Gay guys share some of their most bizarre and bewildering hook-up encounters

Most gay men will have had a hook-up encounter that did not go as planned or threw them a curveball. A recent post on the AskGayBros subreddit prompted hundreds of comments and tales of unusual kinks and potential miscommunications.

“I hooked up with a guy who is visiting and staying at an Airbnb across the street,” said @writerboy1550, who got the ball rolling. “We chatted, had sex, chatted afterward, he was on his way and I found he was a nice guy. I texted him (we had exchanged numbers) and told him ‘Hey that was a good time. If you want to meet up again while you’re here, I’m down 😉.’

“His response: ‘Why do you have to say things in the past tense? Also, I’m sure you have deleted me from your contacts already. 🤷🏽‍♂️.’

“I was like WTF are you talking about?! Make it make sense. Really was bewildered as to what the hell he was on about lol.”

He asked other users if they’d had any of their own “WTF” moments. The replies came rolling in.

Some of them were decidedly NSFW and graphic, but here are some of the milder ones.

Health awareness

For one guy, his partner’s lack of knowledge about sexual health was a big turn-off.

“My WTF moment from a few months ago: Dude and I were vibing. I told him about my various tests and vaccines, disclosed my status, and my being on PrEP. He has not been tested in over five years, does not know his own status, nor is he on PrEP. He doesn’t like to take meds; goes only raw; and insisted that, since he’s strictly a top, it’s on the bottom to take care of himself. Yeah, that went no farther.”

Thomas The Tank Engine

An unexpected tattoo threw this guy off his game.

“I met a guy from Scruff, very handsome. He came over, we ate some food and started getting down to business. After he took his shirt off I realized he had a FULL BACK TATTOO OF THOMAS THE TANK ENGINE and I couldn’t keep it up for the life of me because it was staring into my soul.”

Cash requests

Hookups followed by requests for cash never go down well, it seems.

“Went out with this guy who seemed nice. When we met up he had a black eye and claimed he’d been mugged. Took his word for it and we went to dinner. Had a nice chat, made out in the park nearby, and then he went home. Overall a nice night.

“A few days later I texted him asking when I could kiss him again and he was all like ‘I’ve been hurt before so don’t push me!’ I was taken aback so I backed off, thinking he’d been through trauma. I tried again a few days later by saying hi. He responded with, ‘I left my wallet on the beach, can you send me money so I can buy a steak for my dog?’ I blocked him after that.

“Two years later he tried to Venmo me requesting $3. He sucked when it came to scamming. Too bad though, he was very cute.”

Third parties

Unexpected interruptions from roommates are also usually unwelcome.

“I was in the Bronx, naked with this sketchy but attractive guy in his bed, and he buzzes someone into the apartment,” said one commentator. “Another man walks right in and says, ‘Come on dude why do you have to do this in my bed.’ I’m just sitting there with a hard-on that is quickly shriveling. I get up to get dressed, and the hook-up tells me to just to hang on so he can move some furniture around. Needless to say, I bolted out as fast as I could.”

Drugs and amnesia

Whipping out drugs unannounced is generally unappreciated.

“When I hooked up with my gym crush,” recalled one guy. “He started doing meth in the middle of me giving him head. I was so disappointed and left. He has the most perfect body, not too big and just perfectly toned. I see him occasionally at the gym and I just shake my head in disappointment.”

“Was seeing a guy casually for three months,” offered another man. “[He] ended at the end of Jan this year pretty brutally as he ‘doesn’t want to have care about other people or their feelings’, he then blocks me across Snap, Facebook and Grindr. So naturally he taps me on Grindr at the weekend complimenting my body and not recognizing me other than ‘Your body looks vaguely familiar’. After some blunt conversation from me to see whether he know who he tapped, of course, he didn’t, so I replied with ‘Yeah😂’ and left him on read after that. WTF? he spent three months f*cking and snapping me for me to be ‘vaguely familiar’.”

Another recalled a casual sex buddy trying it on with neighbors.

“I had been f*cking this guy for a bit. He’d always come to my place. The last time I invited him over he thought some other dude who let him into the apartment was me. The other dude also had a friend coming over, probably a bro because he happened to be the straight guy across from my apartment. So they all three walked up the stairs together. I hear my fwb say ‘Oh uhhh ok didn’t know it was a group’ and then get told ‘wtf are you doing’ when he tried to enter their apartment…”

Related:

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Poor hygiene

Someone not washing before a hookup is also frequently frowned upon.

“I went to a hook-up once with a guy staying at a hotel near my place,” remembered one dude, less than fondly. “He was nice. We chatted. His photos were a bit dated but, still cute enough.

“Started fooling around and I realized he wasn’t showered. Then as I reached into the back of his pants, I thought maybe he had pre-lubed in the back….. nope, he was FILTHY back there. I said politely, ‘Make sure you’re clean af because I’m going to be in there a while.’ As soon as he hit the bathroom, I started quietly gathering my things at a super fast pace. I was down to my underwear and no shirt but I had to be fast.

“I ended up in my drawers trying to get my clothes on in a very nice hotel and I swear to God, as I got to the elevator, the doors opened and three men in suits were exiting on my floor. They laughed their asses off as I panic buttoned my pants, no shirt, no shoes, and I couldn’t help but laugh my ass off.

“By the time the elevator got to the ground floor, I was mostly dressed, I got to the valet and gave the dude a $20 and just drive off. I blocked him immediately but forgot he had my Instagram still. He accused me of robbing him, and I had to be the one to explain that he got DOODIE all over my hands and if he didn’t believe me, he could check the sheets I wiped my hands on.”

Although hookups that go wrong can be amusing in hindsight, one well-liked comment came from someone who made a more somber point about the situations some gay men put themselves in to find sex.

“When I think of all the dangerous situations I got myself into when I was a teenager, it’s a miracle I still have all limbs and no HIV.”

Greater communication before meeting someone or hitting the bedroom is never a bad idea! And don’t ever feel embarrassed about asking for a video call with someone if you want to compare their appearance to their photos.

Related:

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And the winner is…?