Sex with someone you shouldn't have.

Yes, and I won't say who or why I won't say. Had sex with a couple of friends girlfriends. Had sex with two of my ex wives friends. And one I will admit to to... a friend of my ex stepson, she was fantastic fun.

The Mother of an ex- girlfriend, my Mother’s second cousin and her daughter as well, my 70 year old neighbor, my 30 year old neighbor…I lived the life of a complete reprobate for a number of years. I am managing things somewhat better now.😛

In high school I was on a traveling volleyball team and I regularly had sex with my coach and the assistant coach who were both married. I also had sex with my boss when I was a waitress.

An older married woman I bowled with. She wanted to use me to get revenge on her husband. I was happy to let her.

If you had sex with someone...you should have.

Quote by Ivanka
Yes, once with a long-time friend that became very awkward und affected our friendship afterward.

A few times dating that had me just shaking my head with regret afterward.
Sometimes they became love-sick, over possessive, or completely changed as a person from when you first met them.

I also regret having sex with my then best friend, it has almost ruined our friendship for the same reason you describe in the last sentence.

Revenge sex is great. The best sex I ever had was with a woman whose boyfriend had been cheating on her. I helped her move some furniture in her apartment Afterwards, we had a couple of beers and chatted. We ended up fucking all night. She had little titties which I really love and a really tight pussy. I didn’t find out until a couple of days later that she fucked me to get back at her boyfriend. They patched things up so I never got to fuck her again but, man, was she a good fuck.

Quote by Cycoape

An older married woman I bowled with. She wanted to use me to get revenge on her husband. I was happy to let her.

Most of my sex partners were persons I shouldn't have done it with.

A woman I met online, she was married and we met maybe half a dozen times for sex. Her husband owned a large commercial generator company and was out of state on business a lot. We needed up fucking all over their very large and lavish house, including in the hot tub on the deck for all the neighbors to see. We also fucked at his place of business…on his big boss desk!

Got a blow job from my friends girlfriend.

Most of the guys I’ve had sex with I probably shouldn’t have but boy was it fun lol

Sex no sext yes.. many many regrets if u can’t do it IRL perhaps (me) should do a hard pass

Never had the opportunity

Happens to the best of us! I enjoyed it though!

Family member

Once I drunkenly took home a horny seventeen year old girl I met at a party. I was twenty-four and should have known better. That was legal in my state, but wouldn’t have been in some others.

The list of people I should have had sex with, but didn’t, is far, far longer. Those missed opportunities drive much of my writing.

My girlfriends twin sister, I didn't even know she had a twin let alone a sister

Like banging your ex-girlfriend's best friend, so the ex gets really mad. Then you know she really still wants you.

We were about 28, my friends wife and I. We were all drinking buddies. One night, the conversation between us came up of, “Would you ever do it?” We both said no. Many drinks later, we fucked on the couch. It was shameless and blameless between the both of us. She had kids, I didn’t. We both got what we wanted, neither of us speaking of it again. She had long, jet black hair. Her eyes were bright and beautiful. Her name is Courtney. I don’t regret it.

Yes my brother in laws ex-wife. Before I was married and a few times after until she moved away. Retrospect probably should not have done so.

My first wife lol. It would have saved a lot of grief 😰.

Quote by cal_teddybear
Has there ever been someone who you shouldn't of had sex with but you still did it? Who was it and did you continue having sex together?

Yes i did. It was my ex gf 18 year old daughter at the time and we still have sex at times now.

Yes...my mother-in-law...she was 50, I was 25. One of the most memorable fucks of my life

My third cousin and I still don’t regret it.

my friend's son and another time also a family member

My best friends daughter and her best friend on the couch right beside him while he was passed out. I had sex with them both since.

Once, I introduced a girl I was friends with in college to an ROTC friend who really liked her. They went on a couple dates but at one point, she came over to my room on a Friday and we were just hanging out and chatting. Guess she felt he was moving too slowly. She ended up spending the night and we kind of spontaneously fucked in the morning. Kept fucking through their whole time dating. Some of the hottest fucking raw sex I've ever had.

My best friends girlfriend gave me blowjob while he slept in the next room. I fingered her while she sucked me.

A neighbours wife in her marital bed while her Ill husband listened.

A teenager on a storeroom floor. The same teenager against the wall in a kitchen.

With a cheating wife in the marital bedroom while her husband played video games a couple of doors down the hallway.

In the cellar while her husband watched TV upstairs.

With a whore while my wife thought I was watching a film at the cinema.

In an office archive with my office assistant at work. On several occasions over a 3 year period. We were both married but wanted more sex. It was great while it lasted.

With a barmaid 8 years my senior. My first fuck to lose my virginity. What a great first time experience.

Yes, My male roommate after my divorce. he told me he was strsight and i thought I was. but he seduced me and made me his slut. I wasn't as straight as i thought. unfortunately I ;oved it

Yes I was 21 and she was 18. It was the ex-GF of my BFF. They were "on a break." She and I went to dinner "as friends" and ended up back at my folks house (they were gone for the weekend). We had a lot of foreplay and after she sucked my cock she said "I need that cock in me." About two years later we got naked again but only foreplay. They ended up getting married and I was the best man. They divorced 15-20 years later.... The weird thing is that her sister took my virginity in high school. To my knowledge, the sisters do not know they both fucked me. And I'm 99.999% sure my buddy doesn't know I messed around with his GF.