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What is your biggest sexual regret, and why?

Realistically I wish I would have slept around more before my first marriage. It wouldn't have happened lol
 
Had a girlfriend in college that got off on me being with other women. Dumbass me, didn't want to do it as much as her. ooooohhhhh.
 
My biggest regret was high school. I was painfully shy and was also pretty clueless when it came to girls, so I hardly dated at all. Then at reunions over the years, I've had several girls tell me they liked me back then and wondered why I never asked them out.

If I could go back in time .... :rolleyes:
 
Mropietaylor69 said:
Had a girlfriend in college that got off on me being with other women. Dumbass me, didn't want to do it as much as her. ooooohhhhh.
Click to expand...

Really? How did that work with her? What was the turn on for her? Did she want a 3some or she just got off on knowing you were with someone other than her?
 
Having being a Dom of 30 years and getting married to a vanilla for 3 years.. I should never have done it.. lol ThanK GOD I now have a great sub.
 
darkknight01 said:
If feel for you.

Do you know where this teacher is now?
Click to expand...

She became a flight attendant for a major US airlines. I had a fling with her a few years later, and got caught by her, unbeknownst to me, pilot fiance butt naked eating her pussy. He was not happy, lol, and that was the last time I saw her.

I found her a facebook a few years ago and creeped on her, though I never friended her as my wife knew we had been pretty heavy into each other before I was married...even as a 50+ year old, she was still sexy as hell.
 
hi

i should have lured my ex bf's dad to do sodomy on me like he did his wife.i regret it to this day.
 
Two genres' of regret. Marrying a vanilla woman and generally not making contact with ladies (especially the ones I caught checking me out) because I was too busy to flirt etc.
 
Miy biggest is

Not fucking the sexy, puffy nippled, hairy pussied, Spanish Girl I help out of a jam by letting her stay with me for a few weeks back in the late eighties..........Maria where are you baby?
 
MarathonATL said:
She became a flight attendant for a major US airlines. I had a fling with her a few years later, and got caught by her, unbeknownst to me, pilot fiance butt naked eating her pussy. He was not happy, lol, and that was the last time I saw her.

I found her a facebook a few years ago and creeped on her, though I never friended her as my wife knew we had been pretty heavy into each other before I was married...even as a 50+ year old, she was still sexy as hell.
Click to expand...

Sounds like you still want her. Maybe you can convince the wife to have a 3some with her.
 
The fall of 1985. I was leaving a job and a place I lived and at my going away party I had the chance to make love to a beautiful woman I had long been attracted too - and I said no. I should have said yes. :)
 
Had the chance to experience receiving anal but chickened out. Ive since lost contact with the couple and have not found anyone new.
 
UhlBWett said:
Not fucking the sexy, puffy nippled, hairy pussied, Spanish Girl I help out of a jam by letting her stay with me for a few weeks back in the late eighties..........Maria where are you baby?
Click to expand...

Was this "Spanish Girl" a friend, co-worker, or someone else you knew? How did you know she had "puffy nipples and a hairy pussy"?
 
Paul_Chance said:
The fall of 1985. I was leaving a job and a place I lived and at my going away party I had the chance to make love to a beautiful woman I had long been attracted too - and I said no. I should have said yes. :)
Click to expand...

Why did you say no?
 
I met her at a local night club.......

darkknight01 said:
Was this "Spanish Girl" a friend, co-worker, or someone else you knew? How did you know she had "puffy nipples and a hairy pussy"?
Click to expand...

I gave her my address, she showed up the next morning. She wasn't shy about her body and often dried off with the bathroom door open after she showered.
 
Probably was

darkknight01 said:
Sounds like an open invitation to me.
Click to expand...

I was going through a divorce at the time and already banging a 19 year old, I was 27 then, so my life was all fucked up. Could have, should have, you know..................
 
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