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What’s your gender? Man
How old are you? 39
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? California
Highest education received: Some college (not currently in college)
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Swinger
How many sexual partners have you had in your life (including oral sex)? 50
How many hookup stories have you here posted before? 0

Buddy’s Fiance

How long ago did this hookup happen? 12 Years

What was your relationship status at the time? Single

How would you best classify this hookup? Group sex

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? My buddy is A, he’s just under 6′, very athletic/muscular, and I’ll admit (yes I noticed) he’s got a big dick! His wife V(his fiance then) looks hispanic. She has dark hair, dark eyes, permanently tan skin, a great pair of DDs with nice sized dark nipples, and she is totally shaved. I am 6′, fairly athletic build, blonde hair, blue eyes and I’m about 7″ down there. Not as big as A, but a little thicker.

I used to work with V and through her met A. We all ended up becoming good friends over the next few years. While I was friends with V first, I definitely got along better with A. We ended up pretty close for a while and had kind of an odd relationship. I really don’t remember exactly how it happened, but A and I ended up always talking about sex and stuff, more so than most guys do. V and I kind of went the other way, we were friendly, but she grew distant the longer I knew her. She was kind of the stuck up, prudish type and didn’t approve of my “man-whore” ways. I got a LOT of random sex back then.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It started one night while I was hanging out with A. I was at his place where he lived with V. She was off at a concert so we had the house to ourselves and were just enjoying the peace/freedom. We had a few beers each and were just watching some BS on TV and eventually ended up talking about sex. He was talking about how much he’d love to see V with someone else while he got to play with her too. I was surprised, but also curious and hinted I’d take the chance if it came.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? A few beers later, V came walking in the door. She seemed bummed I was still there, but she was nice enough. Once she settled in, she came and sat on the couch by A. I was on another adjacent couch at the time. She was really touchy-feely with him right away and kissed him hard, whispering something in his ear when they finished. A got an odd look and glanced conspiratorially at me which I didn’t get at the time. We all chatted a bit more but V kept pulling A in to kiss. I realized she must have been super horny and probably was kinda drunk because she never acted that way, that’s when it dawned on me what A’s look was for. It kept up like that for a bit until A really started pushing her for more. Surprisingly, she was game for it too.

A ended up talking her into stripping down to her panties and a t-shirt (sans bra) while they made out. He was only in sweats too so I ended up watching her jerking him under his pants while he fingered her under her panties and they made out. It was so hot and they were distracted so I figured what the hell and reached down my own pants. They kept at it and eventually A ended up between her legs, pulling her panties aside and having sex in front of me without actually showing anything yet. It was HOT! I even moved from the other couch to sit on the coffee table right next to them, still openly stroking myself under my pants while I watched, hoping for a better view or maybe more. They kept at it and A started working her shirt up. When he got too high once, she said something to him, he replied and she just shrugged. They went back to kissing and pretty soon after her shirt was up to her neck. WOW! She had some of the nicest tits I’d seen! Maybe half dollar sized, dark nipples standing out hard against the pale skin of the rest of her breasts.

Now they were having sex in front of me and her amazing tits were on display for me. I figured “fuck it” and just pulled my pants down and went back to stroking while I watched them. The moment of change came when A noticed me stroking myself next to them. He grabbed her hand and guided it to my dick. I think that’s when she realized/remembered I was partly naked too and that I was watching them. She seemed a bit unsure and surprised, but she went with it and started stroking me though. A told her something that got another shrug and then he slid down her body, finally pulling her panties off as he went, and letting me see her very nice shaved pussy. Once he got her panties all the way off, he started eating her out. I admired the sight for a moment; my friends naked (normally prudish) fiance below me, eyes closed while he ate her pussy in front of me. I decided to go for it. Her hand was already on my dick so mine found her boobs, then my mouth found them, then my mouth found hers.

She seemed hesitant at first, stiff, but then she softened. Her lips opened for mine and soon her tongue was meeting mine equally in passion. God her tits felt nice and she was really kissing me back! I loved how hard her nipples felt under my palms and how she’d moan both from A licking her and when I’d slip down to suck at her breasts. A went back to fucking her and I dared go even farther, slipping a hand down to touch her lips and tease her clit. Yeah I bumped A’s dick, but he didn’t seem to mind and it made it kind of hotter for me too.

