Regretful fantasies of sex with guys you let get away

[heirtothewind]

Have you ever fantasized about how great sex might have been with a handsome guy or guys sporting large packages because you feared rejection, or you feared entrapment by police, or you feared he might be rough trade? I may have missed out on having great sex for all of these reasons simply because the object of my lust seemed too good-looking to be true or safe back in the 70's and 80's.

 

[milwjocknow]

This is a BIG reach of a topic, isn't it? Tell me the fantasy you have of something that might have happened with someone who might have had a big package? Really?

 

[heirtothewind]

In Chicago, 1970, there was an older, muscular guy named Armando who hung out at the Lawson YMCA and at a gay bar nearby, The Normandy. His basket looked huge, and the regulars at that bar said he had 10 inches and liked to fuck. His attention zeroed in on me -- bought me beers, groped my crotch, always made pleasant conversation. One night at closing, he invited me home; however, having been just introduced to anal sex with all the pain of penetration from 6-inch cocks, I feared a 10-incher would really tear up my ass. He may have only wanted to give me a blowjob, but I did not ask his intentions. I just assumed he wanted to throw me face down on the bed and enjoy my screams as he held me down and fucked the bejezus out of me. I declined his invitation but now still fantasize about a great blowjob I might have received, or the feeling of a big cock gently gliding in my ass, or both.

 

[elgarcon]

Have I ever fantasized about the one that got away or the one that might have been? For Sure. It never really has anything to do with whether the guy was hung or not, though.

 

[AlexDB9]

I've regretted a couple guys I let get away but I've never once thought "omg, I can't believe I let that big dick get away."

 

[dylz]

oh, i thought you meant exes/ex-flings and such that you "let get away" and fantasizing about sex you wish you could still be having with them... in which case the answer would be yes for me. but there will be others on the horizon.

 

[billybones]

In Chicago, 1970, there was an older, muscular guy named Armando who hung out at the Lawson YMCA and at a gay bar nearby, The Normandy. His basket looked huge, and the regulars at that bar said he had 10 inches and liked to fuck. His attention zeroed in on me -- bought me beers, groped my crotch, always made pleasant conversation. One night at closing, he invited me home; however, having been just introduced to anal sex with all the pain of penetration from 6-inch cocks, I feared a 10-incher would really tear up my ass. He may have only wanted to give me a blowjob, but I did not ask his intentions. I just assumed he wanted to throw me face down on the bed and enjoy my screams as he held me down and fucked the bejezus out of me. I declined his invitation but now still fantasize about a great blowjob I might have received, or the feeling of a big cock gently gliding in my ass, or both.

Thank god the '70s are over.

 

[wappingite]

Looking back at my sexual habits in the 1980s and 1990s, I let a vast many men get away because I was too shy and reticent, even when they showed direct interest. However, I'm very glad now because I'd probably be dead today if I had taken up every opportunity and if I had been totally uninhibited and extroverted about sex.

 

[Infernal]

There is always one that you regret letting get away. Well, almost. I met this guy. He had some middle eastern ancestry and was all kinds of hot. Very sweet, sexy, hung. We were friends and just hung out, but he wanted things to get more serious. We had chemistry without a doubt. He tried to get me to go to a hotel with him one night after work, but I turned him down. The problem was that he had a boyfriend and even though their relationship was close to death, I didn't want to intrude. His boyfriend was also crazy. Some guy in a bar pissed him off so he slashed him with a razor kind of crazy. I didn't want to be tangled up in that kind of mess. So I let it go. I still have good thought about him though. He kissed me on the neck once and it tingled for hours afterwards.

 

[Joegrant43]

My regret is that I did not let this tall European guy I was seeing fuck me. He had a huge cock and thick, every time we would fool around he would come to be with lube and a condom and always want to fuck me. I had not had anal at this point, of course he was so damn big that it scared me, he was so forceful and persistent in bed. I always wish he had fucked me, it would have been one of those treasure island media fucks that to this damn make me shake with anticipation, I actually tremble watching that kind of sex... Hot! This guy had that hot edge to him, never had the chance with another it cock so I regret not letting him be my first.

 

[Exbiker]

Hmm.

At last count I think I have had ten serious relationships over my thirty years of sex with men...

Luckily, the most recent has now lasted 12 years, and is officially recognised.

Looking back on the others, hardly any of what I valued in any of those men was focused on their penis. I'd like to say 'none', but that might not be entirely true, I suppose. Random thoughts do sometimes drift through the shadows and cobwebs ... But, even at the time of each of those relationships, the specific size, shape, texture and taste of the other man's penis was of hardly any relevance. And certainly, looking back, it plays no role. I think about experiences we had, things we did, places we visited...

The opening poster sounds a bit like someone who does hold on to regret. But for me, memory isn't like that.

Memory is a field of celebration of life, of what did happen. What I did experience. Not what I didn't ... even if I did let certain things pass me by ( not many ! ) that would have been for what seemed sensible reasons at the time. And that's part of being alive too.

:smile:

 

[deleted3782]

At first glance, I have no regrets. Those who know me pretty well might raise an eyebrow, because I dont get much action, and they might assume there are lots who I've let "get away".

I'm generally pretty clueless about guys who want to mess around with me in person, and its been years since I've had a face-to-face encounter that was in some way a legitimate 'the ball is in your court' offer. My friends also say I'm way too picky for my own good, so that might help me filter down the number of "lost opportunities".

Other guys I've had crushes on are straight, so they were a dead end too. All in all, limited interactions and no regrets...and that's ok.