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What is your biggest sexual regret, and why?

Not taking *advantage* of a few younger men who expressed ..interest.
 
I was dating a girl in college, fwb's really, and one weekend she went home. I saw a friend of hers at a party, and we went home and had sex. It was really fun, but someone told the girl I was seeing, and that ended it. She said she knew we were not exclusive, but it bothered her I did it with her friend. The way she explained it and the way she acted just made me feel like a total dick.

Here's a good one I DON'T regret, but for a long time thought I made the wrong decision. Worked with a really hot little Italian girl. One day she invites me to hang out in the afternoon with her on her farm, family had big bucks. I get there and she's had a few beers already and offers me some weed. I had only smoked a few times in my life at that point, but I decided sure. Got really stoned and she starts talking about sexual fantasies and I am beyond excited for the sex I am sure will soon come. Then she says her fantasy is to be gangbanged, I immediately thought, WHORE! Right or wrong, that's what I thought. It got real awkward but, I left about 10 minutes later (and jerked off as soon as I got home!). About 3 years later I am hanging out at Spring Break in Fla and run into some friends of mine. This girls name comes up because one of them went to high school with her. They say she's a ragin whore, confirmed diseases. I explained my experience and they said, seriously she slept with everyone, and has diseases for sure. NO REGRETS!!
 
tiny_tits said:
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.
Click to expand...

If only life had a rewind button. :heart:
 
I met a man as a prospective new friend to spend time with. We met just for coffee to check out the chemistry. He was very pushy from the very beginning. I thought he was pretty appealing though so after a few half-hearted denials I agreed to sit in his car with him. We started making out and his hands started wandering and I gave in and ended up in a hotel room with him. It wasn't great but not bad either. I left feeling like I had been played though. Not a good feeling and I regret being weak.
 
There are a whole bunch of people I wish I had (and maybe could have) slept with in college. I also regret not being up for a threesome that almost happened. It's always easy to second-guess in hindsight and ask yourself "What was I thinking??" but at the time I guess it just didn't feel right. But I've sure spent some time since then imagining how it could have gone...
 
Loving50 said:
I met a man as a prospective new friend to spend time with. We met just for coffee to check out the chemistry. He was very pushy from the very beginning. I thought he was pretty appealing though so after a few half-hearted denials I agreed to sit in his car with him. We started making out and his hands started wandering and I gave in and ended up in a hotel room with him. It wasn't great but not bad either. I left feeling like I had been played though. Not a good feeling and I regret being weak.
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You should always go with your gut feeling.
 
Dogma52 said:
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!
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This made me LOL!

My one sexual regret was having revenge sex when I found out my hubby (now ex) cheated on me. I never told him I cheated, but I knew I had done it, which went against every principle I had. To this day it is still the only regret I have in my life.
 
Not experience being with a sexy, brunette female before I was married....now I'll never know what it's like to be with a woman.... My biggest, most haunting fantasy!
 
BiMommy77 said:
Not experience being with a sexy, brunette female before I was married....now I'll never know what it's like to be with a woman.... My biggest, most haunting fantasy!
Click to expand...

You can't work something out with your hubby?
 
Mrclean_sober said:
I was dating a girl in college, fwb's really,

Here's a good one I DON'T regret, but for a long time thought I made the wrong decision. Worked with a really hot little Italian girl. One day she invites me to hang out in the afternoon with her on her farm, family had big bucks. I get there and she's had a few beers already and offers me some weed. I had only smoked a few times in my life at that point, but I decided sure. Got really stoned and she starts talking about sexual fantasies and I am beyond excited for the sex I am sure will soon come. Then she says her fantasy is to be gangbanged, I immediately thought, WHORE! Right or wrong, that's what I thought. It got real awkward but, I left about 10 minutes later (and jerked off as soon as I got home!). About 3 years later I am hanging out at Spring Break in Fla and run into some friends of mine. This girls name comes up because one of them went to high school with her. They say she's a ragin whore, confirmed diseases. I explained my experience and they said, seriously she slept with everyone, and has diseases for sure. NO REGRETS!!
Click to expand...

Bull shit hear say! You should have fucked the living daylights out of her. Just put a condom on.
 
Mine is fairly simple. I wish I had been more sexually active when I was younger. I'm a disabled guy. So when you have that against you, it's hard to get up the courage to even approach a woman.

Being with someone now for years is okay, but I always wish I had given myself a chance to be with a few women just to see what it was like. To have sewn my oats before settling.

I still think about that and feel terrible I didn't take more chances back then.
 
BiMommy77 said:
Not experience being with a sexy, brunette female before I was married....now I'll never know what it's like to be with a woman.... My biggest, most haunting fantasy!
Click to expand...

Are you saying that this is now ruled out???
 
hi

i should have lured my ex bf's dad to do sodomy on me like he did his wife.
 
I wish I had sex more ! That's really about it. Looking to rectify (sp?) that situation, by the way... Just sayin'...
 
I have no regrets. A lot of mistakes and poor judgement, but no regrets.
 
I had a fling with one of my ex HS teachers when I was out of school a few years and in the military. She was 10 years older than me and very sexual. She turned me onto a lot of things that even I, as a pretty experienced 20 yo, had never done.

One time when I was home on leave, she invited me over to her house and told me that she had her best friend with her. She said they were ready to have a good time. I jumped in my car and on my way to her house I decided to swing by my best friends house to see if he wanted to join me and maybe "party" with her friend.

After several hours of drinking and talking, we ended up with both of us heading to different rooms with our partners, me the ex teacher, him her best friend. The next day, my lover asked me why I had brought my friend...she explained that she was "sometimes" bisexual and the idea was to have a 3 way with her friend and me. I was literally kicking myself...I don't know how it is today, but back in the 80's, as a young man, the opportunity for a 3-way with a couple of bisexual women didn't land your lap everyday!
 
Too many, but the biggest is after a Senior high school pool party I went to thank the hostess, a hot mid-late 30's wife with no kids, and as I went to hug her she did a tonsil check on me with her tongue, my buddy couldn't believe I didn't go for more, but all I could think about was her husband. I was too stupid or naïve one to realize they were probably swingers. Damn, what could of been.
 
I should have tried having sex with a hot guy in high school.

We knew each other but wern't great friends. But he was so hot - bubble butt, soft round lips, cute face.

Should have made the move on him and see where it went. Hopefully to his bed, me pinning him down on it with my swollen cock in his tight little virgin ass.
 
MarathonATL said:
I had a fling with one of my ex HS teachers when I was out of school a few years and in the military. She was 10 years older than me and very sexual. She turned me onto a lot of things that even I, as a pretty experienced 20 yo, had never done.

One time when I was home on leave, she invited me over to her house and told me that she had her best friend with her. She said they were ready to have a good time. I jumped in my car and on my way to her house I decided to swing by my best friends house to see if he wanted to join me and maybe "party" with her friend.

After several hours of drinking and talking, we ended up with both of us heading to different rooms with our partners, me the ex teacher, him her best friend. The next day, my lover asked me why I had brought my friend...she explained that she was "sometimes" bisexual and the idea was to have a 3 way with her friend and me. I was literally kicking myself...I don't know how it is today, but back in the 80's, as a young man, the opportunity for a 3-way with a couple of bisexual women didn't land your lap everyday!
Click to expand...

What was going through your mind when you invited your friend to come along??? :confused:
 
When I was in college there was a girl that had a smoking hot body. She wore hideous glasses so I never pulled the trigger. I found out many years later that she had wanted to date me. And I can only think of the fun I missed by not asking her out.
 
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