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

Tio_Narratore said:
The girl back in 1966 who left early in the morning, taking my dedicated and signed copy of Ginsburg's Howl with her.
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Someday I'd love to hear how you can sleep that deeply when there's a stranger in your bedroom but now you have an interesting story to tell at parties and flea markets. Someday you'll be reunited ( and wouldn't it be hilarious if the seller was that girl? ).
 
I had sex with a co-worker, bad idea, I know. She was really attractive so I was thinking with the small head. As these things do, it ran it's course but not for her. She threatened my job and said she would leave her husband. I'm not going to lie the sex was good but the aggravation wasn't worth it
 
Mine was an older woman I had met in a nightclub. She was married. She wanted to meet at a hotel a few days later and I agreed. So..... I thought it was going to be a one off. But met her again the next week and we actually did it in the women's room at the nightclub. I had told her I lived about thirty miles away. And as my luck would have it. She lived just down the road from me about a half mile. We got together one last time. I was scared shitless that he was going to kill me and I took a job out of state soon after. Definitely not worth it.
 
Oshkosh60 said:
Mine was an older woman I had met in a nightclub. She was married. She wanted to meet at a hotel a few days later and I agreed. So..... I thought it was going to be a one off. But met her again the next week and we actually did it in the women's room at the nightclub. I had told her I lived about thirty miles away. And as my luck would have it. She lived just down the road from me about a half mile. We got together one last time. I was scared shitless that he was going to kill me and I took a job out of state soon after. Definitely not worth it.
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It would've been hot if one day you saw him at a bar and sat down at his table and told him what you'd done with his wife, then introduced him to your wife and asked him to drop her off on his way home.
 
lily_wall_ said:
Me F-ing their husband is the reason they didn't fulfill the last F

Saddest part is I did it twice
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I don’t see that is sad, I see that as you knowing what you want and enjoying your life… Just because it happens to be with someone else’s husband… If you enjoyed the time you’ve spent with them, that’s what’s most important
 
lily_wall_ said:
"Especially" ... I need therapy I know lol
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Well, I will never tell anyone not to seek therapy if they feel it will help them.

I think you are a person who wants what she wants. There is a reasonability to that. I’d rather be you. The person who goes after what she wants, than me, the person who finds reasons not to go after what he wants.

It’s very frustrating staying safe & being the “good guy” and doing the “right thing” it feels good in the moment, but other people clearly have more fun in life than I do.
 
fearless1969 said:
I had sex with a co-worker, bad idea, I know. She was really attractive so I was thinking with the small head. As these things do, it ran it's course but not for her. She threatened my job and said she would leave her husband. I'm not going to lie the sex was good but the aggravation wasn't worth it
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No matter how pretty they are, I bet her husband was also tired of dealing with her shit too. Cynical outlook but the same can be said for men too, I’m certain
 
My relationships have basically never been appropriate.

But... my boss at work..

I was in college. Kind of embarrassed to be working in the cafeteria in the dorms.

My boss was kind if standard issue BBW, about 35- I think. She was always complaining about her husband. From Real serious stuff to minor BS. I tried to be a sympathetic ear.

I think she was sweet on me fir a while. Eventually I noticed she was wearing new clothes, less clothes, and not coincidentally some massive titties.

Our first time she locked up, and we did it right in the kitchen floor.

She was clingy and only moderately attractive and not very bright.

But I was horny, lonely, and prone to hiding from my problems in whoever arms were waiting, so....

Eventually I made up my mind to push her into breaking up with me. I underestimated her low self esteem and desperation.

It was a lot of fun. Probably did a fair amount of psychic damage to both of us.
 
#2 would actually be from the same job. Cafeteria at my college.

The first bad idea was my boss, soon after I started. I had just broken up with my soon ti be first wife and boss lady provided distraction from my heartbreak.

Probably a year later. Future ex wife and I were back together. In fact, I'd just proposed. Tall lithe and thin coworker said we should go celebrate. I think she was flirting with me, I know I was definitely aroused by her attention.

I tried to get our newly divorced NEW boss to come too. It seemed like a a good idea to me! I saw one of three outcomes, boss lady woukd chaperone, be a party proper, or join in and this would become a threesome. So, I'd either get kept out of trouble or thrown deep enough in that I wouldn't care.

Boss said she couldn't and strongly suggested I didn't either. Of course I didn't listen.

I bought some booze that I had no interest in drinking. Hot coworker repeatedly chastised me about keeping up. Soon we were making out. Feeling her toned stomach totally launched my arousal into the stratosphere.

I ended up being half an hour late to a physics test the next morning.

