Describe the weirdest hook-up you ever had

Oh, that story has been told on DataLounge before! But it is funny.

One time a friend hooked up with a kind of bitchy design queen with frosted hair and a fake tan, you know the type. They were in a bed and breakfast in the Hamptons, in a nice room with a canopied bed with all white sheets.

They had a bit of an “accident” during anal they didn’t notice until they were done. But they saw a little dark spot on the comforter. The design queen (the bottom, of course) was mortified! The looked closer, and it was a bay leaf.

That's why you remove them before eating.

I once had a guy I picked up at a gay bar say, “I love you” while we were having sex. We’d known each other for two hours. I tried to laugh it off, but when he didn’t laugh and just kept looking at me I was weirded out… ugh, it was super cringy.

Hat story is a DL classic

I went on a blind date with a guy who looked just like my brother. Nope.

He was into my feet. Which is the most unattractive part of the male body to me. Yuck.

I met a guy and we went back to “his place” on the subway, very late at night. It ended up being in Queens, and took forever to get there. It was a house. I remarked it was interesting he had a whole house and when I asked if it was his he said “Yep.” He insisted we go into the basement, where he had an entire bedroom. Hmm. I spent the night.

In the morning he goes, “My mom’s upstairs she made breakfast. Don’t tell them anything okay? We’re friends! You’re just my friend you slept over, got it?”

I was blindsided and didn’t even ask again about the house, I was just like, “Uhh…”

We get up there and his whole family is there in the kitchen, mom, dad, grandma and I think his younger sister. We eat breakfast at the table with them. He introduces me as his “buddy” and proceeds to just spin a bunch of lies about who I am, where I live, what I do. I’m sitting right there, munching on bacon and nodding. I felt pathetic but didn’t want to cause a whole scene. Then his family starts asking me questions based on the lies he told. I couldn’t leave fast enough.

When I left the house I had no idea where the subway was or anything and was lost for a good while.

I hooked up with a good looking guy who had a great body. I was really into it until I accidentally snatch his wig off.

LOL!

Because good looking guys with nice bodies don't shave their heads; they "wear wigs" that are "snatched" off.

Hooked up with a guy that lived on The Bowery in NYC. We went back to his place, a ratty but large two bedroom. Very late.

We’re in his bedroom having sex with the door open, kind of ajar, and suddenly we hear noises in the apartment. He says, “My roommate must have gotten home.” And gets up and shuts the door. We continue. At some point later we hear the front door loudly slam.

When we’re done we go back into the living room and it’s freezing cold. He says, “My roommate left the window open!” And I look over and the window on the street side (with the fire escape) is wide open. He leans out and calls his roommate’s name a bunch of times to see if he’s out there, then shuts it.

Then we’re sitting on the couch talking and, slowly, he’s like, “Wait a minute.” He realizes his expensive camera and tripod are missing, and some other random things like a blender. We eventually figure out he’d been robbed! The whole time we’d been in his bedroom having sex someone came off the fire escape, took a bunch of stuff, then left through the front door.

He called the police and they came and talked to him. I stuck around for moral support. He was really upset about the camera. They deduced since they lived on the third floor with giant windows and never closed the curtains, people from buildings across the street could case the place, and saw the windows were accessible and might be unlocked. They police told us several times, “We were very lucky.” It’s true, the idea of someone or someones right outside the door robbing the place while we were boinking is creepy as hell. It could have been far worse.

What creeped us out more is we later realized the robber or robbers may have been in the apartment when we came in, and hid.

I once went home with a guy who lived in an apartment that he kept incredibly cold. Then he told me he was a mortician.

I've told this story. It wasn't a hook up. Back in the day on one of the chat platforms I met a guy. Turned out to be a doctor, he seemed decent, we set up a dinner date. I met him outside the restaurant we went in and he went non verbal. Dinner basically lasted 45 minutes and I probably talked for forty. No eye contact, virtually nothing verbal. It was beyond some normal level of this isn't gonna work for me. Of course every insecurity in me was firing at Defcon 5. We never communicated again, so didn't hook up, though as a card carrying gay man I probably would have even after that horrible dinner.

A year later I opened up the paper and saw he'd lost his license for sexual impropriety with patients. So he was a fucking headcase.

Too many to pick just one.

I once met up with a guy who asked me to leave because I wouldn't look at him enough.

And another guy asked me to stop looking at him so much.

I can't win.

Not my story but R12 reminded me of my sister who got carjacked on a blind date with some guy...thankfully it was his car, not her's...they were sitting in his car talking and some guy came up with a gun and threatened them into getting out and they did and guy just sped off in the car. My sister said it had been a really good date so far but that just soured the whole thing and she never heard from him again.

I had a fuck buddy when I worked in the loop in Chi. We would always offer to visit the hotel rooms at lunchtime of any gay elderly visitor who might enjoy watching us fuck. Many, many hot times. Also, one very scary experience…the dude didn’t understand the boundaries and got SUPER pissed when we wouldn’t let him join in. Scary pissed. And screaming at us to get the fuck out. We couldn’t get out fast enough. Grabbed our clothes and ran out of his room (at the W on Adams..lol) naked, and got dressed running down the hall to the elevator.

In my Flyoverstan city, where I am notorious for doing nothing, I went to a gentleman’s apartment. He was nice guy, average looks but had nothing at all. Like mattress and a couch. He was mid 30s. Something was off and I left quickly after.

HOoked up right in the Rijksmuseum, with one of the docents, DURING HOURS!!

I once was hit on at a children’s party—-by the clown. I passed.

It didn't feel weird at the time. More like transgressive, at least until I met the other seminarians.

Made out in the seminary bell tower. He gave great oral, and just as we both were at The Moment (he was jerking off) the bell started bonging 11 PM. Very proudly and loudly.

He left the seminary and ended up marrying a woman and having a kid before he headed to NYC as a choreographer.

I fully expected He left the seminary and ended up with a hearing aid, signing in the hours before landfall.

Hooked up with a guy in the early 2000s via Craigslist. He was looking for a bit of role-playing; we engaged in a bit of digital foreplay exchanging headless torso photos and a few action shots, so set a time to get together. I offered to host but said I needed his name to give to the doorman to let them know to let him in, and he hesitated explaining he worked in a high profile position at a conservative organization but eventually relented. So, he shows up and the whole mood was weird. The photos he was using were at least 10 years old, ironic because I'd told him beforehand that I preferred older guys, but whatever.

Then he started talking about acts that we had not discussed. He was insistent that we had and that was the only reason he'd agreed to meet up. But I was thinking with my little head so proceeded with caution... but ended it rather abruptly when he wanted me to get in position to eat his ass and it was apparent he hadn't showered for at least a couple of days and there were reminders clearly in view. When I said sorry I didn't want to go there he got pissed off and only then did I realize that he had confused me with someone else he was emailing with in response to the ad. The pièce de résistance was when he said "I blew off a much better looking dude to fuck you" and it was clear he meant... me.

Guy from an app told me his friend lived with him and was very old and practically blind but would it be okay if he stayed in the room and watched us. I said no, not okay with that. He said no problem at all, he can just wait in the lobby.

I get to the building, which is fancy and it’s a really nice lobby. There is an extremely and tiny old man sitting in the lobby with an iPad. The guy tells his doorman to have me wait 5 minutes so the doorman has me sit in a chair next to the old guy. We don’t acknowledge each other. Longest 5 minutes of my life.

Many moons ago I had a hookup with a guy who was into blonds. Good for me. Seemed nice enough.

As we were going at it, he kept telling me how perfect I was, how Aryan I looked.. “So blond, so white, so perfect!!” and how he wasn’t worthy of me!

Turns out he had some weird nazi/aryan fetish.

…and when he came he just screamed out, “Surrender Dorothy!”

Sex with a Sri Lankan in a Port-a-Potty along the Hudson while carrying desert to Thanksgiving dinner.

[quote]carrying desert

Gobi? Sahara?

A guy who casually asked me if I ever had the hots for my own father. I looked at him, horrified, and said “hell no.” He then started telling me about doing whatever he could to catch his own father in the shower or otherwise naked. I did not contact him again! Later turns out he was into kid porn and beastiality. Freak

r18, you are the weirdo in that story.

