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

Ssbbw4u1974 said:
It wasn't sex...I was newly separated from my husband, and one night his brother and i got drunk together because he was one of my favorite BIL's... So, at the end of that night, I seduced him into letting me give him a BJ 😳😜😳😜

Weeks later I got drunk and told my husband.
He was soooo pissed 😡 😡

I shouldn't have done that BJ.
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BJ was fine. Shouldn't have told
 
I don't seriously regret any of my previous sexual encounters because the excitement and build up to knowing that you're about to have sex with a stranger can't be beaten. But I can remember one night in 2011 when I started chatting to a girl online who only lived about 6 or 7 miles from me - and she almost immediately sent me a webcam request. Of course I clicked 'allow' and there she was, exactly as she looked in her profile photo. About 15 years younger than me, long dark hair and a very attractive face.
Almost unbelievably she was sitting there facing the screen and allowing me to not only just see her head and shoulders but also her fantastically-shaped large boobs. She was wearing a satin nightgown which was completely open and she hadn't waited to tease me about what might be underneath. Of course my reaction was that I had to meet this girl in person as soon as possible and after probably 45 minutes of increasingly x-rated cyber chat she invited me over there and then. I don't remember or even care what time of night or early morning it was, I just had to get to her and fortunately once she told me her address I was completely familiar with the area where she lived.
She opened the door and I couldn't believe my luck and just hoped that she was alone in the house and this wasn't some nasty trick. She assured me that she lived alone, had no kids - no baggage and no jealous ex boyfriend. She was simply long term single and a bit lonely. She sat opposite me in the same pose as when we had been web-camming. Night gown open and the most amazing boobs just a few feet away from my face. I so badly wanted to get my hands on those boobs and she was obviously inviting me to do so but I decided to delay the moment by simply chatting coolly for as long as I could manage to prolong the moment and she didn't seem to mind.
Eventually of course we drew closer, began kissing and I began caressing her impressive tits. They were probably a C-cup with no loss of firmness, and gravity had by no means taken over. I was rock hard by now and she began to rub the front of my jeans before unzipping them and wrapping her fingers around my cock.
We moved to a more comfortable sofa and she invited me to join her. She pushed herself as far backwards as she could and opened her legs, making me aware that she was wearing tiny lace panties. I instinctively put my head between her legs and began kissing her pussy through the front of her panties and it was at this point that I realised she had a serious hygiene problem in her feminine area.
She tore her panties away in a flash and I must say her pussy looked beautiful in the dim light of the room. Semi-shaven and all very neat and tidy. I was hoping that the smell was just my imagination and would disappear but it didn't. Even so I was still aroused with my head between this gorgeous woman's legs and my mouth against her pussy and of course I still put my tongue inside her. She clearly enjoyed it, reached again for my cock and changed position so that I could fuck her.
To my horror I began to notice that my dick had begun to go soft. It was still semi hard and she was so wet that I managed to slip inside her but with each thrust I was losing my erection. I pulled out and apologised but she was very sympathetic and accepted the situation almost as though it had happened before.
This was the first time it had happened to me, I would have been 50 at the time and didn't think that it was the right time of my life for me to suffer erectile dysfunction.
I never saw the girl again, we said our polite goodbyes and I disappeared into the night but couldn't get rid of the thought of the terrible smell of her pussy which had ruined the encounter for me and almost certainly for her. I began to think that she was such a wonderful person, great body and easy to chat to, attractive face and obviously loved sex but she just needed to cleanse her genitalia before inviting men or potential boyfriends round.
 
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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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Love it and hope to read the story soon🥰
 
Wageslave said:
My ex wife - before I knew how evil she was
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Sleeping with my ex-wife wasn't the mistake.

Sticking around after that first weekend was the mistake.

Totally different trajectory in my 30s if I had embraced the expression, "Raw Dog and Bail." :D

In my lame defense, I lived in a fairly rural area and it wasn't exactly a deep dating pool. Mud puddle is more like it. Attractive woman willing to have sex with me? What red flags? I don't remember any red flags.

Oh, shit, there were red flags. 🤦‍♂️
 
PattiAnnSucks said:
I would have to say, my oldest Uncle. He has such a big hard cock and is such a great lover. He only comes to my town for a family reunion, at Christmas, and I have let him fuck me the last 3 years! I feel so naughty for doing that, but the good feeling afterwards makes it well worth it
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I love my niece also she is my favorite secret slut as you are😜❤️❤️

https://ibb.co/zGgxKkr
 
The one I shouldn't have was a working girl at one of the legal brothels in Nevada. Super fun, but it cost me a bundle! I should have flown to Germany where things are MUCH cheaper!
 
without getting into the too much detail but basically it was a on again off again way too many times ex gf who I was too stubborn to admit we weren't very good for each other but the sex was usually amazing and it's when I learned the phrase "don't stick your dick in crazy" definitely guilty of being young and stupid lol
 
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