Your best missed opportunity

[R. R. Wayne]

We all like to tell about our best sexual adventures. How many of you have a missed opportunity that if you had a do-over, the outcome would have been different? Here are two of mine.

I was a freshman at a small Illinois college. My roommate was a really handsome and bright guy. We got along well and often at night we would jokingly suggest that the other do something sexual to each other. We talked about it a lot and one night my roomie got out of his bed in his tidy whitties and stood next to my bed. I laughed and did nothing.

What I should have done was pulled down his briefs and sucked his cock. He would have done the same to me I am sure, but I was just to timid to put my mouth where my words were.

I had another one a couple of years later with a high school classmate at a different college. We had known each other for about six years. I had no idea he was gay. Good looking coeds flocked to him. One night we went out drinking and ended up in his off-campus apartment. We were both drunk and started to jack off. As we got close to cuming he said he'd love to have his cock sucked. I did nothing. Years later I found out he was gay. Damn. Another missed opportunity and he had a gorgeous 7 inch cock.

[Herculoid Poirot]

I had two beautiful girls ask me to shower with them and I chickened out because I was too shy. I'm still kicking myself.

[mesaharleyrider]

So many times when we just don't have the courage, makes me sad to think of what I missed but one comes to mind, immediately.
It was summer, we were in the backyard pool, just lounging around, having a beer and conversation. The couple with us were new friends and the conversation turned to sex. The women were flirting with each other, it was easy to see the connection they had (consumated a week or so later.) He and I had moved to a deeper part of the pool and he was telling me that he had thought of being with another guy but had never had the courage. As we sat there and he told me his desire, I could see the front of his swim trunks begin to bulge. I told him that I was bi and that I would be glad to be his first if that's what he wanted. My hand was playing with his upper thigh and I was waiting for him to move it higher as the talk got hotter and hotter. He reached across me to grab his beer from the ledge and his hand, accidentally (yea, right) slid across my trunks, he could feel the obvious reaction that I was having.) I moved my hand to his cock, just barely touched him and could feel it begin to pulse through the material. As he came, I just sat there, barely holding on. Shortly after, he moved away, nervously and began to make excuses about an appointment. He and his wife were gone within ten minutes. He, later, told me that, had I asked, he would have taken the suit off and let me have my way with him.

[69luvr]

I met a guy in a mall who was very attractive. He wanted to touch me and I was shy since it was in public. We wnet into a novelty shop that was a bit darkened. He made like he was looking at a poster. I came up behind him and he touched me for all I was worth! I should have done it to him in return but chickened out! I have regretted it ever since.

[innaminka]

I think I snared both my best "opportunities"
(I gather we're talking "quicky" type stuff here.

A Norwegian bush pilot I was forced to "weekend" with (his plane was broken) - Not much to look at .......... but!!!!!!! my toes really did curl!
A finance officer for UK Ministry of tourism. She was an absolute honey. I think she was really the missed opportunity for a long-term relationship. But 20,000 kms is a bit too far to have a "sleep-over"

[darkeyes]

During the Edinburgh festival when I was 17 I met this gorgeous tall vivacious Canadian woman who really gave me the hots.. we sat in Princes Street gardens chatting and it was sooooo obvious I was gaga over her and she knew it.. she chatted me up, was incredibly flirtacious and affectionate and invited me to dinner that night at her hotel and I was over the moon...

Got home.. rushed upstairs into shower, out, started making myself beautiful (at least as beautiful as a scrawny lil 17yo could) put on new dress.. and then in came me mum with long face... knew something was up and it wasnt going to be good... my dad's mother had died.. mum said I cant go out and to pack a bag and get changed into travelling clothes we are off up north and that was that... so that was my biggest missed opportunity and one I often think of... in those days I had no mobbie and athough I left a message at her hotel I never saw sight nor sound of her again.. maybe she thought I was messing her about i cant say, but tbh I didnt really think much of her as we travelled north.. my thoughts were more with gran and my luffly grandad cos there isnt and never has been much more important to me than me family..

