Sex with someone you shouldn't have.

I suppose I have or at least others might say I shouldn’t have but I have the morals of an alley cat and rarely turn any opportunity down.

A few times. But I've been in a sexless marriage for many years and still have lots of urges and needs.

Yes. She was 30 and I was 48. Amazing sex. Dumped six loads in and on her on our first time together. Hadn’t had that much sex in one night in many years.

Yes my mother in law

Yes,5 bosses. Always fun

Quote by Cal2024

Yes,5 bosses. Always fun

At the same time?

My husbands brother as well as his Boss

Yep, and I learned the cardinal rule: don't sh*t where you eat.

I suspect there are a collection of things I shouldn’t done at least in other people’s opinion.

A girl who was under 18 and I was 20. Big mistake for many reasons.

My beautiful brown skin boss. We were both mid 40 s. I was the maintenance superintendent and she was the project manager, built like a brick outhouse. We are ahead on all the work stuff and start talking about our many similar life experiences. Soon the talk is getting intimate. She ask if I ever been with a black lady and I inform her I have not but there is always a first time. She admits to never having been with a white guy. We talk about the complications of work relationships and neither of use wanting to ruin our marriages. She tell me if she did she could see me with her. We finished the day with mutual orgasms.

Not proud, but my step brother's gf when we were growing up. He and I never got along, always thought he was an asshole. His gf did too. They argued a lot. He worked nights and she was alone a lot. She came over, we got closer than we should have, too many hard lemonades, we ended up in the shower together... and so on... Ended in a fist fight with him, and that was that.

My girlfriends mother. Then my girlfriend after we had broken up and she was with another guy.

Yes, many times. Starting with my teachers while I was in college. Now with co-worked and boss. And actually sometime my [removed by mod for ToS] fucked me in return to keep my secret safe.

Well, my true story Gettin’ That A begins like this: “Professor, we shouldn’t be doing this,” she warns in her schoolgirl voice.

My ex Sister in Law

A few times. Good stories with complicated outcomes.

It was the Summer of 1983. My BFF & his GF were on one of their twice-a-year-breakups. I was home from college and she & I decided to go to dinner. She was 18 and I was 21. Dinner, drinks, movie, making out... we left the theatre and returned to my folks house (they were out of town). We were soon naked on the living room floor: kissing, touching, licking, caressing, etc... After a lot of foreplay & oral sex I positioned myself over her in missionary position, and slowly pushed in. She had a wet, tight pussy. I recall fucking for a few minutes and then blacked out..... Sometime after I awake with a blanket on top of us and notice the time. It was just after midnight. She had a 12am curfew. It was a 20-25 minute drive to her house. We quickly cleaned ourselves up and jumped into my car to get her home. The next day she called me in the late afternoon when she knew I'd be home from my summer job. We both admitted we were drunk and tried to put the pieces together of what we did. "I remember telling you to use a condom," she said. I asked, "Did I cum on your tits?" Her reply, "Yes." At the end of our 20 minute phone call we agreed to NEVER tell anyone about our hookup as it would crush her BF, my best friend. Let alone any future women I might be with. To this day I have not told a single person.