A possible sexual moment you let it pass and regret it

[Big Ben IV]

Many years ago I had a couple of Fwb's that I had met on here. Unbeknownst to me they had been talking to each other. Well they had agreed to make my fantasy of a 3sum come true. But things were getting serious between me and a woman I was dating (I'm making my life sound much more exciting than it really was. Lol) so I didn'tgo through with it. Definitely a bone head move.

 

[MaxwellSmart86]

Can't remember if I posted in response to this but I have several moments with an ex-girlfriend that I used to replay in my head imagining a more sexually positive response.

Also had an ex-coworker that I wish I had made a move on.

 

[HampshireBoy]

Like a many people, I have a few "I wonder what would have happened" moments.

As a quite innocent student I was home visiting my family when a friend's older female cousin was visiting. She mentioned that she wasn't sure about going back to her accomodation, she was a student nurse near my Polytechnic. Basically she suggested driving me back to college. I asked her to drop me near my place, which she did - only later did I think "was she reluctant?". When I next saw my mate, he was convinced that I'd bedded her . What made it worse was that I fancied her like crazy, just young and niave and I thought I didn't stand a chance. So I possibly blew it, I'll never know if I really had a chance.

My SIL (from first marriage) and I had a very flirty relationship, when my first marraige was on the rocks she definitely upped her game. One evening I went round to help with some jobs, there I was knelt down sorting out some wiring when I realised she was stood there naked. It was difficult but I made my excuses saying that I was married to her sister and couldn't do it - she even offered only oral, but I said no. The thing is that I am 100% sure that she would have told my wife, if not then after we divorced, so it wouldn;t have been worth it.

 

[strongnsensual]

It took me a looooooong time to learn to read people. Oh, the chances I missed. Some very, very obvious.

The funniest was probably at a work conference. Several of us were at the resort bar and the bartender was apparently hitting on me. I was clueless. Completely. Oddly enough, my wife (before our relationship ever began) was there and she still chuckles about it now and then, very good naturedly!

 

[Tallcajun]

In hindsight there were quit a few missed opportunities. Mostly due me being young and naive.

There were also those where I should have pushed the envelope while in a the relationship.

 

[kinkincguy]

Not necessarily regrets but a lot of missed opportunities I would have grabbed with both hands, literally and figuratively, if I had a do over.

 

[sister jenny]

I wrote a story called something like ”Getting help from my sister” 1 and 2. In one of them there was a scene in a car. The little sister in the front seat was blowing the driver while the big sister and a guy was in the back.
In real life, I was the big sister in the back sitting with who would become my husband. We were all stoned and drunk, going to a party.
But unlike in my story, me and my husband-to-be never did anything in the backseat. We just kinda stared, embarrassed and turned on. But intimidated and shy.
I really regret not doing like my sister and blow my husband-to-be at the same time. I find that thought very exciting.
But I didn’t.

 

[ycym]

I wrote a story called something like ”Getting help from my sister” 1 and 2. In one of them there was a scene in a car. The little sister in the front seat was blowing the driver while the big sister and a guy was in the back.
In real life, I was the big sister in the back sitting with who would become my husband. We were all stoned and drunk, going to a party.
But unlike in my story, me and my husband-to-be never did anything in the backseat. We just kinda stared, embarrassed and turned on. But intimidated and shy.
I really regret not doing like my sister and blow my husband-to-be at the same time. I find that thought very exciting.
But I didn’t.

It is a development. You don't start from 0 to slut. Although for some this goes very fast.
It is often the case that the best response comes into your mind after the situation is gone.

 

[EdgySubMic]

In another thread, I recently described a case of a coworker trying to "engage" but me not following up on her offer. As mentioned there, I thought about it afterwards, but I would not call this regret. I was (and still am) not available by my own choice, so there is nothing to regret.

Thinking back to when I was still a free man, I can't recall any case of sexual regret either. I made my choices, always stood by them, and still do. As far as sexual moments are concerned, regretting doesn't help or change anything anyway: they may be exciting in the moment, but are not that important in the grand scheme of things. And in case one does seem to be that important anyway, e.g., because of potential follow-up consequences, I'd say there is a bigger thing there to regret.

