What is your biggest sexual regret, and why?

[ButtAnalMan]

Nice thread

 

[DocErotic3D]

I have a slew of missed opportunity regrets but only one where I regret following through. I made a pass at one of my best friends from growing up. She grew up and she was incredibly hot. She got mad, deservedly so, and I've never talked with her again.

 

[Candy224]

The guy I'm convinced I'll always still love a little bit was laying right in my bed.. All night and I didn't have sex with him. I wanted to be different then the other girls. But I regret it because I feel like it may have made us closer and if I would have had sex with him maybe I wouldn't still be holding onto him like I still am.. It's a rather complicated situation .

 

[DocErotic3D]

The guy I'm convinced I'll always still love a little bit was laying right in my bed.. All night and I didn't have sex with him. I wanted to be different then the other girls. But I regret it because I feel like it may have made us closer and if I would have had sex with him maybe I wouldn't still be holding onto him like I still am.. It's a rather complicated situation .

I was in a similar situation, but with a girl I loved as much as my (now) wife.

 

[TheLM]

In the past year I've passed on 2 threesoms. (FMF/FFM)

Part of me is glad I passed them up, part of me still wants to do it, because I know I'll never pursue it again.

 

[darkknight01]

In the past year I've passed on 2 threesoms. (FMF/FFM)

Part of me is glad I passed them up, part of me still wants to do it, because I know I'll never pursue it again.

Why did you pass them up?

 

[darkknight01]

The guy I'm convinced I'll always still love a little bit was laying right in my bed.. All night and I didn't have sex with him. I wanted to be different then the other girls. But I regret it because I feel like it may have made us closer and if I would have had sex with him maybe I wouldn't still be holding onto him like I still am.. It's a rather complicated situation .

Did you ever have any other chances with him?

 

[TheLM]

Why did you pass them up?

The first one was because I knew one of the girls was emotionally unstable, and it could have messed her up.

The second one was with more mature women... One was my (at the time) sub, but the other was our mutual friend. Redhead, sexy, but a total and complete slut. My sub and I were put off by the fact that she has had so many sexual partners, and the fact that she'd have refused oral in all ways. We still would have had a great time... And we did all three hang out on multiple occasions, but I never initiated anything. To this day I still could, and may.

 

[darkknight01]

The first one was because I knew one of the girls was emotionally unstable, and it could have messed her up.

The second one was with more mature women... One was my (at the time) sub, but the other was our mutual friend. Redhead, sexy, but a total and complete slut. My sub and I were put off by the fact that she has had so many sexual partners, and the fact that she'd have refused oral in all ways. We still would have had a great time... And we did all three hang out on multiple occasions, but I never initiated anything. To this day I still could, and may.

I think you will have another chance. I've never had a sub or a 3some, so you are one up on me.

 

[junk_yard]

My biggest regret...

We were in the hot tub... four of us, my wife, my friend Sam, his girl friend Brenda and I, all absolutely naked and a bit drunk after a football game. My wife & Sam were very obviously playing with their hands beneath the bubbles. It was so obvious. She had that glazed look in her eyes, they were side by side... meanwhile Brenda was next to me, quietly watching, saying nothing. Me? I was a bit disgusted... not wanting to share my wife with anyone... yet I was willing to fuck most any woman when she wasn't around, and often did.

As Brenda sat so close to me, our knees touching, I never reached out to her... and she was a fine specimen of a woman. About 38 of 40, great figure... obviously very aware of what was happening just a couple of feet from us... and I'm sure, willing to join them with our own mutual play. BUT, I didn't want to share my wife. SO, the more I watched, the angrier I got, finally saying, "it's time to go home."

Why, but why didn't I just say to my wife, "go ahead and fuck him." Or, better yet, why didn't I just reach out to Brenda, and begin our own little foreplay... who knows what would have happened! I'll never know, but I relive that moment, that happened so many years ago, countless times, thinking how different it could have been.

True story... my wife and I divorced a couple of years later. I'm sure Sam finally did fuck her at some point. I'm not sure when... I never fucked Brenda, but always wanted to... Brenda and I remain just friends to this day, as for Sam, not so much, haven't spoken to him in years. Brenda and I have never mentioned that night to each other since.

I have a few other regrets... but this one probably tops my list.

 

[analgirl69]

Not a lesbian but....