I wasn’t sure if this was as far as it would go but then A tapped my shoulder. I got the hint and let him take my place kissing her and feeling her boobs. This left me free to play lower and I wasn’t going to waste it. I got on the couch by her feet and just looked for a moment, A and her were kissing again and his hand was on her breast. I explored with my hands first, sliding them over her legs as she spread them for me, letting me go higher and higher until my hand found her vag. I let my fingers slide over her inviting lips a few times and damn she was wet! I started fingering her and heard her moan which made me want more. I started kissing down her legs, knowing she would feel it and know what was coming, that her fiance’s friend was about to be licking her bare pussy. She didn’t stop me and soon my tongue was buried in her wet slit. God she tasted good too! She squirmed and ground against my mouth so I put my hands on her ass to hold her to me all the while thinking how hot it all was. I licked her for a while until I noticed him move, I stopped to see why and was greeted with the sight of her pretty mouth wrapped around his cock.

Earlier A had warned me V wasn’t on any kind of birth control. We also didn’t have any condoms lying around so I shouldn’t cum in her. I decided to just go for it though and started working my way up between her legs. I could see A watching too, an excited look on his face. I’ll never forget how that moment felt, my cock slipping past her wet lips and sliding all the way into her, bareback. Even as tight as she was I was easily sliding in and out of her. The overall sight and experience was so hot, watching her sucking A, admiring her great naked body on display for me, and feeling her most private area sliding around my cock. I think I decided then that I didn’t care about being careful and that I was going to just let it happen and cum in her when I was ready.

Soon I was getting close. I could feel it building up and knew I was going to fill her up with my seed soon, but right before I could, A wanted another turn. I’m not a total ass, so I stopped and slipped out of V, letting him take my place while I went back to kissing her and fondling that amazing rack. I tried to get her to suck me too, but I guess that’s where she drew the line, only stroking me a bit more. A lost it then, pulling out at the last minute and shooting his cum up on her belly and hip. I thought it just made her look even hotter, a total slutty look for this normal prude.

We switched two more times, taking turns kissing her and feeling her tits then licking and fucking her still soaked pussy. She met every kiss with passion and every thrust with moans. A even lost it again, shooting a second load onto her belly. Probably for the best, but every time I was close we had switched places. In the end, she rolled over a bit and allowed me to jerk myself over her ass. In a single moment of lust fueled insanity, I wondered if I could just grab her hips and pull her up so I could enter her doggy right as I came. Then the moment passed and I was there, my cum now shooting all over her sexy cheeks.

Bonus, A was so horny from it all (he knew I was bi) he even let me suck his cock for a second after it was all over. V didn’t see that of course. Tasting her on his dick was almost enough to get me going again. The only thing stopping me was I knew they were both done. After that, I just got dressed and left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? Nothing good happened after. I remained friends with A but V was awkward. Fairly soon after, we all stopped hanging out. A and I still talk and sometimes hang out, but V won’t come with us. A said they talked about it and she was ok with everything but also kind of not. I still felt great. He tells me that to this day that is the hottest experience of his life and he wished I had cum in her after all (he didn’t want her prego but the thought of my cum filling her up does it for him.).

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal

What were your motives for this hookup? Fun, pleasure, horniness, Intoxication, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Completely wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? A little bit

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? I’ve mentioned it to a few of my friends that don’t know those involved and I never used their names. I also used to talk to A about it sometimes.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Getting to fuck my buddies HOT fiance who turned out way better than expected.

What was the WORST thing about this hookup? Kinda lost a friendship. A and I still talk but it’s rare now and V is totally distant/standoffish.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No change. I love and have always loved casual sex. I even shared my own girlfriend with another friend of mine before that.

All things considered, how POSITIVE was this experience? Somewhat positive

All things considered, how NEGATIVE was this experience? Somewhat negative

What do you think about the Casual Sex Project? Cool site. I love sharing my experience and hope to see what people think of it.

You have a hookup story to share? Submit it here!