What was your most unexpected or random hookup that completely took you by surprise (friend, classmate, roommate, etc)? 😮

A man who came to my conference presentation. I presented, we spoke afterward, saw each other in the bar later, fucked back in my hotel room.

The next day when I saw him he was the main keynote presenter for our conference that day.

My best friend in high school's first cousin. Years later, I picked him up one night at the Club Baths and brought him home with me. We had known each other through my friend, but had never had sex in high school. It was the best sex I'd ever had. He's the man who got away. Actually, I'm the one who did the "getting away," and I've often wondered what would have happened if I'd stayed.

My ex housemate. He was getting divorced and straight when I lived with him so never made a move. Afrer a year of being single he was much less repressed in a lot of ways. We reconnected online and I confessed I’d had the hots for him. I went over to visit him and ended up in a pretty intense session with me sucking him off twice. Gorgeous cock and huge loads. It only happened once and he has since remarried. I wish I could do it again and still jerk off thinking about our encounter.

BILL TAYLOR

Had a good straight lad I knew "peripherally" socially for over fifteen years ask me quite casually for a blow-job one night I saw him out. He knew quite well I was fond of him, and knew I was gay. Previously to this night, he was always a great hugger, but nothing ever tipping me off. He had broken up with his girlfriend recently, and had been complaining about how randy he was. Great time making out, blowing him, fingering him, and cuddling. I believe I got off four or five times that night. Kind of trade-y, as other than the kissing and cuddling, no reciprocation. No regrets though, awesome fantasy come to life!

A buddy of mine at work got in a fight with his wife and asked if he could crash at my place. He showed up buzzed and upset. He left the house without anything so after talking a bit and a couple of beers I got him some clean clothes and he jumped in the shower. I was in bed when he got out and I made the couch up for him to sleep on.

He wobbled into my room and asked if he could chill a bit with me. I thought it strange bc he knows I’m gay. Anyway he mentioned he was sorry to put me out and I said it was cool. At that point he started casually stroking himself through the basketball shorts. I asked if he needed help and he said yes. So I stood him up, turned the lights off, dropped his shorts kneeled down and gave him a blow job.

Really nice cock and body. He fucked my mouth and said you want my load? Here it comes and shot down my throat. I came right then as well. He dropped into bed and I let him sleep with me. The next morning we did it again and on occasion he shows up to get serviced after a night out with his buddies. No complaints here.

That thread about guys eyeflirting made me unexpectedly worked up. Bump!

I was presenting a session at a large conference. This guy in the front row kept giving me the eye. Later in the bar, I was drinking with my coworkers, and he came to join us. After the group disbanded, He and I fucked numerous times in my room. I had to see him the next day as a conference participant while I continued to present. It was hard to make eye contact with him. We continued hooking up throughout the conference.

Ex's best friend.We had just broke up and he basically offered to take me out.We went to a place that was running a happy hour.Two for one.Both of us got pissy drunk and ended up freaking in the car garage.It was good.But he loves his bestie...so we stopped after doing it a few more times in semi-public places (i am a McDonald's bathroom hoe) An we promised we would never tell ex.....

No i don't feel bad about it.My ex was a cheating hoe....