Unplanned Hookups

Yes, A guy who came to install countertops in my house. Very professional, did a great job and when he was all done and about to leave he turns to me and says, "Do you want to fuck around?" Sure and we did

Who hasn't??

^ (psst)... I think the idea of the thread is to talk about when it happened 🙄

Met a guy at intermission of a show. We were each there on our own. When the show was over, he waited outside until he saw me. We went back to his hotel nearby after.

Hott

At a conference. Met him; we talked; we went to my hotel room.

While he was fun, he just wouldnt leave

My grandpa took off his clothes and said “help me with this”. I said “how”? He said “put your mouth on it and go up and down”.

R7, dont know if you're posting as a joke, but I actually have a friend where something similar happened.

R8 I was being raunchy and it was a joke

Do babies cry?

During the early days of the pandemic, when nothing was open, my friend referred me to the guy who cut his hair and was still doing so on the down low in his salon. When I went, I was the only one there. After he cut my hair, one thing led to another and I ended up fucking him in the supply closet.

Mine was a miss. I had someone come over to talk about redoing a bathroom. I explained to him that the woman who I used to do my kitchen had been a designer. He responded by saying that he was also an artist & offered to do a drawing of me.

I had a few romantic encounters in the Senate gym with some gentleman callers

Forgive me Father, for I have sinned. It has been three months since my last confession. I….wait, are you supposed to be in here? Why are you removing your investment? Oh my God!

vestment

Yeah, I met a guy at a state fair. He was an exhibitor and from a different part of the state. This was back in the late '80s

Does a sixth fleet reunion count?

This weird ass at a Renaissance fair wanted to rape my ass.

[...]

Are you all so young that you didn’t experience cruising in the 1980s and early 90s. Walking down the street. Eye contact made with knowing glances of internet. Heads turn after passing. Slow down. One stops and looks in a store window. Other one turns around and then stops to chat. Eventually do one of you live nearby and ably o host. Voila! Orgasm and goodbye.

^ internet not internet. And not with the original intent of looking to get laid. But just a serendipitous encounter.

Um. This was life before the Internet. It’s still out there…just keep your radar tuned (stop staring at your phone on the street, in supermarket, stores, etc. lest you miss the best fuck of your life). I had one truly exceptional post-Internet random hookup: met at an 8th ave / Chelsea Starbucks. About 2011. He was 30ish. I was 40ish. I was about to visit my friend after work. This guy was checking me out, I smiled, and he then walked over to me and began talking. Hot energy. Went to his place. A great 45 minutes.

How many hotel bar hookups?

Unplanned bowel movements

With all of these im like, "sure that happened"

Every SINGLE time I go to the gym.

John Travolta @ r26

Why do you doubt, R25? Men have sex all the time -and in all kinds of places and situations.

I was on a (straight) cruise in February, sitting in the sauna. A guy came in and sat across from me and loosened his towel so I could see his pubes and the top of his dick. He started talking to me and touching himself through his towel. The conversation was innocent, but his hand was clearly busy and he was getting hard. When he saw me getting hard he opened his towel completely and started jacking. At that point another guy was coming in so the towel when back on. I got up to leave and the first guy followed me out. We went back to my cabin and I fucked him.

It happens.

Back in my single days, yes.

Went to the wedding of a girl I knew from college. The groom had all these cute groomsmen and friends there. It was 2 day long affair, and the wedding and reception were at a hotel. This really hot guy had been flirting with all my girlfriends, and had made out with one of them the night before. They were all trying to hook up with him. I was coming back into the hotel lobby from a smoke break (ahhhh…smoking) and ran into him.

He said he was on his way to get something from his room and asked if I wanted to ride up with him. Naive me had no clue. The door had barely shut before he pounced on me and stuck his tongue down my throat. I was shocked, but in a good way. We kissed, blew each other, and stroked each other until we both came. We didn’t talk much, and we pulled our clothes back on and went back downstairs. Just before the elevator doors opened, he grabbed me and kissed me again. Didn’t really talk again that night, or ever again! I did learn years later that he married a woman and has had a couple of kids.

Yes, many times...

R28 I'm a shy guy. I guess I need to get over that.

I have myself no gaydar whatsoever, so if a guy were to send me signals, I'd miss them.

"Yes, A guy who came to install countertops in my house. Very professional, did a great job and when he was all done and about to leave he turns to me and says, "Do you want to fuck around?" Sure and we did"

It helped that, during the entire project, you were standing there, bent over, presenting hole.

It wasn't too difficult for him to figure it out...

