Gay guys share their funniest and sweetest hookup stories

A self-described “hopeless romantic” asked his fellow Redditors for their “funny/sweet hookup stories,” and you know how it goes online: Ask, and you shall receive. Here are some of the best responses… or, at least, as much of them as we can safely print!

The icebreaker

“This one hookup I was with was taking a bit of time to warm up. He only bottomed a few times before and was struggling a bit. … So I leaned in and whispered, ‘No homo.’ He tried to hold back the laughter but couldn’t. Sometimes laughter is the best way to relax your bottom.”

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The butterflies

“I went to a nice lake to watch the sunset with a guy a little younger than me. We found a wishing bench, and I told him that my wish was for him to kiss me, which we did until a haggard drunk approached us. We went back to his place where we explored each other and made love for 4 hours. His roommate eventually walked in, so we froze for a while and waited for the guy to fall asleep (in the same room) before resuming. He … collapsed onto me, where I held him — there, we butterfly kissed as our breathing completely synchronized and we drifted into sleep. Haven’t seen him since. It was like a weirdly beautiful dream.”

The check-in

“I had a FWB in my last city who was great. He’s the reason I was able to get used to bottoming. He was more experienced and used to have me over on the weekends and we’d have a lot of fun together. I got to try new things with him, and it was good for me. One sweet moment in particular stands out. I was having my first threesome with him and another guy I was meeting for the first time that he knew. We were having a great time, and they were going at it for a bit at first before my FWB told me to get on my back. … He leaned in really close and kissed me. Then, with this stupid smile on his face: ‘Hey.’ Me: ‘Hey.’ It was like he was so happy to have me right there in that moment, even with the other guy in the room. He was returning to something familiar and comfortable, and it was as if he was saying, ‘I’ve got you.’ Like, recognizing our sexual companionship over the greater part of a year at that point. It was just really sweet and I think about it a lot!”

The tour guide

“Last spring, I went on my first solo trip to Puerto Vallarta. In my profile, I mentioned I wanted someone to show me around. I met up with a guy my age, and we did just that. On my last full day, he took me to a neighboring island on a little exploring expedition. Once we got back to his apartment, the sun was setting just right. We opened all the windows in his room, and there was this orange hue of sunlight I’ll never forget [that] washed over his bedroom. Normally, I’d never dare do the deed with the windows wide open, but the setting was just too perfect. I topped him and we cuddled until the sun went down. To this day it’s still the most intimate sex I’ve ever had with a guy. I’ll never forget it.”

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The swim captain

“I was attending a swim meet at another university. The captain of that university’s team had agreed to let my team sleep on the floor of his (tiny) living room. When we got there, we realized that there was no way we could all fit, so he offered to let someone sleep in his room, which I took him up on. I laid down [with a] towel as a blanket and hoodie as a pillow. He closed the door, and after about two minutes, he says, ‘You know, there’s plenty of room on my bed.’ (It was a twin XL, and we were both 6-foot-tall swimmer dudes; there was absolutely not room.) The rest of that night was… memorable to say the least, as was getting walked in on by one of my teammates 6 hours later.”

The long-distancers

“Met a boy over the Internet. We spent an amazing 20 days together. Then I moved to Asia. (I’m from Canada.) But I managed to convince him to visit me. We’ve been together for over 3 years now.”

The first date

“15 years ago, I had a hookup with a tall, hot twink. It turned into watching anime and cuddling. He’s my husband now.”