What is your biggest sexual regret, and why?

Being afraid

I married the first man I slept with and was with him for 24 years until he left me four years ago. On a whim a few months back I put a profile up on a dating site and an old acquaintance found me and expressed a great deal of interest. After over four years of celibacy, it didn't take much to get me persuaded to ride the pony. ;) I think the only reason I let it get that far was because I had met him before and didn't feel like I was putting myself in danger by meeting some stranger.

Problem is, he's moved on to other women as he loves the thrill of the chase, and I'm sitting here thinking, what, do I wait until some man decides to approach me? I have no idea how to go about "putting myself out there," as some of the folks here talk about. Part of me wants to, and part of me is very, very afraid to put myself out there. I've ended up taking down my profile on the dating site.

I've had some really lovely chats with Literotica folk here and on Yahoo and have had some lovely hot cyber encounters. But in real life? Not a chance.

Sigh. I know I probably "could" change this regret, but honestly, I don't know if I'm going to be able to, nor am I at all sure *how* to. :mad:
 
I married the first man I slept with and was with him for 24 years until he left me four years ago. On a whim a few months back I put a profile up on a dating site and an old acquaintance found me and expressed a great deal of interest. After over four years of celibacy, it didn't take much to get me persuaded to ride the pony. ;) I think the only reason I let it get that far was because I had met him before and didn't feel like I was putting myself in danger by meeting some stranger.

Problem is, he's moved on to other women as he loves the thrill of the chase, and I'm sitting here thinking, what, do I wait until some man decides to approach me? I have no idea how to go about "putting myself out there," as some of the folks here talk about. Part of me wants to, and part of me is very, very afraid to put myself out there. I've ended up taking down my profile on the dating site.

I've had some really lovely chats with Literotica folk here and on Yahoo and have had some lovely hot cyber encounters. But in real life? Not a chance.

Sigh. I know I probably "could" change this regret, but honestly, I don't know if I'm going to be able to, nor am I at all sure *how* to. :mad:

You have to change the way you think and you have to be more positive and have some fun. Things are not always going to be good, but if you don't take any chances you are not going to be happy. Believe in your dreams and make them happen.

You deserve the best and until you get the best. Enjoy the road while you are getting there.
 
You have to change the way you think and you have to be more positive and have some fun. Things are not always going to be good, but if you don't take any chances you are not going to be happy. Believe in your dreams and make them happen.

You deserve the best and until you get the best. Enjoy the road while you are getting there.

Thanks, darknight...truly, those who know me would characterize me as a positive person! I look men in the eye, I smile, sometimes I flirt, I enjoy life! I just don't get asked out - or in! LOL. But this is a regrets thread, and so I guess that was a little dark!

I don't drink, so I don't tend to go to bars, and being married for so long from a young age, I'm a bit clueless about how to go about things. :) I'm very glad I have internet chat and this board, though. It helps!
 
Thanks, darknight...truly, those who know me would characterize me as a positive person! I look men in the eye, I smile, sometimes I flirt, I enjoy life! I just don't get asked out - or in! LOL. But this is a regrets thread, and so I guess that was a little dark!

I don't drink, so I don't tend to go to bars, and being married for so long from a young age, I'm a bit clueless about how to go about things. :) I'm very glad I have internet chat and this board, though. It helps!

I'm happy to hear that you are a positive person. :D

You will be asked out, get back on that online service and talk to guys. You don't have to go to bars to meet men. Go to places you like to go to, go to a sports game with your g/f's, go to the park, book store, but you have to go out. I'm sure you will meet some great people here too.

I hope to see you around. :D
 
I had the opportunity to have a threesome when I was 17. I didn't take it because I had a boyfriend, and my neighbor- one of the participants- was only 15. I haven't had another opportunity. :(

The other is wasting a ton of time on a kid who I have just begun to realize is never going to fuck me. Moving on...
 
I am intrigued that most of the regrets on this thread describe something the poster ~didn't~ do. A missed opportunity. I have plenty of those kinds of regrets ... the girl in freshman Spanish class in college who never quite let me have her completely ... the girl at my junior prom who made me dance with her and leaned her head back as she clung to me, swinging her blonde hair across her shoulders, practically begging me to kiss her neck ... the alabaster-skinned redhead at church camp. Enough "what ifs" to fuel all kinds of fantasy thoughts ... But I find it difficult to say that my life would have been any better if I had fully known any of those girls. In fact in at least one case, I probably dodged an emotional bullet.

