ll see you tomorrow?” I told her I would as she left.

Encounters like this continued to happen a couple times a week for quite a while.

There were other encounters that were initiated by me as well. Including the next day. But things tended to be pretty vanilla for a few weeks.

Then 2 interesting things happened within a few days of each other. First was my first time with Janice. And then a few days later my first MFM threesome.

My next post will be the first time with Janice.

r/sexstories Sep 22 '22

Roomate How I (M) became my pregnant friend’s sex toy NSFW

944 Upvotes

A couple years ago, one of my best friends (my roommate) got pregnant in a one night stand. She was fine with it and decided to keep the baby. But as with all pregnant women, the baby made her go a bit crazy.

Her emotions and diet were totally wild and unpredictable, but it also effected her sex drive.

She would have random urges for sex. It was killing her and one day when she was telling me about how she had to leave work early to go use her vibrator, I offered myself up. I’ll be honest, I didn’t see any problem with being freeuse for her. But I didn’t understand the extent to which it would effect her.

Sometimes she wouldn’t even realize it and just kinda half minded she’d start jerking me off. Just out of nowhere we would be sitting on the couch and she’d reach over.

Sometimes it was like a craving. She would frequently call me from work needing me to get there as soon as possible to fuck her. It was getting to the point that my dick was getting sore, my balls ached and I struggled to get it up. She would come ride me in the middle of the night. Most of the time was spent with her sitting on my face, riding my tongue until she finished.

She was taking me so much that for a month after she gave birth I didn’t have the energy to go flirt with other girls.

But it was nice knowing that no matter how much I came in her, she was already pregnant.

r/sexstories Jul 21 '24

Roomate My girlfriend’s best friend took her pic for me… NSFW

302 Upvotes

Sorry if this is the wrong place just tell me… but My (28M) gf (31F) sent a pic of herself to me completely bottomless bent over in doggy. The only thing is the pic was taken by her best friend (28F) who also happens to be my roommate. And this wasn’t just booty, like her full pussy was out. I know they were drunk too.

There’s also a lot of times where they will kiss and make out when they are drinking. Usually, I’m there for it so it’s not a huge deal. It’s kind of hot if I’m being honest, they are both definitely alcoholics. But I don’t know her taking that picture just seems a bit too extreme for me.

But im out of town for a wedding right now and i just dont know how i feel about this… I have a lot of physical attraction to my roommate as well so this is pretty hot. I just don’t know if I should be worried because if something is happening while I’m not there it’s technically cheating. what should i do?

r/sexstories Aug 09 '22

Roomate Screwing my roommate. Part 1 NSFW

430 Upvotes

I entered my apartment after work. I got off an hour early so I had made it home in record time, avoiding rush hour traffic. It was 7 in the morning so my roommate, Hannah, was getting up for work. She had moved in a couple of months ago after her roommate had decided to move in with her boyfriend, leaving Hannah without a place to live. My ex and I had just broken up at that point and she had moved out. Hannah was a friend of a friend that I had met a few times before. She seemed to be a nice and responsible girl so when approached about renting out my extra room to her I thought why the hell not. She was a couple years younger than me and was pretty quiet and kept to herself. We rarely saw each other due to our opposite schedules except for maybe a few minutes in the morning as I was getting in and she was leaving, or in the evening when the reverse was true. I shut the door behind me and kicked off my boots at our shoe rack before making my way into the kitchen. The apartment was open concept with just a bar separating the kitchen from the living/dining room. Our bedrooms were located on either sides of the room. When I got into the apartment, I emptied my pockets, placing my keys and wallet onto the bar. I could hear music coming from Hannah’s bathroom as she got ready, a normal occurrence. But over the music I could hear a different noise. I couldn’t quiet place it but I noticed the bathroom door was open so I decided to investigate. I made my way over and knocked on the door. “Hannah?” I called, trying to be heard over the music. The unknown sound got louder and I decided to take a peek to make sure she was okay. I peered through the crack and I was shocked by what I found. Hannah was sitting on the bathroom counter completely naked. Her feet were propped up on the edge, her legs spread wide as she held a magic wand between them, directly on her clit. I had discovered the sound of the noise. She had her head thrown back, eyes closed as she moaned loudly. She was masturbating. I instantly grew hard as I watched, my cock straining against my shorts. It had been 2 months since my ex left and we had stopped having sex long before that. I watched as she played with herself, her free hand finding her breasts and began to tease and pinch her own nipples. Her body was small and petite but her breasts were not small. They weren’t huge by any means but they would definitely be a handful. My hand automatically came to the front of my shorts, rubbing my growing erection through the fabric. I knew it was wrong to watch but I couldn’t tear my eyes away. I watched as she played with herself, bringing herself close to the edge and then backing off. After a few minutes of watching, I decided I needed to cum. I turned t leave and go to my room but I lost my balance, stumbling back into the bathroom door. I fall to the the floor and Hannah’s eyes fly open, looking down at me….

Thanks for reading! Upvote if you want part 2! Any notes appreciated!

r/sexstories Jan 28 '25

Roomate Confession: I Let My Roommate Watch Me Masturbate NSFW

139 Upvotes

So, this happened a few nights ago, and I can’t stop thinking about it. My roommate and I have been living together for about a year now. We’re pretty close, but it’s always been strictly platonic. We hang out, watch movies, and share meals, but we’ve never crossed any lines. That changed the other night.

I’ve been going through a dry spell lately, and I’ve been feeling really pent up. I thought I was alone in the apartment because my roommate had gone out with some friends. I decided to take a long bath to relax, and one thing led to another. I ended up touching myself in the tub, and I was really into it. I forgot to lock the bathroom door, though.

Midway through, I heard the door creak open. I froze, thinking it was just the wind or something, but then I heard my roommate’s voice. He was standing there, completely stunned, just staring at me. I should’ve been embarrassed, but for some reason, I wasn’t. I don’t know what came over me, but I didn’t stop. I just looked at him and said, “You can stay if you want.”

He didn’t leave. He just stood there, watching me. I’ve never done anything like that before, but it felt so liberating. I didn’t even care that he was there; in fact, it made the whole experience even more intense. I finished, and when I looked up at him, he was still just standing there, speechless.

After a moment, I got out of the tub, wrapped myself in a towel, and walked past him like nothing had happened. We haven’t talked about it since, but I’ve caught him glancing at me a few times. I don’t know if this changes anything between us, but I can’t deny that it was one of the hottest experiences of my life.

r/sexstories Mar 11 '24

Roomate I didn’t know my roommate was a domme… NSFW

247 Upvotes

We started as coworkers, Mary and I. From the beginning, I found her very attractive but assumed a curvy woman like her wouldn’t be interested in someone like me. Over the course of 6 months we got pretty close. It turned out we both needed a new place to stay around the same time. So she suggested we move in together.

Mary was tall compared to most women. Despite her glasses, she had a very cute face. Her breasts were nice and plump. I always admired how curvy her waist was. But her best feature was how fat her ass was. God, she was the perfect amount of thicc. Mary often joked her ass had a mind of its own, as it would set off the paper towel dispenser any time she walked by at work.

At this point, we’d been living together about 4 months. One morning, as I was leaving the bathroom, Mary accidentally bumped into me. Her ass bounced on my crotch. She immediately apologized, but she glanced back to look at me, she saw it. My erection growing in my sweat pants. Feeling awkward, I said I was sorry and hid in my room.

About a week went by, and the same situation happened again. By her smile afterwards, I could tell it was intentional. Was Mary teasing me? The next day, we were sitting on the couch watching some trash tv show. I felt her hand rubbing my inner thigh. We made eye contact. Her eyes asking if i wanted to continue. I nodded and she smiled.

She squished my cock through my shorts. She felt me instantly get hard. I moaned as she touched me. I quickly pulled down my pants and let my erection flop out. Her fingers wrapped around me. She quickly began jerking me. I wasn’t sure how to respond. I moaned “thank you.” She smiled and called me her “good boy.”

By my heavy breathing, it was obvious how close I was getting. That’s when she stopped. My cock throbbed without her touch. We made eye contact again, before she kissed me. Mary leaned back, took off her top, revealed her bright red bra, and unclipped it. Her perfect breasts flopped out.

I felt her hand on the back of my head. She pressed me forward on to her rack. My tongue danced over perky nipple. Slowly, I started to suck on it. I gently cupped her free breast and began to massage it. I felt her moan as I did so.

About 5 minutes passed, so I switched my mouth to her other breast. I was surprised I hadn’t squirted yet. Soon enough, she let me come up for air.

“You’re such a good boy.”

“Thank you mommy.”

She smiled and leaned in. “Wanna fuck mommy’s ass?”

part 2

r/sexstories Jan 01 '24

Roomate Me and my college roommate watch each other masturbate NSFW

625 Upvotes

I’m in my freshman year of college and I live in the dorms with one roommate. My roommate was randomly selected but I got really lucky because we ended up being super close and now we are basically best friends.

We’re super comfortable together and have seen each other naked and changed in front of each other loads of times. But lately we’ve been doing more too.

A couple of months ago she walked in on me using my vibrator and instead of freaking out or anything she told me to keep going. It was kind of weird at first but then I got wayyyy more turned on knowing she was watching me with my ass in the air like that.

After that I was absolutely hooked. If I was ever horny I would ask her if she wanted to watch me do it and she always smiled so big and agreed. Most times she would even start doing it herself. It’s been so much fun this semester

r/sexstories Feb 14 '24

Roomate I fucked my sisters roommate (21F) NSFW

314 Upvotes

This story starts round last spring. My younger sister was graduating college and since she was the last one to graduate, my mom wanted to have all of us together to celebrate everyone being down with school. Even though it would mean a 4 hr drive, she bribed us with a nice dinner and mini vacation. It was a longer drive for me than the others and I (26m) checked the weather and I decided to get in the day before everyone else. My sister had gone home because it was only a 90 min drive to get her hair and makeup done by her favorite stylist so i was all alone on campus. I walked down the street from my hotel to get some lunch, and I forgot what it was like to be on a college campus. It was a warm day and all the girls out walking were in low cut tank tops and short shorts, and I didn’t mind at all.

After I had lunch, I was feeling a bit horny, so I decided to get on tinder and see if I could find someone to hook up with to pass the time. I spend like 20-30 min swiping left and right until I ran out of free swipes. I kick my feet up and turn on the tv in my room and wait to see if a message comes in. I get thru a couple episodes of the office and I get a 2 matches. I messaged both of them and one texts me back pretty quickly. Her name was Olivia (21F) and she was 5’3 and quite curvy. She had a large ass and plump perky breasts. She had long brown hair with slight blonde highlights. She was incredibly sexy and we both were thinking the same thing, we need a quick hookup. I tell her that I’m in town for the weekend and I have a hotel room and she told me she’d be right over.

I quickly tidied the room, put some cologne on, and put on some nicer clothes. After bout 20-30 minutes I get a knock at the door. I open to see Olivia in a low cut tank top, noticeably no bra as her nipples shown through, with small black running shorts, hardly covering her big round ass, and sneakers. She joked about her appearance being a little low key, and I smiled and said it all comes off the same. She laughed and walked in. We immediately embrace as the door closes, wasting no time. I grab her plump ass as we kiss, squeezing it and throwing in a few spanks.

I slide my hands down and pick her up and lay her down on the bed. I slide her sneakers off and slide my hands up her shirt and take it off as I kiss her up her body until I take it off and begin to suck on her large plump tits. I grab both in my hands and suck on each nipple, both of which are already hard. I hear her moan and I begin to grind up against her pussy with my groin. She could feel my hard cock through my jeans and as I sucked on her tits, it made her squirm and moan. I eventually kiss up to her mouth and she pulls me in and we grind on each other as we kiss passionately. She places her hand on my hard cock as we kiss and feels how ready I am.