The only big change I'd want to make to my life in hindsight, is one time when I was preparing to ask someone a question that would have been life altering, but then the opportunity was ruined by outside factors just as I was about to ask. That question was not sexual in any way, however, and since neither I nor he had any control over what intervened, there's nothing to regret either. Had I asked an hour earlier, it would not have affected the eventual outcome.

 

[Inthelastrow]

To add another story to this thread, (yes, so many missed opportunities!). I would like to hear some LIT member opinions. When I was just out of college, I was working in an office with an older lady, mid 30's. We worked the same shift and became pretty good friends. Attractive, she was divorced and to my knowledge had not dated in a quite awhile. Because we were on the same shift, she asked me to help move some furniture from a relatives house to her apartment on our day off. It took most of the day so when we finished she invited me to stay for dinner. After dinner we talked a bit, and then just as I was getting ready to leave, we got close and kissed. We made out for a bit, but before we got too hot and heavy, she stopped us and said "You should probably go." Being a respectful young man, I agreed and left. Afterwards we stayed friends and never mentioned that moment, nor did the chance come again. A part of me thinks I should have stayed or tried harder. No regrets as we were friends, but I wonder if she really wanted me to go or not.

 

[CuriousMaleCO]

There was one with my sister. One with a morbidly obese neighbor, and a few others.

 

[fma20fma]

When my ex bf's dad hinted that he was fantasizing of bareback anal sex with me, i didnt respond and now regret.

 

[MamaBitte]

Not asking my mom ...

 

[Bisexguy70]

Once, when I was much younger, I met a girl at a pub. She was about to go home, but scared of leaving due to some very rowdy guys outside the pub. I walked her past them and she stopped by my dorm before heading home. The guys had been shouting something at her when we left, but I didn't catch what it was. When I asked her about it, she put a hand on my thigh and told me they were shouting 'lesbo' and 'dyke' at her - and that she did prefer women.

I had not seen that coming and didn't react well. I turned her down quite coldly and asked her to leave. The next day I tried to find her to let her know she just surprised me, but I never saw her again.

I don't do regret, but I sometimes wonder what it would have been like, if I had been a little more observant and open-minded..

I had a similar situation and knew a guy who was being made fun of being gay. Not that we were close friend's but I certainly could have befriended him. I was over at his house once with a group from a science club. We were both seniors and 18( to follow lit rules). But at the time I probably would have been considered a twink. I was too shy to ask a girl on a date but was so horny to have sex instead of just masturbate.
I think back and realize now I should have tried becoming closer to him. I think of how hot it would have been to suck each others dicks. Exploring each ones body and experimenting with sex. Perhaps going as far as kissing and making love to each other. I wasnt attracted to him per se but I think if we would have been naked in the same room it would be inevitable. Back then being Gay was so looked down upon and so taboo. Damn though I cant help but be rock hard thinking about what could have been. I regret not discovering the intense pleasure from same sex

 

[SPARTAN047]

I remember the times I've been propositioned by guys old enough to be my dad, they were usually the ones who worked for my other friends with me.

There were a couple of yummy mummies... But married.

 

[Elle4u2use2]

1. Turning down advances from lesbians
A) at bar with friends
B) another one groped my breasts
C) slept in bed with one, when an empty bed was near

2. Turning down a pair of brothers

3. Not following through with mmf with 2 men that were strangers but both voyeurs

4. Not fucking the pastor

 

[SPARTAN047]

You're right, of course, but probably every groper thinks the gropee will enjoy it. So don't encourage them lol

That's true. Everyone who groped me thought I loved it anyway since they wouldn't stop. Of any gender.

If you encourage them it'll go too far, yes. Would it be exciting though? Yes, kind of, I'd secretly be very flattered I was hot enough to paw like that. Not that I'm very attractive but that's what anyone thinks when they're groped.

Now if they were my type and someone I fantasized about anyway, I'd probably let them do anything to me with my mouth shut. Provided I'm not in a monogamous relationship.

