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

A coworker’s sister. It was the first time I cheated and it opened up the floodgates for me. It didn’t hurt that she was 10 years older and would do whatever I wanted.

Up until that point I had only flirted with other women and was naive to the whole cheating thing. From then on I’d flirt and try to see how far I could go, which led to having sex with a whole bunch of people with whom I shouldn’t have had sex.
 
Back in college I had a significant other. She had been involved in some scandalous stuff the year before and basically was just trying to lay low and graduate and get the hell out of there. But we started hooking up. It was never an official relationship because she didn't want that but we were basically a couple. But she was clear that we could see other people too. The only one she asked me not to mess around with was one of her housemates. But then there were a lot of mixed messages about that too. Looking back I can see she was just nervous her housemate would steal me from her. But none of us wanted that - we were all just too horny. Our weird little whatever was doomed to end at graduation anyway, but I should have just not done that anyway.
 
Wanderg said:
A coworker’s sister. It was the first time I cheated and it opened up the floodgates for me. It didn’t hurt that she was 10 years older and would do whatever I wanted.

Up until that point I had only flirted with other women and was naive to the whole cheating thing. From then on I’d flirt and try to see how far I could go, which led to having sex with a whole bunch of people with whom I shouldn’t have had sex.
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I have had a few women I should not have had sex with but did maybe I shouldn't have.
Such as my cousin, wife of a friend, and ex gf when we both married to others
Thinking back - it was worth it.
 
"Shouldn't" is kind of a loaded term. There were situations I probably should have avoided because, ethically, they were wrong. But no harm came from them so I do not regret my actions. No harm, no foul.

That being said, there were a few situations where it would have been better if I had said no. One such occurred during my first year of grad school. I was renting a room in a house with two other students - 1 male and 1 female. The woman was the same age as me, and originally from the same part of the country as me. We quickly became friends. (The other guy was local, had his own friends, and we seldom saw him).

Well, one Friday night the woman -- I'll call her Stacy -- and I were home alone. We discussed going out, but decided to stay home. After a few beers we got a little frisky, and ended up in the bedroom. We ended up in bed despite the fact that I did not consider her pretty, except for her legs (which were spectacular) I was not turned on by her figure, and overall I thought her personality was more boring than interesting. We were friends due to the situation we were in. And I was lonely.

We fucked every night for a month. I am normally a lights on kind of guy, but with her it was strictly lights off. I did not want to see her. She was so so at giving head -- not the worst but far from the best -- I did not enjoy going down on her, even though I love going down. I did it out of, I don't know, a sense of obligation I guess. But her pussy was warm, wet and tight, and I enjoyed fucking her. We fucked for hours, but afterward I went back to my room every night. I could not bear the thought of waking up next to her.

She had feelings for me, and I knew it. I did not feel the same for her. I was lonely, she was there, her pussy was available, and I took advantage.

When her period came around we took a few nights off. I never went back to her bed. I did not tell her why, but I basically ghosted her. Our friendship was shattered, and we rarely spoke the rest of the year. The house was cold, she spent all her time with her other friends and I was away as much as possible. I regret sleeping with her, and accept full responsibility for what happened. This was definitely a situation where I should have kept it in my pants.
 
Wanderg said:
A coworker’s sister. It was the first time I cheated and it opened up the floodgates for me. It didn’t hurt that she was 10 years older and would do whatever I wanted.

Up until that point I had only flirted with other women and was naive to the whole cheating thing. From then on I’d flirt and try to see how far I could go, which led to having sex with a whole bunch of people with whom I shouldn’t have had sex.
Click to expand...
I could have written this.
 
Was a woman I had met online years ago, can’t even remember where we met, probably an adult site but maybe a default dating app. Not important.

She was a decent looking Mexican milf. Big pretty eyes, decent body and tits. Always horny. Always wanting dick.

She was married to an overweight police officer and had a dead bedroom as she wasn’t attracted to him anymore and he gave up on sex as she explained. She had an old bf she was hooking up with on the regular as he was able to give her what she needed. My opinion on this is I’m not judging, as I was in a sexless marriage before and understand how it messes with you when basic needs aren’t being met, if she made the decision to cheat, then that was hers to make.

We wanted to hook up, but never had the opportunity with kids, work schedules etc. We were good outlets for each other during this time and would often sext and send daring photos to each other while working from home to spice up the day. We kept in touch this way for nearly two years, every couple of months one of us would flirt and get the conversation hot and it helped us both get what we wanted from each other. We always stayed in contact. Just in case….