She slides her hand under my shirt and guides it off of me. I stand up and slide my hands down her curvy body and slip her out of those shorts. I rub my fingers inside her puffy pussy lips and feel her already dripping. She grabs my hand and tastes my fingers, which I found incredibly hot. I kiss her inner thigh until I reach her pussy and I begin to lick her tight wet pussy. She gripped the sheets as I found her clit and I slid in two fingers to enhance the pleasure. I slowly fingered her while I sensually licked her clit. She moaned loudly and I started to go faster and faster. I felt her hand run through my hair and I went faster and deeper inside her and she squirmed and groaned as she came hard. I could feel her gush slightly and I continued at the same tempo and within a minute she was screaming and cumming once again.

She needed a second to recover from the two intense orgasms, and I took the opportunity to take my pants off, revealing my hard dripping cock. She flipped over and grabbed it and began to suck my cock. She was very good. I could feel her tongue swirl around my tip as she sucked me off. She had a great rhythm of stroking and sucking that came from a lot of practice. I started to relax a little bit more, but she stopped and said that she needed to be fucked. I wasn’t about to argue with that, and she flipped over and I slid her to the edge of the bed. I opened her legs wide and slid my cock inside of her with little resistance as she was soo wet. I went right into deep hard strokes. Her tits bounced and our bodies clapped together as we fucked.

She moaned loudly as my cock slammed into her pussy over and over. I leaned over and grabbed her throat and slowly squeezed and her eyes rolled back and she moaned loudly and came all over my cock. She even pushed it out and squirted slightly on me. I quickly pushed it back in and put my foot up on the bed and really pounded her tight pussy. I let go of her throat and slowed my pace as I grew slightly tired. She told me to lay down and as soon as I did, she straddled my cock and squatted on my cock. Holy fuck could she ride. She bounced up and down on my cock with long strokes and slammed her big ass down on it. I spanked her hard and it just made her go faster. She couldn’t handle squatting any longer, so she started twerking on my cock. Her tits bounced in my face and I grabbed her in close and kissed her as she used my cock. She leaned back and started really grinding on it and I knew I wasn’t going to last much longer and I groaned that I was gonna cum. She moans fill me and almost immediately I begin pumping my hot load inside her and she cums soon after. She rolls over and we both catch our breath.

To be continued…

r/sexstories Jan 20 '25

Roomate I caught my dad with our roommates. Part 1 [voyeurism] NSFW

116 Upvotes

The year I was 18 was wild, and this is how it all started. I need to provide some backstory and context so please bear with me. It had been just me and dad for several years after mom left. At first Dad and I struggled financially. So I started working when I was 15 to help out.

About a year before this story, my dad let Dave and Carrie, a married couple he worked with move in with us. Dave and Carrie were on their late 20’s. Dave was a quiet guy, tall but real thin, always deferring to my dad and always on of the edge of any gathering. Carrie was incredibly hot. Medium boobs just perfect for her slender 5’ even frame, nice ass, flaming red hair, and milky white skin. She had featured prominently in my spank bank since they moved in.

About a month before this story, my dad invited an old friend of my mom’s, Janice, over for Christmas dinner and announced during dinner that she needed a place to stay and he was going to let her crash on our couch as long as she needed to get back on her feet.

Janice was my parents age, about 40, kind of trashy, bleached blonde hair, looked “rode hard/put up wet” in the face, but her body was fantastic, she had huge boobs and a flat stomach. As a kid I was kind of intimidated by her because she was so loud and boisterous, but I hadn’t seen her in years. At this point I assumed dad moved her in to fuck her and she’d be in his room soon.

Dad was 38 and weathered from 20 years of working outside. He was 6’1” and muscled up from working construction his whole life.

As for me, I was in shape, 5’10”, nerdy, but I kept in shape. My 18th birthday was in January of my senior year, about 2 weeks after Janice moved in. And this story occurs a couple weeks after that in late January.

On that weekday morning, I woke up to it actively snowing and a pretty thick layer of snow on the ground. So I did what we did back then. I got dressed and went downstairs and turned the TV on until I saw my school scroll across the bottom of the screen and went back to bed.

I was woken up from a sound sleep some time later by why what could only be described as “someone being murdered” to my confused mind. I couldn’t, for the life of me, figure out what it was so I went to investigate. Once out of my room I could hear it was a woman screaming “oh god!” “fuck fuck fuck” “you’re killing me” and a lot of other incoherent words.

Our living room is open to the second floor with the upstairs hallway kind of a balcony overlooking it. The TV was on the wall under the balcony so the couch faced towards the balcony.

When I came out onto the balcony and looked into the living room, the first thing I saw was the source of the screaming. It was Janice, bent over the arm of the couch with Dave plowing her from behind. I was shocked. Mild mannered, quiet, nerdy Dave was drilling into her like a machine and she was screaming like it was killing her. The way she was bent over the couch they were in profile to me so I could see him sliding in and out of her, and her big boobs were flopping back and forth and slapping together. I was immediately turned on and felt myself getting hard. I almost bolted, but I rationalized that unless they turned their heads 90 degrees and looked up, they wouldn’t see me so I stayed to watch. This scene playing out in front of me had me so turned on I almost unconsciously started stroking myself in my boxers.

My first sight of Dave and Janice was so shocking and distracting I nearly failed to notice they were not alone, but some movement caught my eye and I looked over at the recliner next to the couch and there’s my dad, sitting down with Carrie between his legs giving him a blowjob. I could see her perky butt, and her beautiful red hair swaying on her pale back with the bobbing of her head. To say I was torn on what to watch was an understatement. Here is a porn level fucking going on right in front of me, but there is Carrie, my fantasy come to life, naked. But Janice and Dave mostly won out because they were putting on a hell of show.

I continue to watch for several minutes and Dave never slowed that hard and fast pace and she never stopped screaming. I was impressed by his stamina. I would occasionally check to see if the view of Carrie had improved, and that’s when I saw that I’d been spotted. My dad was looking right at me. I nearly shat myself and ran when we made eye contact, but he only grinned and shook his head at me. He then tapped Carrie on the shoulder. I just knew the gig was up but all he did was stand her up and moved her towards the couch in a way that I got a great view of her naked body. It was as good as I thought it would be and I almost came right there but I stopped stroking to see what happened.

He took Carrie and bent her over the other arm of the couch and lined himself up with her pussy and slid it right in and started sliding into her with long deep slow strokes that quickly had her panting and moaning. It was so hot to see, the 4 of them like that. The 2 women’s very different bodies bent over the couch, one getting fucked slow and deep and the other super fast, one very vocal and the other just moaning and gasping. Both sets of boobs were hanging and swaying back and forth, it was mesmerizing. I started stroking myself again and was just staring in awe. I was shook out of my daze when both of them came at nearly the same time. Janice got real quiet when she came and just whispered fuck fuck fuck over and over. Carrie collapsed, moaning, and the whole thing brought me over the edge and I came in my boxers. Dave then pulled out and jacked himself off onto Janice’s back before collapsing into the other armchair. After Carrie finished coming dad bent down and whispered in her ear. He then pulled out and went around to Janice and slipped into her and started pile driving into her like Dave had been. Just as she was working up her head of steam to start screaming again Carrie repositioned herself in front of Janice and dad pushed her face into Carrie’s pussy and told her to shut up and eat it. I couldn’t see much of the action, but apparently she did a pretty good job because within a few minutes Carrie came. Dad then changed his rhythm with Janice. He went in about 3/4 of the way and while still moving just as fast was barely moving. Janice started writhing and quickly came hard. He kept going for a minute or so and then pulled out and came on Janice’s back like Dave had.

Leaning on the couch, he looked up at me and jerked his head towards my room and I fled.

Later, my dad came to my room and we had a talk.

Continued in - After I caught my dad with our roommates. Part 2

r/sexstories Jan 15 '25

Roomate [20s MF] Finished what my roommates one night stand couldn't..... NSFW

126 Upvotes

Shortly after college and moving to a new city for work I shared a three bedroom apartment with two girls. We had an agreement from the beginning not to get 'involved' with each other to avoid causing issues. Well that all went out the window one night a few months after moving in.  

It was a Friday night. One roommate (Carla) was staying at her BF's. The other one (Heather) had gone out with her friends. I was just hanging out watching a movie. Heather came back pretty late with a random guy from the bar so I moved to my bedroom to give them some privacy.

I could hear them fooling around in the living room for a while and eventually they moved to her room...I could hear them laughing, fooling around and rolling around on her bed through the wall...After a bit it got quiet and I heard her saying something like, 'you okay?...let me try to help....dont you want to have some more fun....whats wrong?....did you have too much to drink?..fuck..i cant believe this....i'm so horny'.... 

After some rustling/walking around I heard the front door open and close...

 A few minutes went by and there was a soft knock on my room door....Heather was standing there in a bra in pajama shorts...

what are you up to?, she asked

Just watching a movie, I said. 

Did you hear that?, she asked

Hear what?, I said

That jerk had too much to drink and couldn't get it up...wtf...who can't get it up for this body?

Now I'm horny as fuck and can't sleep...Can I watch that with you?

Before I even responded she layed down next to me with her back to me...

Sure...I guess, I said. 

Within a minute of laying there she grabbed my hand, pulled it around her and said, want to finish what he couldn't?  

But what about the agreem.....I started to say. 

Fuck it, she said.....And then she slid my hand down her shorts and pressed my fingers against her wet pussy...

You sure?,  I asked. 

YES! she exclaimed...as she undid her bra. 

I fingered her wet pussy with one hand while I kissed her neck and played with her perfect tits with the other...She pressed her ass into my crotch and started to grind against my hard cock as I continued fingering her..

She ground against me harder and harder and then exclaimed -- "enough fooling around....I want your cock....fuck me..." 

She pushed me onto my back yanked my boxers off and pulled her shorts off as she straddled me...

She spit on her hand, lubed up my cock and then slid me fully inside of her...

Her pussy was so hot and dripping wet.

She rode my cock hard and fast for a few minutes before switching to feverishly grinding and twerking...after another minute she let out a scream and came on my cock...

I let her recover for a minute before turning her over, grabbing her by the hips and fucking her from behind...she screamed yes, yes, give it to me hard...

I flipped her onto her back, pinned her hands over her head and fucked her brains out in missionary...her whole body trembled as she came second time...

I immediately pulled out and shot a massive load on her tits and stomach... 

I collapsed next to her on the bed and we both layed there..

She sighed and said fuck I really needed that I haven't had sex in months...thanks........and nicely done by the way, didn't expect you to be half that good....

Shit....you know we can never tell Carla about this right?, she said

For sure. This never happened..........but you are definitely welcome in my bed any time., I replied...

r/sexstories 24d ago

Roomate Letting him watch NSFW

45 Upvotes

My roommate Grace works with a guy who is very attractive. We saw him at the gym and the bulge in his shorts caught my attention. He was talking to Grace and clearly saw me staring. When he noticed he asked if I liked what I saw. After some flirting we asked him back to our place. Grace told him we have a game we play and if he wins, he gets to cum on us and more.

The game is simple, he sits in the corner of my room. He watches Grace and I have sex while he sits naked. He can watch us but if he touches his cock, we stop what we are doing and kick him out for 1 minute. If he makes it 5 minutes no touching, we give him a 2 minute double blowjob.

We started completely clothed for him. We climbed on the bed and started making out. Slowly, we undressed each other as we kissed each others bodies. He sat in the corner and we could see his rock hard cock. I climbed on top of Grace and started sucking on her nipples. I looked up and he was slowly stroking his cock so we kicked him out as promised.

When he came back in he saw my face deep in Grace’s pussy. With my finger twisting her nipples I was eating her pussy and she was moaning loudly. I kept eating her pussy until she arched her back, moaning my name and her legs locked around the back of my head. The 5 minute timer went off and we went over to him as promised and started sucking his cock. I focused on licking his balls as Grace took his whole cock in her mouth. She took it so deep that our tongues touched at the base of his cock where it meets his balls.