I had an affair with a girl. We had were just friends but we experimented once..She suggested, I said ok and then she blackmailed me to keep doing it. We started having sex every time we got together and it made me feel so bad and confused. I horribly regret that. It would have been one thing if I was attracted to girls, but I'm not. I can appreciate the female form. Lol. But that is all. I have never had a crush on a girl- only guys.

I also regret the first guy I slept with. Was forceful and not in a fun way that is fantasy, like I have mentioned I have a preference for. He never listened to no (when I managed to actually get enough courage to say it) even when I was sick. He almost got me pregnant- I said no without a condom but he just didn't care. Thank God I was just late... He used me and treated me like his whore, in and out of the bedroom. No one wants to feel like someone else's trash. But I have a hard time saying no, so I am easily taken advantage of. Finally got the lady balls and dumped his ass.

Thank God I met my husband when I was 15 so I have no more regrets. Sometimes it takes some bad experiences to make you truly appreciate it when you find someone who treats you right.

 

[darkknight01]

My biggest regret...

We were in the hot tub... four of us, my wife, my friend Sam, his girl friend Brenda and I, all absolutely naked and a bit drunk after a football game. My wife & Sam were very obviously playing with their hands beneath the bubbles. It was so obvious. She had that glazed look in her eyes, they were side by side... meanwhile Brenda was next to me, quietly watching, saying nothing. Me? I was a bit disgusted... not wanting to share my wife with anyone... yet I was willing to fuck most any woman when she wasn't around, and often did.

As Brenda sat so close to me, our knees touching, I never reached out to her... and she was a fine specimen of a woman. About 38 of 40, great figure... obviously very aware of what was happening just a couple of feet from us... and I'm sure, willing to join them with our own mutual play. BUT, I didn't want to share my wife. SO, the more I watched, the angrier I got, finally saying, "it's time to go home."

Why, but why didn't I just say to my wife, "go ahead and fuck him." Or, better yet, why didn't I just reach out to Brenda, and begin our own little foreplay... who knows what would have happened! I'll never know, but I relive that moment, that happened so many years ago, countless times, thinking how different it could have been.

True story... my wife and I divorced a couple of years later. I'm sure Sam finally did fuck her at some point. I'm not sure when... I never fucked Brenda, but always wanted to... Brenda and I remain just friends to this day, as for Sam, not so much, haven't spoken to him in years. Brenda and I have never mentioned that night to each other since.

I have a few other regrets... but this one probably tops my list.

Why not bring it back up to Brenda, she was game before, she might be game now.

 

[darkknight01]

I had an affair with a girl. We had were just friends but we experimented once..She suggested, I said ok and then she blackmailed me to keep doing it. We started having sex every time we got together and it made me feel so bad and confused. I horribly regret that. It would have been one thing if I was attracted to girls, but I'm not. I can appreciate the female form. Lol. But that is all. I have never had a crush on a girl- only guys.

I also regret the first guy I slept with. Was forceful and not in a fun way that is fantasy, like I have mentioned I have a preference for. He never listened to no (when I managed to actually get enough courage to say it) even when I was sick. He almost got me pregnant- I said no without a condom but he just didn't care. Thank God I was just late... He used me and treated me like his whore, in and out of the bedroom. No one wants to feel like someone else's trash. But I have a hard time saying no, so I am easily taken advantage of. Finally got the lady balls and dumped his ass.

Thank God I met my husband when I was 15 so I have no more regrets. Sometimes it takes some bad experiences to make you truly appreciate it when you find someone who treats you right.

I'm so sorry this happened to you. This was not of your choice and it's sad that those people took advantage of you. I'm happy to hear you found someone who treats you right.

 

[Jon4Fun916]

I regret that when I was out of town I had the opportunity to take 2 girls home with me and I didn't to be "loyal" to my spouse...and at the end of it all she was just as mad at me for being out getting drunk with some friends as she would have been if I had cheated on her. And two years later we were divorced...so I was loyal for no reason really. 10 years of loyalty for no reward.

 

[Johnnyboy30]

I regret that when I was in high school and college that I did not have sex with girls that were curvy, chubby, chunky or bbw's (however you want to characterize it). I had more than enough opportunities to take but I never went through with it. I woul flirt but never take it farther even though some of them made it very clear that I was going to get laid. I'm not really sure why I don't try harder but I think it's because I didn't think I should hook up with chubby women or that I would be laughed at for trying to pick up a bigger girl.

