It was a bit of a weird situation for me. At the time I considered myself “straight” (despite a certain [blowjob in the public showers](https://www.reddit.com/r/gonewildstories/comments/636oyh/a_show_and_a_bj_in_a_public_shower_mm/) some time before), and my best friend Jay was gay. He’d made several passes at me when we were drunk but, despite the fact that he was fairly attractive and someone I cared for, I always politely turned him down (probably because we were always in mixed company and he wasn’t publicly “out” yet so it would have been pretty bad). It never got awkward for more than a second.
Meanwhile, I had this crush on my friend Kit. Well I say “crush”… Let’s just call it what it is: I thought she was hot as hell. She was pale, slim, big eyes, great smile, and with legs that just went on and on and on… She was an inch taller than me too, so around 6′ 2” or so. Spent a LOT of time thinking about those long, long legs wrapping around me.
Unfortunately she was interested in Jay. Him being gay was just another challenge for her. She wanted what she wanted. It’s one of the reasons I respected her as a friend actually, that whole goal-driven thing.
So to review: Jay wanted me, I wanted Kit, Kit wanted Jay. Fucksakes.
One summer for about a month the three of us found ourselves hanging around together a lot in Jay’s smoke-filled beer-stained attic apartment. (I miss the 90s.) Despite the unrequited sexual tension we were all having a pretty good summer together.
One night Kit calls me up and says her and Jay were going to the movies and did I want to go too? Why not. So we go, and the movie they want to see is called “Threesome”.
Guess what it’s about. Seriously you will never guess.
It’s about three college students who somehow end up roommates. Straight guy, gay guy, straight girl. And guess what? The gay guy wants the straight guy, the straight guy wants the girl, and the girl wants the gay guy.
What. A. Coincidence. Hmmmm…
So we go. We laugh. We watch them inevitably have an R-rated 3-way. Kit gets a little flirty and handsy with both of us, but plays it off as just having a bit of silly fun. It’s all good. Back to Jay’s for beers.
At the time I didn’t think anything was up but in retrospect it’s pretty clear that evening was carefully planned by those two. As we go into his apartment Jay locks the door and says: “Nobody else coming over tonight, just the threesome!” He gives me a wink, I laugh. I sit on the couch, Kit sits on the chair next to it, Jay sits on the couch next to me… and that’s a bit different because Kit’s sitting in Jay’s normal seat but whatever.
We start drinking. I get a good buzz.
And it’s goddamn hot. Like I said this is an attic apartment and Jay didn’t have an air conditioner, so the windows were all open but there wasn’t enough breeze. Kit is fanning herself and complaining about how hot it is in this velvet dress she was wearing.
Listen I’ve got to tell you about this dress. It was tight, showing off the flare of her hips and small breasts, and short. It barely covered her round little butt. From there it was about a mile of legs.
And this is the part I’m pretty sure they planned out.
Jay says: “Well we’re all friends here, I mean, you have a bra on right? Just take that stupid dress off. What were you thinking wearing velvet?”
It DID seem odd…
Kit: “I’m not sitting here in my underwear, I’ll feel weird!”
Jay: “Well I’m hot too. Here, look, we’ll do it too.”
He stands up and pulls off his shirt. Then he looks down at me and says: “Come on man, aren’t you dying?”
I hezitated a bit here. It’s true, I was boiling hot, but I really only had two modes: exhibitionist and shy self-conscious guy. I was in the 2nd phase.
Kit: “Okay, if you guys are going to be in your underwear, I’ll do it. Are you up for it?” And she looks at me…
Fuck, fine.
It was a real shift I had to go through internally then. As I pulled my shirt off and watched as Jay kicked his pants over to the side of the room, I realized I’d be mostly naked with them… And it was something I couldn’t ignore. This “we’re all friends” stuff didn’t change what we were doing… I couldn’t help but start to think of them as sexual creatures now, and I felt a stirring down below that I worried would be a bit embarassing… Considering I was in a pair of Fruit of the Loom briefs.