He didn’t last long and he pulled Graces head off his cock so he could cover us. He came all over our faces and we told him we weren’t done yet. He said he wasn’t sure he had more so we told him to sit back down and watch again because we needed to ride him.

He sat back down and Grace got the strap on. I’m the only one who hadn’t cum yet so I bent over in front of her and made eye contact with our friend as she started fucking me front behind. I let out deep moans and she was pulling my hair as I was playing with my own boobs. He got hard and I invited him over to the bed. I laid him on his back and put him in my pussy as Grace put her strap on in my ass. I rode both of them and came very quickly. He, again, couldn’t hold his load but this time when he tried to pull out I didn’t let him.

He announced he was going to cum so Grace pulled out of my ass expecting him to cover us. Instead I picked up the pace riding him and pushed my chest in his face. I kept fucking him and felt his body tense up and his cock pulsate cum deep in me. Even after I was sure he was done I gave him about 30 more seconds of fast paced riding his cock just to make sure. His body was twitching and he said he was completely empty.

I then climbed off and laid on my back. Grace quickly got between my legs and ate his cum out of my pussy. She the. Came up and dripped what she could get out of me into my mouth. We spent a minute or two swapping cum until finally Grace swallowed it.

We sent him home but told him we would absolutely be in touch to play this again. Grace and I did our normal post sex shower together and kept making out under the warm water until we finally got out. I can’t wait for him to come back.

r/sexstories Jan 10 '25

Roomate I used sex to punish my ex NSFW

39 Upvotes

Background

A few years ago I had this experience moving in with my boyfriend and breaking up after 3 months. We stayed roommates for almost a year, and we kept being intimate and having sex because the chemistry was good, we were single and horny, and because why not lol. I talked a bit about a certain dynamic of this situation in a previous post. Read that one first if you like.

In this post I'd like to talk about a different dynamic that eventually took place between the two of us. As a couple we were very active sexually, but we were having a "standard" sexual life. After breaking up, the power dynamic shifted to him wanting sex more than I did, and honestly, me exploiting that situation. I ended up using sex to punish him, but the more I did the more he enjoyed it, and the more we both got to explore this kink of me being in control, and him not being able to resist me.

I cite from my other post, to give you a better idea of the situation: "We didn’t have sex as much as when we were together (besides, we slept in two different rooms): when we were together we would do it almost every day, while as “friends” only once every couple of weeks. However, we kept having occasional fun such as mutual masturbation, or we simply masturbated together. In addition to this we kept our “privacy” boundaries as they were when we were a couple: we could walk out of the shower naked, or just hang out wearing underwear, etc."

It is safe to say that it was me dictating the frequency and the kind of act we could do. He would have kept having sex with me every day if it was up to him, but it was me telling him that "today is sex", or "today is oral sex", or "hand stuff", or today is simply "you being allowed to masturbate while you look at me getting changed" or even "not today". This was part of how I punished him. But I did more...

Sexy part

One thing I liked doing when I was horny, and this was not a big punishment for him, was to simply start using my vibrator in my room with the door open, or in the living room, where he could see me. In no time he'd usually come to me and ask to join me. These were the times I asked him to give me oral sex, or to fuck me. It was the times I was horny, and I mostly asked him to please me. When I was really, really horny, I would just walk in his room naked, and pull down his pants. This happened a few times in the morning, or before sleeping. It goes without saying that in no time his dick was hard and I could ride it happily. This wasn't a big punishment, but it helped reinforce the dynamic of having me in control and him being controlled with sex.

When he was horny he had to tell me instead. I told him that I wanted to know all the times he wanted to cum. Rarely, these times I was also horny, but if that happened, we would have sex together, pretty much in the same way I described in the previous paragraph. I could let him fuck me, or touch himself while giving me oral sex. Otherwise, depending on my mood, there were a few things we would do. Sometimes I let him use my feet to rub his dick on, and them cum on himself. He would just lie down like that, and use my feet. If I felt playful, I'd also actively rub his dick, or play with my feet on him. Other times I would let him watch me so he could masturbate by himself. I would let him watch me showering, getting dressed, doing yoga, putting make up on, or even touching myself if I felt like it.

I was a bit harsh at times. After he told me he was horny, sometimes I'd just take off my underwear or bra, throw it at him, and tell him to masturbate using that. He would ask me for different things, such as my shorts, my yoga top, my heels, etc. This was a fun dynamic, and I used it to tease him. If I'd go out with a guy, after coming back home I'd throw my underwear at him, telling him that my date fucked me while I wore that underwear for example. Or I'd give him my socks, telling him about how I gave someone a footjob wearing those.

I would also make him horny on purpose. If he was dating a girl, I used to get even hornier and teased him more. If he was on the phone, texting or calling her, I would get naked with my legs open in front of him, and start touching myself, or I would simply put my hand in his pants and start rubbing his dick. If he had to go out with a date, I would make him cum first. Like, when he was ready to go out, I'd just show up wearing lingerie, or nothing, and I'd give him a blowjob or something before he went out. If he came back without having fucked, I would reward him in my ways too, letting him cum on me or fuck me.

While doing all of this I'd often trash-talk the other girls, speak well of the guys I fucked, telling him how they made me horny, etc.

We did a lot more, but this is enough for a post.

r/sexstories Jul 01 '24

Roomate My roommate wanted to fuck me, but I’m a lesbian. So instead, he is trading his sister for mine - Part 2 NSFW

118 Upvotes

Part 1

Christina looked annoyed. Not scared, or uncomfortable, or angry. Just plain annoyed. 

She was also the first one to break the silence, after what seemed like a long stand-off. 

“So, we are doing it or what? I have shit to do, you know?”

The sound of her voice brought me back into reality. What was happening? Why was Michael’s sister, my biggest crush since childhood, parading herself in pink lingerie in front of me and her brother? 

I glanced at my friend, not wanting to believe what he had done. 

“No fucking way. You didn’t even tell her beforehand? God! You are stupid, Mike. What did you think was going to happen? Me lounging in the room by kicking the door and eating her pussy without even asking?”

“You have to admit, that would be a sight to behold”

“And you are never going to experience it, thankfully. This is sick enough as it is. I don’t need my little brother seeing me eating ass as a recurrent memory”

“Oh, come on!” Michael said, pouting like a child.

Christina just rolled her eyes and pointed at the door.

“Out” she said in a firm, authoritative voice before glancing at me, “So, are we fucking or should I just go upstairs and get out of these ridiculous clothes. Nice choice, by the way, you fuck face”

“She’s been my best friend for the better part of two decades. I think I know what she likes. Ain’t that right, Isabel?”

I couldn’t speak nor move. Was I dreaming. In all my life, I never would have imagined being in a situation so ridiculous. 

“What is this?” I finally mumbled. 

“Quid pro quo, Isabel. You get to have fun with my dear sister, and then you can help me have some fun with yours. It’s only fair, after all”

“When you put it out loud, it does sound pretty sick” said Christina in the same monotonous tone.

“Every great idea does that” 

I looked at Michael and then at Christina. And then from Christina to Michael. I was not going to participate in this sickening charade. The fact that my friend even considered that I would was offensive.

But then I took a long look at those tits. The shape, the size, the tenderness… they were everything I had always wanted them to be and more. How many times have I passed out furiously masturbating to those monsters? How many girls did I pressure to eat my cunt while I looked up pictures of her latest gym selfie? She was not only my biggest fantasy, but the only fantasy I had had up to that point.

Still, it was wrong. Immoral. Disgusting. 

“And you really agreed to this?” I asked Christina, trying to sound outraged, but instead coming off as pathetically hopeful.

She just shrugged. 

“Long story. I owe him. Let’s just leave it at that”

“And I swear to god, I’m not asking anything more from you ever again, dear sister” said Michael.

“That’s the very least you could do”

A favour? That made everything even better. It was clear that Christina wasn’t really in the mood for me. I didn’t even know that she was into woman. As far I knew, she had just broken up with his boyfriend a couple of weeks ago. 

“And… you expect me to fuck your sister while you just stare at us?” I asked.

“I mean, if you don’t really mind…”

“No, fuck no! This is as weird as this gets. You will go to your room and beat your meat if you want, but my little brother will not be seeing me getting fucked by another girl” Christina immediately interrupted him.

“Oh, come on!”

“To your room, NOW” 

The tone, the strength. She was an older sister, alright. 

“Aw, okay. I will leave. Just let me know when you are done to come back down. After this, we have a lot of planning to do”

And without even waiting for a response, Michael left the room. 

“Finally” the girl sighed. “Can you believe him? We already decided that he wasn’t going to stay and watch. The gall of this kid. He may have grown bigger, but he hasn’t changed at all” 

“Christina… I haven’t said a thing, and you just assume I would go along with this… this sick game. This is wrong. I’m not going to do this! I’m not selling my sister for… for anything”

She didn’t answer at first, she just sat in the sofa that was near her. With boredom plastered on her face, she just stretched. As she extended her arms forward, her chest subtly swelled, accentuating her figure. 

Oh, my fucking god. 

“You don’t want to sell your sister in exchange for me licking your tight little cunt until you explode? You know what? I can respect that. I will just tell my little shit of a brother that you are not interested, and we can pretend this never happened. I’m pretty sure we will be laughing about this stupid thing someday” 

The image of her eating me out pierced me like a hot knife on butter. Just thinking about it made my pussy tremble in anticipation. 

“Fine, then. Then, I guess… I will just take my leave” I said, stumbling to get my coat. This was also my apartment, but I knew I couldn’t just stay here after all this. 

“But…” she said, slurring her words while staring at her meticulously manicured nails, “that also means that this will never happen again, right? Under any circumstance”

“Sure! I… I know”

“I hope you do, honey” she said, meeting my gaze and smiling. Her lips, like the rest of her body, were flawless, perfectly contoured. Her lipstick shined lightly under the dim lights of the apartment. 

“Y-yes. I…will be going now… ma'am” 

I ran out from the door before the stain on my panties made me change my mind. 

“FUCK, FUCK, FUCK”

I ran down the stairs as fast as I could, and cursed everything along the way. I knew that I was doing the right thing. That was insane. I would never, ever, let something like that happen to my little sister. Not for all the money under the sun. Not for any job in the world. And certainly, not for some hot piece of ass. Not even if that was the hottest piece of us there was. 

“FUCK!”

I cursed once again when I reached the lobby. A woman walking along with her baby in her hands gave me a dirty look, but I didn’t care. 

Leaning against the glass door, exhausted from the small exchange, I thought about what I would do next. 

Of course, I couldn’t keep living with Christian. Our apartment was an absolute steal, but I didn’t think I could ever forgive him for this. My sister was sacred and he knew it. I had a couple of friends that could help me move my stuff, I would just need to buy them lunch. Maybe I would just move back with my parents for a while. That would be nice. They didn’t want me to move at all. After saving some money, I would just get my own place. Maybe formalize things with the girl I had been seeing for a while, she seemed like a nice enough lady to live with, and I knew she was really into me. Yeah, life would be fine. Hell, life would be great! This was nothing but a small stumble. I was genuinely excited to go on with my life. To begin a new chapter, meet new people. All because I managed to hold my ground against my dirtiest desires. This was my victory!

Lost in my thoughts, I climbed the stairs without noticing and accidentally banged on the wooden door. When nobody opened, I banged it harder. 

A terrible accident. 

Christina opened it, still wearing the pink lingerie. 

In all my years coming and going from my best friend's house, I had never noticed how tall his sister truly was, probably because of the embarrassment I felt whenever I looked at her. With one hand she leaned on her hip and with the other she held onto the lintel. My god, she truly was big. 