R9- It's all good as long as he was not wearing a RATTY KOREAN WIG.

OP, was his name Noah, tall thin black guy?

Met a guy at a bar in London. Went home with him and he had dingleberries all over his asshole. True story. Like, WTF, dude?

[quote] We would always offer to visit the hotel rooms at lunchtime of any gay elderly visitor who might enjoy watching us fuck. Many, many hot times. Also, one very scary experience…the dude didn’t understand the boundaries and got SUPER pissed when we wouldn’t let him join in.

This sounds odd. How do you figure out who wants to watch.

R25, I can't follow that story.

Any weird celebrity hookups?

Ex sportscaster in a more populated Eastern Midwest state. Ended up being a weekend in Suagatuck.

R35, I should clarify. It was a regular fuck buddy, we both had boyfriends, and both worked (didn’t live) downtown , so needed a hook-up place. We’d get on manhunt (ha!) and look for an eldergay staying in the loop who wanted to watch us fuck. Typically found one and typically had a ball…except for the one time.

R22 I had sex with a seminarian many years ago, out in a cornfield out the back of the monastery. Wasnt weird but damn it was hot. Fuck that was a good day

I hooked up with a cute younger guy who once we got into bed I realized he'd made it so tightly that the corners must've been plomb bomb-aligned with creases by Martha Stewart's magazine and we could hardly move or turn, it was to cramped. Then his roommate slowly opened the door unexpectedly and sleepwalked into the room, around the bed à la a "Paranormal" movie sequel, and exited slowly shutting the door behind him while my equally sheets-restrained bed partner laughed it off.

I hooked up with an older guy off Craigslist who turned out to be into submission and body worship. I went over to his apartment for some great head, and he swallowed as I finished. He immediately said I should never allow anyone to spit because it's an insult, and he asked me to store all my cum in a jar when I jerked off so he could drink it the next time I came over. I was convinced I had just hooked up with a serial killer and couldn't leave fast enough.

I did go back one more time, though, without a cum jar.

Random hookup online. Got a hotel room and fucked him for hours. Two days later I am seated in a restaurant next to this family of four. Dad is the guy I fucked. Awkward.

Oof, so many odd or downright weird ones. It will be hard to narrow down. I may need more than one post! Yes, I was a slut.

In the early/mid 2000s I lived near a big university, at the same time Craigslist became a thing. It was like shooting fish in a barrel. Aside from several hot college guys, I hooked up with two older guys who fit this thread. One wanted me to suck him off but was really weird about being seen and eventually told me he'd wear a cowboy hat, sunglasses and bandana over his face. He shows up - beautiful body, tall guy, big dick. As he gets close he starts talking more and especially as he's shooting, and he tells me to take it, I realize why he wanted his face hidden - he was a well known TV anchor. The second older guy wasn't shy about hiding his face but he had a weird frottage fetish. And I don't mean frottage itself was weird but that he wanted to stand behind me as I sat on the couch and rub his dick all over my hair...? Anyway, nice dick, nice load. Three days later a sports team from the university is interviewed and he's shown as part of the coaching tea (I won't say more as someone might guess who it is).

I also not long ago posted this in another thread about married men or something like that - but I had a fuck buddy that I really got on great with. Nice guy and we talked a lot. Small guy, sort of looked a bit like Chris Meloni or Ethan Embry with dark hair, but shorter, around 5'5 or 5'6. Intense, beautiful, fucked like a champ, came like a geyser. I knew he was married and that he lived in the same suburban county where I'd grown up - he was vague about where. A few months later I am visiting a sibling in said suburban community and in walks the classmate of one of my sibling's children.....and then that classmate's parents, and of course he was the dad. Super awkward. We both kept our cool, though.

I've posted this before, but years ago in San Francisco I was picked up by a guy who was WAY out of my league — he looked like a firefighter from those beefcake calendars. We went back to his place in Japantown ...

... where he started talking about how "fun" shitting in someone's mouth could be, had I ever tried it, I wouldn't have to touch it or anything, just give it a try and take a dump in his mouth.

I said absolutely not and he sheepishly asked if it was OK if I left because he wanted to go back to the bar and try again. I got out of there as fast as I could. He wasn't threatening — he was actually really nice — but I understood why someone who looked like him had trouble picking up guys.

R9 = Neely O'Hara.

As for more weird hookups.....hard to choose. I was a somewhat beefy guy with broad shoulders and people made a lot of weird assumptions about me based on that.The weirdest was the shorter guy who had a fetish for.....uh, riding men like a horse and having the man neigh? Sorry, I'm not SJP, bitch!

Then there was the guy who wanted to fatten me up and wanted me to wear a white shirt with food stains (!!)

There was the guy that saw current, clearly lit photos of just about every inch of me (no dick shots) and then met me and said, "You misrepresented yourself in your photos, I was looking for something else."

Which was followed, within a few weeks, by a guy who actively and aggressively pursued me, took me to dinner, flirted with me all night and then said, as we were leaving, "I'm sorry, I'm not interested in another date. I really only date Asian men." After those two I was kinda done for a long time!

I hooked up with a Sri Lankan guy in Chicago and he was wearing some sort of garb. He lit candles and was chanting and it kinda threw me off....but damn he was a great fuck. Big cock, too.

I also remember meeting a guy on an app in Chicago...and it ended up being a friend of a friend that I'd already met. He seemed like such a sort of mild mannered, almost milquetoast guy, very buttoned down. But he had a nice long fat cock and shoots ENORMOUS loads. The only frustration is that he always wanted to give me a facial....and I wanted to take it and swallow!!!

Have had a few weird ones that started well and then yes, someone's hygiene wasn't on point - either the guy's ass just stank, or his balls did, or he had dingleberries, or just seriously ripe BO, and I just left every time it happened (maybe 4 or 5 times over the years??) At least two of those times I think the guys had some sort of stank or shit fetish and probably thought it was hot to reel an unsuspecting trick in, but I was not having any of it. Ugh. A little after the gym sweat is one thing, but.....ugh. I can't deal with scat or funk. Just no.

I met a guy online and invited him to my place. Big mistake. He had attractive features and was in shape.....but he was super scruffy and looked (and smelled) like he hadn't showered in a month. He smelled like weed, unwashed clothes, and B.O.

I made an excuse to get him to leave

Ha! R47 the same thing happened to me re: the pics. Sent tons of pics I took that day to the guy, show up at his hotel and get "you don't look like your pics, this isn't gonna work" routine. I just said thanks and left shook my head and said to myself "what the fuck?" What was so weird was that he pursued me. Fortunately his hotel was close to my apartment and I didn't go out of my way. I think some guys get off on that game.

[quote]I was convinced I had just hooked up with a serial killer and couldn't leave fast enough.

[quote]I did go back one more time, though

Hook-up culture neatly summarised in two lines

OP, did he have a brain tumor or bullet wound scar?

My favorite thread.

I was a desk clerk in college, and was turned on by a swarthy Cuban man who checked in. He asked me to come up to his room when my shift ended. He was well-built, with nipples I could chew on all day, a hefty cock, thick balls and an oversized bush.

We were up all night and showered together. He then told me he travelled to colleges all over the country, and he had a guy he could sleep with at every college. He wanted me to be his port of call whenever he visited my college. This is when AIDS was just starting to go around. I declined the offer and got myself tested every three months for years. I was Huckleberry Hound. Thank goodness I never tested positive, but it hung like a cloud over me for a good ten years.

Some of you are such sordid whores. My word.

R11 is a mega-bitch and I love him.

Used to hook up with a guy who did the “Elvis”. Would get off grinding on me while clothed. He was great looking but had a small dick—also like (young) Elvis.

I met this nice guy at a party. He was thin and a bit " nerdy" with glasses and a a quiet seriousness. After spending most of the evening together, I drove him home, where he invited me into his house. Of course, I went. We started making out and got naked. I had heard that the thin guys have the biggest cocks ; this was true in his case. After a while of making out and fondling, he said that he wanted to fuck me. I agreed and we went into his bedroom. He started fingering my ass, but pulled out and said that he wanted me to talk on the phone to his friend while I was being fucked. I thought it was the weirdest thing,. but was excited at the same time. I agreed, so he got his phone, called his friend, gave the phone to me, and got me to talk to him. We did for a couple minutes when the guy announced that he was going to fuck me. I let out a scream as he started. The friend kept asking me questions about what I was feeling and what he was doing throughout. I'm sure he was jerking off as we were talking. The guy came with a loud scream, grabbed the phone, and told his friend that he'd pick him up tomorrow for work. Then he pulled out. We kissed for a few minutes and I got dressed and went home. It was weird, but I still get hard remembering it.

