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Ever slept with someone you shouldn't have?
Topic Started: Aug 11 2012, 12:08 PM (4,603 Views)
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Post your stories here!

I'll go first:

I've had sex with my boyfriend's brother. It was interesting to note their differences & similarities. My bf his hairy; his brother is smooth. They both have horse cocks. My bf has ugly feet; his brother's feet are totally hot. They are both bottoms. My bf isn't a very good kisser; his brother is. On the whole, sex with the brother was much hotter, maybe because of the "forbidden fruit" factor.
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Tybee
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Many, MANY times. But that was all in my much younger days when I was much less discriminating. Plus back in those days we didn't have the dangers we have today. It was all conducted with wild abandon. Yes, we were whores darlin'! :shhh
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Slept with both my sisters bf's. Meh.

I had permission beforehand, btw.
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Guest
Aug 11 2012, 12:45 PM
Slept with both my sisters bf's. Meh.

I had permission beforehand, btw.
Does your sister date gay men exclusively?
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Tybee
Aug 11 2012, 12:12 PM
Many, MANY times. But that was all in my much younger days when I was much less discriminating. Plus back in those days we didn't have the dangers we have today. It was all conducted with wild abandon. Yes, we were whores darlin'! :shhh
Like who, Tybee? A boss? Co-worker? Mailman? Your sister's husband? Enquiring minds want to know!
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Tybee
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Oh GAWD no! One thing I always was at work was 100% professional. Never once in 33 years did a dip my tootsies in the work pool. And no mailmen or any other "service" people. I've always kept a respectable distance between vendors and my private life because they never mix well. And most definitely not either of my sister's husbands or boyfriends or my brother's friends. Those 2 evil creatures went away to boarding school by the time I started high school anyway and I always spent the summers away so by then I rarely had much contact with any of their friends, or them (thank the stars in heaven).

No, other than my local pals through the years, my slut years dalliances were mainly with impromptu meetups in bars (and various other venues I won't go into :shhh ) all over America and eventually the world. I traveled almost continuously around the country for many years and then my job entailed a lot of travel abroad. Lots of unknown, never to be seen or heard from again, quickies and overnighters.

Ah, happy days! :rofl
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Well, most of the sex I've had has involved some sort of boundary crossing. I guess because I'm lazy and it's always been easiest. I had a fling with a roommate's boyfriend once. And my college geology instructor, who I'm pretty sure had Aspberger's. The guy who comes to read the gas meter is a pretty regular fuck these days.
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I think there's a difference between regrets and should't haves.

I have several regrets but only two real shouldn't haves.

One was a onetime co-worker of my father's who remained a family friend. When we first met him, he was an ex-priest married to a much younger woman, and had two young girls. Shortly after that the marriage broke up (with the young wife becoming known as the neighborhood tramp, named in at least one other divorce) and he began hanging out alone, or when he had time with his girls, on holidays or at our family summer cottage. A nice man, I always liked him, but never felt an attraction to him, never had any inkling he might be attracted to me.

Then when I was a university student, around 20, he asked me to help him move, said he would pay me and give me pizza and beer, and did I have any friends who could help. No friends were available on such short notice. But he was moving from a two-bedroom apartment to a three-bedroom apartment in the same building. It was pretty easy, just load the elevator. It went quickly, we got drunk on beer and scotch, went for a swim in the indoor pool late that evening when no one else was there, he got frisky... back down to his bedroom for the night
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Tybee
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Speaking of teachers, I did have one of my former high school teachers slide a tongue into my ear one night in a bar when I was in college. It went absolutely nowhere, because it was a woman. :shhh
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Fucked a guy showing an open house. Really regretted that. Not classy at all. It happened in the guest bedroom but still......
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Most of them.
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apartment four
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Post 8 was me.

What I didn't count was all the women I fucked to make myself straight. Didn't work, obviously.

Most of them were older. Had they been men, they would be called predators.
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Erna
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Yes, every man we ever slept with for free.
Edited by Erna, Aug 14 2012, 11:50 AM.
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MrsPatrickCampbell
Aug 14 2012, 10:24 AM
Yes, every single man we ever slept with for free.
Even your Blatino husbear?
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Erna
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yes
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MrsPatrickCampbell
Aug 14 2012, 10:24 AM
Yes, every man we ever slept with for free.
Your regret/shame is de minimis when compared to theirs.
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MrsPatrickCrapsmell
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Indeed, but most who paid were in the throes of dementia, therefore incapable of feeling guilt!

Trolling nursing homes has worked out very well for us.

Discuss.
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I have recently entered the pasty white middle-aged ass of a man with whom society says I should not engage in physical relations of a sexual nature. I did it anyway and have no regrets.
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i had slept with my boyfriend's brother, while i am pregnant of his child, i really regret it. i dont know what he thought when he asked me to have sex with me, and foolishly i just cant refuse it. but for some reason, now i cant keep my mind of thinking about my boyfriend's brother . he already say sorry about what we have done and never text me again.

my boyfriend dont know about it yet, i really want to tell him about the truth, but i am scared that he would leave me and i cant take care of our baby alone, but if i dont tell him, i feel like i am a liar for my whole life.

i feel very discust about myself, and if i dont carrying his baby, i probably done a suicidal already..