Jeez, I know this thread is still in its early days, but I already feel like the city whore. It would be easier for me to say where I haven’t had a random hook up. In the early 80’s when I was in my early 20’s i was travelling on a couple decker bus in London. It was a weekday morning and almost empty, the conductor played with and sucked my cock in the stairwell for about a minute between stops. Late at night on the underground platform somebody might just look at you, the next minute you are down a quite hallway exit having a quick wank together. I sat opposite a guy in an otherwise empty tube carriage once and we had a quick play between stations. I was in Harrods menswear department in the 90’s shopping. I tried on a pair of expensive trousers, the assistant who served me came into the changing room to to hem up the bottoms for me. I hadn’t fully zipped up the trousers or fastened them and was clearly displaying a a full upright hard on through my pants. He was of course on his knees whilst sorting the hems and he did the polite thing my servicing my cock.

Passport control at my airport- he followed me to the bathroom.

Just blowjobs/wanking in the gym, all non-verbally agreed

Bump

What r34 said. In the 1970s, I used to meet guys on the street, at the supermarket, or on the subway. Of course, I lived (or shopped) in zip codes 10023, 10003, and 10011. When I moved to DC, I met a guy who became a boyfriend while we were both looking for sweaters at Jos. A. Bank.

I sometimes laugh when someone on DL goes on about "shit on my dick." It wasn't something you really thought about those days. Surprise anal can mean all kinds of surprises.

[quote] had one truly exceptional post-Internet random hookup: met at an 8th ave / Chelsea Starbucks. About 2011. He was 30ish. I was 40ish. I was about to visit my friend after work. This guy was checking me out, I smiled, and he then walked over to me and began talking. Hot energy. Went to his place. A great 45 minutes.

Crap! That may have actually been me!!

I went out of the gym late. I headed to the parking lot when I noticed that a guy, whom I used to see working out, was going out of the gym too. He looked at me and slowed down. I asked him if he wanted a ride because it was rainy and he said yes. Within one minute in my car we agreed to go to his place to fuck. Et voila....a Greek with very exciting moany grunts.

In the swimming pool area there was that hot old guy wearing sunglasses. I passed in front of him twice to pick up my drink from the bar, but he never gave me the look. I thought I wasn't his type. An hour later I enetred the elevator and he was there and he started to talk and asked if I liked the city. I told him he was hot and immediately we started to kiss. I asked if he would like to join me in my room and he said yes. A Dutch daddy who jerked off the biggest amount of cum I have ever seen.

Any surprise anal?

At the Minneapolis airport men's room, it did not work out

Bump

Cigar shop just before closing. I bought what I wanted and the clerk locked the door, took me into the humidor and gave me an eye-rolling, pelvis-thrusting professional suck job.

We're still (distant) friends.

As a gal, unfortunately the nuns rearing us did not prepare us to expect desire and all its temptations. Everything was okay while still confined to an all-girls learning institution yet afterwards, having broken away from such constraints and oversight sometimes a chance encounter led to mid-day tension relief.

The only downside was being convinced it was unnatural until I realized it wasn't.

Many times in many places. Was at a conference in Atlanta at the Westin Peachtree Plaza. I think I was arriving late morning and going up a very long (2 or 3 stories at least) escalator. Linked eyes with a very handsome guy coming down. He scampered off at the first possible opportunity and followed me up the escalator. The next thing I knew we were in his hotel room. He was a flight attendant This was 2009. so not so very long ago. He was Portuguese, based in London. In NYC in the early 1980s it could be anywhere at any time. People followed me home, I followed people home - one guy invited me to his hotel room at the Waldorf Astoria after we met somewhere else. In Florida in the 80s and 90s if you were still at a bar during the blue light special near closing time, anyone was fair game. I guess if you have your gaydar set on maximum, many opportunities "arise". Now I'm in the invisible age of gay men, and when I pass attractive men in pairs, one will turn to the other and say "did you just feel a little gust of wind?" I don't regret any of those unplanned hookups - well, there were a few coyote dates, and a few potential maniacal axe murderer hookups, like the guy who went out to his car after he arrived at my place because he needed his luggage and didn't want to leave his GUN in his car.......

R44 what was the build up?

[quote] Now I'm in the invisible age of gay men, and when I pass attractive men in pairs, one will turn to the other and say "did you just feel a little gust of wind?"

Lmao!

I grew up fat, no one cared.

Bump

One late morning a gas co. employee knocked on my door, waking me up. I slunk to the door in my bathrobe, groggy. He was there to turn off that utility as I hadn’t paid bill for a few months. I wasn’t poor, just flighty.