I was teaching high school and it was Parent/Teacher Night. It finished about 8pm and we didn't have school the next day, so I went to the baths to relax. I was sitting in the steam room when I felt a hand fondling my dick. I looked over and there was one of the dads I had just spoken with about his son. He smiled at me and blew me right in the steam room. After I came, we left. showered, and sat for a conversation. He told me that his wife was at a conference and the kids were at home, so he thought he'd take a break and " get some steam." I never looked at his kid the same way again.

I’m glad I’m not single. Since millennials and especially Gen Z were raised with limitless access to porn at any time, they are probably really into freaky shit right off the bat. Some probably can’t even get off with “normal” sex.

Craigslist hookup. Exchanged pics and the dude was gorgeous. Reminded me of a young Alec Baldwin except he had these big doe eyes. He showed up and he looked just like his pics but he was dirty. Like filthy, face had dirt on it, clothes were tattered. And the smell...

He told me he just got off work and asked to take a shower. He did, then we exchanged oral. As he was putting his clothes back on I noticed something fall out of his pocket. I picked it up and turns out is was his pass/paperwork for the homeless shelter down the street. He just sort of shrugged and said sorry. Told him to hit me up if he ever needed a quick shower and bj. Never saw him again.

Had another kid who was one of the best hookups I've ever had. Just my type, nerdy skaterish, and we actually had a lot in common. He stayed the night and everything seemed like this may be a hookup that could be the start of at least a friendship. Until I heard screaming from a few doors down. Some guy was knocking on every door of my apartment building screaming "I know you're here, your car is in the lot" and spewing all sorts of threats. Kid panics, says sorry and punches out the screen of my bedroom window and jumps out from the 2nd floor.

Both of these happened within a month of each other.

I can’t hook up with someone with bad BO—no matter how hot they are.

I once had a hookup with a trick who wanted a ride home after and I had parked downtown in a huge parking garage. It took 45 minutes for us to find my car. He was not amused.

OP, your story reminded my of this kindertrauma tale The Velvet Ribbon. I really want to know what would happen if he removed his cap.

College boy? And for ten years you were worried a hot trick shot AIDS into you? And you never once listened to the nurse or doctor, on those dozens of trips to the clinic, and neverread an article in the press, that the window for that risk was a couple months? 10 years!?

I was in college and living in Paris and Geneva. I bet a Thai boy in Geneva who quickly became my almost live in servant and sex slave. He just wanted to serve, needed to serve. Meanwhile, during my days in Paris I met a Moroccan boy who spoke no English and little French. He also was into serving. They were both very rich aimless boys stored in these cities by their embarrassed families. 1980s. The sex wasn't kinky at all. I didn't cosplay being a master for any of the service. They would say they wanted to do something for me so I gave them daily and weekly projects. The weirdest thing was they both cried during sex. I wasn't a rough fucker and I don't have a huge cock. And I used a condom, these were the AIDS years. So after I would ask if they don't want to have sex and they said they did. The next time fucking, rinse repeat. The crying. It was all very strange and I knew it and liked how weird it was but after 2 months I let them go from my life.

R60 has actually been touched by a hobo.

Met a guy online. His body was hot, thick muscular guy, nicely furry, and a big dick. I drive to his place, it is in an older neighborhood. He invites me in, and looks just like his pics. The place is odd though, decorated in very old lady style but fuck it he is hot and hung. We go to his bedroom which is not as bad. We fuck and it's hot, then there is a knock on his door. "Robert, do you have a friend over?" I hear in old lady's voice. "YES MOM, I TOLD YOU I WAS HAVING A FRIEND OVER," he yells at the door. "I need your help," she says softly. He rolls his eyes pulls on some shorts looks at me and says be right back. He opened the door and this little grey-haired old lady was peaking in shooting daggers at me. He is gone for about 20 minutes so I got dressed to leave. He comes back and begs me to stay. He wants to fuck again. I told him he never mentioned he lived with his mother. Other way round. He lives with her. I let is slide because...that dick...and he could fuck but the whole second time I am thinking his mom is peering in the door watching me get plowed. He asked me to spend the night but I told him I had to go. He called me about 20 times after that to hook up again but he could not come to my place or go out on a date or anything because of his mother. Finally, I just told him I was really odd having sex with his mother in the house and if he wanted to see me like a normal person he could. Never heard from him again.

My current boyfriend... I kind of love him and am very fond of him and feel an instinctive protectiveness of him... I think he's been badly hurt in the past, probably by nasty parents, but he won't say. He's an adequate lay... my feelings for him are what turn me on.

His weird twist: he always calls it his penis. Never dick, never cock. It's always penis. Suck my penis. It's like having sex with a textbook. And he never tells me he's going to cum and never makes much noise when he cums, which feels a bit... lonely sometimes. But he's under my skin. There's a lot going on with him. It feels a bit like dating Roman Roy. But I'm fond of him and I am trying to sort out what to do because... it's kinda weird and I'm not sure I like it. But right now the affection and concern always wins out.

R68 guys who make no noise when they cum or even just tell you they're going to cum are the worst! I've always found it so weird.

I love when guys are verbal, too. Maybe not in that never shuts up porny way. But especially when a guy cums, I want to hear him moaning, telling me to take his load, etc.

Once I fucked a guy in the back of his van which was filled with random junk. As I was getting ready to leave, I realized my ID wasn't in my pocket. So I had to frantically rummage through all of this junk for several minutes. Finally found it on the floor.

In LA in some odd little dirty gay bar. I walk in around 12:30 am, almost last call and the bar is empty. I decide one beer for the road before I call it a night. 15 minutes later in walks this sexy tall MFer, We look at each other and nod and that's it. I eye him once again in the mirror behind the bar. He gets up to go and I follow him. Get into my car and follow him home. We had great sex without ever saying a word to each other. Left when the deed was done.

Another LA hookup via the old chatrooms. I show up at the guy's place and he meets me at the Apt elevator. Dude is hot! And we start fooling around in the elevator. Make it into his place and go at it for about an hour until he hears some crying in the next room. He has two kids in there! Time out while he gets them water. I wasn't freaked out enough to leave yet, so we go one more time.

San Francisco - In some leather bar and hook up with this very hot guy. Brought him back to my place for a night of piggy wild sex. The following week I go in for an eye exam and guess who's staring into my eyes. Neither of us said a word.

San Francisc again - another divey sex bar. Hot Hot guy hits on me and we fool around some in the bar before leaving together. As we get to the parking lot, I ask "your place?" Ooops he doesn't have a place. Kind of homeless. This was after the dotcom crash and he was a programmer. Had to fuck him in my car. (I don't like bringing strangers back to my place...too much)

How am I still alive? Sheesh

Not only are you alive R72, but you can still see.

You must have done the ophthalmologist well.

R67 Was his name Seymour Skinner and was his mother named Agnus?

I got fucked on a replica of Henry Hudson's ship, the Half Moon, on the river in Albany, New York, by the caretaker who was living on it while construction was being finished. The sex was hot, it was just the location that was weird.

Some LA weatherman. Like to have rocks of meth shoved up his ass. Wonder whatever happened to him.

What was the cabin like on the Half Moon?

R77, there wasn't a "cabin". He fucked me on a futon on the floor of the unfinished wooden interior.

This is the type of thread that EST dreams are made of.

[quote] A few months later I am visiting a sibling in said suburban community and in walks the classmate of one of my sibling's children.....

R44 round these here parts we call a "sibling's children" a niece or a nephew.

R80 aren't you a clever little cuntling!

I deliberately left the gender of my sibling as well as her child/children out of my story. Sorry if it left you extremely tender to the touch!

Every story involves a hot guy with a hot body/dick, no one admits to fucking the ugly guys with micropeen

R81 displacement. May I suggest the Sheboygan Conservatory's EST Writing Workshop?

