Reddit gays detail their most “surreal” sexual encounters

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Followers of the r/askgaybros subreddit took a NSFW trip down memory lane recently after one user asked them for the “most surreal, unexpected sexual encounter” they had ever experienced. And it seems like everyone had a story to share: That one thread got more than 285 comments. Here are some highlights from the conversation, lightly censored and edited for readability.

The lonely roommate

“When I was in college, I had a semi-crush on my straight roommate, him being more popular and all. One day, I got home from a four-day trip, and he said that he missed me and wanted to know if I wanted to get naked and join him in his bedroom for the night. I joined him, and it was hot. I didn’t identify as gay or bi at the time.”

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“I came home for the summer after my freshman year of college, I went on Grindr, and I saw a childhood friend’s dad on there. I knew he and his wife recently just got divorced, but I didn’t know why. I took a shot and messaged him. I ended up at his place, and he f*cked me all over his apartment all night. The next day, I hung out with his son but didn’t tell him what I did the night before.”

The laughing fit

“I don’t know if this counts, but my boyfriend and I are having hella foreplay, I keep edging, and then he gives me a handjob, and I literally start moaning like I’ve never before, loud and sensual, ‘cause it felt so amazing. I proceed to make eye contact with him, and I burst out laughing in the midst and I come right in the middle of a intense laughter fit—like, dry heaving laughing—and it was so intense orgasmically but a weird surreal experience.”

Related: Guys reveal their hottest-ever sexual encounters

The barracks hook-up

“I was doing a desk job in the Navy in the mid ‘90s. My closest coworkers were a quartermaster and a second lieutenant from the Army. I was doing rounds in the barracks on a night watch, heard sounds, and unlocked a door and found those two going at it. For the remaining months, they did everything they could to avoid being in the office. I kept grinning, and their faces kept changing between 50 shades of red.”

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The party hosts

“Once in college, I was over at my friends’ house with a bunch of people. The hosts were an engaged gay couple, and they loved to host fire pit nights at their place. Anyway, we were all having a good time, drinking and enjoying the night. People eventually started to leave, and it was down to just me, the hosts, and one of our coworkers. One of the hosts ‘turned in’ for the night, and the rest of us chatted a little longer. After a while, the coworker left, and the other host asked if I wanted to stay and cuddle with them both. (Not the first time we had done that, mind you, but nothing sexual happened the other time.) So I said sure because it was already late, but when we went to the bedroom, the one who went to bed early was awake and waiting for us in the bed naked. We proceeded to have amazing sex till way too early in the morning. Still the best sex I’ve had.”

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The airport connection

“I was at the airport traveling to Budapest from my country, and my brother was coming with me as well, so we were just waiting for the doors of the plane to open in 20 minutes, and I was on Grindr checking guys out, and then I realized that was someone who was two meters away from me. He had a blank profile, and he messaged me, so then I looked around me and there’s a chubby bear (my type) that’s sitting right in front me, and literally the moment I looked at him, he also looked at me, and we both smiled, although we didn’t even say anything to each other on the chat beside him saying, ‘Hey.’ So, he stands up and goes to the bathroom that’s nearby, and I tell my brother that I’m going to the bathroom real quick as well…”

The shower run-in

“At college, I was a bit nervous about telling my roommates that I was gay, so I pretty much avoided them. One day, I was running late to class and got in the bathroom to take a shower. One of my roommates was there, and I just screamed, ‘Sorry!’ And before I could leave, he said, ‘You can join.’”

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The parking garage meet-up

“I was in Vegas for New Year’s and had just hooked up with someone, and as I was leaving the hotel to the parking structure, in comes another guy to the elevator, no words exchanged. Then I get to the floor of my car, and we both go separate ways. Then I turn on Grindr a couple of minutes later inside my car. Turns out, that same guy asked if it was me in the elevator, since I had no pic on my profile and neither did he. I was surprised, and he said he had also just hooked up with someone as well and was leaving. So I told him to meet me in my car’s back seat and hook up again.”

Related: Gay guys tell the tales of their most spontaneous hookups

The Army buddy

“I remember I had this one Army buddy. He was like the straightest-acting guy in the Army. Anyway, I went to his and his wife’s house. His wife was out on business. At first, he touched my leg and such, and I didn’t think he was serious. Then he grabbed my crotch and things escalated from there, and we had sex. A week later, I heard he left his wife and was out as gay.”

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The bi carpenter

“I worked on a building site in upstate New York with a tower wrapped in tarpaulin and balconies overlooking the Hudson. I used to go up there for lunch with one of the bi carpenters I was sort of seeing, and we’d kiss and jerk off then go back down and join the guys when lunch was finished. If only they knew.”

The six-way

“I was at a conference for LGBTQ+ students. As I’m sure you can imagine, Grindr was hot that night. I ended up meeting a guy outside in the smoking area. … While we were outside smoking, another guy comes outside in his dressing gown and tells us that the hotel has a 24-hour spa with a hot tub and sauna. We end up going down there 15 minutes later … and we were not alone. Ended up having several hours of six-way fun until everyone paired off. The guy I ended up with wasn’t my first choice, but I was really, really happy with how the morning turned out. Not only was it the most unexpected fun I’ve ever had, but it opened my eyes to guys I wouldn’t ordinarily have gone for. 12/10 would conference again.”

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The porn actor

“I had the DVD of a random porn and there was one scene where I thought the guy was so butch and hot, and it was always my go-to to get off. About a year of doing that, I hook up with a guy who knows this porn actor who is my fantasy. He texts him and the dude meets up with us, and I take him home. I was getting f*cked up at the time — 3+ years clean and sober now — and I decide to put on the DVD while we are f*cking around. He thought it was weird and kinda lost interest. SMH.”

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