Ever had a random hookup turn romantic?

[NHeat]

Recently I met a couple guys online for hookups that turned very sensual and romantic. I'm not always down for that kind of thing but it was nice. Lots of kissing, eye contact, missionary fucking, etc. Both guys happened to be younger and shorter than me, which made me topping easy.

Just wondering if anyone else has ever experienced this from a random hookup? 

[BlueSaphir]

I feel in love with two guys in my life. But the first guy didn’t felt the same. He fucked me like I was his girl though. Despite having a girlfriend that time. 
 

Recently, for awhile. Another fuck buddy I enjoyed for years and turn into a heated love interest. I found out he is divorced and I had to find out on my own terms he has 3 sons with her. He doesn’t know I know he has kids. But I understand we may not have a romantic relationship because of his complex relationship with the ex wife and their kids. But he knows how to fuck and he makes feel like I am a significant for him. 

[Tiboer]

Absolutely love when you find an emotional connection with someone who was just supposed to be a hook up.  Sometimes it goes further than just sex.  Other times, because of emotional commitments (like married men), it has to just stay sex.

For me, one stands out—met at the bathhouse.  He was my sexual and intellectual  ideal—I would have married him if I could.  But he was married and had a kid—so I could just spend time with him at the bathhouse.     
 

Sadly, I haven’t seen since the pandemic.

 

[viking8x6]

At one point, I was dating someone I had met in a public restroom. He got cold feet and left me to go back to his girlfriend. Then 6 months later I saw him at the video store with another guy.

Moral: Don't try to date closet cases. It doesn't end well.

[NYBBGUY58]

I certainly have. Connections sometimes just occur and can feel all sorts of ways. Given the, uh, close quarters sex may feel extremely intimate.

[ffabbian]

Many times, some are hook ups that I may never see again, others have turned into friendships, FWB of BFs. I've had romantic connections in unexpected places with men that turned into a relationship, twice wirh men i met at a Sauna and once wirh a guy in at an orgy that became my bf

 

[Sfmike64]

Many years ago, I knew a couple in Boston who met in a cruisy t-room in Harvard Square, and were together for 25 years.

[DJ2023]

I’d like to have a relationship with a guy of a similar dirty mind to mine. 

[thebigpig]

I've two random hookups turn romantic. One guy was my second load of the day but we ended up clicking. We were together a little over a year. The other guy started out as a one time thing, then it became a regular thing, and before we knew it we were dating. It really snuck up on us and we're still together. 

[hungry_hole]

On 5/24/2025 at 12:48 PM, Tiboer said:

Absolutely love when you find an emotional connection with someone who was just supposed to be a hook up.

Many years ago I met a Latino guy at the sauna Spa Excess in Toronto. We met in the dark area in the 3rd floor in the very dark room at the end. I started sucking his cock, uncut, we then kissed and he turned me around and he fucked me an bred me, while he groaned in Spanish "Te voy a preñar" (I'm going to breed you) so I responded in Spanish "Dame tu leche". I was so horny that I came while he pumped his load in my hole. So I left the dark area with him and we talked a bit at the bar on the first floor. We were supposed to meet later to exchange info, but he disappeared. He was hot 20-something guy from Chile.

I once visited Santiago, Chile, and placed an ad looking for anon action, door of apartment open, walk-in, etc, stuff that Chileans were not used to seeing. I waited with a hood on, and eventually the guy started fucking me. After sex I took the hood off and he says "I remember you from the sauna in Toronto!".

I was there for 3 weeks so for the next three weeks we spent every day together, travelling to different places in Chile. When you first meet at a sauna and have bareback sex, and then establish emotional ties, there is nothing to hide or pretend to be.

[lycis]

Married mine.

To be fair, it wasn't totally random in a Grindr way. But was at a gay bar with a friend, and a friend of my friend I had never met came over and started chatting/hanging out with us. We all went home together to hang out. One thing lead to another and the friend of a friend started huffing pits, and slyly revealing the jockstrap he had underneath (clearly was trying to hook up at the bar!).

I end up dragging him to the guest room and pounding the hell out of him. The way he fucked was just... so perfectly in sync with me. We then started meeting up every weekend to fuck, and turned out we were the exact same level of piggy. I had never been with anyone before that shared even 1/4th of my kinks so someone who checked every box was almost panic attack inducing it was so hot lmao. We got up to a lot of bullshit including giant 100 person Folsom orgies, house rental orgies, steamworks adventures...

Ultimately though he was a really lovely, honest person with the heart of a lion that inspires you to do your best. The kind of guy you could trust with anything. Tie in the fact that he laughs at my stupid jokes and gets my sense of humor, then follow that with him helping me through a very hard event that happened in my life, deciding to propose was easy.

The only thing we haven't done is me whoring him out in a cumdump session on grindr/sniffies...super into that scene, but I'm more of a switch so it feels hard to push things in such a dom top direction. Also covid happened and ever since then his sex life aspirations have cooled off a lot. He's a lot more into fisting/toy/kink play now. I still have a bit of a desire to get up to bullshit though. Navigating new waters and all that 🙂

Edited yesterday at 06:45 PM by lycis

[Olderkinkybiguy]

It’s happened several times. It’s nice when sexual attraction turns more intimate and a mental bond can form. Two times we ended up in a long term relationship and moved in together. Once two people learn what the other enjoys, intimacy can freely flow and being together can reach new heights. 

[a2nudist]

I met my husband through what was supposed to be a quick fuck after work one night back in 2001.   Turns out I was the first to fuck him as he had only done oral with guys before.   After I dropped my load and was getting dressed he got out of me where I worked and showed up the next day at my office.    So after a few more fuck sessions we started dating.   And when gay marriage became legal we were married.    Now it's been 24 years.  Long time for a hook-up!

[Njn0mc]

Yea. Very many years ago.  I know i fell in love with my master. He taught me all kinds of things and the way he played mind games with me i started to think of him all the time. Even when he would make me play with his friends alone or make me go to their homes I did my best for my master.

He was good looking great body and great hands.  I do still think of him occasionally.

[bbslutdanny]

There's been quite a few hook ups where I've really connected with that person. I remember meeting this guy and we shared very similar interests in almost everything, and I could see myself starting a relationship, but something always goes wrong...