Your biggest regret sexually

chigitychaunc

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I hooked up with a crazy chick who had the most perfect breasts and vise grip tight puss. We only actually hung out knce and screwed twice that night after a week or two of chatting online. On my way out the door that night she hit me with an "i love you". In retrospect i shouldve dipped in that honeypot one more time. But who knows, i most definitely dodged a bullet. Perhaps if i went in ankther time she wouldve poked the condom or something. She was baby obsessed. What i find funny is i looked her up like 2 years later on FB and her current bf looked like he could be my twin.
 

curtdude

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My biggest regret was no taking advantage of Peter. I knew Peter from high school and suspected he may be gay. I met up with him when we were 18 at a mall we shared some small talk while waiting for the elevator. When yhe doors opened we stepped in the ride seemed forever. I could not help starring at the bulge in his shorts it was massive i could feel myself getting hard too we got to our floor and we walked out of the elevator he smiled at me saying goodbye and we parted i did not get his number to keep in touch my regret not gettin that number to find out what was hiding behind that bulge later i found out from a friend he was gay and living up north
 

ronin001

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I young lady I met and sort of dated, she was gorgeous half European and half black, tall and well educated. Sadly she was slightly unstable, so we never had a physical relationship.

Later she became sort of famous in a C list / level of fame, Yes I get to say I dated her; but not that I had sex with her.
 

Upperdown

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Depends on the day:

If I'm feeling like I wanted to do more bad things then I have a list of females that I should have pursued harder. Including some friends' girlfriends. One girl in particular was all chalked up and ready to F*ing go. I didn't go for her and that didn't slow her down. She was sitting on the couch next to me sucking on her tits. Her boyfriend was sleeping less that 10 feet away.

Sometimes I feel the other way and genuinely wish I hadn't done some things. I fucked my girlfriends best friend and that was, in retrospect, a bad idea. That same girl pops up on both ends; she jumped in bed with me years later and I turned her down. I absolutely should have fucked her...maybe
 

Trott.lint

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Depends on the day:

If I'm feeling like I wanted to do more bad things then I have a list of females that I should have pursued harder. Including some friends' girlfriends. One girl in particular was all chalked up and ready to F*ing go. I didn't go for her and that didn't slow her down. She was sitting on the couch next to me sucking on her tits. Her boyfriend was sleeping less that 10 feet away.

Sometimes I feel the other way and genuinely wish I hadn't done some things. I fucked my girlfriends best friend and that was, in retrospect, a bad idea. That same girl pops up on both ends; she jumped in bed with me years later and I turned her down. I absolutely should have fucked her...maybe

Friends' girlfriends? Surely not!
 

Over-reaching

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I hooked up with a crazy chick who had the most perfect breasts and vise grip tight puss. We only actually hung out knce and screwed twice that night after a week or two of chatting online. On my way out the door that night she hit me with an "i love you". In retrospect i shouldve dipped in that honeypot one more time. But who knows, i most definitely dodged a bullet. Perhaps if i went in ankther time she wouldve poked the condom or something. She was baby obsessed. What i find funny is i looked her up like 2 years later on FB and her current bf looked like he could be my twin.
Sounds to me as if you did the wise thing...
 
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Getting a bj from a mate's gf when I was 18. Tame I know - but seemed unforgivable at the time.

She was hot tho - in a slightly unhinged, early Jolie kinda way.
 

ronin001

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Getting a bj from a mate's gf when I was 18. Tame I know - but seemed unforgivable at the time.

She was hot tho - in a slightly unhinged, early Jolie kinda way.

Early Joll, sounds like he was a bit if a rogue :cool:
 

notthatguy

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Was having a discussion with a group of friends after a funeral of one of my friend's parents about lifetime regrets. I said that we have to fuck more often as no one ever said on their death bed, "I wish I had cum less often."
 

linntg

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Not trying something with the guy i was sharing my cabin at an cruise.He had a big bulge and he was freaking hot.