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What's your biggest ever sexual regret?

  • Thread starterSwingingChris
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I love my wife, and my kids, and the life we have, but before I met Louise I was with another girl called Vicky in my late teens. She was hot, and had the morals of an alley cat.

She lived at home with her parents, her sisters (she was the oldest of three), and her mum’s boyfriend, who she’d previously dated too. Every time we went out clubbing she’d be off dancing with other guys, justifying it as “don’t worry, I’m coming home with you”, and she would disappear to the bathroom with my friends - most times I called her my buddy Tony would answer.

We weren’t together long. We were young (me 19, her 17), and split up because she got pregnant to a bus driver while we were dating, but before we slept together. Her daughter’s now 20, I guess; I’ve not seen her in a long time.

Like I say, I love my family and the quiet desperation of suburbia, but sometimes I wonder what would have happened if Vicky and me had settled down and lived inside a porn film.
 
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I have a few, but my biggest regret would HAVE TO BE not knowing anything about being a cleanup cuckold and having these very strong desires about being a cock sucker back in my earlier days, the mid 70's. My wife and I had a few 3sums with this guy Ed, a work friend of mine back in the early 80's. We were in our late 20's. I love to think back to those 3sums and wish I could have sucked Ed's big fat uncut cock. Being him and my wife's cleanup instead of just getting sloppy seconds. WOW! the thought of licking up Ed's cum from my wife and sucking his big fat cock clean.

I just never had any gay thoughts about sucking cock back in my younger day's my teen's 20's or 30's. Been a cock sucking wannabe since my 40's.
 
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SwingingChris said:
Mine is saying no when my wife (girlfriend back then, 27ish years ago) asked if she could piss on me.
Mine is not introducing my wife to BBC much earlier when she was more innocent.
 
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happydad said:
GEttinger embrassedcwhen an incident happened, in the house I should have stayed in the room
What incident?
 
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happydad said:
GEttinger embrassedcwhen an incident happened, in the house I should have stayed in the room
Please more
 
Pretending, even to myself, that i an a man. Wasted so much time not enjoying being as much of a woman as i can for a real Man. And also caused unnedessary pain and stress to those real women i pretended to ... including my wife.
 
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powerful11 said:
One night me and my ex-wife were driving in New York City by Park Ave., South and 28th St. was an open lot parking lot with a pimps hang out in their lady’s yes my sexy blonde wife ask one of pimp to come over
To my car she told him through the window that she can suck a fuck better than any of his ladies and was way better looking He asked me to pull it into the lot which I did he open the door and she stepped halfway out while still sitting with her legs, spread. He’s referring to her as she pulled out his cock and suck his cock the other pimps came over and before I knew it they have her in the back seat of my Cadillac with the back doors open she was bent over the seat sucking one of guy sitting down in the backseat of the car she bent over and behind her, was other black guy fucking the shit out of her.
My regret is we didn’t have cameras back, then just happen back in 1989 summer about 2am anyways they all fucked her and 3 or 4 ass fucked her made her do ass to mouth after 3 or 4 of them, took her to the back wall of the parking lot, made her kneel on the cardboard and they begin to piss on her. Her top was off. The skirt was pulled up into my surprise. She enjoy the golden shower.
The following day shouldn’t want to talk about it a few months later, she told me after work she went back a few times and see if she works from 4pm to 12 midnight
She told me her fantasy was to be owned by pimps. She thought I would be mad instead, I told her I loved hearing about it

IMG_0481.jpeg IMG_3862.jpeg IMG_3859.jpeg IMG_3860.jpeg IMG_3880.jpeg IMG_3988.jpeg
That's the hottest story I've read in a long time!
 
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before we got married. We fantasised about my wife having other guys. One of my friends saw her in her lingerie and it was hot him seeing her. She was nervous to have fun with him, so didn’t take it any further. On our wedding day, I had trouble with the zip on her wedding dress when we got back after being married. My friend stayed as he was taking us to the airport. He ended up helping me to get her wedding dress off, but we did nothing else. I wish he would have taken things further!
 
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I once had a blindfold gang bang for my sub gf and in it I had some guys I meet online plus one of her friends. She never knew who fucked her but her friend who was really excited to fuck her, kept trying to drop hints and clues. Like everytime they would meet and I got pretty pissed off and almost kicked his ass. He calmed down and finally kept it a secert but I haven't done any of those since then.

On the plus side it was stupid hot
 
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SlimJims said:
I once had a blindfold gang bang for my sub gf and in it I had some guys I meet online plus one of her friends. She never knew who fucked her but her friend who was really excited to fuck her, kept trying to drop hints and clues. Like everytime they would meet and I got pretty pissed off and almost kicked his ass. He calmed down and finally kept it a secert but I haven't done any of those since then.

On the plus side it was stupid hot
That is hot. Had she asked that no one she knew to be involved?
 
No I told her that there could be anyone I choose but I'll protect her. Originally I didn't want people who know her there but it was too hot of an idea
SwingingChris said:
That is hot. Had she asked that no one she knew to be involve
 
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SlimJims said:
No I told her that there could be anyone I choose but I'll protect her. Originally I didn't want people who know her there but it was too hot of an idea
Fuck yes.
 
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That I didn't admit to myself that I was bisexual back when I was young... And that I didn't "sow my wild oats" with anything that was breathing...
 
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Exgf and I had just finished fucking when she said her 2 year younger sister hated having sex with her bf because it was terrible. Asked if I'd fuck her since she knew i.was nice. I said no
 
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When I was a teen, the old, white haired security guard lured me into his empty house to let me fish in their pond. Bit soon he said to come on the stool between his legs and kept talking to me while casually squeezing my CROTCH. I was an obsessive compulsive wanker at that age but I got scared and left just as he invited me round to the back of the house to see his filthy servant quarters. I left. To this day, I imagine being stripped and fondled by this man. What a loss. Being hypersexual, I paid a street ***** in Bangladesh to fuck me for 20 bucks,around 84 ents. I fucked her often and we developed a deep bond. I would be 19 on Paris before I had the guts to enter and adult cinema and wank off a total stranger. My wife has no idea of my fondness for cock to this day.
 
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happydad said:
Not getting into swinging earlier in pur marriage
i wish that i & the ex wife would have getting into swinging earlier in owe marriage
 
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not having my wife fuck other men when we was married
 
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