:'(
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Jansen
Oct 6 2015, 11:08 PM
i had slept with my boyfriend's brother, while i am pregnant of his child, i really regret it. i dont know what he thought when he asked me to have sex with me, and foolishly i just cant refuse it. but for some reason, now i cant keep my mind of thinking about my boyfriend's brother . he already say sorry about what we have done and never text me again.

my boyfriend dont know about it yet, i really want to tell him about the truth, but i am scared that he would leave me and i cant take care of our baby alone, but if i dont tell him, i feel like i am a liar for my whole life.

i feel very discust about myself, and if i dont carrying his baby, i probably done a suicidal already..

:'(
Get help, and talk to your boyfriend.
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Erna
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Yes, many times.

We seem to attract sociopaths.
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Tybee
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A few times. Especially the ones who after one roll in the hay thought it was OK to ask me for a loan they solemnly promised to pay back. Of course that really meant "can you loan me $5000.00 which I will never pay back, and indeed the second I get the money you'll never see or hear from me again, or be able to find me".
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Tybee
Oct 7 2015, 07:57 AM
A few times. Especially the ones who after one roll in the hay thought it was OK to ask me for a loan they solemnly promised to pay back. Of course that really meant "can you loan me $5000.00 which I will never pay back, and indeed the second I get the money you'll never see or hear from me again, or be able to find me".
How did you meet those men? In bars, or via personal ads? Or were they prostitutes?

A friend of mine had a partner who forged his name on a check, and once he found that out he kicked him out.
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Tybee
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No, they were all either introductions by a mutual "friends", or someone I met on my own at some stupid fancy party I'd been invited to. It took half a lifetime, but I finally gave up accepting these invitations & introductions when I came to the realization that 99.9% of the people I met were nothing more than fancy dressed users & losers, and the sort of people whose acquaintance would end up only making me unhappy.
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Erna
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Tybee
Oct 7 2015, 09:47 AM
No, they were all either introductions by a mutual "friends", or someone I met on my own at some stupid fancy party I'd been invited to. It took half a lifetime, but I finally gave up accepting these invitations & introductions when I came to the realization that 99.9% of the people I met were nothing more than fancy dressed users & losers, and the sort of people whose acquaintance would end up only making me unhappy.
"...neither a borrower nor a lender be...."
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Tybee
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Mrs Patrick Campbell
Oct 7 2015, 11:34 AM
"...neither a borrower nor a lender be...."
Absolument! :lol
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Tybee
Aug 11 2012, 02:58 PM
Oh GAWD no! One thing I always was at work was 100% professional. Never once in 33 years did a dip my tootsies in the work pool. And no mailmen or any other "service" people. I've always kept a respectable distance between vendors and my private life because they never mix well. And most definitely not either of my sister's husbands or boyfriends or my brother's friends. Those 2 evil creatures went away to boarding school by the time I started high school anyway and I always spent the summers away so by then I rarely had much contact with any of their friends, or them (thank the stars in heaven).

No, other than my local pals through the years, my slut years dalliances were mainly with impromptu meetups in bars (and various other venues I won't go into :shhh ) all over America and eventually the world. I traveled almost continuously around the country for many years and then my job entailed a lot of travel abroad. Lots of unknown, never to be seen or heard from again, quickies and overnighters.

Ah, happy days! :rofl
Did you meet men in bath houses, public bathrooms, gym locker rooms, and adult book stores?
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Tybee
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What part of "I won't go into" don't you understand?
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Erna
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Fortunately most of our Hershey Highway encounters have been good ones, i.e., they resulted in increases to our bank account!
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Mrs Patrick Campbell
Oct 8 2015, 01:59 AM
Fortunately most of our Hershey Highway encounters have been good ones, i.e., they resulted in increases to our bank account!
What's the most unique/odd thing a client/john wanted to do that you did?
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Erna
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A rather famous tv/movie star who perspired about 20 years ago just wanted someone to talk to while he drank in his Beverly Hills house. Sad.
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Mrs Patrick Campbell
Oct 8 2015, 10:32 AM
A rather famous tv/movie star who perspired about 20 years ago just wanted someone to talk to while he drank in his Beverly Hills house. Sad.
OK who was he? Can you at least provide a hint?

I meant more like fetishes/kinks like you sometimes hear about people paying prostitues to fulfill.
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Erna
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he had sizemeat but we never wanted to touch it and, thank God, we never were required to!
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Mrs Patrick Campbell
Oct 8 2015, 11:13 AM
he had sizemeat but we never wanted to touch it and, thank God, we never were required to!
A bisexual man I met in a bar in college told me how he was a street hustler in the 80s in NYC and had male and female clients including a Colombian $ugar mama, and he said how some of his older male clients just wanted to have a younger man to talk to while they ate food and sex was not involved.
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I had sex (at different times) with several tinymeats. I was totally turned off by their Cheeto*-sized, erect wieners but went through with it anyway.

Isn't tinymeat something you might want to confess before you even meet?
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Oct 10 2015, 10:22 AM
I had sex (at different times) with several tinymeats. I was totally turned off by their Cheeto*-sized, erect wieners but went through with it anyway.

Isn't tinymeat something you might want to confess before you even meet?
My friend's ex is a size queen and they were in an open relationship and he had sex with someone that has tinymeat and he told everyone at the bar who it was, as we all knew him socially, and my friend's then partner said, "If I were that small I'd kill myself!" :eek
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