In college I fucked my best friend’s girlfriend. It was so wrong but the hottest sex of my life. [MF] [cheating]

Hello all, I wanted to share this story because I shared some more recent stories here a while back and everyone seemed to enjoy them. This story happened many years ago but is 100% true and was one of the hottest events of my life. It’s a long read because I wanted to include all important build up details. I want to give a disclaimer that I totally understand my actions in this story made me a piece of shit. I want to assure you I’d never do anything like this now, and I was in a very shitty phase of my life where yes i was very selfish and yes I’d done some asshole things. I was 22 and I think all of us make shitty decisions and that’s what I did. I’m way more mature now and would never do anything like this now. But regardless, it still let to some very hot sex.

When I was 22 and finishing up college I rented a house with three of my good friends. This story mostly surrounds me (Jay), and my roommate Sam. The other guys are Adam and Max but they play much smaller rolls. A little backstory has to be discussed here. Each of us had our share of girlfriends/hookups/whatever during college. But Sam was different. He was kind of picky and kind of quiet and awkward with girls. As for me, I had had a serious girlfriend from high school that I was kind of on again off again with and she had cheated on me once and we kinda moved past it. Honestly, things were dying between us but I was at that age where I was too weak to just break it off and thought I was going to “save the relationship.”

As for Sam, our senior year of college he finally met this beautiful girl, Jen. It seemed out of left field because he hadn’t dated anyone then he’s suddenly with this absolute knock out. To this day she’s the most beautiful woman any of my close friends have ever dated. She was petite, with bright almost bleach blonde hair and bright blue eyes. She was probably about 5’4 and 110 lbs, petite but with curves and boobs (34 B come to find out), and outrageously perfect ass and legs.

She was also VERY flirty, very fun/outgoing, and was the kind of girl who you could tell had every fucking guy wrapped around the finger from the time she was 12 or 13 probably.

And I fucking hated her. Hated is a strong word actually. I never hated her. But while everyone else was fawning over her I always found her a bit annoying. She was one of those people that got by by batting her eyes at everybody. Every guy that came by the house found all her stupid jokes HILARIOUS. I remember a time when we had a bicycle she tried to ride and really struggled and the guys thought it was so adorable and cute and everyone wanted to teach her and my god it was sickening.

But she was undeniably beautiful. And sensual. And sexy. While Sam was reserved about talking about their sex lives, she was fine with it. She’d talk about how she needed sex every day, we’d hear her screaming from his room practically every night, she’d walk around the house dressed in impossibly tight shorts, tank tops, sometimes even her underwear. And on halloween…good god. The sluttiest Dorothy you’ve ever seen.

Even my girlfriend and the other girls loved her.

But eventually of course there was some trouble in paradise. We partied a lot back then and she would get drunk and Sam would get drunk and they’d get into it.

One night in the summer after our last year of college everything changed with us. I was actually on a break with my gf at the time and went out with Jen, Sam, and a few of our other friends. Sam got drunk and was an asshole and when we got home went to his room to pout and pass out leaving Jen with me.

We sat on the back deck, at the edge, right on the would of the deck. She and I were talking about she and Sam’s issue and she kept kind of scooting closer to me. Then we talked about us. She said she always thought I “hated her.” I told her that that wasn’t true but yeah I wasn’t always her biggest fan. She told me she always liked me and wished that we could be better friends even if it was just for Sam’s sake.

It was dark and on our deck no one could see us. I realized that she had scooted to the point where she was actually touching me. I was sitting with me knees bent up and my arms resting on my knees. As we talked she put a hand on my knee. I noticed her kind of slowly riding it up while we talked and laughed. We actually had a good time with it.

We ended up talking about sex…she talking mostly about how his inexperience and lack of confidence bothered her. I remember kind of telling her that wasn’t a problem for me (yeah I was a douche) but that I’m sure as he got more experience it would be better. By this point she was running her hand up my thigh under my shorts, clearly crossing the line.

As her hand reached the point where she was actually under my boxers I grabbed her hand and pulled it out. “I…can’t…” I told her. I held her hand in mine. “It’s not you…and look I liked where that was going but come on…it’s Sam. We can’t go there.”