OK R82 - My micropeen story - I was in LA needed a hookup - was one of those nights where I was pent up and had to have it. I chatted with a guy on line, looked very handsome. I show up there and he's just like his pic so we go at it and he's hesitant to take off his underwear, so I just pull them off and saw the tiniest peen ever. Almost a clit. Well, I could give a fuck, he had a nice ass. I fucked him so hard he had no idea what hit him. He really wanted me to stay and linger, but in those days I was a hit and run type of guy

We only allow Micropeen EST's if the unfortunate man is also devastatingly handsome and a middle eastern prince or the son of a plutocrat.

R79 Thank you! Definitely getting a Penthouse Forum vibe.

I've had a few micropeen disappointments too but that's not really "weird", just disappointing and sad.

The one I really clearly remember was not "devastatingly handsome" but it was one of those Gronk/Brett Favre deals - a guy that worked at a farm supply store. I assumed big and beefy + butch and confident meant hung, or at least sufficient to work with, but holy fuck, it was sad. He kept saying "it's cold, he'll wake up" and like the third time he said it I was like, dude, it's July. That was the end of that.

When you’re hung enough, almost every guy is a disappointment.

One man wanted me to zip him into a body bag. That was the sex. So I did.

I hooked up with a guy who had a short (but relatively thick) penis. We actually had a drinks date before the hookup. After the hookup, I never heard from him and I didn't try to contact him.

Fast forward maybe 2 years or so and we run into each other at a bar. He's chatting me up and it dawns on me that this short-peen fucker doesn't even remember that we already hooked up. So, of course, I reminded him.

Later, I discussed this with a friend. Told friend that short-peen never tried to contact me, again, yet was apparently attracted to me. (Evidenced by trying to pick me up, a second time, in the bar.) Friend said: "He knows he can only get away with that shit (short peen), once."

Or you're just a particularly unmemorable fuck

Maybe, R91.

I met a guy on AOL who asked if I was into roleplay. He was handsome in his photo so I was like, sure, let's play. He lived not too too far from me and told me he'd wear his work uniform when we hooked up and I thought, okay, that's cool.

There was only two things wrong: the photo ended up being about 10 (or more) years and 50 (or more) pounds prior to our meet up. And oh, apparently his "work" uniform was a Batman costume. I simply said, "no" in the kindest tone possible and closed my door.

Classic thread already.

Another happening but not in my Flyoverstan city, got ghosted by a guy who lived 2 doors down.

Happened but it didn’t, in my Floyoverstan city

diaper fetishist. I tried to go along but it was silly.

The guy kept stopping and would frantically run to the bathroom about every 10 minutes and call an automated recording. I couldn’t make out what it was saying. Once everything finally came off, I saw that he was wearing an ankle bracelet.

HA (R20) I was a volunteer @ the Rijksmuseum 20 years ago for 3 years & yes, this happened quite often. I met my husband of 15 years there! We visited a couple of years ago & still have a couple friends working there. They said all the new ones are sluts..... It's still going on!!

Fat whores! Love your stories! Keep them coming.

I met a guy who insisted on letting his yappy little dog in the bedroom. It was like a Tasmanian Devil, jumping on the bed barking and gyrating while we were trying to fuck.

R101 guys who don’t lock the pooch up are a no-go for me.

I was raped.

The weird part was his socks didn't match.

Were they blue?

I always thought the story about going to a guy's apartment and it being filled with porcelain dolls was a gay urban myth, until it happened to me! They filled the living room (fifty or more, at least) so much that you couldn't sit in there. The bedroom was a closet that barely fit a queen-sized bed. What's worse is that his partner was home and he expected me to hook up with both of them. I only did because his cock was huge and really thick.

[quote] I only did because his cock was huge and really thick.

The original guy, or his partner?

The original guy

I guess you could say it was a package deal. 😎

I hooked up with a guy who strongly resembled Niles from Frasier and wasn't super interested in him, but rumor had it that his tall, hairy husband liked to join in sometimes. The second or third time "Niles" and I hooked up, the husband did join, then husband and I hooked up a few times after. Husband had the perfect dick to ride for hours.

Obese, living with mother, pockmarked, body odour, criminal record, old photos, filthy house and yet it almost always comes down to I only did because his cock was huge and really thick.

I met a guy through Craiglist (no photo) in town on business who described himself as a bear. When he opened the door, he was several bears (did you know the group noun for bears is either sleuth or sloth? He was one, I was not the other.) I am not being unfair. I know my place in the pecking order and I promise, most of DL would like to stone me to death for being what I am. But this one, he was massive! Shaped like Jabba the Hutt. And short of breath. And with a pill organizer that would have been at home behind the counter at the pharmacy. I did not do it because his cock was huge and really thick. I assume because it was buried beneath folds of huge and really thick. He took my feeble excuse gracefully. At least I could have outrun him, which I can't always say.

I’ve told this story before. It’s funny now but at the time kinda traumatic. I picked up this incredibly hot marine type. I was early 20’s he was late 30’s. Built like a fucking god. Gorgeous. He comes to my place. Takes his shirt off. 8 pack. Pecs perfect. His entire upper body was a 10. He throws me on the bed. Giant cock. We make out. Perfect kisser. He takes his pants off and I realize both legs are prosthetics. He proceeds to take them off and throw them in the corner. He starts to hump me with these two stumps. He cums after he fucks me. Slaps them back on and takes off. I never see him again.

That's a leg up.

I would totally get into hot sex with an soldier/marine etc who had prosthetics. Not b/c it's a fetish but just, it wouldn't be an issue.

BUT I would want, you know, a little heads up before we got naked!

[quote] I always thought the story about going to a guy's apartment and it being filled with porcelain dolls was a gay urban myth, until it happened to me!

Mine wasn't porcelain dolls. I went home with a guy at the bar who was in head to toe leather, had a beard and hairy chest, and looked great. When I used his bathroom it was filled with flowers and two giant bowls of flower-shaped scented soap. He made those soaps and proceeded to give me a tour of his soap making setup, as his Peggy Lee CD began to play in the background.

We had a lovely chat and became somewhat friends/acquaintances after that, but I was bummed out that the package was, uh, not quite as initially advertised.

I had a bartender fetish. I would make it my business to fuck around with a bartender, but it had to be in the bar. I had plenty of fun with a number of them, but this one bartender wanted to blow me but not in the bar, so I met him later at his place and couldn't get it up because...he was not in the bar!

I’ve told this story before on DL.

Back in the ‘90s, I was flying from JFK to Rome business class on a 747 Jet. Business class was the upper chamber on the 747, with bathrooms at the bottom of the stairs. I sat alone in the compartment until almost departure when a group of men suddenly arrived and filled every available seat. It turns out that they were a group of Franciscan seminarians from Pittsburgh making a pilgrimage to Assisi.

After we took off and were fed, the FAs set up a help-yourself bar at the front of the cabin and promptly disappeared. My seatmate and I were both Scotch drinkers, and the other boys were heavy drinkers. After a few rounds and a lot of laughter, my seatmate begins feeling my upper thigh. Long story short, I ended up having sex with a few seminarians, mainly in the bathrooms, but also hand jobs at the seats. It was a wild night.

^That's a fun story.

30 years ago, I went home with a guy from the gym. We had chatted regularly and was a genuinely nice guy. A downtown, finance guy a Clark Kent type that anyone would like. We had chatted a few times and fooled around for a minute in the sauna and he invited me home to his new place that he had been excited about. Great, he opens the door to the apartment and it looks like grandma's place. Heavy, button-tufted sofa, a curio cabinet with Hummels, or some shit. And doilies, lots of layered doiles, under glass. I expected to see a wicker basket with yarn and needles next to the rocking chair. It's a little Norman Bates but so what.

We get naked and we have a good connection, he's chatty, but fine. Then he starts talking about mom. And the voice in my head screams "NOOOOOOOOOO!" I was already close to coming when this happened so I said something like. "Shut up and let me finish before she hears us" and jerked myself off. Really, anything but mom.

R119 -I went home with a built finance bro type from the gym after a few workouts worth of giving each other the eye. He was handsome, late 30s and a killer body. Then we got to his apartment - it was well decorated, for an ultra conservative, 60-something DAR matron. Very beige, heavy traditional furniture, lots of bland mall art and the bed was made with about a dozed piled damask pillows. It would have been better if his mom DID live there too.

