Ssbbw4u1974
🪻🍃🎧💋🤠
- Joined
- Sep 19, 2021
- Posts
- 14,744
You're very right, he kept his mouth shut, even after I confessed
Who is a person you have had sex with, but probably shouldn’t have?
- Thread starter GoGreenGoWhite
- Start date
Leaderoft5b
Virgin
- Joined
- Apr 19, 2025
- Posts
- 46
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.
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.
Last edited:
HotwifeBrooksideKC
Literotica Guru
- Joined
- Dec 27, 2023
- Posts
- 1,712
A really good friends ex husband
RedmanReaction19
Red Master
- Joined
- Aug 27, 2025
- Posts
- 782
No doubt he would have been happy to have the BJs continue, even if there was a chance of repairing the marriage. Once he tried your mouth, he would always want it.
peekingone
Always behaves
- Joined
- Nov 4, 2005
- Posts
- 48,978
Love it and hope to read the story soon
At least you can block them.
Wriggle
Chaotic Neutral
- Joined
- May 19, 2023
- Posts
- 11,460
After I've saved all the audios, pics and vids....
MongoSex
Experienced
- Joined
- May 21, 2025
- Posts
- 149
Absolutely!
Sir_Timo_Volodok
Experienced
- Joined
- Jun 2, 2025
- Posts
- 236
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."
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.
Waiter519123
Not a Virgin lol
- Joined
- Aug 17, 2024
- Posts
- 3,858
Adrock1981
shake that thang
- Joined
- Jan 24, 2021
- Posts
- 1,362
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
WendyTrilby
Third Rail Rider
- Joined
- Nov 8, 2022
- Posts
- 228
I lived in New York for a few years while finishing my graduate degree. Davy was in my cohort—handsome, charming, and effortlessly social. We were part of the same close-knit academic group, the kind that studies hard and then relaxes together in lively restaurants and dim bars. It was innocent. Fun. Harmless.
Until the night it wasn’t.
He had tickets to a Broadway show and invited me along. Just the two of us. We were classmates, nothing more. Still, over dinner, the conversation drifted into flirtation, then into confession territory. We even compared “body counts”.
Then his friend Dan walked by.
Dan joined us for a drink and, as he was leaving, casually mentioned Davy’s upcoming wedding. That was news to me, something Davy forgot to mention while talking about how many women he had slept with. The mood shifted. The flirtation cooled.
Davy walked me home afterward, all gentlemanly restraint, stopping at my stoop. That should have been the end of it. Instead, I asked him, half-teasing and half-serious, if he wanted to add one more body to his count before closing that chapter for good.
He came upstairs, and we added each other’s bodies to our respective counts. It felt wrong, considering the line we were crossing, but that also made it feel so good. Besides, this was pretty much a one-and-done. I knew we would never see each other again after the semester ended. After all, he was moving to LA, and I had my life set on staying in New York.
A few months later, he was married and gone. I finished my degree and, eventually, life being life, I moved to Los Angeles to take a job at a Talent Agency in Beverly Hills
I landed a job and quickly became close to a coworker named Amelia. She was (is) great. The kind of person you instantly trust.
New to LA, I was grateful when she invited me to a beach gathering with friends. And that’s where I met her husband.
Yeah, you guessed it, it was Davy. What are the odds?
We both masked the shock in record time. “Oh my God, weren’t you in my program at NYU?” we said, performing casual recognition like seasoned actors. It was convincing enough.
This story doesn’t end with Davy and me getting it back on. That never happened again. It ends with Amelia and me becoming the best of friends. The kind who share everything. Well, almost everything. The only thing I’ve never shared is that once, years ago in New York, I fucked the hell out of her husband, or maybe he fucked the hell out of me, it’s kind of a burr now. I tell Amelia everything, far more than I even share on these forum pages, but that’s the secret I won’t share, because I care about Amelia and maybe a little about Davy.
Until the night it wasn’t.
He had tickets to a Broadway show and invited me along. Just the two of us. We were classmates, nothing more. Still, over dinner, the conversation drifted into flirtation, then into confession territory. We even compared “body counts”.
Then his friend Dan walked by.
Dan joined us for a drink and, as he was leaving, casually mentioned Davy’s upcoming wedding. That was news to me, something Davy forgot to mention while talking about how many women he had slept with. The mood shifted. The flirtation cooled.
Davy walked me home afterward, all gentlemanly restraint, stopping at my stoop. That should have been the end of it. Instead, I asked him, half-teasing and half-serious, if he wanted to add one more body to his count before closing that chapter for good.
He came upstairs, and we added each other’s bodies to our respective counts. It felt wrong, considering the line we were crossing, but that also made it feel so good. Besides, this was pretty much a one-and-done. I knew we would never see each other again after the semester ended. After all, he was moving to LA, and I had my life set on staying in New York.
A few months later, he was married and gone. I finished my degree and, eventually, life being life, I moved to Los Angeles to take a job at a Talent Agency in Beverly Hills
I landed a job and quickly became close to a coworker named Amelia. She was (is) great. The kind of person you instantly trust.
New to LA, I was grateful when she invited me to a beach gathering with friends. And that’s where I met her husband.
Yeah, you guessed it, it was Davy. What are the odds?
We both masked the shock in record time. “Oh my God, weren’t you in my program at NYU?” we said, performing casual recognition like seasoned actors. It was convincing enough.
This story doesn’t end with Davy and me getting it back on. That never happened again. It ends with Amelia and me becoming the best of friends. The kind who share everything. Well, almost everything. The only thing I’ve never shared is that once, years ago in New York, I fucked the hell out of her husband, or maybe he fucked the hell out of me, it’s kind of a burr now. I tell Amelia everything, far more than I even share on these forum pages, but that’s the secret I won’t share, because I care about Amelia and maybe a little about Davy.
BobbyandtheCabin
Dreamer
- Joined
- Dec 12, 2022
- Posts
- 360
I was about 20 and had a boss who was pretty volatile and generally not great. His mrs was about 10 years older and had a thing for me. He had us all over at his once, lost his shit, and kicked us all out including her.
Next thing I know, I'm in the middle of fucking her back in my dorm.
We continued meeting up to fuck in secret for about another 6 months. It was wild. I'm talking 3-4 hour sessions of none stop exploration and adventure. She was hungry for it all. Facefucking, making her squirt, anal (though the latter i'm honestly not keen on). She would tell me over and over how I'm so much longer and thicker than him, and the more of a bellend he was the more I'd love the fact I was doing this.
Not sure I'd take such glee in being a home-wrecker now... but, you know...
Next thing I know, I'm in the middle of fucking her back in my dorm.
We continued meeting up to fuck in secret for about another 6 months. It was wild. I'm talking 3-4 hour sessions of none stop exploration and adventure. She was hungry for it all. Facefucking, making her squirt, anal (though the latter i'm honestly not keen on). She would tell me over and over how I'm so much longer and thicker than him, and the more of a bellend he was the more I'd love the fact I was doing this.
Not sure I'd take such glee in being a home-wrecker now... but, you know...
Similar threads
