37 Straight Guys Confess The Gayest Thing They’ve Ever Done
"My friend told me he was gay...I was so surprised I nearly choked on his penis."
1. My friend told me he was gay…I was so surprised I nearly choked on his penis.
“My friend told me he was gay…I was so surprised I nearly choked on his penis.”
2. Full anal but made sure the balls didn’t touch.
“Full anal but made sure the balls didn’t touch.”
3. Pissed on each other. He started it.
“Pissed on each other. He started it.”
4. I shared a pizza with one guy. Never again.
“I shared a pizza with one guy. Never again.”
5. I did over an hour of naked karaoke duets with another dude at a nudist resort. There were a lot of Elvis songs.
“I did over an hour of naked karaoke duets with another dude at a nudist resort. There were a lot of Elvis songs.
I also made out with a bisexual guy at a swinger party. My wife and some other women said it would be hot. It didn’t do anything for me but the women were into it. That was less gay than the naked Karaoke.”
6. I accidentally touched a guy’s hand while I was giving him his change. I guess you could say Im a flaming homosexual.
“I accidentally touched a guy’s hand while I was giving him his change. I guess you could say I’m a flaming homosexual.”
7. Butt sex but I said no homo so it wasn’t gay.
“Butt sex but I said no homo so it wasn’t gay.”
8. Drunk naked rollerblading in a park with erotic posing with my best friend, Peyton.
“Drunk naked rollerblading in a park with erotic posing with my best friend, Peyton. I was very drunk.”
9. I told my buddy, ‘That’s a nice tie’ once, but what I really meant was put your dick in my mouth but in a platonic sort of way.
“I told my buddy, ‘That’s a nice tie’ once, but what I really meant was put your dick in my mouth but in a platonic sort of way. No homo.”
10. Watched the first four episodes of Gilmore Girls.
“Watched the first four episodes of Gilmore Girls.”
11. I showed a crowd of dudes my dick for a snow cone.
“Either when I kissed a dude or the time I showed a crowd of dudes my dick for a snow cone. Both at Burning Man.”
—5pt
12. In high school my and my friend put little Barbie-sized cowboy hats on our erections and had a stand off at high noon.
“In high school my and my friend put little Barbie-sized cowboy hats on our erections and had a stand off at high noon.”
13. I once had a guy lick cream off my chest while I was wearing a bikini.
“I once had a guy lick cream off my chest while I was wearing a bikini.”
14. In a matter of minutes we’re both jerking off on the couch next to each other.
“Jerked off with a friend.
It was in high school. I was spending the night at my friend’s house. It was a sweltering summer night, so my friend and I were in just our boxers, hanging out in his back house.
Porn somehow comes on TV (I can’t remember if he put it in a DVD or what). We’re just talking about the girls and next thing I know my friend is obviously hard and rubbing himself. I start to do it too. In a matter of minutes we’re both jerking off on the couch next to each other. He cums really fast and I immediately feel awkward. I finally end up cumming…into a sock. It was weird because we just acted like nothing happened. He turned off the porn and we started playing Mario Kart. Never talked about it again and we were friends for years.”
15. My mother looked out the window to check on us and saw us both dicks in the air.
“One time in high school me and a buddy were swimming in my pool and for reasons unknown my buddy floated on his back, stuck only his dick out of the water and made the jaws duh-nuh noise repeatedly. So I did the same for a good ten minutes. My mother looked out the window to check on us and saw us both dicks in the air. That was a weird conversation with her later that day.”
16. Me and a friend one time raced to see who could jerk off faster.
“As drunk teenagers me and a friend one time raced to see who could jerk off faster. He won, I was a little weirded out that he came in like 12 seconds. Another time he held my dick while I took a piss. I was holding his too if you’re wondering.”
—dBob
17. I had to hold my friend’s dick for a good minute whilst he pissed in my parents’ garden.
“On New Year’s Eve my friend got extremely drunk and got somebody to duct tape two liter bottles of cider to his hands so that he couldn’t use them until he finished the bottles. I was outside in the garden and he came up and said in the most desperate voice ever “i really need to piss, please man..” so i helped him pull his pants down to his ankles. He just looked at me with that same sad desperate look and said “i’ll piss on my shorts, you’ll have to..”
I had to hold my friends dick for a good minute whilst he pissed in my parents’ garden because he taped alcohol too his hands.”
18. Me and a group of friends used to put porn on the TV and jerk off with each of us in different chairs in the living room.
“In middle school me and a group of friends used to put porn on the TV and jerk off with each of us in different chairs in the living room. We never really looked at each other or talked about it to much.