He was nice enough, and ok in bed - but that apartment made me realize we really had absolutely nothing in common.

^^ To be fair, I’m sure he would have found my apartment equally weird and off-putting.

Love this thread.

Back in MySpace days, I was single for five months. There was a guy who I wasn’t interested in because in all of his pics he was making goofy faces or in costume. But one day he made me laugh while messaging and I was bored and lonely, I decided to meet him in a neighborhood bar. In walks this tall, handsome, debonair man wearing amazing clothes with fantastic hair. I was ecstatic that this was the guy. Really,whoever looks BETTER than their pics? Within two minutes of meeting me he asks if I want to go smoke meth. I told him I never had, but would try it because he was hot. We went to his friend’s house and it was sketchy. We smoked meth and I hated it. Then we all went to a bar. He continued to smoke it for hours. I got wasted drunk. His friend was trying to get with me whenever the guy was out of ear shot. I wasn’t into it. I went to the guy’s house from MySpace. I started to give him head and vomited all over him. Then I passed out. Whenever I woke up during the night (light sleeper) he was watching BDSM on his laptop. For whatever reason, we kept seeing each other for a few weeks. He was a complete mess. I later found out he was the trust fund son of a very wealthy realtor.

He asked if he could put it in my "tootie".

I declined and ran for the hills.

I condole you R124, in remembrance of the guy who told me, as we were stripping down fter lots of fun kissing and foreplay, that he wanted to bang me in my pooper.

He followed that with a comment about how hard his pee pee was, and I was outta there.

I haven't laughed this much in a thread in ages. And speaking of laughing here's one of my memorable hookups.

I was touring in a Broadway show and we were in Singapore. I met this very, very British guy with red hair in a bar who had seen that evening's performance. Cyril was in Singapore for an extended work trip - banking, finance or something - and had been there for months. He was sexy, and I love a British accent. Eventually we went to his hotel. He said he hadn't had any sex since he'd been there. The gay scene in Singapore was very underground, and he was really ready to go. When we got into his room we got naked quickly and got to it. He had a very nice body, a great dick and he was assertive and energetic. He was a real turn on. As things heated up, he began saying, 'Ohhh, specTACulah', 'that feels absolutely specTACulah on my cock', 'do that again, it's specTACulah'!, 'Cyril is having a specTACulah time'. SpecTACulah this, specTACulah that. I really did dig his accent, but hearing him say 'specTACulah!' over and over and over, the way someone might say, 'fuck, oh fuck, fuck yeah, fuck, fuuuuuck' except there was none of that - only the word 'SPECTACULAH' in every utterance. Well, it was still some good sex, so I kinda blocked it out and he kept on...'specTACulahly' you might say until he was ready to shoot and when he did he was screaming it.

Afterward I started giggling. After his repeated pleas to tell him what I thought was funny, I told him I hadn't ever heard someone repeat a word like 'spectacular' during sex so much. He admitted to saying it a little but thought I was exaggerating, insisting he probably only said it a couple of times. It took me a while to convince him that it was more than he thought...A LOT more, but he simply didn't realize how much he said it. I could tell he was a little embarrassed, and I told him that I had a good time despite that.

We hooked up three or four more times while I was there. Now being self-conscious, the poor guy tried and tried to stifle his urge to use the word when we were having sex but when he was cumming he simply couldn't help himself. During one orgasm, he started laughing after saying it and then I started laughing, and we collapsed on the bed kind of in hysterics. He turned out to really be a lot of fun.

Weird you say?

Huge Dominican bodybuilder on Scruff - mid 30’s, handsome, 6 foot, 250 pounds of muscle.

We’re naked in his bed and I start chewing on his enormous pecs when he stars in with “I need you to fuck my pussy. Please fuck my pussy…” over and over.

The dick-wilting vibe was strong, but I did manage to rally and fuck his…. “pussy.” Sigh.

I did it in the locker room while the wrestling team was at practice with some guy I met on the street.

Did someone say wrestling?

When I was young, I fucked a few guys I picked up in AA meetings. One particular meeting, held at the detox center, had some rough characters. I was going through a weird phase in life and I was drawn to the scruffiest men I could find. Fucked a guy in a halfway house, he would sneak me into his little room with a single bed. Once I went back to a guy's place, a ramshackle house and his roommate was home. He had just gotten out of prison. Ended up fucking them both. Met a guy at the downtown library once and you can guess what happened next.

On the 3rd hook up, he revealed he was 5 years older and a child molester. Found his name and googled it to find a news article and his listing in the database. Also had a guy lock his keys in the car, saw him a couple times after with his undisclosed partner and years after that denied being a bottom. He couldn’t handle what the short guy gave him.

R128 Ooof, been there. And I'm always super clear about what I like/want.

Interesting that it's often big muscly guys who play along at the bar or wherever you meet them.....and then once you're in bed they turn into big ole bottoms. I hooked up with a beautiful Polish bodybuilder in Toronto who was all top at the bar....and then whimpered and called me "daddy" the second we got back to his place.

AOL M4M Miami- I drove my rent a car from an airport hotel to meet a "hot Cuban top". I drove to Hialeah to some rickety apt. complex and the guy who answered the door had the physical presence of Ariana Grande. I mean 4'10 and 85 pounds, 10 of it, georgous, flowing hair. I looked past him to his one room studio and the entire wall was filled with 8x10 photos in 99cent frames, of ALL the Grande Dames. Harlow, Colbert, Judy, Joan, Kate, Rita,a dozen more, and a big poster of Marilyn. I burst out laughing, I hugged the guy and said no baby, you're cute, but not tonight.

OP's fuckbuddy was obviously either bald on top and embarrassed by it, or had some sort of scar he didn't want him to see.

He tried to bottom for me and cried with the tip going in.

“ He was a complete mess.”

R123 Oh, honey…he’s not the only mess in that sorry.

Amen R137

r128 can I has his number?

Met a guy in Riverside Park - we messed around a bit in the park, and then went to get something to eat. After we were finished eating, he revealed that he was unable to digest solid food, and that the food he just ate went to a plastic stomach that he emptied every day. He got his nourishment intravenously, and ate solid food for social reasons only.

I was on vacation in Florida a few years ago, decided to check out one of the local gay bars. Met a handsome "older" gentleman, we talked a bit and started making out. He asked if I'd like to go back to his place, and I said sure. When we got there, he asked if he could play me something on his baby grand piano. Ok, weird, but ok. He then performs the most angst-ridden version of "Desperado" I've ever heard.

Picked up a French guy in a club in London. Brought him back to my apartment and he started pretending he was a dog and barking and pulling my laces with his teeth. At first I thought oh thats cute but then he wouldn't stop and when I told him to stop he said in broken English "I told you in the club I wanted to be your little pup and you said ok". To be fair to him he spoke only in French to me in between kissed and I was just like oui bien. Oh well. He ended up leaving as he told me he could only get hard by behaving like a dog. The next day I thought I must have dropped acid and it was all a dream but then I saw him in the same club a few weeks later. I had told my friends about it not knowing if it was a dream or reality and the night we were all out together in that same club and he was there I pointed him out and the bitchy cunts went over and started barking at him. Poor guy 🐶🐶

r112 was that in San Diego? Had a similar hook-up, I was surprised but didn't care. He told me he doesn't tell guys because it should not matter. It really didn't Like you said he was hot as fuck and could lay some pipe lol.

In NYC I went out in drag one night and got picked up by a burly type. He took me to some tiny studio underground, off a parking garage or something. (It later occurred to me that maybe this was some fuck pad he’d secured years ago, and that he actually lived somewhere else.) (I hope so!)

Anyway, at some point he mentioned he was getting married the next day. Which I found striking.

[quote]Met a guy at the downtown library once and you can guess what happened next.

We could, R131 but you're boring as fuck and we don't care.