But if I were to express one thing I actually did that I now regret ... it would be something that didn't actually end in a sexual encounter. I had been chatting online with a girl, who was really just a friend but who I talked a lot about sex with. I told her about this really cute intern in my office ... an intern who was just a little bit crazy. Just crazy enough, I thought, to give in to a guy who was not only somewhat older, but also a staffer in a political office, and who was also taken. She was graduating and leaving our office, so (at the urging of the online friend) I used that as an excuse to take her for coffee, just to chat about working in politics and give her advice to send her on her way. I was flirty, and touchy, grabbing her hand and squeezing it when she told me she got a Teach for America position, letting our knees touch under the table. I gave her a hug and kiss on the cheek in both greeting and parting. I went back and told my online friend, and she encouraged me to pursue this girl more ... so I actually went back to the coffee shop right then and told this girl I wanted to hang out again ... and she said she'd like that ... but then when I called her later she asked what was going on, and in that conversation and a little bit of an email exchange, I was a little more forward, and she was more resistant. I let her know what I wanted and asked how she had not felt anything between us. She became judgmental, and angry, and threatening. It turns out, I think, that she had actually felt just a spark of something between us, which should have been left as a yummy little morsel of sexual tension and flirtation, but which I made into a real sexual pursuit. And being a slightly crazy college kid, she actually enjoyed the drama more than the attention or possibility of anything sexual between us.

Why do I regret this? I was reckless. I let this online girl (who was also a little bit of a drama-loving crazy person herself) push me into something unsafe. I let purely physical desires put me in danger. I had not yet made "official" vows to my wife ... but I had made promises. She was my fiancee at the time. I did not consider ~who~ might be worth breaking those promises for. I did not think about ~who~ I would break those rules for. I pursued someone who did not necessarily want me, who did not have my best interest at heart, and who could very easily have hurt not only me but many people around me.

Now ... there are circumstances in which I would break those rules. Find a way around the vows I have since made. And some of you may judge me for that, and you've every right to do so. But there is one ... one in particular ... for whom I would, because of who she is and what she is for me, but also because I know she would go out of her way to see that no one is hurt. That we both stay safe. She won't allow me to be reckless ... she won't allow my urges to overwhelm my common sense.

Which brings be back to a regret of something I haven't done ... which is to say ... I regret that I have not yet been with ... fully and truly with ... this one. This one for whom I would break rules ... the one I could never, ever regret.
 
That I was circumcised as an infant.

Based upon what I now feel, having mostly restored my foreskin, I missed some mind blowing sex. I will always regret missing what I could have had, taken from me when I was helpless.

This. A part of me was taken without my consent. I have since discovered that orgasm isn't limited to my penis and prostate but the full blown sensations of a penile orgasm will always be denied me. It upsets me that people think that what's best for their kids somehow includes such a barbaric practice. Humans managed just fine without this procedure for a very long time.

I regret not learning sooner that orgasms can be felt in virtually any part of the body. I'd have another 30 years of practice under my belt.
 
I am intrigued that most of the regrets on this thread describe something the poster ~didn't~ do. A missed opportunity. I have plenty of those kinds of regrets ... the girl in freshman Spanish class in college who never quite let me have her completely ... the girl at my junior prom who made me dance with her and leaned her head back as she clung to me, swinging her blonde hair across her shoulders, practically begging me to kiss her neck ... the alabaster-skinned redhead at church camp. Enough "what ifs" to fuel all kinds of fantasy thoughts ... But I find it difficult to say that my life would have been any better if I had fully known any of those girls. In fact in at least one case, I probably dodged an emotional bullet.

But if I were to express one thing I actually did that I now regret ... it would be something that didn't actually end in a sexual encounter. I had been chatting online with a girl, who was really just a friend but who I talked a lot about sex with. I told her about this really cute intern in my office ... an intern who was just a little bit crazy. Just crazy enough, I thought, to give in to a guy who was not only somewhat older, but also a staffer in a political office, and who was also taken. She was graduating and leaving our office, so (at the urging of the online friend) I used that as an excuse to take her for coffee, just to chat about working in politics and give her advice to send her on her way. I was flirty, and touchy, grabbing her hand and squeezing it when she told me she got a Teach for America position, letting our knees touch under the table. I gave her a hug and kiss on the cheek in both greeting and parting. I went back and told my online friend, and she encouraged me to pursue this girl more ... so I actually went back to the coffee shop right then and told this girl I wanted to hang out again ... and she said she'd like that ... but then when I called her later she asked what was going on, and in that conversation and a little bit of an email exchange, I was a little more forward, and she was more resistant. I let her know what I wanted and asked how she had not felt anything between us. She became judgmental, and angry, and threatening. It turns out, I think, that she had actually felt just a spark of something between us, which should have been left as a yummy little morsel of sexual tension and flirtation, but which I made into a real sexual pursuit. And being a slightly crazy college kid, she actually enjoyed the drama more than the attention or possibility of anything sexual between us.