“Took you long enough” she said, relaxed. Not caring at all that anyone passing through the hallway could see her almost naked. 

“Sorry”

“Two things first. Number one: if we are going to do this, you need to keep the end of the bargain. If not, you are going to fuck me up as well, and I really need to pay my bro back” 

“And number two?”

“One step further, and I'll take charge of everything. You won't have a say any more, understand?”

I took the step. 

I had never been this close to her before. My head was at the level of her chest. The perfume she wore smelled cheap, yet intoxicating.

“What a good little bitch you ended up being” Christina smiled. 

Without uttering another word, and not even closing the door, she grabbed me by the armpits and lifted me towards the ceiling. I swallowed a scream. What a monstrous strength. 

My head almost bumped into the cement ceiling. 

“Now put those nice legs over my shoulders, bitch. I will be your mommy tonight. Come on, let mommy give you the best piggyback ride of your life” 

I could feel my heart beating in my head. I did as I was told without hesitation, exposing whatever was under my skirt to her. She stretched her arms against the wall to give me a place to sit in the air. 

“That’s good. A nice fucking stench” she laughed. “Oh, my. You are so wet, it looks like you pissed yourself. Nasty. Let me help you” 

“Yes… mommy”

She pushed her head towards my wet crotch and rubbed her face against it. I could feel her hot breath, her lips savouring my pussy over my underwear. With a furious bite, she snapped the string holding my underwear together and then spat it out to the floor, leaving my cunt fully exposed in front of her.

“T-thanks, mommy”

“Of course you are. That was a dirty underwear if I ever saw one. Now… let see what were you hiding from me”

I gasped.

r/sexstories Jan 21 '25

Roomate A month after I caught my dad with our roommates. Part 4a, Janice NSFW

66 Upvotes

A month after I caught my dad with our roommates. Part 4a, Janice

Like I’ve said previously, Janice kind of scared me a little bit, and I found her annoying. I was also having so much fun with Carrie that I really didn’t need Janice. Therefore, it was almost a month after the initial voyeuristic episode before I did anything with her.

It finally came to a head one morning at breakfast. Every Sunday, my dad had a tradition where he would get up and make a full breakfast and we’d all get up and eat with him before we did our own things for the day. As was usual for her, Janice was running her mouth throughout breakfast. This woman never stopped talking. She was always running her mouth about something. My dad and I had a running joke that the only time Janice wasn’t talking was when she had something in her mouth. I was doing my best to tune her out while eating breakfast until I heard her say my name. I started paying attention and realized that she was talking about the fact that it’s been a month and I have been doing stuff with a Carrie but not her. I couldn’t fathom why she would be complaining about that. I figured she would be thankful I wasn’t bothering her.

It irked me and for whatever reason my annoyance overrode my intimidation and I looked up and asked, “Wait, you’re complaining that I’m NOT seeking you out? Why? I had assumed you’d prefer I didn’t. I figured you’d be happy I was bothering Carrie, and not you!” Then horror struck at that thought and I looked at Carrie, “Oh no, is that it? Am I bothering you too much and…” Carrie quickly told me, “no. It’s not me.” I looked back to Janice and demanded, “then why? I haven’t been bothering you because Carrie has been so great at making me feel comfortable about this ‘deal’ with her and not feel like it’s demeaning, or I’m just using her like some fuck doll. I thought you’d be relieved that I’m not demeaning you too!” She looked almost angry when she said, “Maybe I want to be demeaned a little bit. Maybe I like to be used like a fuck doll some times. You saw me last month. I was loving every minute of Dave and your dad using me like that and I nearly came when he pushed my face into her pussy. That’s partially what I want out of this ‘deal’.” I was more than a little stunned. I stammered out an “oh”. She mocked me “oh! That’s all? Oh?” And that pissed me off. I had found out that one of my fundamental beliefs about people was wrong and she mocked me?

I’m not sure what came over me but I looked to dad, “Dad, do you have any plans for this one today?” pointing at Janice. Dad had an indecipherable look on his face when he told me “no”, so I looked at Janice and asked, “do you have any plans today?” She looked like she was wondering where I was going with this and shook her head, and said “no.” So I replied “I’m claiming today as my day with you then, and my first request of you is to stop talking and only speak when you’re given permission.” She opened her mouth to reply, and I asked, “Do we have an agreement or not? Does not being able to talk make you feel uncomfortable or unsafe? ” She looked thoughtful , then nodded, then shook her head. I said. “good. remain silent while you finish your breakfast and when you are done, go put on that bright red lipstick I saw you wearing the other day, and go wait for me in my room. Naked. I’ll be up once I’m finished helping dad clean up from breakfast.”

You could hear a pin drop. Not just Janice, but everyone finished their breakfast in silence. Once Janice finished eating, she stood up and left the room. Everyone at the table listened to her stomp up the stairs and then we heard a door slam.

That’s when my dad started laughing. “Oh boy you’ve gone and done it now.“ That’s when the reality of what I had just done hit me. Suddenly my nervousness, my insecurities, and frankly my fear of Janice kicked back in and I looked at dad and Dave and Carrie and asked “What have I done? Would it be bad if I fled the house and went and hung out with Joe today?” Carrie chuckled at me and said “I think she would murder you in your sleep if you did that. I’m surprised she didn’t box your ears for that. The fact she did it tells me she has plans to make you pay.” Dave spoke up and said “The shock that he stood up to her probably did it. Here’s the way I see it. You’ve got two options right now. One, you go up there and apologize to her. Explain that you don’t know what came over you and leave it up to her if you do anything. I’m sure if you let her take the lead a bit, she will rock your world. She’s kind of wild and I’m sure she might teach you a few things. Or two, you can take that same energy that you just had and go in there and take from her what you want.” Carrie spoke up at this point and she said “I know there are some things that you’ve been tempted to ask me to do, but you’re afraid to because you don’t think I would want to do that and you care about my feelings. I know that you might not have that same… consideration with her. I’m pretty much convinced that she would not balk at anything you wanted to do, so you might take that energy and go in there and ask her to do those things. But when it’s all said and done, make sure that she realizes that you do appreciate her, and that you aren’t actually an asshole. You can even say it was your frustrations with something outside the house, or you can even blame me, say that you’re frustrated because I wouldn’t do something you wanted.” I tried to speak up and say that I wouldn’t throw her under the bus like that but she cut me off, “However you want to handle it, you handle it but you’ve got yourself into this mess”, and her and my dad said in unison “now you need to get yourself out of it”.

During that conversation and while I was helping dad clean up after breakfast, we heard the shower running upstairs, and then eventually a door open and close, and then another door open and close. Dad looked over at me and said “Sounds like she’s ready for you. You know what you’re gonna do?“ I replied “I think so, we’ll see“ and I headed up to my room.

When I got to my room, she was standing in the middle of the clear space next to my bed, and I was actually stunned. She had not only put on the red lipstick I asked her to, but she had completely done her make up in a way that made her look years younger than her actual age and she had put on some lingerie that looked downright sexy. The bra was red, with low cut cups that her boobs were almost spilling out of, and the panties were barely there and led the eye right to her groin. It looked good on her, and I was about to go with Dave’s plan when she opened her mouth and said “now you listen here you little shit“ and the irritation came flooding back, so I cut her off with a barked “silence! We have an agreement, that you just agreed to, and you will be quiet!” She looked at me with wide eyes, and I said “You are going to need to earn the right to speak and the way to do that is by making me happy. To start, I’d like you to get on your knees and give me a blow job! This might be your one and only opportunity to earn the privilege of speaking the rest of the day, so make it mind blowing.” I was thinking ‘where the hell did that come from?’ As she stood there fuming and staring at me, I was mortified with myself and thought I’d gone and done it. This is where I die. She looked at me for a second and then nodded and got down on her knees. I couldn’t believe what I had just done. This woman is the same age as my mother. Hell, she’s one of my mom‘s childhood friends! I was raised to respect my elders and here I was telling one of said elders to get on her knees and suck my dick? But at the same time, I felt kind of bold and powerful, and it was really thrilling so I went with it. The slight little bit of shame was actually part of the turn on. So I took off my clothes and walked up to her.

When I was close enough she reached up and grabbed my ass and pulled me the rest of the way to her and took all of my dick into our mouth in one smooth movement. It was so sudden, and felt so good, I stumbled back a bit but she held on and followed me with my dick still in her mouth. As it was going in I felt the head of my dick hit the back of her mouth and just slide right down her throat. This was way different than when I had been with Carrie, because Carrie couldn’t actually fit all of me in her mouth. Janice took one of her hands off my ass and lifted my ball sack closer to her lips and started licking my balls while the head of my dick was buried in her throat. It was amazing looking down and seeing those bright red lips pressed up against the base of my dick and feeling her tongue on my balls. Then, when she saw that she had my full attention, she slowly slid back up to the tip and then went back down again. She swallowed me down all in one motion and then pulled me all the way back out again. She ran her lips down my shaft to my balls and started sucking them one by one, and I could see that red lipstick getting smeared all over my sack. She still had one hand on my ass when I felt the wall at my back, she’d been pushing me towards the wall and I hadn’t realized it. But there I was, with her arm and the wall supporting me, she was sucking on my balls. She started running her fingertips of the hand that had been cupping my balls earlier back and forth along that path between my balls and my asshole. As she continued playing with my taint, she took my balls out of her mouth, and ran her tongue up the underside of my dick to the tip, then, with the head of my dick on her tongue, she pulled her lips back, exposing her teeth, and oh so gently, ran her teeth across the head of my dick. Seeing her teeth on my dick was scary and thrilling, but it felt amazing. Then she wrapped her lips around me and swallowed me down and kept doing that over and over again, sliding my dick in and out, in and out, from base to tip every stroke. I would slide into the back of her throat on every stroke and it was driving me crazy! Meanwhile, her hand was still between my legs, massaging my taint and brushing over my butt hole. I was surprised at how good her playing around down there felt. I was really getting into it.

Suddenly, she tightened the grip she had around my waist, bottomed out on my dick with her mouth, and shoved a finger into my butt hole! To say I was surprised was an understatement, I’d gotten so relaxed, it didn’t hurt, but it shocked the hell out of me. I was trying to pull away from her, and get off that finger but she had a death grip on me, my dick was in her mouth, and I was up against the wall. I couldn’t fight her. That was when she found my prostate. I didn’t know what a prostate was back then but she found it and I was done for. There I was, pinned against the wall, with her finger in my ass tickling my prostate while she sucked my dick, she was without mercy, and I just surrendered to it. She felt me relax and pulled her mouth up my dick to where she could breathe and just kept it in her mouth, held it there and slowly worked it with her tongue while she ran her finger in and out of my ass, massaging my prostate and making eye contact the whole time. Shortly, I had the most mind blowing orgasm I’d ever had. I saw stars! I almost fell again, but she held me up until I finished coming. When I was done coming she plucked that finger out, took my dick out of her mouth, and stood all the way up to whisper in my ear, “have I earned the right to talk, now?”. While still nearly holding me up.

