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Who is a person you have had sex with, but probably shouldn’t have?

There were a few that weren't good ideas. My close friend's ex, a couple of friends of an ex of mine but especially the guy I met at a bar and went home with who was really into choking without consent. Don't make impulsive decisions when you're drinking!
 
Gone_and_Back said:
There were a few that weren't good ideas. My close friend's ex, a couple of friends of an ex of mine but especially the guy I met at a bar and went home with who was really into choking without consent. Don't make impulsive decisions when you're drinking!
Click to expand...
Always gotta be careful!!!
 
My boss. She took my virginity. i was 18, she was 40. She owned the hotel i worked at, was single and, so I doscovered, liked them young. She had a lunatic brother who was in prison for hospitalising her ex-husband for cheating on her. Maybe it's because she took my cherry or maybe it's because she knew exactly what he wanted in bed (and on the stairs, in the pool, in her car, on the roof, in the sauna, in her ass, with her sister, in a cemetary, at the cinema, in several restaurants, up against the washing machine while it's on final spin) but the couple of years I worked there was probably the best sex I ever had. The last time we were fucking (in the sauna) she asked me if I was going to leave her or cheat on her. Luckily my gap year was imminent and i went to the U.S. for just over 12 months.

My aunt's wife. That was a tricky one.

And by extension, though it so nearly did/didn't appen, almost my aunt. Even trickier.

Ex's sister.

(The same) Ex's mother.

(Still the same) Ex's cousin (in my defence - literally ALL the women in that family were gorgeous and very liberal, in more ways than one)

Sister's best friend.

Another boss - this time at one of those esoteric head shops that sold bongs, lace shawls, incense, candles, tarot cards, plastic skulls, played way too much Stevie Nicks and singing bowl/rainstick music over the soundsystem - all that sort of thing. She TOTALLY seduced me.

One of my university lecturers. I was 21. The archetypal lost weekend. This is a total life experience that likely deserves as much a stand alone write up as the hotel boss. Three days of complete carnal abandon. Took me home with her on the Friday, stopped me in the hallway of her very remote cottage on the way in and said "Whatever we do to and with each other ends on Monday morning and will never be spoken of. If you don't agree, you can make your own way home now."
 
Dai_Hard said:
My boss. She took my virginity. i was 18, she was 40. She owned the hotel i worked at, was single and, so I doscovered, liked them young. She had a lunatic brother who was in prison for hospitalising her ex-husband for cheating on her. Maybe it's because she took my cherry or maybe it's because she knew exactly what he wanted in bed (and on the stairs, in the pool, in her car, on the roof, in the sauna, in her ass, with her sister, in a cemetary, at the cinema, in several restaurants, up against the washing machine while it's on final spin) but the couple of years I worked there was probably the best sex I ever had. The last time we were fucking (in the sauna) she asked me if I was going to leave her or cheat on her. Luckily my gap year was imminent and i went to the U.S. for just over 12 months.

My aunt's wife. That was a tricky one.

And by extension, though it so nearly did/didn't appen, almost my aunt. Even trickier.

Ex's sister.

(The same) Ex's mother.

(Still the same) Ex's cousin (in my defence - literally ALL the women in that family were gorgeous and very liberal, in more ways than one)

Sister's best friend.

Another boss - this time at one of those esoteric head shops that sold bongs, lace shawls, incense, candles, tarot cards, plastic skulls, played way too much Stevie Nicks and singing bowl/rainstick music over the soundsystem - all that sort of thing. She TOTALLY seduced me.

One of my university lecturers. I was 21. The archetypal lost weekend. This is a total life experience that likely deserves as much a stand alone write up as the hotel boss. Three days of complete carnal abandon. Took me home with her on the Friday, stopped me in the hallway of her very remote cottage on the way in and said "Whatever we do to and with each other ends on Monday morning and will never be spoken of. If you don't agree, you can make your own way home now."
Click to expand...
Love ex's sis. Did same with my ex's stepsis and her bff lol
 
AnthonyT0715 said:
Love ex's sis. Did same with my ex's stepsis and her bff lol
Click to expand...
I've kind of always had (even though I'm 55 now!) a thing for older women, which clearly had a genesis in my mother's pretty vocal post-marriage sex life that I recall starting when I was about 12 years old. I'd hear "things" in the middle of the night over weekends, and they seemed to coincide with the "new man" arriving on the scene. It took for my best friend at school (a girl) to explain what was happening! She showed me one of her dad's "adult interest" tapes! I was 15 by then and so incredibly, unbeliveaby naive. The result of a VERY repressed, VERY strict Roman catholic upbringing!
 
There were several, but the one that comes to mind at the moment was a tech consultant hired by the firm I work for who was significantly younger than me. It started shortly after he began working with us, and continued for the 6-month length of his contract. He was unmarried at the time but I was not. My husband never found out, even though once our relationship started we usually "got together" at least weekly, and sometimes more often.
 
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