Why do I regret this? I was reckless. I let this online girl (who was also a little bit of a drama-loving crazy person herself) push me into something unsafe. I let purely physical desires put me in danger. I had not yet made "official" vows to my wife ... but I had made promises. She was my fiancee at the time. I did not consider ~who~ might be worth breaking those promises for. I did not think about ~who~ I would break those rules for. I pursued someone who did not necessarily want me, who did not have my best interest at heart, and who could very easily have hurt not only me but many people around me.

Now ... there are circumstances in which I would break those rules. Find a way around the vows I have since made. And some of you may judge me for that, and you've every right to do so. But there is one ... one in particular ... for whom I would, because of who she is and what she is for me, but also because I know she would go out of her way to see that no one is hurt. That we both stay safe. She won't allow me to be reckless ... she won't allow my urges to overwhelm my common sense.

Which brings be back to a regret of something I haven't done ... which is to say ... I regret that I have not yet been with ... fully and truly with ... this one. This one for whom I would break rules ... the one I could never, ever regret.

I wouldn't judge you for your decision. You have to do what feels right in your heart.
 
Which brings be back to a regret of something I haven't done ... which is to say ... I regret that I have not yet been with ... fully and truly with ... this one. This one for whom I would break rules ... the one I could never, ever regret.

I share your exact feelings, lover. And I miss you so terribly today.

By the way.... Can you see bolded words at Lit when using your phone?
 
You haven't killed this thread, it sometime takes a little bump to get things flowing back again. :)

No worries!! I swear I kill threads all the time! I comment... and they just die!!!

My main sexual regret.... is not having more sex!!! I've had a sad amount ( i feel ) for a 32 yr old woman. I swear I'm not going to have this same regret 30 years from now. I am planning a trip to hedo! Just hopping I won't regret that....
 
Well it is kind of my fault, since I knew what I was getting into, my friend warned me, but I went through with it anyway, but still, thanks for saying that. Yeah, I feel pretty disgusting everytime I think about it, and no, my friends and I don't really talk about 'feelings', and I don't have a therapist or anything like that, I'm just hoping that I'll stop looking at it as such a big deal, I guess I'm just sensitive.
(Assuming you were talking to me anyway, if you weren't just ignore this hah, and sorry for being such a downer haha)

I'm sorry about the emotions you have wrapped up in that. If you can see the logic in it.. then think about how the hurt doesn't help you, and see if you can let it go. If you try looking for the silver lining in the storm cloud... well hell. You had the bravery to go ahead and do something to change a situation you were frustrated with!! That's something poeple all over the planet don't have the gumption to do!! I sure wish I could just get out there and get over my fears. Did it back fire? yes and no. You accomplished mission, even if the so called "execution" could have been better. Millionaires are the people who dared to try, failed, and dared again. Seriously.

You went for something, and achieved your initial goal. Now you have more experience, and a reference point for the next time. With the "virgin" pressure off.. you can now start figuring out what you want to do! A lot of people seem to have the " I regret loosing my virginity the way I did"... but you still have the "good experience virginity" to loose ! :) Go find it! (when you're ready :)
 
No worries!! I swear I kill threads all the time! I comment... and they just die!!!

My main sexual regret.... is not having more sex!!! I've had a sad amount ( i feel ) for a 32 yr old woman. I swear I'm not going to have this same regret 30 years from now. I am planning a trip to hedo! Just hopping I won't regret that....

Well I don't believe you are a thread killa. Some threads just need a bump and they start right back up again.

I'm sure you will not have to do much to get your average up now that you are putting yourself out there. Don't get all wrapped up about it and have fun.

I've heard mixed reviews about hedo. If you go, let us know how you liked it.
 
choices...