[pepperjack]

Had a cute, sexy, petite young female arrive at my home once to give me a Kirby vacuum cleaner demonstration; the two of us alone in the privacy of my home on my day off from work when I tend to be the horniest. She was very subtly erotic, indulging in double entendres ( " If you had a bed here...I could show you how good this sucks.") When I responded "Well, that's upstairs," she reacted noticeably. I'm no expert on body language but I am intuitive, discerning & often accurate. So, I was ambivalent, unsure about how to proceed because I have been toyed with by wily females before. I didn't want some sort criminal charge levied against me because she might have been using sex to sell her product. Just one of my missed opportunities.

[niftyshellshock]

Was in another country at a gym. Was walking by with a towel past a row of mirrors and I see this tall, fit, muscular man drying off near me. I take a second look and see that he has a thick, long, cock, about eight inches FLACCID just there. I wanted to approach him and say something, but I choked up.

Really wanted to have that in me :)

[3waytrey]

Was in another country at a gym. Was walking by with a towel past a row of mirrors and I see this tall, fit, muscular man drying off near me. I take a second look and see that he has a thick, long, cock, about eight inches FLACCID just there. I wanted to approach him and say something, but I choked up.

Really wanted to have that in me :) DAMN!! Or just suck it!! wow

[fredtyg]

I'm sure there's more, but these are two that come to mind right off the top of my head:

We'd just moved to the town I still live in. My best friend's girl followed us a week or so later. Jim and her used to sleep in the same bed in the room next to mine. I usually slept alone.

One night after we'd gone to bed, Jim came into my room and said, "Michelle thought you might want to join us". Wow! A threesome, and I would have loved to jump Michelle's bones. I might have even got a taste of Jim's cock had I had the nerve. As it was I just said, "Nah. I'll be fine".

Still hate myself for passing that one up. Never had the chance again.

Then there's a guy I used to work with:

I was in my early 20s and thought he was pretty good looking. Simple minded, but good looking. In the back of my mind I had the hots for him but was still struggling with my homosexuality back then so never seriously thought of doing him.

At one point he started saying publicly he'd like to try sucking dick- something not at all that acceptable back in the early 80s. He was too simple minded to care, though. I couldn't say anything in support because we were around other people, most of the time.

One day after work we were in the locker room by ourselves changing clothes and getting ready to go home. I was standing in front of my locker and he came over next to me, reached down and made a motion as if we was grabbing my cock- opening and closing his hand right in front of my crotch. Looking back I think he was interested and it was the perfect time to move on him.

I just stood there and didn't say a thing. He stopped after a few minutes and we went our separate ways home.

It just kills me to this day that if I would have just opened my pants and offered to let him put his hands around my cock and balls he probably would have done it. We probably could have done something once he did that. I'm sure at the very least I could have suggested we go to either of our houses and continue the cock play which probably would have resulted in us sucking each other off. No doubt in my mind, but I didn't have the nerve.

I blew it. Years later I made a move on him but the moment had passed and he refused my proposition.

[Gearbox]

I was walking my dog late at night through a secluded lane one night years ago, when along came a bloke I knew casually. I had been told by my gay friend that he was gay. (I had/have no gaydar). He was muscular and attractive but also a bit of a wreck at times. I had picked him off the pavement having drunk himself unconscious to take him home, a while before.lol So had no interest getting involved with him.
But that night he stopped me to talk. He asked where I lived, and made it plain he was up for sex, gaydar or not. As he talked he began playing with himself in his pocket, and the brazenness of it got my cock to swell my jeans. We both eyed each other and I'm sure he knew I was bi before that and I'd be interested. I was! I wanted to pin him up against the fence and take out all my m-m frustration out on him. BUT I had a gf, and I was scared to tap into that, at that time.
We parted with nothing happening. He moved away later, and I do regret being scared of myself back then. He gave me an excellent opportunity, but I just wasn't ready.

[dondiego20716]

When I was younger, and before I finally came to the realization that I was bisexual, I used to frequent adult book stores to watch videos in the booths. The ones that I went to in those days did not have glory holes. I was still fairly naive about their existence.

I was still fairly inexperienced having sucked off one friend in college when I was visiting a new video store near me. I dropped my tokens and started watching a movie in a booth. I hears something to the side of me and when I looked to my left I saw a huge black cock coming through a hole in the wall. It was about six inches long and flaccid. I freaked out and bolted out of the store while the video was still playing. I wish I had gotten on my knees and sucked him off.