I met a guy on a board (before apps) in L.A. He listed his height at 5'2". He was a little person. He still was cute and had a great body and I am into guys smaller than me. We get naked and he has a killer body but...yeah the equipment is on par with the height. Still I am way turned on by the big/little juxtaposition. I am kneeling on the bed and he is standing as we make out, my hand cupping his tiny little muscle ass and I am dying to fuck him when he says "I want to fuck you." I am thinking okay, let him go first before I get to plow that tiny little ass. All I feel is pressure against my hole. I doubt he even got it in but he is putting on a good show and cums all over my ass. So I get up and lay over him and kiss him as I try to pry his little legs apart for my turn. "Ah. I don't get fucked.." he said. I hopped up out of bed went to his bathroom took a towel and wiped his load off and threw it on the floor, Got dressed faster than I ever have and said cya!

The posts about dogs and dolls reminded me of a weird hookup of mine.

Met a couple online in the days of the aol chat rooms. They, too, had a tiny yappy dog. But they shut the bedroom door with him on the other side of the door.

He scratched and jumped against the door for a bit. Either he stopped… or we stopped noticing.

Sex was good. Fun was had. They opened the bedroom door. Tiny yappy dog had shredded their roommate’s collection of antique dolls. Utter pandemonium, screaming, blaming. I slithered out quietly.

Mid 70s. Met this hot looking short and shaggy haired guy in a local "sex joint". Very Italian studly looking. We go back to his apartment and start getting busy. I went down to my knees and unbuttoned his jeans and slid them down his legs, then I pulled his boxers down and what appeared before me was God like. The heavens opened up and the angels began to sing. It was like a small arm. After a few minutes of me giving him the most energetic service I'd ever given to that point he removed the rest of his clothes and laid back onto the bed. He motioned for me to crawl up on to of him so we could kiss. As we were playing tonsil hockey I nonchalantly reached up with both hands to grab his head so I could really dig deep with my tongue. Then it happened. As I grabbed his head there was a weird feeling that I was scalping him as his hair started moving. I looked up and his hairline had moved from a normal position on his forehead to almost just above his nose. He made absolutely no mention of it I had to assume because he was in the throes of deep lust and passion. So I thought quickly and rammed my tongue back down his throat and with my hands worked his hair back up to some semblance of where I thought it should be.

When we finished up he made a quick exit to the bedroom and a minute or so later came out after he had taken care of the hair malfunction. To this day I've never seen a man who had a more lifelike looking full wig.

I hooked up with this doctor who was very good looking and really nice. We went to his house and started making out on the couch. He then said that we should go into the bedroom. As he opened the door, I noticed what looked like a heat lamp shining very brightly. Next to his bed was a large cage which contained a huge iguana; the light was keeping it warm. I thought I was on the set of a kinky movie. We undressed and started having sex on the bed. All the while he was pounding my ass, the iguana was noticeably moving around in the cage. It was weird, but the sex was so great that I went back several times. The dr. and Godzilla.....good times.

R146 = toxic vers

[quote]we were all out together in that same club and he was there I pointed him out and the bitchy cunts went over and started barking at him. Poor guy 🐶🐶

LOL

I noticed a non-regular clubgoer at Limelight where I was working the ropes at Disco 2000, or maybe the Friday party. I figured with all the drug attention the club was getting in 1994 he might be some sort of law enforcement (white sneakers). He was.

He also lived about two blocks from me on the West side (low 100s), so after a few times seeing him at the club we chatted and shared a cab uptown. He invited me over and since he was a DEA guy, I figured, why not?

It was all great and fun until he came close to climaxing while I was fucking him and he started COCK-A-DOODLE DOOING like a freaking rooster! He also wouldn't rest and immediately went into rounds 2, 3 and 4, each time crowing like a deranged rooster. At some point, he decided to start calling me "Mommy". Aaaaand scene! I hustled my ass out of there and ran home at 5:30am in our shitty neighborhood.

He also had a verbal tic of saying "It's all good" a hundred times in a conversation.

Only two or three years later he tried picking me up on the street having completely forgotten who I was. Yikes!

Just moved to NYC, young 20-something. Went to G Lounge in Chelsea, met a cute guy and go back to his place, he lived across the street. Great apartment, clearly had money, didn't want to have full sex that night because he wanted to get to know me, I'm totally his type, etc.

Fine. We sleep with our underwear on (tighty whities for him), cuddled, made out, could this be love at first sight?

In the morning we start making out again, things get more heated, I remove my underwear and straddle him, grinding deep onto his hard dick through his underwear.

Look down, realize my dirty ass left a giant skid mark on the front of his Calvin Kleins.

He acted like he didn't notice it but there's no way he couldn't.

Date over. Never to be heard from again.

Scene.

To be fair R153, I'd have tossed you out as well.

This thread is the funniest thing I’ve read in such a long time. Thank you to everyone that has posted so far.

I've posted about his over the years, and it ended up becoming a Meme of sorts.

I was cruising in my car, driving to a location known for guys hanging out looking for sex. I saw this tall thin guy with glasses who looked at me and smiled. I smiled back. I found him very cute, but I was also pretty horny, so perhaps my judgment was altered. He gets in his car and follows me to my house. He follows me upstairs. I lay on the bed, he yanks my pants down and while kneeling on the floor gives me an insanely good blow job. He makes me cum, he swallows, all without saying a word the whole time.

He then looks up from my dick and says to me "DAAAT'S DA SUCK JOB!"

It was then I realized that he was a bit 'special'. I was mortified and got him out of my house as politely and quickly as possible. Poor guy, well, I guess he had fun, so whatever. It was still great head....

I thought dats da suck job guy came over to the apartment and said that after he was sucked off by the guy in the apartment. He would just buzz up and say something like "I wAnT tO fUcK NoW." because he was "special". And there were repeat visits.

No, R157. My story is as it happened. Anything else you've heard is just someone else elaborating, perhaps.

R148, great story, especially this part:

[quote] his hairline had moved from a normal position on his forehead to almost just above his nose.... So I thought quickly and rammed my tongue back down his throat and with my hands worked his hair back up to some semblance of where I thought it should be.

Nobody's perfect and this story proves it.

Really good looking Brazilian guy with the scariest cock I’ve ever seen - very thin and long stalk and an absolutely enormous cock head. There was no way that I could do anything with it it so I left.

Hooked up with a guy who was a mutual friend of my ex. Just as we’re getting into it, he lets slip that my ex used to cheat on me with him “all the time”. This was news to me, although it turns out my ex was the biggest whore that ever whored so I shouldn’t have been astonished. He was surprised that I was upset by this revelation. To say it killed the mood was an understatement.

Regarding micro/small cocked guys, I love topping them as they’re usually so grateful.

I was on the third date with a small-dicked guy. He cooked dinner…very nice guy.

He had a small, needy, yapping dog, so he wisely put it on the the first floor balcony before we hit the bedroom. After some wine, we didn’t hear him, and sure enough, the dog escaped and we found it dead in the parking lot.

Needless to say, I didn’t get any that night.

One guy I hooked up with had a cat that sat near the bed while we were hooking up....and just stared at us the whole time

R162 that's AWFUL!

R162. And the worst part is I dumped him a couple weeks later.

I see him out about once every 6 months and I still get a dirty look from him.

And it was 22 fucking years ago!

Not the weirdest for me, but one that I could see being weird for HIM.

I was out at the only place to go on a Sunday night. Flirted with a guy, ended up buying him a drink and then we danced a bit. We both got a bit handstand on the dance floor, anyone could see our bulges were growing before their eyes. I asked him to come home with me.

Once home, we make out, start to get naked, etc. He’s a sexy, swarthy Brazilian with a big cock, hairy pits and didn’t wear deodorant. I’m in heaven, smelling, kissing, sucking, tasting, and feeling him do the exact same with me.

We flip. We flip. We fuck each other. The session lasts an hour or so. He has to leave, since the next day is Monday. We exchange numbers while dressing a bit in the bedroom, and he goes to the front to find his socks and shoes. I randomly pat myself down and realize my wallet isn’t in my back pocket.

I quickly walk out front to see if he may have my wallet, but I do it under the very weak guise of being cute and still envelopes in after glow from some really amazing sex. I grab at him, pull him close to me, but I’m really patting him down as if I could feel my wallet. He makes his move to leave, and I start to get REALLY weird, so he gets MORE determined to get out on be on his way. He leaves my unit’s door and I’m following him down the stairs to the building’s foyer, still grabbing at him in a way I think should be innocent and playful. I don’t feel my wallet on him and I watch him hurry down the street.

