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

It’s a long list…

At the top of it, my ex-wife’s 19 year old sister. She was there waiting for me when I picked up the last of my things. Wearing a sheer lingerie top that left little to the imagination. Introduced herself. Started verbally and physically flirting. I got aroused but pushed her away, “One crazy bitch was enough, thanks.”

Her retort, “Wouldn’t you like to help me piss her off?” Then she lifted her skirt to expose her naked ass. That broke the tiny bit of self control I was clinging to.

So we fucked in my ex-wife’s living room. Left the wet spot on the couch in her favorite spot.. It was THAT petty.

Then she helped me load my car.

She of course, IMMEDIATELY told my ex-wife. Like, my phone rang before I was two miles away. I ignored it.

All four tires got slashed on my car that week. Worth it. Sad part is I’m only 80% sure it was the ex. Sister seemed crazy enough to do it too. Chaotic Neutral that one.

At least I got a proper orgasm after a long sexless marriage that wrecked my self esteem. The fastest way to get over a woman is to get inside a new one. :D
 
Oh, goodness…I feel as though this is a whole can of worms.

I suppose the one who stands out for me at the moment is a man I work with. He’s married, though he was on the brink of separation at the time, and is currently separated from his wife (no, I am not the reason why - I am very discreet). I was also having a rough time in my personal life, and we were friends. We would commiserate. I had done him a (platonic) favour at work, so he said he owed me a coffee. I didn’t take it seriously.

Then he texted me on a Sunday morning and asked if I was at home. I said I was, and he said he’d be there in twenty minutes with my coffee. It surprised me - I wasn’t expecting it. I let him up, and we drank some coffee and had some congenial conversation. It was all very normal. Then, when he was leaving, he kissed me. It was shocking. And electric.

Three days later he was back when we were finished work, feverishly fucking me. I knew it was a bad idea - he hadn’t called it with his wife yet, though it was clearly headed that way. It was wrong. And we were also not a match - diametrically opposed in so many other ways. But I couldn’t get that kiss out of my head, and he was so insistent. The sex was delicious.

We've never done it again, though he very clearly wants to.
 
My freshly divorced colleague from my old work!!! She came out of a sexless marriage and hooked up at a business trip.... After that we were fucking on each given chance, even at the office on working hours!!! Almost got fired becasue she was too damm loud!!!
 
Most of them really. A lot of the time, the sex has been amazing but I have an unfortunate habit of letting it take over real life. After nearly 50 years, I think I've proved my earlier theory (which I never had the sense to subscribe to) that whores would have been cheaper in the long run...!!
 
ladventures said:
My mother’s best friend when I was 18 and she was 35. Her husband had cheated on her, and I was definitely used for revenge or evening up the score, but I loved every minute of it.

She was very discreet. I don’t think anyone else ever knew. I don’t think she wanted to tell her husband or rub his face in it. But she liked having a secret affair, while she knew about his.

They stayed together for 10 more years and even came to my wedding together.

The relationship went on the summer before I went to college. It continued a few times when I would visit home during college breaks.

The craziest time was when I came home for Thanksgiving, my mom’s friend immediately asked me to come over, supposedly to fix something at her house. We had amazing sex - she had an IUD. With college girls, I usually had to use a condom or pull out.

I came twice that afternoon with her. Then, that night my girlfriend arrived home from her college. We had not seen each other in two months, so of course she wanted sex immediately.

She was shocked at how long I lasted, and I couldn’t tell her the neighborhood MILF had drained me earlier.
Click to expand...
Awww, this is one of the cutest confessions I ever read. 🥰🥰
 
justagirlLMA said:
Same here!! Most of the men I had sex with always wanted the basic missionary. LAMEEOOO. So I am definitely interested in reading other people's stories.

Maybe I can get some ideas of what I would love to do in the future.
Click to expand...
I have a few different (non-stupid) things you might enjoy.
 
That’s really not a fair question. Why shouldn’t we have? If the person is down to fuck then so be it.
 
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