Did you ever fuck a friend?

Yes. Ive kissed a lot of my friends. And for a while I was a third for a couple I was friends with. It worked well. They were both attractive, I was comfortable with them and nobody had any extra feelings or weirdness. It was just fun. So we all hooked up on a regular basis.

We liked to hang out and one drunk evening it turned into sex. She was my first woman.I was their first, but not last third. I think its rare you can sleep with friends and remain friends, and I was extremely lucky to have this experience.
 
I have. On two different occasions that come to mind at the moment, it didn't go so well, and that in turn kind of tainted the friendship.

On the other hand, I've had deep friendships that started with sex...
 
Summer break in college I stayed on campus for work. A friend I worked with and her roommate were sitting on the ground of their patio listening to music and drinking way too much. While we're sitting there I feel my friends hand reach under the back of my shorts, move up my leg, grab my cock and pull it back down the leg of my shorts where she began to stroke it. It was obvious what was happening, but her roommate just ignored it and we kept talking. Eventually the roommate left and we went inside where she very aggressively kissed me and then opened my shorts and sucked my cock. It felt really good and I could have easily come in her mouth, but in my drunken stupidity I pulled her head off my cock, pushed her on her back, pulled down her shorts and fucked her hard and fast. Unfortunately, our relationship became awkward after that and never really recovered.

My wife also did in college. She was hanging out with a group of friends in the dorms. Most of the friends left and it was just her and one guy. They talked and listened to music and then the guy asked her to slow dance to a song. That's pretty much a guaranteed way to get in her pants. They start kissing, he played with her tits, and then their clothes came off and he fucked her. According to her it was just two good friends who needed a good fuck. They stayed friends after and never hooked up again.
 
So, I haven’t known this guy long—he’s a colleague at the office, super timid but genuinely kind. He’s helped me out tons, and I’ll admit, I might’ve taken his kindness for granted, passing off some of my work to him when I was swamped. I’m not proud of it, but I’ve stopped doing that, even if it means my stuff gets delayed. Anyway, being new at the company, we clicked fast. We’ve become drinking buddies, hanging out after work, and I realized he’s stuck in this miserable situation with his toxic girlfriend. She’s got him wrapped around her finger, doing whatever she demands, and it honestly breaks my heart to see him so beaten down.

So, I invited him to my place one night when he was having another fight with her—some silly drama, as usual. Nobody at work, at least in my department, knows much about our personal lives. They don’t care, and I don’t share that I’m engaged or that my fiancée and I are in a semi-open relationship, exploring things. We’ve got two rental apartments—she stays at hers while finishing her master’s degree, and I’m at mine when work’s intense, but we’ll move in together soon.

Anyway, he comes over, and we’re having our usual deep talks over drinks. I’m trying to convince him he deserves better, someone who’d actually make him happy. Then, out of nowhere, my mind wanders, and I start imagining him with my fiancée. I don’t know what sparked it—maybe the whiskey, maybe the vibe—but it got me buzzing. So, I pull out my phone and show him a picture from her Instagram, passing her off as a single friend. I ask if he’d be into meeting someone like her. His eyes light up, and he’s all in, saying she’s gorgeous, his voice getting this hungry edge. It sent a thrill through me, my heart racing at how much he wanted her.

I couldn’t resist pushing it further. On a whim, I text her to let her know I’m bringing my friend over, telling her to dress sexy and play along as my ‘friend.’ She’s game—she loves the thrill of our dynamic. We head to her place, and the second he sees her, he’s hooked. She’s wearing this tight dress that hugs every curve, her smile teasing, and he’s practically tripping over himself to charm her. We go out for dinner and drinks, and the whole time, he’s flirting hard—leaning in close, laughing at her jokes, his hand brushing hers. The air’s electric, and I’m feeding off it, watching them spark.

On the way back, I play it cool and say I’ve got work early, suggesting he take her home instead. His face lights up—they both gets the hint. I head back to my place, buzzing with anticipation. Later, he tells me it was the hottest night of his life, like he’d never experienced anything like her. The way he described it—her touch, her confidence—damn, it got me worked up all over again. It’s wild how this stuff turns me on, Thanks for letting me spill this.
 
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