I go back upstairs and do a more thorough examination of my bedroom, the scene of the crime if you will. My wallet is about two feet under the bed, probably kicked there by me when I pushed the poor guy onto his back and leapt upon him an hour before.

And no. I never got a call or text from him in the following days.

R140 OMG! *gag* What we’re all wondering: did he have an ASS?!

This guy I met around 2011-ish in London after chatting on Gaydar. We met for coffee in Southwark, and we hit it off. He’s the sexy, masculine professional type, so I’m all for hooking up. Arriving at his ‘flat’ in Bankside, it turns out to be a penthouse on the Thames waterfront with postcard views through floor to ceiling windows with Paul’s Cathedral dead centre, I was doing my best to act nonchalant, but this was the most impressive place I’ve ever travelled for a hookup. We start snogging on his sofa, and he quickly asks to eat my hole. Not one to refuse such an offer, I obliged. A couple minutes later he’s suddenly blowing air through my sphincter like a balloon and asking me to fart in his face. Whoa, that went from zero to non disclosed fetish in 60 seconds. However, I was so full of air, I couldn’t help it, and just let it out, and he went right back in blowing me back up. A couple more rounds, and he’s really intensifying, and I realise this is probably just the tip of his fetish iceberg…a brown one. I got up and said no thanks ‘it’s not really my scene’, dressed and left. He wasn’t too put off, and I’m sure I wasn’t the first or last in this situation. Mind you, all of this is happening framed in view of St Paul’s. If you’re ever walking along that area south of the Thames, look up and remember my story.

Israeli therapist, handsome dude in his 40's. We get to his place, start making out on the bed. He starts getting verbal with this hushed, urgent tone in his voice, asking if we can move to the nearest chair. We move, make out for 30 seconds, then we have to move to another chair. Another 30 seconds of necking, we need to move to another chair. And so on and so on and so on and so on and so on.

I politely excused myself after roughly 10 minutes of second base musical chairs.

R169, do you have any idea why this guy kept wanting to change chairs? Was it a chair fetish?

Certainly not the weirdest but the latest weird one. It happened today. I met a guy on sniffies and he was all into meeting me. I get to his place and he seems a bit wild-eyed, but not crazy. He said he had smoked a little pot and that made him incredibly horny. He also had poppers. I was cool with all that. We started messing around, pretty vanilla. Lots of groaning and such. He had porn on his big screen tv in the bedroom. Great. We lay back for a moment. And I hear his breathing is kind of heavy. A minute later, he's snoring. I mean out cold and snoring to beat the band. I jerked off to the porn and left. Totally out. I get up, get dressed, pet his adorable dog, and leave. I suspect he was up all night doing meth and it wore off. No proof, just a feeling from his rapid-speak.

R169 that is really weird!

I had sex with a guy and he referred to sex as a "session". Weird! I was appalled that I had sunk so low.

R153, of all the hos on this thread, you’re the trashiest.

I was maybe 22 and a buddy of mine and I had driven from LA to Palm Springs for the weekend. I had a big thing for daddies back then, so I was in heaven out there. I met this very Average Joe looking guy, about 45 or so. Tall, beefy, and very masculine. Looked like any suburban soccer dad and acted like one too. My catnip.

I left my friend to go back to the guy's place and hook up. He has a nice enough house, but I realize he's super drunk. Not sure how that happened (he didn't seem that way in the bar). But that was fine. I was buzzed too.

We start kissing and it's going good! Then he spanks me. Which was fine by me. I like a little aggression. Then another spank. Then he gets physical with me. Pins me down. I'm a decent sized guy, but he was much stronger. I panic a bit. But then calm down. I assume this is just his thing. And, you know, I'm game. I just don't want to be killed!

This is where it gets weird. He starts calling me Billy (not my name). For some reason. At first I correct him. I tell him my real name. Again, he's drunk. Easy to forget a name.

But he spanks me again. Hard. And forcefully tells me that I'm Billy. I start to get it. This his kink. His "Billy" kink. He then goes on to tell me this long elaborate story about how I, "Billy", am the worst neighborhood kid on the block and all the dads talk about how much they want to punish me. So that's what he's going to do.

I forgot the details, but this was a twenty minute story about my fictional Other, the street we all lived on, the other dads. All these storylines. It was so bizarre. But oddly, quite Compelling. The man had clearly given this porn-y tall tale a ton of thought! Mind you, I'm like pinned under him the entire time. Being spanked every now and then. And his pretty big dick is flopping around near my face. I could think of worse places to be!

But it was just too strange. And I started to feel like I needed to escape. The guy was probably harmless. But I'd played his game long enough. I finally asked for a drink. When he went to make it, I got out of there.

R175, what a waste.

Something that stays with me is I once found myself in bed with a really tall, very very very muscular man. I hadn’t really tuned in on his body at first as he was wearing a loose coat when we met.

It was distracting when he was on top of me and I realized this man could probably snap my neck with his pinkie. I know I’m an inner drama queen, but it kind of took on a “Sleeping with the Enemy” vibe.

Went home with a guy from The Works in about 1997. He lived behind Lincoln Center. Seemed cool enough. Went back to his place and we started making out Ang groping on his living room sofa. He excused himself, disappeared into the bedroom, and reappeared in the doorway three minutes later, nude but for a fringe vest and a guitar slung over his shoulder, with which he proceeded to serenade me. Badly.

I quickly decided we’d better get straight to the fucking so he’d stop singing and I could make a graceful exit.

Made it to his bedroom, where his bed was covered with 40+ Beanie Babies, each of which had to be individually introduced. 😳😳😳

Shockingly, the sex was actually pretty damn good after the pre-show, but I thought to myself never again.

Smash cut to six years later. I’m now in a Broadway show, and go out with a fellow cast member and his friend who had seen the show that night. The friend was very smart, very my type physically, and we clicked and he asked me to go back to his place.

I had a strange feeling we’d met before, but I couldn’t quite place from where. As soon as I entered his pad, it hit me: “Beanie Babies.” Yes, he’d grown a beard, lost the glasses and buffed up,, but it was Beanie Babies guy.

The kicker was a few days later when I recounted the story during therapy,, and when I got to the part “And you’ll never guess who it was…” I heard my shrink say from behind me (I was in Freudian analysis and doing the couch trip,) “Oh, No… not Beanie Babies?”

I guffawed, not only because of the absurdity, but because I was utterly thrilled that he’d actually been paying attention for all those years!

R176, I really did try and see it through. Gave it the old college try. Or high school try, if I was still Billy.

It was hot at times. But it's just got too weird. I don't regret getting out when I did.

[quote]Any weird celebrity hookups?

Not a huge celebrity, although a huge celebrity. I worked for a tech company in the early 2000s that was basically run out of a big loft apartment in Chelsea, w28th st. Actually thinking of this, this will be a 2 parter (lots of weird sex in NYC over the course of 20 years). Anyway when my boss would go on trips, I would use his apartment/office to set up a gloryhole to host guys since I couldn't do it at my place and always fantasized about trying it. Anyway, one of the guys who came over was Roger Bart. This was before the Producers on Broadway. He wasn't out, (never was I don't think). But he had a big beautiful cock to suck on. We hooked up one more time at his place on the UWS using the similar gloryhole setup at his place using a curtain between a living room and kitchen.

And this exact same apartment on 28th Street. was in the same building that used to host a sex club and a very early "Frat 24 hour Video" dorms called Apartment24 . Although the guys there were hardly frat boys. One was an aspiring magician, one just a retail queen and the other was dating Benny Medina at the time. Anyway the aspiring magician was a buddy and I had to sign a waiver to go and hangout with him. We hooked up a couple of times in the apartment on camera. I tried to hide my face as much as possible. But I have seen video you can't find anymore of me jacking off in the background.

The Studio? In the Flower District.

I remember that place.😈

r190 how big is Roger Bart? I heard huge. We talking double digits?

Started flirting with a guy at Rawhide on 8th Ave back around 2001. The entire bar seemed to be crackling with sexual energy that night. We go back to his place and seconds after he swallows my load his phone rings. He let's the answering machine answer. It's his father leaving a message that his mother had just died. I spent the rest of the night just cradling this grieving man. He was so sweet and so very sad.

with sexual energy.

