What's your biggest sexual regret?

Here's every single one in a nutshell, from first to last.

First. Went out a few times, spent a few nights together, but nothing sexual. End up in bed again one night, things getting heavy, for some reason kind of have a freak out and start saying things to make it stop. At this point in my life I've had sex quite a bit, but felt different this time. Was a really weird/bad time in my life, so maybe it was for the best, but still a regret. We ended up being friends for a while until she moved away.

Second. First date, off to a bad start. I'm quiet, nervous, kind of awkward. She's different, we end up not having too much in common, but both sticking it out. Go out for dinner, have some drinks, hit a bar. I drink, and drink, and drink. End up almost getting in a fight, she's into it. Bar closes, go get more food, almost get into another fight, she's into it. At this point I'm in full drunk asshole mode, she's still into it, telling me about all the kinky things she's into and how she loves to be dominated and aggressive guys. Last thing I remember is sitting on the hotel bed, she's rubbing my leg, giving me the eyes. That's it. I passed out. Next morning back to being awkward and quiet. She was more into drunk aggressive me than sober quiet me. Probably for the best it never happened, but still.

Third. First date, super nice girl, get along well. Go out for dinner, have some drinks, end up at a bar. I drink, and drink, and drink, but no fights this time. She's flirty, everything's going good. End up back at the hotel, she goes to have a shower and comes out in nothing but panties, I'm still drinking at this point. We fool around and once again I pass out. Wake up in the middle of the night, wake her up, fool around more, but pass out again. Wake up sober in the morning, go out again, but she's uncomfortably clingy now, like we just got married last night clingy. The whole day is super uncomfortable for me. She wants to get together again at my place the following weekend, say okay, cut off all contact. Again, probably for the best nothing happened, but still.

Fourth. Quite a bit older now, been through some heavy relationships, seeing a much younger girl, almost 10 years younger than me. She's stacked, blonde, not much in the face, but the body of a goddess. We go out a few times, she spends a few nights at might place, we fool around quite a bit. The more we go out the more the age difference becomes apparent. She's only been out of high school two years, I've been out of high school for almost a decade. I've traveled all over the world, she hasn't left the country. I've had numerous relationships and experiences, she's a virgin. I couldn't do it, she deserved better and I wasn't looking for a relationship, just sex.

That's it.

/r/AskReddit Thread