I regret not fucking Janis Joplin.

 

Three non-experiences from my student time.

I was about 20 years old when I walked down the staircase of a department store. Two attractive girls, sitting on the stairs, giggling, both asking me 'hey, don't I know you?' For some reason I didn't get that as an invitation but for a long time I had fantasies of a threesome with them.

About the same age, I was on a three-day course somewhere else in the country, and we (my fellow students and I) stayed at the dorm of the institute. There were students from another school too, and a girl who apparently had the reputation of being the school's slut, hit on me. In the last evening she was really trying to get me, talking some real horny dirty talk, while another boy from her school couldn't keep her hands off her. I was thinking to suggest a threesome but for some reason I didn't have the guts to.

While riding my bicycle to the nearby grocery store, a guy wistled and yelled at me. When I looked up he made wanking movements. I had never thought of doing anything with a guy before, but back home I couldn't help getting horny for the idea.

Fast forward to a few years ago, a friend of my wife's niece took the opportunity of me being alone to completely go for it and hit on me. I must say I've never been so tempted. But she's as much an unreliable bitch as she is smoking hot, and also I knew I really didn't want to cheat on my wife, so I do NOT regret that I have fought the temptation. I did tell my wife, though, about her attempts. And every now and then when I'm horny, I still think about how it would have been to fuck her.

 

Pigpen was in Charlie Brown. I think.

 

I should have let this guy cum deep in my asshole cause i still curious about the feeling of warm cum filling me up and i should have swallowed a sexy tranny load.

 

Pigpen was a dirty boy.

 

I regret that when Lisa and her date came in to the bedroom where Colleen and I were having sex that I didn't take more advantage of the situation.

 

Good one

 

Gang bang. It's not too late, but highly unlikely now.

 

@BlackJade - what makes it so unlikely?

 

There are things I have done and have been done to me I think about too much but I honestly don't regret any sexual act.

 

My regrets basically boil down to not having the courage to go after what I wanted. I'm a lot more assertive now, much more able to ask for what I want, but still I know opportunities pass by me.

The big one I regret is not trying to make a move on my mom when I still lived with her.