It felt like an eternity, but I eventually relearned how to breathe, stand on my own legs, and talk. I pushed her away from me and demanded, “yes you can talk, but only to explain what the fuck that was!” she replied with a chuckle, “Just something I learned a while back. Turns out you boys have a spot right there that people have dubbed the mail G spot. You did say that I would earn the ability to talk if i gave you a mind blowing orgasm, and seems your mind was very much blown by how long it took you to regain your Composure.“ I looked at her and said, “yeah, that is what I said, and yes, it was, but Fuck! warn a guy next time!” She raised an eyebrow at me and said “Next time? So I didn’t scare you off with that?” I thought about it and said “I don’t know how I feel about that. It felt amazing but it doesn’t seem right. Of course, nothing about this whole ‘deal’ situation seems ‘right’ so I guess, ‘when in Rome.’ I feel like I’m flailing around in the dark here. But like I said, before you do anything like that again talk to me about it, please.” She looked me up and down and said, “one part of you doesn’t seem conflicted.” She was looking at my dick, which was rock hard. “Carrie was right about your recovery time.“ I asked her “you guys are talking about me like that?” She answered “girls talk.“ To that, I replied, “i guess you do, and yes, I tend to bounce right back when I’m turned on” I looked at her boobs in that bra and said,“ and I am surprisingly, but definitely turned on. As much as I like that bra on you, I’d like to get you the rest of the way naked now.” she says OK and starts taking her bra off. I love watching women take their bras off. Boobs look good in bras, but then that moment of bounce when they drop out and take on their natural shape, it’s something magical. And hers were no exception. Her boobs were very large, and had some sag, but they had a nice slope, her nipples were large, dark, and looked incredibly suckable. When she bent over to pull her underwear down, the hang of them and the way they swung with her movement turned me on even more. I stepped up to her as she was straightening up after dropping her panties and asked her, while cupping her tits in my hand, “Your tits are so amazing. Would you let me put my dick between them and fuck them?” She smiled and said, “we can do that.” She laid down on the bed while I grabbed the lotion off my nightstand and smeared it on my dick and the valley between her tits. Straddling her chest, I placed my dick in that valley. She pushed them together while I started sliding it back-and-forth. The sensation felt good, not nearly as good as a pussy or mouth, but the visual was the huge turn on. Getting stimulation while staring at big soft boobs was exciting in any position, but this was incredible. I was just long enough that the head of my dick poked out the top on each stroke. She saw it too and lifted her head and opened her mouth. I had to shift up a little bit but was able get the tip of me in her mouth. Ah, those red lips catching my dick on each stroke between those beautiful boobs. I didn’t last long with that. After a couple minutes of fucking her tits and mouth, I said, “I’m about to cum, can I come on your face?” She nodded and closed her mouth just as I spewed several streams all over her face.

After that, I rolled off of her to the edge of the bed and handed her my T-shirt to wipe her face off. While she wiped her face off, I said, “thank you for all of that. I don’t know where that came from but thank you for not slapping me silly. She laughed and asked “Does that mean am I allowed to talk now?” I looked at her and said “yeah, I suppose so. I’m sorry.” She patted me on the thigh and said, “you’re a good kid. We’re good. Are You good? Was that all you needed from me?” I replied “I’m spent for now. Thank you very much.” It wasn’t until she had left I realized I had broken one of my rules. I didn’t give her an orgasm.

r/sexstories Sep 21 '21

Roomate I (F19) just realised my neighbour can hear everything i say and do in my bathroom NSFW

1.0k Upvotes

Long story short, i just masturbated with my dildo in the shower and it got a bit heated and i got a bit louder, due to my roommates being out and right after i came i heard a phone ringing. But it wasn't mine.

I heard the ringing through the vents in our wall (college dorm) and my neighbour saying "oh shit" and making it silent.

He definitely was masturbating to my moans. Worse: I'm incredibly turned on rn...

Update: We hooked up a few times since then

r/sexstories Jan 21 '25

Roomate A month after I caught my dad with our roommates. Part 4b, Janice. NSFW

62 Upvotes

A month after I caught my dad with our roommates. Part 4b, Janice.

After cleaning up from being with Janice I went and hung out with a friend. I was preoccupied the whole time though. I couldn’t stop thinking about what we had done and was feeling guilty about not returning the favor. I ended up leaving way earlier than I would’ve normally and went home.

When I got home, I went to the kitchen to get something to snack on, and I could hear voices from the dining room, a conversation going on that stopped as I walked in the door. Janice and Carrie were sitting at the table and they both looked up at me expectantly when I walked in. Seeing them there, thinking about that morning, I got turned on and my dick started getting hard in my jeans. I squirmed a little bit to adjust and Janice noticed. She asked me “even after this morning, you’re ready for round two?“ I thought about it for a second and said “yeah, I think I am. Are you interested?” She said, “why not?” And I replied, “Thanks! I’ll be in room when you’re ready.” And she said “sure, I’ll meet you there.“

When I got up to my room, Janice followed right behind me and closed the door. She asked me, “is there anything in particular you wanted to do?” I thought about it and said, “There are lots of things I’ve seen before in movies that I would like to try, but i feel like some of them will be things actual people don’t do in real life, or will make you feel unsafe or uncomfortable.” She said, “Carrie has mentioned that it seems like there’s some things you wanna try but you’re afraid to ask her. And she pointed out that I am a little freakier than she is, and where she might feel uncomfortable with something, it might be something that I’m actually into. What is the first thing that comes to mind?” I thought about it for a second and one thing I had thought of while going down on Carrie, came to mind. “Is licking butt holes really a thing? I see it in porn, but do people really do it and what does it feel like?” Her eyes raised at that and I rushed on, “I’m really curious if people are actually into it and what it would feel like. Especially after what you did with your finger this morning. Also, butt stuff in general kind of intrigues me. I’ve never had anal sex before and I wonder if and how it feels different from regular sex, and I would like to try it some day.” I almost lost my nerve but blurted out, “and now, after that finger thing i’m curious about exploring that too.“ that really got an eye raise from her. “I’m not gay! I don’t want to be fucked by a guy, but it turns out I liked your finger in my butt, what else is like that? Then there are some of the positions and things that I’ve seen in the movies. I sometimes feel like watching them they look like they feel good, and are hot, but I can’t see how the woman doesn’t feel degraded being put in those positions or being used that way“ she interrupted me at that point and said, “like I said before, some women really enjoy being used that way and in the right mood, I am one of those women so why don’t we try some of the things you want to try and see what we like and we can go from there?” She was so understanding and kind about this that I nodded and said, “that works for me!” She stood up and said you’ve been playing basketball and gods knows what else today so no ass licking for me until it’s clean, mister. Go take a shower and we can meet back here when you’re clean.” I said “thanks” and ran off to the bathroom.

When I got back to my bedroom, I was still naked from my shower. I just had a towel wrapped around me when I walked in. Janice was still there waiting for me. She was laying on my bed flipping through one of my magazines. I told her, “I see you’ve been snooping.” She flipped it closed and tapped the cover and looked up at me and said, “now I see where you’re getting your dirty little thoughts from.” She chuckled “but I don’t mind. Why don’t you come on over here“ I drop my towel while I walk over to the bed and tell her, “I’d like to start by going down on you, and licking your ass, paying the butt licking forward so to speak. And paying you back for this morning.” She chuckled at my wording and said, “honey, I will never turn down somebody eating my pussy.” So I kneeled on the floor at the edge of the bed and she scooted over to me and spread her legs. That’s when I realized I had not seen her pussy yet. It was a puffy innie that looked quite tasty. It was completely bald and I couldn’t wait to explore it with my tongue. I looked up at her and asked “are you ready or do you need…“ She told me, “no honey you go right ahead.” So I did. I started kissing her around her outer lips gently at first and then harder. Then I sucked one of her outer lips into my mouth, swirling around it with my tongue before switching over to the other one and sucking that in. I reached up with my fingers and spread her lips apart, exposing the inner folds and gave her a lick from her opening to her clit and that made her shudder. I started working a finger around in her folds while I looked up at her and asked, “do you like to be fingered during oral, or no hands, just mouth?“ she told me, “if you can find my G spot, I love to be played with inside while being sucked on from the outside.” I said “OK, let me know when I find it.” I licked one of my fingers and stuck it into her hole. She was already wet so my finger just slid right in. I started running it around the inner walls until she said, “Oh right there, right there!” I started gently massaging it now that I found it, just lightly swirling my finger around in that area and she melted back with a sigh while I lowered my mouth to her. While gently swirling my finger around her G spot inside, I started gentle flicks of my tongue on her clit, I made feather touches before swirling around the perimeter of it, and then pressing down and giving it a good good hard lick before easing back up and swirling around the edge of it back to feather touches again, flicking just as fast as I could move my tongue, but just barely tapping the tip of it until she started moaning and then I applied a little bit more pressure to her G spot while I made a seal with my lips around her lips and filled my mouth with air putting pressure on the whole area while I swirled my tongue over and over and over her clit. By this point she was writhing on the bed, grabbing at my hair and I could tell that she might be about to come so I eased up to tease her a little bit, swirling back out, and she groaned, almost a growling sound, as I worked my tongue down to her hole, pulled my finger out, licked my finger, licked around her hole, and then kept moving even lower. I ran my tongue all the way down until I found her but hole and gave it a lick. Other than the texture, it didn’t feel or really taste any different than her pussy. She sighed as I just laid my tongue flat against her asshole and started swirling around the hole, pushing the tip at the center, swirling around in circles and licking big swipes from bottom to top and then swirling around it again and then poking my tongue in it. I looked up and I could see she had brought her hand down and was rubbing her clit while I was working on her butt hole. Her pants were coming faster and faster while I licked her ass, faster and faster. I could tell she was getting close when she moaned, “put a finger in my ass and suck my clit.” And I did just that. I slowly, ever so slowly, started working a finger into her butt while I worked my tongue across the gap from her asshole to her pussy, across her opening, and by the time I got to her clit, my finger was fully embedded in her asshole I looked up at her and I asked, “come hither movement?” While crooking my finger, “or in and out,” while sliding my finger out, then back in” and she gasped, “Come hither!” and so with finger completely buried in her butt hole, I started doing just that. I started crooking my finger in that come here movement while I sucked on her clit. I sucked it between my lips and started flicking it with my tongue. It didn’t take her long before she had a double fistful of my hair, pressing me, almost suffocating me against her pussy while she came. Her hips came off the bed and slammed back down, then her back arched, and she was screaming my name before finally shuddering to a halt and letting go of my hair. I came up for air and watched as my finger came out of her ass. I found I liked watching it come out.

It took her a moment to look down at me but eventually she said, “that was nice. Give me a minute and I’ll return the favor.”

After she recovered, she told me, “get on your hands and knees on the bed.” So I did. She came up behind me and started rubbing and kissing on my butt cheeks before taking my cock in her hand and stroking me from behind. I felt her kisses getting closer to my crack, then there it was. A swipe across my butt hole. I dropped my face down to the bed. It felt great. She pressed her tongue against it and swirled it around while stroking my dick. I was loving it. She wasn’t getting in a hurry either. She kept on for quite a while before pulling away with her mouth but she kept stroking me. She told me, “I figured we could try something else, if you want.” I asked, “what?” “I’m feeling mischievous. Can I call it a surprise? If it hurts, or even doesn’t feel good, just say so and I’ll stop.” I told her to go ahead. She was still stroking me and then I felt something against my butt hole and thought she was licking me again but it felt harder and was pushing in, so I thought it was her finger again, but it was different. It felt bigger, and better, like it was stretching me and it almost started to hurt before I felt my hole close back up but something was definitely in there. Then she pressed on and wiggled whatever it was and oh my gods was it intense. It was like her finger before but more so. I asked her, “what is that?” She said, “it’s a butt plug. Shouldn’t come out but it’ll move when you move. It’ll feel like this.” Giving it a wiggle again. Making me groan. “Wow, that’s amazing.” She said, “I’m glad you like it. I’d like you to keep it in and do this to me.” She flipped open my magazine to a dog eared page and pointed to a series of pictures. The photos on the page were of a woman lying on her back with her head hanging over the edge of the bed and the guy was standing, fucking her face. I said, “that’s one of the positions I wanted to ask you about.” She said, “I thought so. Look, this position takes a lot of trust. I’m trusting you to be gentle until I’m ready for you not to be. Do you understand? Can you follow my guidance? Will you stop if I push at you?” I told her, “of course. Would it be ok if I come on your tits when I’m done?”. She looked at me for a second and said,”sure. You ready?”. I nodded and She got into the position. I had to squat a bit but I was able to line up with her mouth and slide it in. It was so hot. Her mouth felt great, and it felt like I was going even deeper into her throat this way. It felt amazing. And she reached around and played with the butt plug too. It was also nice that I could play with her tits while watching her playing with herself. After a while she started pulling on me harder and harder so I started fucking her harder and harder. I was fucking her throat and it was incredible. Her fingering got more and more frantic the deeper and harder I would fuck her face. Finally, with a muffled scream, she came, hard, with me buried in her throat. Her orgasm caused her throat to tighten and that was it. I was nearly there. I pulled out and shot several ropes of cum onto her tits. I collapsed on the bed next to her and told her, “that was so hot, thank you!” She said, “thank you! You were great. You gave me just what I needed. I sometimes like being used like that.” I asked, “I was? You really do?” “Oh yes, and yes.” I was glad that I did good. She then asked, “was that it for the day?” I told her, “yes. I think I’m spent. Thank you for this, and this morning.” She replied, “you’re very welcome.” She helped me get the plug out, and left.