Since high school and college, I have had a number of experiences with bigger women and they ALL have been incredible. I think I even have a bit of a fetish for bigger girls . Too bad I missed out on some sexy women because of my own hang ups.

 

[needsnewstart]

regret not trying more stuff with the same sex, i am m, fooled around with best friend when i was a teen, am totally into the female gender physically. but i wish i had been a little more open when i was younger with other guys.

 

[eastsidegent]

I regret being to shy....too scared to make a move. And I regret having had opportunities to have sex with some wonderful women, but I didn't in fear of ruining friendships, etc. I wish I had been with them as I think of them often and realize now that relationships do change. I wouldn't be talking to those women less now had we been together.

 

[mike2010fc]

.....

 

[whynotjustsayit]

Everything? Is that allowed for a response? I've mostly had messed up sexual encounters from a young age. I never got to fall in love with a woman and be totally open about sex as we explore each others bodies. My memories are just hundreds of random drunken sexual hookups. Now I'm maybe just too cynical to have the kind of honest, innocent encounter that I've always dreamt of. Sex is only mechanical now. Lit has been healing because it's been nice to hear other people's experiences and know that we all suffer in some way.

Mike

Lit is a very healing place in that regard, I agree.

 

[Sweet_Jenna]

Hmmm... my biggest regret is from my college days. I was at a party, playing some kind of drinking game with these two smokin' hot guys. Each time my turn was over, I had to either drink or kiss one of the guys. I was smart enough to realize at some point that I had had enough to drink, and just resolved to ending each turn with a kiss. I alternated between the two guys, and each kiss grew more and more consuming. Then the kisses started to involve roaming hands and some playful groping (over clothes). It was awesome, and could easily have led to a threesome if I had indicated I was interested/willing. If I could go back and do it again, things would happen differently.

 

[intriguedwriter]

I was 24 and he was 38, lithe and tanned. And sensual, said he could teach me all kinds of things.
I got scared off, but wish I hadnt. It was many years ago now. I regret saying no to him. I had 'issues' then that took me a while to get through.

 

[cuckold_tales]

Back when I was shy and retiring, a guy I work with kept hitting on me, but I'd always turn him down out of loyalty to my boyfriend. Now, he's working someplace else, and I haven't seen him lately.

 

[Ray Roberts]

Rejected what was on offer, then women scorned beware!

My wife and I were at a party of one of my golf friends, at the party another friend who I played golf with regularly was their with his wife and daughter who although married had come to visit her parents she would have been 23 and myself about 30.

We ended up chatting together and then dancing while my wife was socialising elswhere. Eventually I moved on to chat with others and then my wife came up to me and said the wife of my friend had asked her to ask me if I would take their daughter home as she was not feeling well. Full of innocence I agreed and I drove her back to her parents house without much being said.

Once there she insisted that I come in for a cup of coffee and then she asked if I would take care of the coffee while she went upstairs. I got the shock of my life, she was absolutely naked and what a figure as an ex model. She simply said "Like what you see, come and get it" I on the other hand could only think of my wife and kids and the trouble this could all end up with. So I said sorry I've got to go. Then she went berserk started swearing and chucking things at me. Cups plates crashing around me as I hi-tailed it out.

I've always regretted that opportunity and the strife it still caused because I foolishly spilled the beans to my wife and they had a slanging match in the street. I might as well have taken my chance, but then you have to learn from your mistakes.

 

[chatman2]

chaman2

Most were because I was shy when young.
This one I just recalled.
My first one I just recalled being after my first affair was over as I had transfered. I had a 19 yr old high school girl that worked next door to my office and she had a crush on me. I was 23 and married and felt she needed a single man. I later found out she ended up having a fling with her boss. My co worker told me all along I was a fool for not hooking up with her. She only came in when our secretary was out of the office.

 

[ButtAnalMan]

Hmmm... my biggest regret is from my college days. I was at a party, playing some kind of drinking game with these two smokin' hot guys. Each time my turn was over, I had to either drink or kiss one of the guys. I was smart enough to realize at some point that I had had enough to drink, and just resolved to ending each turn with a kiss. I alternated between the two guys, and each kiss grew more and more consuming. Then the kisses started to involve roaming hands and some playful groping (over clothes). It was awesome, and could easily have led to a threesome if I had indicated I was interested/willing. If I could go back and do it again, things would happen differently.

You do not need to regret. You can search for it.