[NjbiGuy01]

I walked in on a couple at a party in an apartment in NYC. Big-ass apartment on Central Park West. Here's a guy about to fuck this cute gal in a skirt, and I was looking for the bathroom. I walk in and say "oops sorry' and he says "no, man it's cool, she digs it with two guys"...I was just so taken with the situation, I said "eh no-thanks..." I was more worried about the friend who's party it was, not having a rubber, my friend thinking badly of me for jumping in and doing "that"....man, today I would have played with both the guy and gal...lol.

[foreverbi]

When I kook over my vast span of 62 years I see so many "missed opportunities" it makes me want to cry or kick myself in the head. One was with one of my best friends in HS. We went out EVERY weekend and "practiced" sucking our own dicks. Now I see that he was comfortable with being partially nude with another man (me), so he probably would have been open to my putting his dick in my mouth. This is something I desperately wanted to do.

[foreverbi]

Another "Missed Opportunity" was another HS classmate of mine (or ours really). He had a humongous cock & he shot a mouth FILLING load of cum when the time was right. I remember spending a lot of time in the shed with him. He went with my other friend and I when we went out to "practice" trying to suck our own cocks. I remember sleeping in the same bed with either of my HS buddies & we were both nude or in our underwear. Oh how I wanted to get his big cock in my mouth & coax a load of cum from him & then swallow it.

MANY MANY years after high school we met at the bank I was working at. He asked me if I wanted to do lunch & catch up on each others life, We started talking about work. He told me that he got called back to the railroad that had laid him off 10-15 years ago. He told what his wages were going to be & I asked what do you have to do for that kind of money & he said (maybe he was just kidding) "For that kind of money I will set on a bench & suck every ones dick.) I was taken aback by this comment & said hell I would do that for nothing. When he did''t say anything about my comment - I just let it die.

Can anyone tell me if I "missed an opportunity" with either of these guys. You better believe I would handle all of these scenarios differently & I think I would have got to suck at least one of the dicks.

[foreverbi]

Another "Missed Opportunity" was another HS classmate of mine (or ours really). He had a humongous cock & he shot a mouth FILLING load of cum when the time was right. I remember spending a lot of time in the shed with him. He went with my other friend and I when we went out to "practice" trying to suck our own cocks. I remember sleeping in the same bed with either of my HS buddies & we were both nude or in our underwear. Oh how I wanted to get his big cock in my mouth & coax a load of cum from him & then swallow it.

MANY MANY years after high school we met at the bank I was working at. He asked me if I wanted to do lunch & catch up on each others life, We started talking about work. He told me that he got called back to the railroad that had laid him off 10-15 years ago. He told what his wages were going to be & I asked what do you have to do for that kind of money & he said (maybe he was just kidding) "For that kind of money I will set on a bench & suck every ones dick.) I was taken aback by this comment & said hell I would do that for nothing. When he did''t say anything about my comment - I just let it die.

Can anyone tell me if I "missed an opportunity" with either of these guys. You better believe I would handle all of these scenarios differently & I think I would have got to suck at least one of the dicks.

[FunE1]

My "missed opportunity" took place at my first military assignment.

I was (a very young) 18 and just arrived on base. Dorm were co-ed, so there were women on the same floor as the men. In the room across the hall from me was just the most beautiful girl I'd ever seen. She was tall, blonde, nicely built, and had the most captivating smile you can imagine. Best of all, she was new to the base, too, so when she saw me moving in, she introduced herself and we became fast friends. She was 3 years older than me, super adventurous, outgoing, vivacious... I loved everything about her.

At this point I had limited sexual experience: some MM play in jr/sr high and 1 MF experience (while stoned... and which I forgot about, actually, for a number of years), and NO actual dating experience. So, despite my crazy, lovesick attraction for this girl, I just had no idea what to do, despite my serious desire for her and despite the fact that we spent most of our free, nonworking time together, including a handful of road trips, sunbathing at the local nudist spot, romantic dinners, etc., etc.

Finally, after some time of this type of being with each other, she came over to my room one night wearing only her robe, and she just walked up to me and said, "Do you want me?" At which point my brain just fizzled and the words, "I don't know" slipped out of my mouth before even I realized what I was saying.