 

[Mostlyherefortheporn]

In law school, I became very close with a married female classmate. Probably too close. We spent a lot of time alone together, both while studying and socially, and were fairly affectionate with each other, I never made a serious move on her, even though there were times she was literally sitting on my lap. I told myself that I had the relationship i wanted with her. I meant it at the time, but now I wonder what it would have been like. She had a very high sex drive (bordering on nymphomania, it seemed) and was extremely uninhibited. Sex would probably have been amazing and I think she would probably have responded if I had initiated something. Or just responded differently to a few situations,

On the other hand, she was a high-strung drama queen with issues. None of her marriages have lasted very long and she’s spent the past few decades alienating partners by cheating on them (among other things). By the time we graduated, I had matured enough that I didn’t want to deal with her craziness snd we drifted apart. Honestly, I most likely dodged a bullet with her, so to speak.

More recently, I had a relationship with a professional acquaintance I had a crush on for the better part of a decade before we got together. Timing was never right for us, even after we started dating, but I occasionally wonder what would have happened if we had gotten together sooner. Sex more then lived up to the fantasies so I wish we wouldn’t have waited so long to sleep together, Truthfully, everything about her exceeded the fantasy, so I really wish things had worked out differently,

Also, as part of my job, I recently spent a lot of time with a local sports reporter. She’s way too young for me, but we hit it off and i ended up really enjoying the time we spent together. She has a great personality and was fun and funny to be around. I also found her to be gorgeous. Absolutely nothing happened because of the age difference and the fact that she works for a client, but both of us are workaholics with no social life, so it’s a little hard not to wonder how much fun we could have had together.

 

[zoso682001]

In another thread, I recently described a case of a coworker trying to "engage" but me not following up on her offer. As mentioned there, I thought about it afterwards, but I would not call this regret. I was (and still am) not available by my own choice, so there is nothing to regret.

Thinking back to when I was still a free man, I can't recall any case of sexual regret either. I made my choices, always stood by them, and still do. As far as sexual moments are concerned, regretting doesn't help or change anything anyway: they may be exciting in the moment, but are not that important in the grand scheme of things. And in case one does seem to be that important anyway, e.g., because of potential follow-up consequences, I'd say there is a bigger thing there to regret.

The only big change I'd want to make to my life in hindsight, is one time when I was preparing to ask someone a question that would have been life altering, but then the opportunity was ruined by outside factors just as I was about to ask. That question was not sexual in any way, however, and since neither I nor he had any control over what intervened, there's nothing to regret either. Had I asked an hour earlier, it would not have affected the eventual outcome.

Sometimes it's not regret but only wonder .

 

[Elle4u2use2]

1. Turning down advances from lesbians
A) at bar with friends
B) another one groped my breasts
C) slept in bed with one, when an empty bed was near

2. Turning down a pair of brothers

3. Not following through with mmf with 2 men that were strangers but both voyeurs

4. Not fucking the pastor

Not sleeping with the brothers haunts me to this day

 

[ericalauren]

When I was in college, there was a queer/trans speed dating event on Valentine's Day. I couldn't go because I had two classes and then was too exhausted to go afterwards. I'm still bummed I missed it!

 

[Sgts19]

When I was growing up a girl who lived around the corner was rubbing up against me all the time but I was so shy I never did anything but think of her and jerk off. She was what I call a butterface, Playboy body throw at least 2 bags over her head.

During the summers I worked at a resort town on the beach, wore the uniform and badge. I was propositioned several times a week, yes, I was week and took a lot up on their offer. One I still kick myself in the ass over was girl who I found out was a model was hitting on me the whole week and because of one thing or another I never took her up on it.

 

[SPARTAN047]

I sometimes regret not going to trans and gay orgies I was invited to when some people on Fabguys got hotel rooms and set them up. I did have them in trans clubs, but being a dirty hoe means I wanted more. I was trying to be self aware and not be an STD ridden cum dumpster. I've always looked for monogamous lovers since the beginning, but the lack of them means I should've tried to enjoy the sex.

 

[Stopokochac]

I was on the beach in the Caribbean and this girl couldn't take her eyes off of me and was even taking pictures of me, but I just could not think of a reason to approach her or what to say. I'm horrible at thinking on the fly. I literally didn't come up with something 'til YEARS later. I still kick myself for it, because it's so rare for a girl to show interest first, and I genuinely think if I made a move, I would've gotten laid.