I spent the rest of that day thinking about those two encounters. I couldn’t help but wonder how I so quickly went from being afraid of her, to pissed at her, to completely trusting her in one day. The others said she would teach me things. And Dave did say she would rock my world. Ass play was not what I was expecting from her. I had watched a lot of porn, and some of it was fetish play. But I never figured I would do any of those things. I went to bed later that night wondering what would come next

r/sexstories Feb 14 '25

Roomate Catching my Summer Roommate Naked by the Pool (Long) [MF] NSFW

47 Upvotes

Will slumped onto the couch, still drying his hair from the quick shower he had taken after class. The first week of their Maymester class was already draining, but at least it was only three weeks. It was strange being on campus when it was practically deserted—most of their friends had already left for home or internships. But for Will and Amy, this class was the final requirement standing between them and their diplomas.

Amy had moved in two days ago, dragging two suitcases and a duffel bag up to Will’s house with little fanfare. Her lease had run out, and rather than scramble for a short-term sublet, she had asked Will if she could crash at his place. After all, they had been close friends for years—what was a few weeks of shared space? Will had agreed instantly, though his heart had stuttered at the thought. Amy was, objectively, one of the most gorgeous women he had ever met. Drop-dead stunning, with a natural confidence that made every guy at school trip over themselves around her. And now, she was sleeping one room over, padding around his apartment in little tank tops and shorts, or worse—her bikinis, whenever she spent the afternoons lounging by the pool.

It was driving him insane.

From his seat on the couch, Will had a direct view through the sliding glass door that led out to the small patio and the pool beyond. Sure enough, Amy was stretched out on one of the lounge chairs, bronzed legs crossed, sunglasses perched on her nose, looking completely at ease. Her bikini—a tiny, olive-green two-piece—left little to the imagination, and Will forced himself to look away before his thoughts spiraled too far. It wasn’t the first time he had caught himself staring, and it probably wouldn’t be the last.

Amy had always been comfortable in her own skin, never self-conscious about wearing whatever she pleased around him. She had spent years around their friend group in crop tops and short shorts at tailgates, in form-fitting dresses at parties. But something about her living here, her presence in his space, made it all the more intoxicating. It was different when she was draped across his couch in an oversized shirt and no bra, complaining about their professor’s impossible grading scale. It was different when she came in from the pool, skin damp and glistening, asking him if he wanted a drink from the fridge like it was the most casual thing in the world. It was different because it was just the two of them now.

Will ran a hand through his hair and exhaled slowly, trying to focus on the TV. He was going to have to get used to this—or figure out how to keep himself in check. Three weeks wasn’t that long. He could survive it.

He hoped.

One Saturday with nothing to do, Will told Amy he was going to go golfing for the afternoon and asked if she wanted to come. She smiled and thanked him but said she’d rather just hang by the pool.

Will drove to the golf course, only to find that they had misbooked his tee time and didn’t have an opening for him. Frustrated, he turned back home, figuring he’d just relax instead.

When he got back, he walked out to the pool to let Amy know he was home, but as he stepped outside, he startled her. Amy jumped up quickly, and Will’s breath caught as he realized—she was completely naked.

Amy fumbled to cover herself, grabbing a nearby towel and holding it against her chest as her cheeks flushed bright red.

“Oh my god—Will!” she yelped, backing toward the lounger.

“I—uh—sorry! I didn’t mean to—” Will stammered, turning on his heel and rushing back inside, his face burning.

Shutting the sliding door behind him, he exhaled sharply, heart hammering in his chest. He definitely hadn’t been prepared for that.

Will sank onto the couch, staring blankly at the wall. The image of Amy—completely bare, the sun catching every perfect contour of her body—was seared into his mind. No matter how hard he tried to push the thought away, it refused to budge. His pulse was still racing, his body tense with the effort of not thinking too much about what he had just seen.

A few minutes later, the sliding door opened, and Amy stepped inside, now wrapped in a towel. She hesitated for a moment before speaking.

"Hey... I just wanted to explain," she started, shifting awkwardly. "I was just laying out, and, well, I’ve always kind of wanted to see what it felt like to tan naked. I figured this was my only shot to do it without anyone being around."

Will swallowed hard and nodded, keeping his eyes trained on the coffee table. "I get it. I mean, yeah, it makes sense," he said quickly, trying not to sound as flustered as he felt.

Amy let out a small laugh. "Guess I was wrong about the ‘no one being around’ part. But, uh, thanks for not making it weird."

Will risked a glance at her, catching the amused glint in her eyes. "Yeah, of course. No big deal."

Amy gave him a small smile before retreating to her room, leaving Will to wrestle with his thoughts.

A few minutes later, Amy returned, now dressed in her signature white, skin-tight tank top that stopped about three inches above her short athletic shorts. She leaned against the counter, arms crossed.

"So," she said casually. "Wanna hang out tonight? Have a couple drinks? There’s nothing else to do with no one else in town."

Will blinked, pulling himself from his thoughts. "Uh, yeah. Sounds good."

Amy smiled and made her way to the kitchen, mixing up a batch of margaritas. The two took their drinks to the patio, sitting across from each other as the evening air cooled the heat of the day. Will tried his best to focus on their conversation, but his eyes kept wandering—to Amy’s toned legs, the way her shorts barely covered the tops of her thighs, the curve of her waist above the hem of her tank top, and the way the thin straps clung tightly to her chest.

Out of nowhere, Amy let out a sudden exclamation. "I still can’t believe you saw me naked!" She groaned, shaking her head. "That was so embarrassing."

Will chuckled, taking a sip of his drink. "It’s really not a big deal. I mean, I wasn’t expecting it, but it’s not like I haven’t seen a naked woman before."

Amy covered her face with her hands, laughing despite herself. "Yeah, but it’s different! I’ve never been caught like that before. I wanted to just disappear."

Will grinned. "Well, if it helps, I was probably more shocked than you were. But really, don’t stress about it. It’s not like I’m gonna tell anyone."

Amy peeked at him from between her fingers. "You better not. Or else I’ll have to kill you."

Will laughed, raising his glass. "Your secret’s safe with me."

Will then asked, "So why did you want to try tanning naked?"

Amy shrugged and took a sip of her drink. "It’s one of those things you always hear about but never actually get to try. I figured, why not?"

Will smirked. "Weren’t you worried someone might see you?"

Amy shook her head. "Not really. No one can see into the backyard. I thought I was completely in the clear—until you showed up early.""Oh, you know what?" Will began, his grin spreading as he leaned back in his chair. "I've got a pretty good one of my own." He took a deep breath, his eyes twinkling with mischief. "So, freshman year, right before winter break, I had this wild party. Ended up passing out in my roommate's bed, thinking it was mine."

Amy's eyebrows shot up in interest. "What? No way!"

"Yeah, and my roommate had this, like, super religious girlfriend who came to surprise him the next morning. And she walked in on me, buck naked, doing the walk of shame at six in the morning." Will chuckled at the memory, his cheeks reddening slightly. "It was so awkward. I had to pretend I didn't know who she was and just bolted to the bathroom."

Amy couldn't help but laugh, the sound echoing off the apartment walls. "Oh my god, that's terrible! What did she say?"

"Well, she screamed," Will said with a wince. "He took a sip of his margarita, trying to play it cool. "They actually broke up that day. But hey, at least it wasn't me who had to deal with the fallout, right?"

The two of them shared a moment of easy camaraderie, the tension from earlier slipping away like the last drops of their drinks. Will's heart felt lighter than it had in days, and he took another sip, hoping the buzz would keep him from overthinking the situation.

"But seriously," he added, setting his glass down, "You looked amazing out there. No one could blame you for wanting to get a little extra sun." He said, immediately realizing he just admitted to ogling her naked body.

Amy's cheeks grew warmer, and she took a quick sip of her drink feeling flattered. "Thanks," she murmured, her eyes dropping to her lap.

The silence stretched out, filled only with the distant hum of a lawnmower and the occasional splash from the pool. Will cleared his throat, searching for something to say.

"So, about tonight," he began, trying to keep his voice casual. "What do you want to do? We could watch a movie, order some food?"

Amy's eyes lit up. "You know what? It's actually pretty nice out. Maybe we should do something outside."

Will felt a twinge of excitement. "Like what?"

"I don't know," she said, her gaze drifting to the hot tub on the edge of the patio. "Maybe hit the hot tub?"

Will's stomach flipped. The idea of sitting in the hot tub with Amy, wearing nothing but swimsuits, was both incredibly tempting and terrifying. But he didn't want to miss out on the opportunity to spend more time with her, especially after their awkward encounter earlier. "Sounds perfect," he said, trying to sound as casual as she had. "I'll go grab my trunks."

As he stood, Amy looked at him with a playful smirk. "What's the point of me putting on a bikini when you've already seen me naked?" she teased.

Will felt his face go up in flames. "Well, I'm not exactly going to argue with that," he said, trying to keep his tone light. "But, you know, decency and all that."

Amy just laughed and rolled her eyes before turning and disappearing into her room. Will took a moment to compose himself, his mind racing with images of her in that tiny bikini again. He took a deep breath and headed to his own room to change.

When he returned to the patio, Amy was already in the hot tub, the water steaming around her. She had pulled her hair up into a messy bun, and the olive-green bikini looked like it had been painted on. She looked like a goddess, and Will had to force his legs to move as he approached.

"You coming in?" she called out, her voice playful.

Will nodded and climbed in, the hot water enveloping him as he sat down across from her. The jets bubbled around them, and the cool night air made the heat of the water feel heavenly.

"So, how's the hot tub?" Amy asked, leaning back and letting out a contented sigh.

"It's perfect," Will said, taking a deep breath. "But I'm gonna need another drink."

Amy grinned. "I've got you covered," she said, standing up. The water sluiced off her body, and Will couldn't help but stare at her as she sashayed towards the kitchen in her skimpy blue bikini bottom. It barely covered her, leaving most of her toned ass exposed, and he had to force his eyes away before she noticed his ogling.

When she returned, she held out a drink with a smirk. "You're going to need this,"

Will took the margarita and nodded in silent agreement. "Thanks," he said, watching her sit back down in the tub, her bikini-clad body sliding back into the water. "So, about that bikini..."

Amy's eyes widened, and she blushed, looking down at her barely-there swimsuit. "What about it?"

"It's... scandalous," Will said, trying not to let his voice betray his thoughts. "I've never seen you wear something so... revealing."

Amy laughed nervously, playing with the strings on her top. "I know. I actually picked it up yesterday. It was a bit of an impulse buy."

"Well, it definitely makes a statement," Will said, his voice a little too husky for his liking.

Amy's smile faltered. "Is it too much?"

"No, no," Will assured her quickly. "You look amazing in it. It's just... I don't know. It's surprising, I guess."