But hey, Jay had tighty whities too (boxer briefs weren’t really a thing in the 90s… So glad they’re here now!), so I didn’t feel so awkward about that part, and I sure as hell was enjoying watching Kit strip off that dress to reveal white lacy underwear, a lacy bra holding her A-cups, and that incredible long body of hers.
Jay grabbed a fresh round of beers for everyone before sitting back down on the couch next to me, his naked leg leaning against mine and his arm around the back of the couch behind me. Whenever I turned to talk to him I was faced with that hairy chest of his that made me want to run my fingers through it… I found myself staring at one point in my buzzed state of mind. I really wanted to feel what his chest felt like underneath my palm for some reason, to feel more of the heat his body was already radiating towards me.
The conversation was then turned (purposefully I am now convinced) to the movie, and to friendship, and how it made sense that they crossed all those “lines” because they loved each other.
Jay makes his first move: “Ya people are so weird about touching. If you love someone there’s physical contact, right?” And he grabs my knee to punctuate the point.
“Sure,” I say, and pat him on the chest. It’s firmer than I thought, despite his not being all that muscular. I curl my fingertips in his chest hair just slightly before pulling my hands away.
Just then, Kit comes over and sits at our feet on the floor. “Who wants a foot massage?”
It just dawns on me then that the coffee table was moved over to the corner today. Well that’s convenient…
I put up my hand and Kit gets to work rubbing my feet and looking up at me with those big doe eyes of hers. Her fingers are long and sensuous, and if the heat and the beer hadn’t relaxed me before I was definitely feeling a lot more at ease now.
Jay starts talking in my ear about how long we’ve known each other. We talk a bit about our history. He talks about how close he feels to me. I feel the same, and actually grab his hand that’s now slung over my shoulder and intertwine my fingers with it. It feels good. I feel really connected to these two people.
Kit says something similar, how she feels really lucky to be our friend, talks a bit about her bond with Jay, her bond with me.
Jay says: “I love you man. I mean not in a boyfriend way but you know…”
And ya. He had alterior motives. I knew that even then. But I also think he meant it. I love/loved him, after all, quite sincerely.
I remember looking over at him, at his angular jaw with his stubble that never went away, and it just felt right to connect with him then. I let go of his hand, placed my hand on his cheek, and kissed him.
The rest was a whirlwind. He kissed me back passionately, and I found myself feeling all these emotions I didn’t even have names for. Excitement mixed with relief mixed with joy and… Well something else, because as we made out on the couch I didn’t even realize I’d become hard until his hand brushed my cock as he stroked my thigh.
I realized then that I had grown an incredibly obvious hard on with Kit sitting on the floor in front of me. Embarrassed, I looked at her and saw her looking down at the outline of my cock.
“Sorry,” I stammered.
“Don’t be,” she said as she reached up and started rubbing me through my underwear. She looked up with a smile and I just moaned and leaned back as Jay started nibbling at my ear. I turned and started making out with him again. Before I knew what was happening I was stripped of my underwear, and Kit was slowly licking the length of my cock.
Soon Jay lost his underwear too, and I began stroking him with my free hand. His cock felt hard, hot, and incredible. It was the first time I’d ever touched another man’s dick, and it was amazing. I wanted him to cum right then and there, to feel him pulsing in my hand. I stroked him as expertly as I could, hoping he liked it the way I did.
Meanwhile, Kit upped her game and started sucking me in earnest, expertly bobbing her head up and down as if she’d done this before. (Which she had. Like I said: if she wanted something, she got it!) It was almost too much for me, and I had to wave Kit off before I came. I looked at her, and said: “Hey, I thought we had a deal. Why are you wearing all that?”
She smiled, stood up, and dropped her bra to reveal two very round A-cups with small dark nipples. Next went her underwear, and I gasped. She was perfectly clean shaven. “Excuse me,” I said to Jay, as I leaned forward, grabbed her by the hips, and started licking her pussy.