I answered an ad placed by a college student for massage. So, I went to his place, which was an apt near the local college campus. He was good looking enough, so I decided to come in. He had a mattress on the floor, candles lit, and a bottle of massage oil next to the mattress. We exchanged a few comments, but I could see that he was really anxious. He told me to get undressed and lie face down on the mattress which I did. He also stripped and immediately went for my ass. He rubbed it with oil, inserted his finger, and began to breathe heavily. All of a sudden, he mounted me, and fucked my brains out. He was whispering the filthiest things in my ear about how he was going to make me his bitch and how I would be his hole whenever he wanted. I realized I was being raped ( or was it, since I liked it?). He finished in about ten minutes of intense pounding and sat down, panting heavily. I got dressed and left pretty quickly. Even though it was very strange, I remember it with great excitement.

Back in the 90s in NYC there was this drag performer, club kid, who was always flirting with me when out. If any of you remember Aqua with the goldfish tank breasts. Anyway I finally went home with him one night. I walked him home still dressed up from the club. We got to his place and he was doing this sexy fem seductress act, and I said that I prefer boys. And he went to his room and 10 minutes later came back as a boy. And I said I liked him better that way. And he started to cry a bit before sitting on my dick. It was sweet. He was kind of nerdy and sweet, my type. And I don’t think he was used to people liking him for himself.

Well if any of you know, Aqua went on to do some pretty Amazing things with her husband.

Who is Aqua's husband and what have they done?

That's actually pretty sweet and pretty decent of you (assuming it's true) r183. So many people would likely bail in two seconds when shit got real like that. I'd like to think I could stick around and comfort someone at what was probably the worst moment of his life if that happened (and with sexual energy no less!)

R185 are you Jack?

That’s Josh Kilmer-Purcell, R185, one of the original authenticated DL posters who used this place as his own personal promotional blog before making very ordinary soap.

Actually, I think r185 is Brent. R186 is the one who needs help with the Google Machine.

TBH, Josh wrote at least one good book before he moved to soap.

'I Am Not Myself These Days: A Memoir' or 'Candy Everybody Wants'

There are those that say he found a lot of inspiration for his books at DataLounge.

Had a fuck buddy who came over on Saturday nights but had to leave by 10 because he said he had to go to church on Sunday mornings which I thought was sweet. The fuck buddy thing evolved into dating. I really liked him and he was gorgeous. Eventually he told me he was a priest but wanted us to see eachother exclusively. No thanks. I don't share my men with God.

I had a similar experience, R192. I was sitting in the steam room of the local bathhouse, when a very handsome man in his 40's walked in naked and sat on the top . He began playing with himself, so I decided to explore. We ended up in his room for what was the most intense session I have had in many years. He fucked me for what seemed like and hour and kissed me as if we had been lovers. He wanted to keep seeing me, but wanted it to be in the bathhouse; I agreed and it went on for several months. One day I was walking downtown and saw him across the street wearing clerical garb, which led me to do some investigation. I found out that he was a very popular priest at a church on the other side of town. When I confronted him with it, he admitted that he was not only a priest, but the pastor of the parish. Despite all of the "baggage," he wanted to continue seeing me - we are still seeing each other to this day, six yrs later. Not very often, but very passionately when we do.

Oh, it's all coming back, now.

You guys are ALL right, but I am not Brent. This was way before he met his husband, circa 1996/97. Very sweet guy. I was younger myself and it was an exciting time.

R193 reminded me of another hookup I had, not with a priest, but a seminary student. He was "straight," not out and very little experience with men. Actually no real experience except with a Transsexual Dom he submitted to. This particular Dom had instructed him to find a "real" man to fuck him and for him to take videos of it and talk to her on the phone while he did it. He was a sexy closeted country boy. Picture a Josh Lucas type. He was living in the seminary in Chelsea at the time. I didn't live that far from there. I met him at night by the entrance gate and he led me into his dorm like living space. He had his own big room but you could tell the living space was communal. He was the kind that needed to be a bit high, out of it, to do anything with a guy. But he was so sexy and he took dick no problem. Actually he was a better bottom than a lot more experienced bottoms I've been with. He wanted me to video him getting fucked. I am not a videoing kind of guy, but I did it for him. I am glad I did, because I go back to the videos sometimes to get off. A couple of years later, during covid of all times, I fucked him in the empty apartment next to mine bent over the kitchen sink. He had such an amazing ass and his guilt mixed with his intense hunger for dick and needing to take it was so hot.

BTW, there are a lot more guys who are living "straight" lives that just want to get fucked in the ass than you would think. They really do fetishize gay sex (I know actual sexual acts aren't fetishes, but I don't know how else to express it) and want to try it for themselves. They aren't necessarily turned on by men, but intensely turned on by being used by a man. Sometimes they don't even get hard or cum, they just want someone to use their ass to get off. I've had at least five quickies like this. Anyone else encounter guys like this?

If I was blowing/fucking a priest I'd make damn sure he was wearing his collar when we did it!

R171. Good on you for not raping the dude.

I know meth have when I see it.

Just go through the hot arrested thread and you’ll see it.

I hooked up with a guy that worked on on one of our construction jobs. I had no complaints .... until .... we'd had a nice fuck session and after he said he wanted to go to a dance club. We went to a place just off the beach. I was wearing thong-type shoes. I tell him I'm not in a dancing mood, let's just get a drink, no dancing. Next thing I know he's on his knees crawling around the floor. He slips off my thongs and begins sucking and licking my toes. Not just licking, he was making goddamned love to them. He was running his tongue in and out between my toes and caressing my feet. This was in a well lit room with lots of people. I look down at my dirty feet and am skeezed beyond belief. Get UP! I tell him WTF. Who does this shit.

[quote] —I guess I'm a whore

Perhaps, R193, but it sounds like your beau is trying to supplant God Himself by trying to recreate the immaculate conception with your whore ass!

A lot of hookups are weird, period. Men are strange creatures. Some have strange mannerisms, strange interests and, at times, strange hygiene habits.

R199 I have had strangers kiss and suck on my toes in dance clubs as well. Once a guy started rubbing my feet after asking to see them on a busy sidewalk.

Met a guy on aol (I'm old) and we had a nice hookup. Afterwards he asked if he could shower. I said sure and handed him a brand new white fluffy towel that my mom had given me. After he left I went into the bathroom and the towel was hanging on the shower rod covered in smeared shit. It looked like he wiped his ass with it. Maybe HE didn't have a good time?

[quote]I have had strangers kiss and suck on my toes in dance clubs as well. Once a guy started rubbing my feet after asking to see them on a busy sidewalk.

Who has been to the Cock in NYC? Did that survive Covid? Anyone I literally had a guy following me around and every time I would stop in that packed back room, who would go down and eat my ass. He seemed normal in every other way, but he just loved eating my ass. It was kind of hot standing there like nothing was going on (the place is SO Packed you really can't see what's going on down between people) while he was tonguing my hole, just sipping my drink. It felt good too. I barely saw him, and just felt his mouth. I was also drunk and possibly high AF.

R202 well shit I'm in shocked disbelief. What the actual fuck. Did you like it? I will admit it felt strangely nice. It was embarrassing though.

The Student Union at Indiana University was notoriously cruisy. Back in the 80s, part of it was a sort of hotel. I met a guy with a really kind face and nice smile in a hallway where I was sitting and reading. He motioned for me to follow him and we ended up in his room. He laid down on the bed and I followed suit. He reached for my dick and pushed my shorts down. I reached for his and my hand met HARD PLASTIC.

Turns out he was missing both legs and his gonads. He detached the apparatus he slid into to ambulate and, well, he was a stump. I was shocked, but also quite young and polite. I let him blow me but as soon as I came, I newped out of there. He scribbled his phone number on a piece of paper and shoved it at me. I’d done my good deed, but was not going to repeat it.

Stumped.

Key West Met a an English guy 30’s in the 90’s had a cane but not strange or a turn off. He had prostatic leg, he had lost it in the Falkland War by stepping on a mine. Some of the best sex I’ve ever had as he was a cum hungry bottom and I love to top him. His shorter leg let go deep. Stayed for a week with me. If you’re reading the JB I treasure that time.