I invited him in to sit on the couch while I wrote a check, and as I started becoming more awake I realized he was fairly attractive. And MANSPREADING, with his arms across the back of the couch. I also realized I was sitting kind of close to someone while very naked under a thin robe.

I said, “You must meet a lot of crazy, interesting people doing your job.”

“Yeah” he said.

“Do they ever offer you sex when you come by?”

“Oh, yeah!”

“Do you ever say yes?”

“Oh, yeah!”

“….. um, do you want to have sex now?”

“Oh, yeah!”

And so, reader, I blew him.

r38 - I mean, shit (literally) happens, but 'surprise/unplanned' anal is definitely not something I've engaged with for that very reason. Call me a prisspot, but whether I'm topping or bottoming, going in without any preparation just isn't for me. I did get an unplanned blowjob from a handsome nigh clerk at 7/11 once. It was 2am in a suburban location so the chances of being walked in on were pretty slim, but, still, it was fun!

R51 hot! What did he look like, Ms. Eyre?

I felt rather slutty writing that, as I don’t remember EXACTLY what he looked like, just his type. I kind of mix him up with another straight-acting guy I hooked up with during that period.

He was probably 5’10”, thin but fit. Perhaps 40? Dark hair a little long. Maybe 1/4 Hispanic…? His skin had a little color. He had the kind of dick that was perfect for practical purposes. Bigger and fatter than most but not like it was going to destroy you, or maker you puke when deepthroating. But definitely the feeling of, “Okay, this is a real DICK I’m working with!”

In retrospect he must have had the greatest job for a swinger guy like him. This was slutty, upscale West Hollywood and I bet men, women and trans were dropping to their knees whenever he showed up to shut off their gas.

It’s probably the porniest thing that ever happened to me. I’m glad my bill wasn’t on automated debit back then!

I stayed in an old hotel once for work. I was sitting with my laptop in the hotel bar - no one else there but the bartender and me. I asked the ol "Do you ever hook up with hotel visitors?" He said he fantasizes about it a lot, wants to, but has to be super careful because he will get fired if anyone found out. I leave the bar, put my room # on the check, and about an hour later he knocks on the door. It was a fantastic fuck.

Was minding my own business at the library….yada yada yada… I was sucking the librarian

I was at the Shell Station ....

I was at a weekend conference and ended up chatting with the president of my (statewide) union. Next thing I knew I was in his room giving him a foot rub -and then a blow job. He was sweet and very sexy. The following year I approached him at the same conference and he clearly remembered me, but we didn't hook up again. It's weird when you're in a room with 500 people listening to to a speech and you want to tell everyone, "I've had him," but you know you can't...

I went out to check the mail….yada yada yada….3 guys had taken turns fucking me

This was many years ago but I was at an outdoor restaurant at the beach in the summer having dinner with my friends - we were sitting right out front on the sidewalk. I looked up and coming down the street were a group of guys, obviously friends out for the night. One of the guys stood out to me, he was practically lit up with a spotlight, and I it was like I was strike by a bolt of lightning - he was the exact perfect conjuring of my dream man. We locked eyes and stared at each other as he and his friends hit closer. My friends caught on and so did his and they all practically pushed us together as they came up on us. I stood up and we just stared at each other like no one else was around and leaned in and just hugged each other, like it was a long-lost reunion. I can’t even describe the feeling but I knew something big had happened, some fate, some destiny, something profound. We looked at each other and at our friends and he said “do you want to get out of here?” and off we went, all if our friends calling to us and laughing and giving us a hard time. We went to my place, to my room in my shared house, and we had the most amazing sex I’ve ever had before or since. He was literally the hottest man, my absolute archetype of perfect man and I was his as well. We could not keep our hands or mouths off each other and spent the rest of the weekend together. He was on vacation from a city far away from mine and we tried to make it work but it was just too difficult and I was too young to realize how significant it was. We connected again years later through Facebook but we were both married off by then. I still think about him all the time and I fantasize about us having a life together. I’m thankful I even had that weekend though because I know that’s rare.

Wow. That's something, R60!

Well, don't give up, maybe both of your husbands will drop dead.

Yes, lots, for decades. It’s called a date or cruising and getting lucky.

R54 You're such a great descriptive writer! Thanks!

r62... OK.... wanna post just one example? We'll wait.

Ah- unplanned- that would be casual cruising that produces a “hit”- yeah- lots- and for decades.

R56 You yada yada'd the best part?

r58 lmao

R64, In a bar, on the street, on the beach, in the gym, at a party… shall I go on?

r60 WOW, perfect story. So glad you had that experience just once in your life! If only everyone could.

R68 Well then, you were obviously the bottom in these stories ;)