She bit her lip and looked up at me. And that’s where she had me. Looking back now I know that’s where she had me. It was the sexiest look I’ve ever seen.

“I know,” she said simply. “But I just…I don’t know what it is…” she leaned in clearly trying to kiss me. She got close but I pulled back.

“Jen I’m sorry. Look, I want to. Trust me…goddamnit, I want to. I can’t do this to Sam though.”

We talked a bit more but I made a break for it and went inside. For a long time I wondered what if…..

Flash forward 6 months. I’m back with my gf who had fucked multiple guys during our break while i had fucked my right hand but otherwise had come up empty. We weren’t doing well but kept it together. More convenience than anything. Jen and Sam were getting more volatile. They’d go on a vacation one week and be in love and come home talking about moving into together and then have a knock down drag out where they’d scream at each other for an hour and wouldn’t speak to each other for a week.

We knew we’d be out of the house within the next six months so our house became the prime party spot. New Years we had a blow out fight. What’s important to know is that our one roommate, Adam, was actually out of town.

We had a ton of randoms over, good times were had, everyone got pretty drunk. My gf actually got completely shitfaced and vomited outside 4 or 5 times and was put to bed around 1 AM. Things were winding down around 230 or 3, with about 10 people left. Sam and Jen had a big blow out fight. I’m talking screaming, yelling, Sam punching a wall. It had something to do with Sam actually talking to anther girl and flirting with her at the party. But Sam ended up locking himself in the bedroom so Jen couldn’t get in. Like a baby, locked himself in so Jen couldn’t get in.

Jen flips out and wants to drive home. This was obviously a horrible idea so one of my other friends and I went and stopped her. We convinced her not to drive but she stayed outside. The other friend went inside because it was cold, leaving Jen and I alone.

Being a drunk idiot, I actually tried to reason with her about what happened with Sam and talk her down but she wasn’t having it. She kept screaming about how he wanted to fuck the “fat whore” that he had been flirting with. This is when I confronted her. We were standing near the front door of the house and I just said it.

“Jen, how can you even be mad…for fucks sake you tried to kiss me a few months ago and I’m his best friend.”

“What are you talking about? I never tried to kiss you. YOU tried to kiss me,” she said.

“What the fuck are you talking about? Jen you had your fucking hand up my shorts and leaned in twice to try to kiss me and I said no.”

I don’t know what made me do what I did next. I wouldn’t do anything like this now, and wouldn’t have even six months before this particular night. I guess it was just all the shit I’d been through in life and in my relationship and the shit I’d seen them go through recently.

Jen started to walk away and I grabbed her arm. “Bullshit Jen. You tried to kiss me, and you fucking know it. And I’ll tell you what. You want to make a move? Do it. You want to kiss me? I won’t turn you down now. But don’t bullshit me. You know what happened. And I wanted it but said no. But you want it to happen? I’m game. Go for it.”

She looked at me almost confused. “I gotta figure out what the fuck is going on,” she said and went back inside.

I went inside to the kitchen (there was a side door there). I could hear Jen down the hall knocking on Sam’s door, yelling and screaming and telling him to let her in. I heard him open it at one point, couldn’t hear him clearly but heard him say “bitch” and “fuck” a lot then slam the door.

Jen comes walking through the kitchen moments later and simply says, “Fuck Jay, maybe i should have just taken you up on your offer.”

I know I described Jen’s looks before, but tonight was a whole new ball game. This girl knew how to dress, she knows how to make herself up and how to look damn good. Tonight she was wearing a black little cocktail dress (probably cost a couple hundred bucks) with a nice little push up bra under it that made her boobs look big and delicious. Her hair looked amazing and her face was so pretty. She also had on some sexy little stockings.

She stood with me in the kitchen and we quietly discussed what was going on. There were still 3 or 4 people left at the party but they had passed out in the living room which was around the corner from the kitchen. So we were the only two up.