I think my biggest regrets are having sex with people just for attention (sounds a tad pathetic...eeeek!). Although, I was quite willing, and for the most part - they were satisfying encounters.....I wish i'd had a bit more self esteem and felt like I was participating because I wanted to as opposed to that being the only way to get attention.

Enough rambling! :)
 
I think my biggest regrets are having sex with people just for attention (sounds a tad pathetic...eeeek!). Although, I was quite willing, and for the most part - they were satisfying encounters.....I wish i'd had a bit more self esteem and felt like I was participating because I wanted to as opposed to that being the only way to get attention.

Enough rambling! :)

And I have all this attention to give, but can't find the girl that needs it. :mad:
 
My biggest regret is the girl who came over to say good by when I moved from New Mexico years ago. We had been flirts for years and I had seriously pursued her at one time but the timing was never right. Anyway she came over and suggested we get some ice cream and we went to get some and brought it back. She then said "I always eat ice cream in my underwear" so sure lets strip down. Then we just ate the ice cream. It wasn't untill weeks later it clicked that was my chance...
 
I've heard mixed reviews about hedo. If you go, let us know how you liked it.

Oooh, what's hedo? (wishing this board had the eating popcorn smiley)

...toddling off to Google now.....

OMG. yes, yes, report back...sounds amazing even from the scrubbed-vanilla website which only hints... :cool:
 
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Oooh, what's hedo? (wishing this board had the eating popcorn smiley)

...toddling off to Google now.....

OMG. yes, yes, report back...sounds amazing even from the scrubbed-vanilla website which only hints... :cool:

If you go, please give us a full report on how you liked it.
 
I wish I had not been so oblivious in High School. Now 20 years later I find out about chances I missed out on because of fear of rejection or failure to notice a lady was interested in me until it was too late. Wish I could repeat High School, just with my head out of my ass this time.
 
I wish I had not been so oblivious in High School. Now 20 years later I find out about chances I missed out on because of fear of rejection or failure to notice a lady was interested in me until it was too late. Wish I could repeat High School, just with my head out of my ass this time.

It would be nice to have a reset button in life. :)
 
O. Henry story:

Man sells soul to devil for a watch to stop time when he reached the happiest point in his life. Went unused until the devil ask for its return on that long black train to hell.

(Yes, I'm just trying to get my post count up by being inane.)
 
more than a few.....

one that really sticks out was in my younger days right after high school. I was working at airport security with this very pretty girl who had eventually told me she was gay. during my time working there I had begun a serious relationship with an on again off again girl that I had always wanted.

during my final week of work after giving my notice the pretty lesbian girl confesses that she has been attracted to me and would like me to be the first man she has slept with. we grope and touch each other all day in complete overdrive ..her face was completely flushed red with desire..we take our break together and try to find anywhere to fuck...we end up huddled in a corner hands down each others pants making each other cum while humping away at each other totally clothed. her passion was incredible!! she was whispering how she wanted to have sex with me and her girlfriend at the same time and have me fuck her in her ass....all things my young mind was just beginning to process..

one of the reasons I could not do anything that day was my then girlfriend had my car and was picking me up after work. I had the rest of the week to get with the other girl..I had such a great night with my then girlfriend that I felt that for the first time i wanted to be in a true committed relationship...

I never finished my week at work or saw my potential bucket list girl again.

this one kills me.

kills me.
 
one that really sticks out was in my younger days right after high school. I was working at airport security with this very pretty girl who had eventually told me she was gay. during my time working there I had begun a serious relationship with an on again off again girl that I had always wanted.

during my final week of work after giving my notice the pretty lesbian girl confesses that she has been attracted to me and would like me to be the first man she has slept with. we grope and touch each other all day in complete overdrive ..her face was completely flushed red with desire..we take our break together and try to find anywhere to fuck...we end up huddled in a corner hands down each others pants making each other cum while humping away at each other totally clothed. her passion was incredible!! she was whispering how she wanted to have sex with me and her girlfriend at the same time and have me fuck her in her ass....all things my young mind was just beginning to process..

one of the reasons I could not do anything that day was my then girlfriend had my car and was picking me up after work. I had the rest of the week to get with the other girl..I had such a great night with my then girlfriend that I felt that for the first time i wanted to be in a true committed relationship...

I never finished my week at work or saw my potential bucket list girl again.

this one kills me.

kills me.

Yes, that one would kill me every time I saw an attractive lesbian. I feel for you.
 
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