She and I traded places and Jay shuffled down, so that she could suck him while I ate her pussy. I glanced up at one point and saw Jay’s expression was clearly one of ecstasy, and Kit’s one of victory.
With my right hand I stroked Jay’s balls, feeling Kit’s breath and saliva as she worked on his shaft. My left hand was busy pumping a pair of fingers in her, rubbing the roof of her vagina while I sucked and flicked my tongue across her clit. She was the first of us to cum, letting Jay’s cock drop out of her mouth as she moaned loudly. Her hips pumped at my face while she came, and by the time she waved me off her incredible legs were quivering.
I sat back on the floor, proud of my handiwork, but still hard and ready for action. Kit sat up and grabbed a random beer from the side table, trying to catch her breath. Jay was leaning back on the couch, grinning, slowly stroking himself and looking at me on the floor.
I forgot how much I love it when people look at me naked.
“You like what you see?” I asked him, standing up. He nodded, and stood up with me. He grabbed me then, more aggressively than I’d ever been grabbed before, and pulled me to him for a hot and passionate kiss. We thrust our hips together, grinding our hard cocks together while his whiskers scratched at my face and tongue explored my mouth.
It was so… Well the weirdness of it wasn’t lost on me. I was used to the softness of women. This was different. It was wrong, it was animalistic, it was… I didn’t know what it was, but I liked it.
He pulled me over to the bedroom then and threw me backwards onto the bed. I laughed, and he climbed on with me in a 69 position. I was face to face with another man’s cock for the first time. I was excited but hesitant, and it wasn’t until I felt his warm mouth working on my cock that I knew for sure I was up for it. Fuck he could suck cock…
He was about the same size as me, average, but cut. That cock head started to look real good, and the moment I put it in my mouth I knew I’d made the right decision. I felt like a complete pervert, so deeply wrong wrong wrong… but also so goddamn right. I found myself working his cock feverishly, sucking hard while licking his shaft back and forth with my tongue every time I bobbed my head. His hairy legs and balls were filling my vision and I found myself running my hands all over him, as if I wanted to touch every bit of him all at once.
Meanwhile, he was expertly working my cock and once again I felt myself getting close. But before I could cum, Jay tensed and I felt him start to pulse. I had to make a split-second decision then – I’d never eaten my own cum and didn’t know what it would be like.
Fuck it. I’ve gone this far. Go all the way. I shoved him as deep as I could as he started pumping loads of cum into my mouth, which I swallowed as quickly as I could to avoid chickening out.
So wrong, and so right.
He rolled back, working my cock with his hand then, gasping for breath. I looked up and saw Kit had crawled onto the bed with us at some point, and she took advantage of Jay’s state to start kissing him. I reached over and started stroking those long legs of hers, and she looked down at me and then over to my hard cock.
“I think it’s time I returned the favor,” she said with a smile. She climbed over Jay and sat herself down over my cock, gently rubbing it up and down with her still-wet pussy. “Condom?” I asked. “I’m on the pill,” she said as she slipped my cock into her.
Her pussy felt soft, warm, and heavenly. It gripped me tightly as she started pumping her hips, leaning down as she fucked me and kissing me deeply. I remember how incredible it was to run my hands across her body at last, but after awhile I couldn’t help myself and wrapped my arms around her, gripping her tightly as I thrust up into her fast and hard as I came.
We spent the next couple of hours drinking, smoking, and hanging out naked on Jamie’s bed. After a few hours we fooled around again a little, but I’ll admit… those details are a bit hazy.
Like this story? I love PMs! Tell me / show me how you liked it and what it made you do!
Source: reddit.com/r/gonewildstories/comments/64mb43/threesome_straight_guy_doing_gay_things_long_mmf
So so good. But just as an FYI you changed Jays name in the last paragraph. May want to edit that ;)
Was it a one time thing? Did things ever get awkward afterwards?
Oh my god finally someone else who’s seen that movie
I’d love more.
That was a fantastic story. I would love to have friends that close!
Dear god, it’s like my life story! Haha. Yet, I’m Jay.