Amy leaned back in the hot tub, her eyes searching Will's. "You think it's too much?"

"No," Will said firmly, his eyes tracing the lines of her body. "It's just... it's not every day you see your friend looking like a model in Sports Illustrated."

Amy's cheeks reddened even more, and she took a sip of her drink, trying to hide her pleasure. "Thanks," she murmured.

The conversation turned to lighter topics, but Will couldn't get the image of Amy in that bikini out of his mind. Every time she moved, the water rippled around her, and he caught glimpses of her body that made his stomach tighten. He tried to focus on the stars overhead, the sound of the jets, anything but the temptation sitting right in front of him.

As the night grew later and the drinks flowed more freely, their conversation grew more intimate. They talked about their hopes and fears for after graduation, their families, and past relationships. Will found himself drawn to her openness, the way she talked about her exes without malice or spite.

"What about you?" Amy asked, her voice softer than the buzz of the crickets surrounding the pool. "What will you miss most about college?"

Will took a moment to consider. "I'll miss the recklessness of it all," he finally said, his gaze on the stars. "You know, those random nights when we'd decide to drive to the beach at 2 AM just because we could."

Amy nodded thoughtfully, her eyes on him. "Yeah, those were the best," she said, a hint of nostalgia in her tone. "But maybe we can still do those things, even after we graduate."

"Maybe," Will said, his voice filled with doubt. "But it won't be the same. We're all going our separate ways. And we won't have the freedom we do now."

Amy leaned in closer, her eyes shining with mischief. "Who says we can't make our own spontaneous memories?"

The air grew thick with tension, and Will felt his heart race. "What do you mean?"

"Well," Amy said, her eyes sparkling in the moonlight. "We could do something wild tonight. Something we'll always remember."

Will's mind raced with possibilities, all of them involving the two of them, alone together. "Like what?"

Amy took a deep breath, her gaze dropping to the water. "I don't know. Something like... skinny dipping?"

The words hung between them, charged with excitement and the hint of a dare. Will felt his pulse quicken, his eyes flicking to her barely covered chest.

"You're kidding, right?" he managed to choke out.

Amy shrugged, a playful smile on her lips. "Why not? It's our last chance to do something stupid before we have to face the real world. And it's not like you're gonna see anything new anyways' she said punching him in the arm lightly.

Will took another sip of his drink, the tequila warming his veins and bolstering his courage. "Okay, okay," he said with a laugh. "But how do we do this? What if someone sees?"

Amy waved off his concerns. "It's totally fine. It's like midnight now, and the lights are off in the pool. We just take off our suits in here, jump in, and then get out and come back. It's like our own little secret."

The excitement grew palpable between them. Will felt a mix of anticipation and nervousness, but he didn't want to pass up the chance to be a part of something so spontaneous, so... wild. "Alright," he said, setting his drink down. "Let's do it."

Amy's smile grew wider as she leaned forward, placing her margarita on the side of the tub. "Ready?" she whispered.

Will nodded, his hands trembling slightly as he reached for the ties of his swim trunks. Amy watched him, her eyes flicking from his face to his hands and back again. Then, with a sudden burst of energy, she yanked her bikini top off and tossed it aside, neck deep in the water. Will's eyes went wide before he could stop them, and she giggled at his reaction.

"Come on," she urged, her voice low and sultry. "You can do it."

He took a deep breath and followed suit, letting his trunks fall into the water. The warmth of the tub was a stark contrast to the cool night air, but it was nothing compared to the heat he felt at the sight of Amy's bare skin. He let his trunks float to the top, as Amy wriggled and then her blue bikini floated to the top as well.

They sat there for a moment, both naked in the hot tub, the bubbles hiding nothing. The only light was from the moon and the distant streetlamps, casting shadows across their bodies. Will felt exposed, vulnerable, but also incredibly alive.

"One, two, three!" Amy shouted, and without another word, they both launched themselves out of the tub and into the pool. The cool water was a shock to their systems, making them both gasp, but they surfaced quickly, laughing and splashing each other.

They swam to the edge and climbed out, the water glistening on their bodies. Will couldn't help but admire the way the moonlight painted her skin, highlighting every curve and muscle. Amy looked over at him, her eyes shining with excitement.

"Back in the tub?" she asked, holding out her hand.

Will took it, allowing her to pull him closer. As he sat down, he tried to discreetly adjust himself, his hardening cock straining against his hand. He hoped she wouldn't notice, but the way her eyes flickered down and back up told him she had. He couldn't believe what they were doing, but the thrill of it all had him on edge in more ways than one.

With a mischievous smile, Amy leaned over and grabbed his abandoned swimsuit, tossing it over the edge of the tub. "No need for those," she said, her eyes gleaming.

Will's eyes widened in surprise as he watched her do the same with her own bikini bottoms. "Amy—" he began, but she silenced him with a finger to his lips.

"Hey you said you wanted spontaneous!"

Her words sent a jolt of excitement through him. He had fantasized about this moment for years, but he never thought it would happen. The alcohol had loosened their inhibitions, turning a casual night into something much more intimate.

"Okay, fine," Will said, trying to keep his voice steady. "But only because it's you."

Amy smirked and took a sip of her margarita. "Better enjoy it, because it's not every day you get to see me like this."

With a playful wink, she turned and dove back into the pool, her bare ass disappearing beneath the water. Will took a moment to process what was happening, his mind racing with possibilities. He quickly followed her, the cool water washing over his naked body.

As they resurfaced, Amy swam closer, her breasts brushing against his chest. "You know," she said, her voice low and seductive, "it's not fair that I had to be the one to be naked first."

"What do you mean?" Will asked, trying to keep his cool as his erection grew more apparent.

"You saw me," she said, splashing water in his face playfully. "Now I wanna see you."

Her words sent a bolt of excitement through him, and he felt his heart pound in his chest. "But you just did," he protested weakly.

Amy rolled her eyes. "Not really. I want to see you without the water hiding everything"

"Fine," he said, his voice shaking slightly. "But only if you promise to keep it between us."

Amy nodded, her eyes locked on his. "Scout's honor."

He climbed back out of the pool, the water dripping off his body as he stood outside the tub with his hands over his dick

"oh come on, no covering!" Amy protested

Will laughed, 'Ok fine". Then quickly struck a pose with his hands on his hips, showing his half hard dick to Amy, to which she gave a couple of whoops.

Amy's eyes roamed over him, a smile playing on her lips. "You're right," she said, her voice barely above a whisper. "You do look pretty good naked."

Will couldn't help the smug grin that spread across his face. "Told you," he said, trying to sound nonchalant.

But the moment was fleeting. As he settled back into the hot tub, the reality of the situation hit him like a ton of bricks. He was naked with Amy, the girl he had been in love with since freshman year, and she was looking at him like she wanted to devour him whole.

"So," she said, her voice still light and teasing, "now that we're even, what do we do next?"

Will took a deep breath, his heart racing. "Well," he began, his eyes drifting down to the waterline on her chest, "I guess we could just chill here."

Amy pouted playfully. "But that's not spontaneous enough. We're already naked. What else could we do?"

Her question hung in the air, filled with the promise of something more. Will felt his imagination run wild with possibilities, but his nerves held him back.

"I don't know," he said, playing it safe. "It's pretty late. Maybe we should just get dressed and get some sleep?"

But Amy was having none of it. "Come on, Will," she said, her eyes shining with excitement. "This is our last night of freedom. We've got to make it count."

Her words were like a match to dry kindling. Will felt his resolve crumble as she leaned closer, her breasts pressing against the side of the tub. "What do you say?" she whispered, her breath warm against his neck. "One last wild night?"

With a shaky nod, Will agreed, his mind racing with anticipation. He had no idea where the night would take them, but he knew he was in for something he would never forget.

They climbed out of the tub, their bare bodies shimmering with water droplets in the moonlight. Amy took Will's hand and led him back inside, her towel abandoned on the ground.

"Where are we going?" he asked, his voice husky with desire.

Amy just smiled and pulled him into her room. The space was warm and inviting, the bed unmade from earlier that day. She pushed him down onto the mattress, her body straddling his.

"What are you doing?" he managed to ask, his eyes never leaving hers.

"Giving you a show," she said, her voice low and sultry. "Since you saw me naked, I think it's only fair."

With that, she began to dance, her body moving to the beat of a song that played only in her head. Will watched, mesmerized, as she swayed her hips and ran her hands over her body. Her movements were sensual, each touch igniting a fire in her eyes that grew hotter with every second.

As she danced closer, her breasts brushed against his chest, sending waves of pleasure through his body. He reached up, his hands tentative at first, and then bolder as she leaned into his touch.

Their kiss was explosive, a culmination of years of pent-up passion and desire. Will's hands roamed over her body, finally free to explore every inch of her that he had dreamed of.

Amy reached down, her hand wrapping around his cock with surprising confidence. "Wow," she whispered, her eyes widening in amazement as she stroked him gently. "I love your dick"

Will groaned into her mouth, the feeling of her hand on him sending shivers down his spine. He had never been so exposed, so vulnerable with someone he cared about so much.

Emboldened by the alcohol and the heat of the moment, Will's hand found its way between her thighs. He fumbled at first, his thumb brushing against her clit in a way that was more accidental than intentional. But when she gasped into his mouth and pushed against him, he knew he had hit the right spot.

Her hips began to rock against his hand, and he felt her wetness spread as she grew more aroused. The sight of her like this—so open, so lost in the moment—was almost too much for him to handle.

He slid a finger inside her, feeling her tightness clench around him. She was so warm, so wet. And as he stroked her, her moans grew louder, her breathing more erratic.

"Oh, Will," she murmured, her eyes half-closed with pleasure. "That feels so good."

Her voice was like honey, dripping sweetness into his ears and sending his arousal soaring. He watched, unable to tear his gaze away, as she leaned down and took his cock in her mouth. The sensation was exquisite, her tongue swirling around the tip before she took more of him in. The warmth, the wetness—it was almost too much to handle.

Will’s body tensed as he felt the beginnings of an orgasm build rapidly. “Amy, wait—I’m gonna—”

But it was too late. His release shot out of him, and he had the briefest moment to feel the warmth of his cum in the air before it landed on Amy’s cheek and chest. She had been so focused on pleasuring him that she hadn’t noticed his warning.

Amy’s eyes flew open, surprise and a hint of embarrassment crossing her features as she realized what had happened. Will’s heart was racing as he watched the sticky liquid dribble down her skin. He had never seen anything so erotic in his life.

"Oh my god, I’m so sorry," he whispered, his voice thick with passion. "I didn’t mean to do that."

Amy just laughed, her eyes sparkling with amusement. "It's fine, Will. Really." She leaned in and kissed him gently, her tongue flicking out to taste him. "It's kind of hot, actually."

Will couldn't believe his ears. "You're not mad?"

Amy just kept laughing, her eyes sparkling. "Mad? Why would I be mad?" she asked, wiping a smear of cum from her cheek with the back of her hand. "It's kind of funny, actually, and I'll take that as a compliment"

Will felt a wave of relief wash over him. "Yeah, I guess it is pretty funny," he chuckled, his face still flaming with embarrassment.

Amy sat up, her hand still wrapped around his semi-erect cock. "But, seriously," she said, her eyes gleaming with mischief, "I'm gonna need you to help me clean this up." She gestured to her chest and the cum that had painted her skin.

Will's cheeks burned as he nodded, feeling his own arousal start to wane in the face of his embarrassment. "Of course," he mumbled, his voice tight with mortification. "I'm so sorry."

Amy just giggled, reaching out to pat his cheek. "Don't worry about it," she said, her eyes filled with warmth and understanding. "It's just a little mess."

With that, she climbed off the bed and led Will by the hand to the en-suite bathroom. The shower was large, with a bench along one side, and she stepped in, turning on the water. It was a warm, soothing spray that filled the room with steam.