Sometimes you gotta run one out right?”
19. He jacked me off. I nutted.
“Took a shower with another guy. He jacked me off. I nutted.
Never again.”
20. He slipped money in my shorts to give me a HJ.
“Gay for pay story: Close friend in HS apparently liked me the entire time. Shouldn’t have been oblivious after the times he tried to get my girlfriend and I to be physical for him to watch.
Anyway, kept asking questions about my masturbating, for details of my dick and eventually slipped money in my shorts to give me a HJ. I laid back and accepted, with my friend eventually trying to turn it into a BJ.
Years later, we both messed around.”
21. Accidentally went on a date with a dude.
“Finally, I can tell this story.
I am a standup comedian, and one Saturday night, I did a show for about 200 people at a club in Cincinnati. After the show, I get a Facebook friend request from a dude who was at the show, and he talks about how I was funny and he said that I was the cutest guy in the club that night. I was on such a comedy high (it was my first paid weekend) that I thought nothing of it. We talked for a little bit through Facebook IM.
Thinking he was just a fan of comedy, I accepted his offer to get lunch with him at a restaurant near where I lived at the time. We go, eat, and have a pretty decent conversation.
Afterwards, we shake hands, and go our separate ways. The moment I pull up to my apartment, my phone buzzes, and it’s a text from that dude. The text said (and I quote) “Do you have any interest in being more than friends?”
Everything hit me at once. I felt like a moron.
TL;DR – Accidentally went on a date with a dude.”
22. I had gay sex with a Russian, he called his mom during said sex and felt horrible about it.
“When I was in Uni, I experimented with my dorm mate, an exchange student from Russia in my freshman year.
We didn’t do anything besides hold hands and cuddle for awhile, then the ‘incident’ happened.
We were wrapped in a blanket, watching god knows what in the dead of night and I wanted to do more than just kiss.
I looked at him and he knew what was up. I bent over the couch and he stood behind me.
But wait! There’s more, everything was going normally until he pulled out his phone. He started yelling in Russian, which was a total boner killer for me but he was still going at it.
The yelling went on until he came and starting crying.
Apparently, he felt so guilty having gay sex, he called his mom and told her what was happening then hung up before she could respond (and presumably disown him).
After that we just drifted apart, he switched to a single person dorm and I got a new dorm mate after that.
No homo, I think he’s alright now.
TL;DR – I had gay sex with a Russian, he called his mom during said sex and felt horrible about it.”
23. He fucked me and it was pretty good.
“Hung out with a guy I sort’ve knew through someone else. I knew he was gay. We would hang out a few times, just chatting and watching TV at his place.
At some point we went quiet and he moved closer to me. We made out for a while. Then our hands moved to each other’s crotches and so soon enough we blew each other. His dick was pretty big. It was a lot of fun to give head.
On that basis I figured, “why not?”. He fucked me and it was pretty good. After a while it started to hurt but I insisted he finished first. Gotta see it through if you’ve agreed to have a dick in your ass.
After all that was over we cuddled for a bit and watched some more TV then I went home. Saw him a few times after that with mutual friends but never hooked up again, but it never got weird. Just had some fun. I’m with a long time girlfriend now. She knows about it and is cool with it.
10/10 would recommend.”
24. I’ve gotten brojobs before.
“I’ve gotten brojobs before.
I’m not attracted to men and cannot see myself in a serious relationship with a man but I like brojobs just for the pleasure. I’ve also gotten bjs from women. Men are much better at it and seem to like it more than most women.”
25. We were ‘those girls’, but with dicks.
“Drunken makeouts with other guys at parties for laughs. We were ‘those girls’, but with dicks. Way creepier.”
26. We were all sweaty and completely naked, grunting while lifting huge weight.
“Three of us. All big, pretty hairy guys. Got drunk at the pub. Went back to one of our houses to carry on drinking in his backgarden.
He had weights and a bench in his garage. We were at the stage of drunk where you have the burning desire to prove your masculinity. It was a really hot, humid summer night, so we dragged the bench out into the backgarden.
One thing led to another… And before long, we were all sweaty and completely naked, grunting while lifting huge weights and shouting deliberately campy slogans like ‘PUSH IT!’ and “FEEL THE BURN!” Apparently, his neighbors never looked at him the same again.
To this day, the gayest thing I’ve ever done. And I’ve done a guy in the butt.”
27. Stopped him when his penis touched my butt.
“Thought I might be gay. So I and my best friend at the time tried having sex. I went bottom. Stopped him when his penis touched my butt.”