We talked for a bit and I came back with it. “Well, you’re getting fucked over, I’m getting fucked over…the offer stands Jen. I’m not going to lie, I’ve wanted you since last summer when YOU tried to kiss ME (I smiled at her to let her know i was just messing with her). I can’t just sit around and want this and not go after it…”

She said how she always thought I hated me. How she didn’t like me for the longest time because she felt like I never gave her a chance. How I had been an asshole to her for a long time. And how for some reason, she was insanely attracted to me ever since the summer.

“It doesn’t make sense, you’re not what I should want…but I sooo sooo want you…” I remember her saying.

“I know what you mean, it doesn’t make sense but I’m tired of fucking fighting it. I never wanted to like you, but I can’t fucking help it. I want you so bad…”

And I kissed her. She was in the corner of the kitchen where the counter comes to a point. I kissed her long and hard. I felt her tongue slip into my mouth and we began to make out. God it was so good. We fell in an immediate rhythm with it. It was like we’d done this a thousand times. It became more and more passionate, her hands behind my head pulling me into her as our tongues danced together.

My hands got more and more risky. I can them down her sides and to her ass, pulling her to me with both my hands on her tight ass over her dress. I ran my hands up and felt her boobs, are kiss never breaking…the hotness of it only being increased because of the sleeping people in the next room. Fuck, the sleeping boyfriend and girlfriend each in other rooms of the house made it insane!

She pushed me against the door of the kitchen, our kiss becoming more intense and crazy, my hands still exploring her. We only broke the kiss when we heard someone stir in the next room. They quieted back down and we realized the threat of them hearing/seeing was over.

Jen leaned into me and whispered into my ear, “Come on Jay…I want more…”

“Okay I’m good with more!” I said like a 14 year old. “Let’s do more.”

“Where though?” she said. “We can’t just fuck in the kitchen with people lying all over the house.

In a stroke of genius I said, “Let’s go to the basement. With the wood steps and door we’ll have plenty of warning if anyone comes down and we can just say we’re playing ping pong or something if someone does come down.”

I didn’t even get a reply, she just started walking towards the steps. Holy shit.

Before we even got to the bottom she was kissing me again. We went into a corner and made out just as passionately as before. Our hands were all over each other, with her grabbing my cock which by now was rock hard and me with my hands all over her ass and boobs.

Finally I yanked her dress down and there they were, her perfectly shaped tits, perkier than any I think I’ve ever seen. They looked so goddamn delicious, and her nipples were already hard. I began rubbing them and feeling them, and then moved my face down and began licking and sucking them. I could feel her nipples get even harder in my mouth, and she was pulling my head into her tits to get me to lick and suck on them even more. She was moaning in such a hot little soft voice. I couldn’t get enough of her boobs. Her breathing became harsh and sexy, each lick eliciting another exhalation from her.

I sucked on her nipples and played with her tits for several minutes and ran my hand up under her dress and began to play with her clit. She was already soaked, and I could feel from her pussy that she was shaved completely bald. We began kissing as I continued to finger her clit and her pussy when out of the blue she pushed me back onto a recliner that we had in the basement. It was kind of an old shitty recliner that I literally don’t think I’d ever sat in before.

She gave me a devilish look and reached down and grabbed my belt and unfastened it. She unbuckled and unzipped my pants and pulled them down to my knees and grabbed my cock. “Holy fuck you’re big, I want your cock so fucking bad,” she said.

Now, don’t get me wrong…I’m not trying to write a story here to make it look like I’m some kind of sex hero with a huge cock. I’m really not that big…maybe a little bigger than average but it’s not like I’m carrying around a 10 inch porn star penis. But that’s legitimately what she said and damnit maybe it was just a little showmanship but I’m not a guy to turn down a compliment.

My god was she good. She started just using a hand at the base and her mouth. She worked around one side of the head of my cock, then the other, then would take the entire head of my penis in her mouth. She started slow and soft, and then went deeper, taking every last inch of me in her mouth. And the eye contact, my god the eye contact. She would look up at me with the most sexual, dirty look and then just go down harder and faster with her mouth all the way down until she had all of me in her throat.

She added both hands at one point and would alternate, sometimes taking them off all together and just using her mouth. It was an amazing blow job but I didn’t want to cum that way. After 10 minutes or so she had pulled off of me for a second and I looked at her and just said, “your turn.”