And of course she left. And of course, it was never the same after that. I was just so insecure of myself at that time, I couldn't even bring myself to go to her and say, "Are you kidding me? OF COURSE I WANT YOU!!" So we drifted apart... in a few months she started dating a guy who was 10 years older than she was. They are still together now after 27 years. I'm divorcing for the 3rd time.

I try not to live in regret over stuff I've done, good or bad, preferring to take the lessons those experiences have taught, but there are days when I sit and wonder just what "might have been" had I had the courage to just say "yes" to that one question on that one night...

Sorry if this got a bit long and maudlin, but I've never been asked this question so have never told anybody about this before.
Thanks for the good question.

[Emotional Masochist]

Well i hve had many missed opportunities, but at the moment whenever im asked i always think of two.

The first being with my best friend( same story i shared before). We got ridiculously drunk at a bar with my brother and when we got hoime my brother went off to bed. me and my best friend were just hanging out in my kitchen when he suddenly pinned me to the fridge and kissed me. was hot was amazing but I remembered i had a girlfriend and so did he. so i had to throw him off me.... i have thought about that moment so often since it happened if only he had waited till we were single. :rolleyes:

the other one i always remember was at the prom after party at a hotel. I was there with my friend as i had been kicked out of my highschool the year before. was sort of funny so he was trying to show off to this girl and ended up completely wasted in like an hour. so me and this girl put him to bed and it was funny cause me and her are lying in bed together and she is flirting like crazy with me. but here is my friend who is absolutely in love with herso i had to turn her down. but the night doesn end there. i spend the rest of the night taking care of my drunk friend and a couple other drunks who are dropped off in my care for the rest of the night and drink my self straight through the night. end up going out for a smoke at about 6am. and meet two girls from the party. we start chatting and they listen to my sob tale of an after party and they ask me to come upstairs with themand they will szee if they can make it better. here is my biggest regret. i declined as i had to go check on the dunk ones and just wanted to enjopy my smoke. i blame the alcohol for my stupidity and lack of confidence.

[Northerner]

So many come to mind.

The earliest is when I was 13, in a tent in a friend's back yard, the usual kiddy stuff ensues. I don't know who suggested the dare, but it was to try to lower your mouth over the other guy's cock without touching. I was extremely tempted to clamp down and suck, but I was oh so conscious of the taboos about being gay, or being a "cocksucker." I still kick myself for missing that chance. I'd do him today for sure.

Next one was in my late teens with a young lady I was quite attracted to. Unfortunately she was my best friend's live-in girlfriend. Now understand that the three of us had indulged in some MFM action, so it's not like he hadn't watched us having sex, but that was over, and he wasn't there this time. We were on our own while he was at work, the tension between us was intense, we were just leaving an empty apartment when I bumped into her, she turned, grabbed me, and kissed me. I reciprocated, but then pulled back and said "let's get out of here before we do something we will both regret." To this day I think it was the right thing to do, but that doesn't mean I don't kick myself for missing the chance anyway. Almost 40 years later I'd still like a rematch :-)

N

[androgynous34]

When I was about 14 years old a friend who was 15 spent the night sleeping in my bed with me after we both woke up and every one left the house. He rolled over and said for me to take my paints off not sure what he wanted I obliged and he said lay on your side and he laid next to me and I could fell his dick trying to penetrate me. I had never experienced this and I wasn’t quite sure what he was trying to do. This was a new experience, I didn’t mind the sensation of his cock rubbing and pushing against my ass hole. After about 15 minutes he said you are too tight. I told him roll over on to his side and I tried to penetrate him but lost interest quickly.
The net day I was dropped off at his house. He was in his bedroom and I went into see him he was jerking off and I was amazed and fascinated at the sight I stood there and watched as cum shot out of his cock and ran down the sides. It didn’t excite me but it was fascinating and I could have watched him forever. Although we never had the this opportunity again I often thought if I could relive this experience I would of loved to feel him inside me and suck that beautiful cock dry.

[Sum14fun]

I have one.

I was just getting over a bad cold. I walked to the Kroger around the corner from my house to get another thing of night quil. The fresh air and walk did me some good after being kopped up for several days. While equating down picking my medication off the shelf a black guy (my fetish) asked if I had a boyfriend. I said no so he asked if I wanted one. I said not right now. Hind sight 20/20 I would have said yes and left with him after getting my medicine. Bummer though would have been nice maybe.