28. Guys give the best head, generally speaking.
“I’ve had my dick sucked by a handful of men.
Maybe I’m not totally straight, but I’m at the far, far end of the bell curve in terms of female sexual partners. I’m 37 and have been tending bar my whole adult life, so it comes with the territory.
I used to be totally open about my hetero-flexibility with the girls I dated, but one who I really liked got super freaked out about it and now I just keep my mouth shut. But I’m not ashamed at all. It’s true: Guys give the best head, generally speaking. :D”
29. We would play the boner game with the goal of achieving the fastest boner.
“Join the Marines…
Boot camp, 97 guys lined up naked, ass to balls, and then we have to run through the shower room to take our shower…
While in France, there were 6 guys to a room. Every night we would play the jerk off the game and with the goal of all of us choking the clown at the same time until we came. The winner went to sleep first.
In Korea, while waiting we decided to play gay chicken… the gay guy won.
While in a formation for a change of command ceremony, we would play the boner game with the goal of achieving the fastest boner. Once a boner was achieved we would make a clicking sound. We did this to pass the time.”
30. I played ‘gay chicken’ in the Navy.
“There is an unspoken rule in the Navy. ‘Never let anyone know that something bothers you’ There is also a game known as ‘gay chicken.’ Basically, do everything you can, just shy of actual penetration, to make the other guy cringe or give up. In the interest of not having dick in your face constantly you do your best to not react when someone pulls some gay moves on you. In that context I have done, or had done to me, just about everything except bj, hj, and sex. Never had another guy get me off, nor have I assisted a guy in getting off. Not gay underway, not queer at the pier. edit Totaly straight, married with 2 kids. Just not bothered by gay guys. Not into it, not against it.”
31. One time I sucked this guy’s dick in the woods.
“One time I sucked this guy’s dick in the woods. There was something just so primal about it. Two sapiens rubbing each other in the wild… no homo.”
32. Shared a straw with a friend.
“Shared a straw with a friend. We were at a movie, Suicide Squad I think. Crappy movie, the straw tasted nice though.
Oh, and rubbed my ass against his crotch.”
33. Friend and I had heard of 69ing so we decided to try it out.
“Friend and I had heard of 69ing so we decided to try it out. Pretty fucking great. I’m straight but I’ll suck some dick every now and then.”
34. He used his mouth to blow air into my butthole so I could fart really loud.
“When you are a man and you have a best friend you would take a bullet for no questions asked, many questionably gay things can occur with no questions or explanation. I’m only 23 and I have had the same 2 best friends for 11 years. One of them is a dad of twins now. The one who is a dad has used his mouth to blow air into my butthole so I could fart really loud.”
35. We decided it would be hilarious if someone got slapped in the face with someone else’s dick.
“In high school I used to have weekly sleepovers with my friends. There would be upwards of 12 people sleeping over at my house. It was chaos and my parents are angels for putting up with it. Quite a few things of questionable sexual orientation happened at these sleepovers but I’ll pick out a couple highlights.
The first one that came to mind was when we decided it would be hilarious if someone got slapped in the face with someone else’s dick. Don’t remember how we decided who was going to be the slapper and who would be the slapee, but eventually we decided two people would get slapped. So they did. And we recorded it. In slow motion. All videos were deleted because nobody could bear to have them on their phone, but I wish I had the video still because the slapees deny it ever happening. I wasn’t the slapper or one of the slapees, but I was still there and encouraging what they were doing. There was a foreign exchange student who was hanging out with us that night. Never talked to him again.
The second thing that came to mind happened as a result of our first trip to a sex shop. Most of us were 18 now and so we went and bought a dildo for the hell of it. We got it back to my house (At one of our sleepovers again) and one of the first things someone did with it was put it in their pants and stuck it out their fly. Don’t remember who it was, but someone grabbed a fat wad of Vaseline, slapped it on the dildo and started giving him a few strokes. So naturally, we all gave it a few strokes. While it was still in the guys pants.
So yeah, I guess the gayest thing I’ve ever done is jerk off a dildo while it stuck out the fly of another mans pants.”
36. I think all the gay jokes and dick drawings me and my friends made over the years totals to one giant gay orgy.
“I think all the gay jokes and dick drawings me and my friends made over the years totals to one giant gay orgy.”
37. Made out with another bearded dude for thirty seconds for free drinks.
“This club I’m Barcelona has this thing sometimes that if you and another straight guy make out for 30 seconds you get free drinks all night.
So this Norwegian guy and I made out so we could have free drinks. I didn’t like it. We both had big beards and I didn’t like feeling his hair in mine.
But hey, free booze.”
