What's your biggest sexual regret?

I had a 3some that could've been really hot but instead I busted a nut in my girlfriend in like 3 minutes which ruined it for everybody. Damnit I should I have busted on her back. It was my first real glimpse of heaven though - I was hitting my girlfriend doggystyle and all was fine but then then I slipped a couple fingers into her hot friend and that's all it took, I blew my load.

A few weeks before that was our first attempt - I happened to have some "magic" mushrooms, which I foolishly let the hot friend eat before we got started... she ended up sitting on my lap in her underwear telling me how bad of a person she was. It was still kind of hot but not quite what I was going for.

Before weed was legal, I had 2 girls come home with me from a bar because I had some killer buds at my apartment. I made out with one of them and boned the everloving shit out of the other. I should've boned them both. That's a minor regret.

After a bachelorette party, at my brother's house, a few people were sleeping over on the couches & whatnot. I ended up between two girls. I was making out with one girl while reaching back & fingering another girl. They were kind of competing for my boner. In the end, neither of them got it. I could choose only one, so I chose the finger girl because hey that's 2nd base as opposed to makeout girl who only on 1st... but finger girl cut me off at 2nd and I ended up sleeping my boner off, on the floor. That whole situation is just regretful.

I've had lots of other opportunities but I don't regret missing them because I feel like I've dodged a lot of bullets in my life by avoiding the whole dick-in-crazy thing.

/r/AskReddit Thread