I remained in the recliner but turned it to face a weight bench that was next to it. I had her put her leg up on it. I should mention she had never fixed her dress, so it was still pulled down and her wonderful breasts were still fully exposed. I hiked her dress up and pulled her thigh highs down. She had a black sheer thong on which I pulled all the way off.

Finally I got to lay eyes on her beautiful pussy. She had what would be described as a true “innie” just a nice little pussy which was shaved completely bald (come to find out, she had had it waxed about two days before that). You could actually see her pussy glistening a bit from being so wet. It was amazing.

I reached around and grabbed her ass to pull her closer to me and while sitting in the chair began licking her clit. I started softly, her sweet taste and wetness immediately apparent. I did small circles on her clit and started very gently. She placed both her hands on my head and kind of guided me into her.

I’ve always considered myself good at oral but really gave her extra attention and tried to be as considerate as possible. I continued licking her clit, occasionally sucking on it a bit and taking it between my lips. I picked up the speed slowly but surely to kind of follow the rhythm of her breathing. I would move down and bury my tongue into her pussy, which was soaked by that point, and then move back up and work her clit some more.

I continued this sort of pattern, fingering her pussy while I was licking her clit and then moving down and plunging my tongue in and out of her vagina itself, both which she seemed to absolutely love. She was digging her nails into the back of her neck and moaning softly. I moved up when I could feel that she was close and worked on her clit…picking up speed. Going faster…faster…faster. What was so hot is that she was moaning VERY quietly…almost more just harsh breathing or panting. She never got into the fake pornstar type screaming…just breathing really fast.

And then… “I’m cumming I’m cumming I’m cumming.” She said this very quickly and almost in an under her breath type muttering kind of way. I held her ass as she almost fell backwards, her hands balancing on the weight bench. I stuck with her as long as I could, my tongue flicking across her clit as long as I could until she was completely horizontal on the weight bench panting. She had her hands on her boobs and was lying there with her eyes closed.

I honestly thought things might end there. But oh was I wrong. She finally sat up, her boobs still hanging out, her dress hiked up, and her hair all askew. “I need to fuck you…now,” she said, standing up and grabbing my hand.

And here’s the tiny detail that cinched this whole night together. Adam wasn’t home. He had gone somewhere else for New years and his bedroom was completely open and unused. Jen led me directly up the stairs, we checked quickly to see everyone in the living room was passed out, and went to Adam’s bedroom. Now, here’s maybe the most fucked up thing about this whole situation. Adam’s room was actually adjacent and shared a wall with Sam’s room….and the idea of that almost upped the ante and turned me on more than anything. Judge me if you want, but I think the taboo nature of this kind of thing would turn a lot of people on.

We went in and locked the door and before I could take a step Jen jumped on me and wrapped her legs around my waist. We began making out, my hands on her ass to keep her draped over me. She was so light and sexy, she felt tiny in my hands and it was hot being able to just walk around holding her so easily.

We continued making out and I carried her to the bed. It was dark in the room but the streetlight outside allowed us to see each other pretty well. She had put her stockings back on but not her panties. I lifted her legs and butt and she slid the stockings off. I helped her unzip her dress and dropped my pants, the entire process taking 30 seconds and we were lying there nude together.

I stood over her at the edge of the bed and she guided my cock towards her pussy. I pushed in slowly but was able to push in in one stroke because she was so wet. MY GOD was she incredibly tight. I know every story, every porno, every whatever talks about how a girls pussy is “so tight” but I’m not kidding. Of all the women I’ve been with she was by far the tightest. It was like she was constantly doing kegels with me inside of her.

I pushed in and out of her slowly, the warmth and wetness of her pussy practically making me cum with just the first few strokes. She gasped and bit her bottom lip as I began to slide into a rhythm, her rocking her ass up against me allowing me to go even deeper inside her.

I began to get a good rhythm going at medium speed, Jen playing with her tits while I fucked her. I eventually pushed her back farther on the bed and we got into more traditional missionary, me lying on top of her, us occasionally kissing. She again was breathing heavily, moaning very softly and quietly. It was a huge turn on because most girls I’ve been with have been louder and it was kinda hot with her trying to keep quiet.

