What is your biggest sexual regret, and why?

I have many but when I was dating after my divorce I went out with a woman whom became more of a friend once we realized being a couple was not realistic. I was at work one evening and she stopped by and was all upset because her new boyfriend dumped her. I got cleaned up and took her out to dinner and a movie. She begged me to go back to her place and have a few drinks but I knew where that would lead and it wasn't fair to her. If I fucked her the relationship would have not been healthy for either of us.

A few weeks later she told me how badly she needed oral servitude that night and to top it off she admitted to being a squirter and a big one at that. She smelled good and I bet her Nectar would have been like pure sugar. Talked about a missed opportunity.

It sounds like opportunity came knocking at your door twice and you didn't answer it both times. :(
 
I used to fool around with this guy in high school, making out, letting him feel my tits etc. On a couple of occasions I gave him head, but we never actually had sex because I didn't want him to see me naked. He had the biggest cock I've ever seen in the flesh, and I regret that I never got the chance to try and take it inside me. It might be for the best though, as it could have meant I always wanted them that big in the future.

Stargirl69, It look like you do crave to have them big.
 
Biggest regret is one I can't control: having grown up before the Internet. If I had had the 'net when I was younger, it would have opened whole new horizons to me. I was shy in high school; perhaps the 'net would have changed that.
 
hi

school days.i had sex wit a clsmate.no condom.so we went for anal start to finish.somehow in the frenzy he entered vag and finished there.i had to face infection and later preg scare.it was a mess and hell for some days. The guy just vanished due to scare of the consequences and left me to fend for myself.i regret that experience.
 
I was 19, she was 23. She was the sister of my girlfriend and a beauty pageant winner. She was perfect and we were home alone!
We played records and drank white Russians (first time for me) until she suddenly announced she was going to get ready for bed.
Thinking it was time for me to leave, I got up, but she asked me if I was joining her!!! OMG..... a dream about to come true.
So I went into the bathroom to freshen up, only to awaken a few hours later, wrapped around the toilet. I guess I passed out!
I looked in her bedroom, there she was, laying in bed with a see thru nightie on.... she woke up, saw me, and asked if I was coming to bed now.
I mumbled no and went home instead!!!!
OMG.... I have regretted that decision to this very day!
 
hi

Biggest regret is one I can't control: having grown up before the Internet. If I had had the 'net when I was younger, it would have opened whole new horizons to me. I was shy in high school; perhaps the 'net would have changed that.

now that you have internet why not try another innings?
 
It sounds like opportunity came knocking at your door twice and you didn't answer it both times. :(

Sounds more to me that he recognized the right thing to do, and did it. Not everything in the universe revolves around your cock, you know.
 
Sounds more to me that he recognized the right thing to do, and did it. Not everything in the universe revolves around your cock, you know.

Yes, you are right. Not everything in the universe revolves around sex. He was a single man and she was a single woman. She was giving him signals both times. Maybe there was something more going on than he explained, maybe not.
 
school days.i had sex wit a clsmate.no condom.so we went for anal start to finish.somehow in the frenzy he entered vag and finished there.i had to face infection and later preg scare.it was a mess and hell for some days. The guy just vanished due to scare of the consequences and left me to fend for myself.i regret that experience.

You mean "when you were 18", right?
 
I regret sucking my (male) best friend's brother's cock. Why do I regret it? Because he asked me if I'd ever done anything with his brother and so help me but I lied and said no when on reality I have fucked his brother (my best friend). I only regret getting physical with his brother because it was done so on the basis of a lie. I wish I would have said "Yes...I've sucked his cock too and we've fucked a few times." Then I wish he would've looked at me and said, "Well now it's my turn."
 
I regret sucking my (male) best friend's brother's cock. Why do I regret it? Because he asked me if I'd ever done anything with his brother and so help me but I lied and said no when on reality I have fucked his brother (my best friend). I only regret getting physical with his brother because it was done so on the basis of a lie. I wish I would have said "Yes...I've sucked his cock too and we've fucked a few times." Then I wish he would've looked at me and said, "Well now it's my turn."

That's hot!
 
Not having a fifteen inch cock, as all the other guys on this site do:D
 
I only regret things I didn't do... I think I probably have more relationship/emotional regrets than anything I regret sexually.

Although... now that I think about it... Once upon a time, I reestablished contact with an ex-girlfriend with whom I had had great chemistry. I was going to be in her area (having moved away some years prior) and so we got together for dinner and later went back to her place. We ended up having sex and it was terrible. I think she had a good time, but I realized I had really moved on and it was a mistake. Needless to say she was pissed off. Didn't want to be the asshole there, but sometimes it happens...
 
A few years ago a friend of a friend (female- and hot) kissed me, i kissed her back, then she ran her hand up my shirt. I chickened out and pulled away. Many times since I have wanted a re-do.
 
The summer between high school and college an older woman (mid-30's) from our church shamelessly flirted with me. I'll always regret not having had the courage to let her "educate" me in the ways of the world....
 
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