To my great regretvI started avoiding my coworker after that and married the future ex.

What I SHOULD have done was apologized to my fiancee for proposing before I was ready and started avoiding HER.

A relationship with tall and lithe was inadvisable. She was a recovering addict who'd lost custody of her kids and I was a college kid with, supposably, great expectations. BUT I really regretted just trying to ghost her. That was very uncool of me. She didn't deserve that.
 
I grew up loving the movie The Graduate—filmmaking at its best. But last year, I found myself living out the movie. The thing is, I remember my college graduation like it was yesterday, so in my mind, I’m the graduate.

Last fall, I was running across the UCLA campus when I saw Ryan, the oldest son of my college BFF Janey. He's a student there, and we started talking. Janey and Pete (his parents) now live in San Francisco, and with Thanksgiving coming up, I offered to drive him to the airport—that’s a big deal in LA. The flight was crazy early (like 5:30 AM), so I offered to let him sleep at my place so I wouldn’t have to drive to UCLA and then to the airport.

I picked him up the night before; we went to dinner, then to my place, and had a very nice time. I’ll save the details for a lit story, but I’m pretty sure I made the first move, and by 3:45 AM, when we finally headed to the airport, we hadn’t slept at all.

Later in the day, Janey FaceTimes me while I’m at my brother’s house for festivities to wish me a happy Thanksgiving. We talk as usual, and I can see Ryan in the background. He takes the phone from his mom and makes sure to thank me for “everything.”

Not sure why, but when I could see no one was behind him, I flashed a boob at him, like I was some high school cheerleader. Perhaps it was an invitation for another time

I took a screenshot of him before he handed the phone back to Janey. We wrapped up the call, and then I got a text from Ryan asking if I wouldn’t mind picking him up at the airport on Sunday.

Then I thought of the movie “The Graduate” again and suddenly realized I wasn’t the graduate; I was Mrs. Robinson!

And you know what, I’m good with that. She was probably the most normal person in that movie. And yes, I did “pick him up” at the airport.
 
WendyTrilby said:
I grew up loving the movie The Graduate—filmmaking at its best. But last year, I found myself living out the movie. The thing is, I remember my college graduation like it was yesterday, so in my mind, I’m the graduate.

Last fall, I was running across the UCLA campus when I saw Ryan, the oldest son of my college BFF Janey. He's a student there, and we started talking. Janey and Pete (his parents) now live in San Francisco, and with Thanksgiving coming up, I offered to drive him to the airport—that’s a big deal in LA. The flight was crazy early (like 5:30 AM), so I offered to let him sleep at my place so I wouldn’t have to drive to UCLA and then to the airport.

I picked him up the night before; we went to dinner, then to my place, and had a very nice time. I’ll save the details for a lit story, but I’m pretty sure I made the first move, and by 3:45 AM, when we finally headed to the airport, we hadn’t slept at all.

Later in the day, Janey FaceTimes me while I’m at my brother’s house for festivities to wish me a happy Thanksgiving. We talk as usual, and I can see Ryan in the background. He takes the phone from his mom and makes sure to thank me for “everything.”

Not sure why, but when I could see no one was behind him, I flashed a boob at him, like I was some high school cheerleader. Perhaps it was an invitation for another time

I took a screenshot of him before he handed the phone back to Janey. We wrapped up the call, and then I got a text from Ryan asking if I wouldn’t mind picking him up at the airport on Sunday.

Then I thought of the movie “The Graduate” again and suddenly realized I wasn’t the graduate; I was Mrs. Robinson!

And you know what, I’m good with that. She was probably the most normal person in that movie. And yes, I did “pick him up” at the airport.
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You definitely made a fantasy come true
 
Co-worker over the holiday.

At a new job, I got paired up with a young woman thousands of miles from her country. Gave her a ride home because the buses were on their holiday schedule and she'd be out there for hours. It started as a kind gesture and ended with the two of us calling off while I dehydrated myself inside all of her holes.

When I heard her making her kids breakfast in the morning, I felt a little guilty.

10/10 would destroy with her kids downstairs again.
 
Wageslave said:
My ex wife - before I knew how evil she was
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Yep! Lol

My ex wasn't EVIL, despite a few compelling points to the contrary. But we weren't a good match, and I was AT LEAST 5 years of age and experience too young fir that kind if committment.
 
MisterWolf26 said:
Yep! Lol

My ex wasn't EVIL, despite a few compelling points to the contrary. But we weren't a good match, and I was AT LEAST 5 years of age and experience too young fir that kind if committment.
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People are people. They change with or without you. Monogamy and soulmates are not realistic.
 
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