She was soaking wet and I was going pretty fast when she said she was going to cum soon. I remember the hotttest thing, at one point she grimaced a bit and honestly said, “Oh my god your dick is so much bigger than Jay’s…I just feel so much…more.” This was a total ego stroke I’m sure but turned me on like crazy and I started fucking her harder. She kept telling me to go harder and faster and I picked up the speed as much as I could without making too much noise.

I was fucking her hard and fast, the sound of her wetness and my body slamming into her the only sounds besides her breathing. Finally she did start to moan a little louder. She grabbed my thighs and dug her finger nails into me. I covered her mouth with my hand as she was getting loud and I really didn’t want to get caught. Finally she let out an “oh my god. oh my god. oh my god.” She let out a little squeal and I could feel her pussy tighten even more as she had an orgasm. I slowed down and let her come down off the orgasm.

I told her to flip around which she was happy to do. And here’s where I get to tell you the full story about Jen’s ass. As great as the rest of her body was, her ass was absolutely to die for. She was a big time yoga/pilates person and was incredibly toned. As she got up on all fours her incredibly tight ass was just there for the taking. It was perfectly round and the curve of her waist-hips-ass was just breathtaking. There was a tremendous curve to each side of her ass, her pale skin shining. And it was so tight.

I grabbed her ass with both hands and pulled her to me, my cock becoming buried in her pussy again. I began rocking, not quite starting as slowly as when we were in missionary. She was again breathing hard and moaning very very quietly. I would spank her (softly because unfortunately any harder would have made a lot of noise) here and there. I fucked her hard and deep, burying myself as deep inside her with each stroke, Jen occasionally pushing her ass to meet me and add some force to our fucking.

We fucked in doggy style for a long time…probably 15 minutes or so, occasionally turning her to the side a bit to change the angle. I had that great drunk dick where I could stay hard but it was hard to cum. She came once and I needed a quick rest because my mouth was so dry.

“Let me take care of you,” she said. “You need to cum to or I’ll fee like I didn’t do my job.” She smiled at me.

I laid back and Jen climbed on top of me. My lord she was a site to see. She leaned forward and kissed me deeply. I felt her reach behind herself and guide me into her. She began rocking her hips, riding me and grabbing her tits. She kept telling me how good I felt and how good I was over and over. She’d ride me and say how good it was, how badly she needed me and had wanted this.

Within a couple minutes she was bouncing on my cock, back on her haunches a bit really riding me up and down using one hand on me for balance and the other pinching her nipple. She kept riding me, picking up the pace faster and faster, coming impossibly close to coming all the way off of me before smashing herself all the way down…my dick all the way inside of her.

She had a good rhythm going and was moaning again, telling me she was getting close and so was I. After going for so long I knew I was about to cum. She was bouncing on me, her tits bouncing just ever so slightly and her breathing hard and grinding on me, fucking me hard.

“Jen I’m gonna cum soon, like really soon…just warning you,” I said, somewhat awkwardly but felt like I should tell her.

“Good,” she said, leaning forward to kiss me and then increasing the intensity of her grinding even more. She rubbed her ass back and forth on me, keeping me deep inside her. “Cum baby…”

And I did. I grabbed her hips and ass and she pushed herself down on me as deep as I could go, very slowly doing circles with her body on my cock.

“OH…GOD…yes” she said in a loud whisper, kind of realizing she was a bit too loud for a second. “God I can feel you. Fuck it feels so good.” She rode me until the last pump of cum was inside of her.

She stayed on me for several more minutes, the two of us kissing and talking and laughing about how insane what we just did was. We both got somewhat worried about getting caught (obviously), so I left her in Adam’s room to sleep and went back up to my room. The next day I went down and she was already gone. The feeling of everything was insane. I went to Adam’s room to make sure we fixed the bed and it was already made. There on the floor were Jen’s stockings, which I took and kept as a souvenir of the craziest night of sex of my life.

Source: reddit.com/r/gonewildstories/comments/5hv1fy/in_college_i_fucked_my_best_friends_girlfriend_it