Finally, after talking about it for so long, she was in the area and had 30 minutes to visit which we always said was all we’d need, so she stopped by one morning and it was exactly as we discussed so many times.

I answered the door and as soon as it was closed she dropped to her knees and sucked my cock. With 30 min we knew we had no time to waste since all we wanted was sex from the other. She was very good at it, must have been practicing on her side guy often lol. Then I picked her up and sat her on my table, pulled her jeans down started fucking her as we made out. This lead to my bedroom where we fully undressed and I bent her over and mounted her big Latina ass from behind. She was moaning on my cock and I was loving her wet married pussy. Pushed her head down and angled in deeper as she started to climax and I wasn’t far behind her. Great nut to fill her up.

Our 30 min was soon up so she got dressed, cleaned up, and I kissed her on her way out the door, both satisfied having finally acted on our long held desire.

Never saw her again as she soon got a new car that had tracking on it and she was worried of visiting again. I probably shouldn’t have fucked her, but married pussy has an appeal and she wasn’t the first I’ve enjoyed.
 
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AZsurfer45 said:
Was a woman I had met online years ago, can’t even remember where we met, probably an adult site but maybe a default dating app. Not important.

She was a decent looking Mexican milf. Big pretty eyes, decent body and tits. Always horny. Always wanting dick.

She was married to an overweight police officer and had a dead bedroom as she wasn’t attracted to him anymore and he gave up on sex as she explained. She had an old bf she was booking up with on the regular as he was able to give her what she needed. My opinion on this is I’m not judging, as I was in a sexless marriage and understand how it messes with you when basic needs aren’t being met, if she made the decision to cheat, then that was hers to make.

We wanted to hook up, but never had the opportunity with kids, work schedules etc. We were good outlets for each other during this time and would often sext and send daring photos to each other while working from home to spice up the day. We kept in touch this way for nearly two years, every couple of months one of us would flirt and get the conversation hot and it helped us both get what we wanted from each other. We always stayed in contact. Just in case….

Finally, after talking about it for so long, she was in the area and had 30 minutes to visit which we always said was all we’d need, so she stopped by one morning and it was exactly as we discussed so many times.

I answered the door and as soon as it was closed she dropped to her knees and sucked my cock. With 30 min we knew we had no time to waste since all we wanted was sex from the other. She was very good at it, must have been practicing on her side guy often lol. Then I picked her up and sat her on my table, pulled her jeans down started fucking her as we made out. This lead to my bedroom where we fully undressed and I bent her over and mounted her big Latina ass from behind. She was moaning on my cock and I was loving her wet married pussy. Pushed her head down and angled in deeper as she started to climax and I wasn’t far behind her. Great nut to fill her up.

Our 30 min was soon up so she got dressed, cleaned up, and I kissed her on her way out the door, both satisfied having finally acted on our long held desire.

Never saw her again as she soon got a new car that had tracking on it and she was worried of visiting again. I probably shouldn’t have fucked her, but married pussy has an appeal and she wasn’t the first I’ve enjoyed.
Click to expand...
I'm not seeing why she is in the "shouldn't have category." She was already cheating, you didn't convince her to do anything she didn't want to do or wasn't already doing. Sounds like you filled each other's needs and no one go hurt. I would have no regrets in that situation.
 
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In my late twenties I was dating a cute , funny , sexy girl named Sue who was up for anything sexually . After dating for months I thought about asking her to move in with me. She was bipolar and as long as she was taking her medication she was almost perfect. Unfortunately she would stop taking her medication because she didn't think she needed it. She would turn into somebody I barely recognized and after a few days would end up being committed till they got her back on her meds and straightened out. I put up with these manic episodes twice before I bowed out. I haven't seen her in thirty five years and often wonder how her and her now husband are doing in life. I still feel guilty for not standing by her longer , but it was just to much.
 
When I was in my twenties I met a girl at a work Christmas party. I had seen her around - she was a true beauty, blue eyes and the porcelain skin.

It turns out she had a boyfriend and was 18. We both liked each other so neither would break it off. She was wild in bed, she loved telling me how my cock was bigger than her boyfriends, and we would fuck sometimes in a small office she had access to after work.

Should I have done it? Probably not. Do I regret it? lol, not one bit.
 
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