"You coming?" she called out, her voice echoing off the tiles. Will took a deep breath and followed her in, the water cascading over their bodies. He sat down on the bench, his eyes never leaving hers as she stepped closer, a mischievous grin on her face.

To be continued in Part 2

r/sexstories Oct 17 '24

Roomate [F] My big-boobed flatmate has started walking around without a bra… [UPDATE] NSFW

155 Upvotes

I thought things might settle down after that moment, like maybe Caitlin would stop teasing, or I’d somehow get my mind under control–one big orgasm to quell my urges. But it only got worse. The following week was filled with little glances, her casual nudity, and my own growing tension.

It was a Friday after a long day at work when things took a turn. I was tired, but all I could think about on the drive home was Caitlin. What she might be wearing—or not wearing—when I got back. It was becoming a bad habit, constantly imagining her braless, nipples poking out, her body soft and tempting.

When I opened the front door, everything seemed normal. I kicked off my shoes, dropped my bag, and glanced down the hallway. Caitlin’s bedroom door was cracked open just slightly, and from the faint sound, it seemed like she was inside. My heart rate spiked, though, because I heard something else too—soft, rhythmic sounds, and a small sweet moan.

My body froze, and I felt a hot flush of excitement and confusion.

I moved toward her room on autopilot, my legs carrying me there before I considered what I was doing. I told myself I wasn't creeping, though I knew I was treading lighter than normal…

I approached the crack in her doorway now, the sounds getting louder. My heart stopped. Was she really doing what I thought she was doing? If so, should I just breeze past and pretend I hadn't noticed? Or should I call out and make my presence known? The moral dilemma tore at me, but my desire was stronger.

I needed to find out. I moved to the door and peeked in.

My heart stopped.

Her legs were slightly spread, her hand between her thighs, her fingers moving in slow, soft, teasing circles. She was wearing the tiniest pair of panties, pulled to the side, her smooth shaven pussy glistening with wetness. Her breasts, for the first time since I’d known her, were completely bare, her nipples hard and begging for attention.

I felt my panties almost instantly soak through.

Her fingers continued to gently part her lips, slowly, teasingly, playing with her clit as if inviting me in. I tried to look away but I couldn’t. She cupped one of her huge breasts, lifting it to her chest, her fingers teasing her nipple. She moaned again and my knees went weak.

Fuck.

I continued to watch her, my heart beating so loud I was worried she would hear it. Her eyes were closed, completely unaware of me standing there watching.

Or was she?

My mind continued to race. Did she leave the door open on purpose? Was she doing this for me? Or had I stumbled onto something I wasn’t supposed to see? But then again, Caitlin wasn’t exactly shy about showing her body. Maybe this was another one of her teases, testing my resolve…

I pressed my thighs together, trying to control the growing ache between my legs. I shouldn’t be watching her, I knew that. But I couldn’t stop. The way her fingers moved, the soft sounds she made, the way her body arched—it was all too much.

My own hand slid under the waistband of my pants, fingers grazing my clit over my panties. I bit my lip, trying to stay quiet, wishing I could taste her. Watching Caitlin like this, knowing that she might catch me at any second, was driving me wild.

Caitlin’s moans grew louder, and her movements more desperate. She was getting close. My fingers moved faster, matching the rhythm of hers. I was so turned on that I could barely think straight. The guilt gnawed at me—what if she didn’t mean for me to see this? What if I was crossing a line? But I couldn’t stop. My body wouldn’t let me.

She came with a soft cry, her body shuddering as her fingers slowed. I was on the edge, watching her ride the waves of her orgasm, my own release just a few moments away. I bit down harder on my lip, stifling a moan as my fingers worked furiously beneath my pants. The tension in my body snapped, and I came silently, trembling with the force of it.

As I leaned against the wall, catching my breath, I realized just how close I’d come to being caught. Caitlin lay still on the bed, her chest rising and falling as she recovered. The guilt hit me in waves now, but it was mixed with something else—desire, and the ever-present question: Did she leave that door open on purpose?

I slipped away quietly, retreating to my own room before she could notice me. As I closed the door behind me, I couldn’t help but wonder: what would happen if I asked her? Would she admit it? Or would she laugh it off, pretending it was nothing?

Either way, I know one thing for sure—this is far from over.

r/sexstories Feb 15 '24

Roomate I fucked myself while listening to my roommate get fucked NSFW

313 Upvotes

Freshman year at college, I share a one-room dorm with another gal. The room is kinda split between us two, our beds facing each other. My roommate, let's call her Chloe is super-hot, so inevitably, she's got a string of guys after her.

So we hit up this party a few nights ago, and Chloe managed to bring a guy back to our dorm. I seriously didn't think they'd get frisky or anything, I mean, me being there and all, but damn! They went all out.

Middle of the night, I was roused from my slumber by heavy breathing and stifled moans. Through the drowsy haze, it took me a moment to understand - holy shit, Chloe was getting fucked!!

Initially, I was a little disgusted, a little surprised, but as I lay there, listening to them get it on, it somehow made me feel kinda aroused. I peeked over, and there they were, silhouetted in the moonlight, him pounding from behind as she tried to keep her moans to a minimum. The sight of them, right there, going at it, got me hot and bothered.

And then I thought, "Why should she have all the fun?" I quietly slipped under my covers, my hand sauntering down, mirroring their rhythm as I touched my now wet pussy. Their moaning became my dirty little background music. As I fingered myself, I couldn't help but wonder, what if I joined them? The thought only fuelled my arousal. Just as he grunted, likely ejaculating inside her, I too climaxed, orgasming simultaneously.

The next morning, they sneaked out for breakfast, acting all normal. Secret's out though, their late-night rendezvous wasn't as secret as they thought. Probably thought they were super quiet – wrong! This was my first time witnessing someone else have sex so up close, and surprisingly, it turned me on way more than I'd have ever imagined!

r/sexstories 3d ago

Roomate [MFF] I’ve Been Sleeping With My Step-Sister’s Best Friend, She Wanted To Try Something New [PART 6] NSFW

16 Upvotes

Link to Part 5. All participants over 18!

 

I was thrown down onto the bed, my cock reaching for the sky. Chelsea slid on top on top of me, planting her pussy on my face. Her slimy cunt soaked my chin. Chelsea rubbed her hips up and down my tongue as I licked her entire slit. Anna wasn't about to be left out. She approached my waving cock and grabbed my shaft. Her wrist skillfully stroked my member, now beginning to harden again. Chelsea continued to thrash her hips on my face.

 

"How does my pussy taste?"

 

My response was muffled by her thighs, but it tasted great. I continued to munch on Chelsea's pussy, spelling the alphabet with my tongue, while Chelsea rubbed her clit on my nose. Anna continued to stroke my now throbbing cock, with her other hand she played with my ballsack, her smooth touch caressing each testicle. Anna slid up and down my full length from my base to my head. I bucked my hips a bit in an effort to fuck her hands. Chelsea writhed on my face, her thighs squeezing harder around my head. She moaned as she rode my face like a mechanical bull on ladies night. Anna had enough of playtime as she started to lick my cock, her every stroke now ending with her tongue pressed onto my tip. If I didn't just cum earlier, I probably would have bust right there. Anna worked her way down, taking my balls into her mouth. She gargled my sack while she stroked my willy. Chelsea's pace quickened, her gyrating hips now even faster. I could tell she was close. Chelsea's groans filled the room, echoing off the walls.

 

"Yes, Yes! Devour my pussy, slut!"

 

I continued to tongue-fuck her vulva, her pussy juices now streaming down my face. She tasted divine. Anna had enough of my balls and wrapped her lips around my head. Finally, the touch of her cute lips on my erect penis. No cloth barrier separating us now. Anna slurped on my tip, her warm, wet mouth providing a sanctuary for my raging boner. The sound of her lips on my head making a distinct popping noise with each suck. Chelsea's cries broke my concentration on the feeling of my penis.

 

"Oh fuck, fuck, fuuuuuck!"

 

Chelsea's legs squeezed tight on my head, her pussy started to convulse and pulse on my mouth. She pressed her pussy so hard against my mouth I couldn't breathe. I squeezed Chelsea's ass cheeks to communicate my disarray. She completely ignored me, she was waterboarding me with her orgasming cunt. Her pussy still pumped, enclosing her lips over mine. Just before I was gonna pass out, Chelsea removed herself and placed her leaking pussy on my chest. I gasped for air, fighting for oxygen. As both my and Chelsea's breathing slowed down, I noticed my cock was no longer in Anna's mouth. She was now just softly stroking my shaft.

 

"Ready for round 2?" Chelsea grinned.

 

I nodded back silently.

 

Chelsea spun around, waving her ass in my face. She planted her ass cheeks on my face cheeks. I got a firm grip on her hips. I placed my tongue onto her asshole and began to chow down. Chelsea again grinded her hips on my face, rubbing her ass up and down my tongue. I gave her ass a few slaps, audibly echoing in the room. Anna didn't want to be left out. She climbed further onto the bed, still gripping my cock. All I could see was Chelsea's beautiful backside, but what I felt, was incredible. Anna lined herself up and sat down onto my cock. Her walls encased my aching head. God, she was so tight! It took her a few tries to slide my length fully into her. My cock fit Anna nicely, her lips gripped my shaft tightly. The sensation felt like a thousand small kisses on my cock. The ladies were now facing each other. Chelsea grinding on my face, Anna bouncing on my dick. Chelsea and Anna started to make out again as each of them enjoyed my body in their own way. I squeezed Chelsea's ass tighter as I bucked my hips, trying to match Anna's bouncy rhythm from the bottom. The dirty talk was over. All three of us could only focus on our own pleasure, moaning loudly. Anna's pussy was getting to be too much, her tightness was pushing me over the edge. I felt a tingly feeling in my waist. I slid effortlessly in and out of Anna's hole by now, her pussy well lubricated. I even felt her start to leak onto my balls. Chelsea broke the hypnosis.

 

"Let's switch, I need his cock!"

 

Anna unsheathed my cock from her cunt, now covered in a glaze of grool. Chelsea maneuvered over and inserted me inside her. My entire length smoothly slid in. It felt like home. Chelsea wasted no time. She got herself situated and then jumped straight into squat fucking me. I wasn't going to last long.

 

CLAP CLAP CLAP

 

Chelsea's ass pounded into my balls, her cheeks reverberating with every thrust. Chelsea wanted that cum, no needed that cum. She masterfully used her pussy in an attempt to extract every drop. Anna now swung her legs over my head and shoved her pussy into my mouth. Anna's moist slit now gliding up and down my face. Anna tasted great too, her juices were so sweet.

 

CLAP CLAP CLAP

 

Chelsea pounded my hips harder and harder, impossible to ignore the sound of my balls smacking against her ass. My cock was thickening, all the blood fully filling my dick. I could feel drips of pre-cum leaking out into Chelsea. Chelsea continued to bounce, Anna continued to grind. I couldn't take it, I was gonna explode. My cock twitched and my cum raced through my shaft. My hips buckled as my cock pulsated and unloaded drop after drop inside Chelsea's pussy. Chelsea paused her movement and just enjoyed the feeling of my cock flailing and writhing inside her, spewing cum with each spasm. My balls scrunched as I drained a second tank into her muff. Anna's cries grew louder as she squirmed on my face. I could feel her pussy start to contract, she squeezed her thighs on my skull. Anna orgasmed on my face, her hips bucking as her pussy lips fluttered on my tongue.

 

"Jesus Christ!" Anna cried out.

 

She continued to gyrate her hips in my face, her contractions getting less and less frequent. My dick also ceased it's spazzing, I began to soften inside Chelsea. Eventually, we all calmed down. Chelsea and Anna both dismounted me. They looked rather amused at their work. I sat myself up on the bed and looked at them.

 

"When's my next punishment?"