Ever had a missed an opportunity in your past ...? (18+ only)

[Silmende]

I still don't know and probably never will if there really was more, but I have thought for a long time there was.
At some point, for other reasons, I confessed my feelings for him. He didn't reciprocate there and then. But, he was also not saying "I don't". He was not being clear either way. And I can't help but wonder what would have happened had I crossed the line into something I shouldn't have, because he's married and we could never have reality.
Things got complicated and messed up and he's now having an affair with the woman that used to be my best friend. I still don't know why he and I aren't even talking when he asked to remain friends but his actions showed more and more avoidance whereas his last words before I walked away didn't.
It still hurts me every single day, he's the first person on my mind in the morning and the last before I go to sleep. I broke our friendship 8 months ago over getting hurt with his actions and my feelings, and, I don't know. The situation at the time was unhealthy for me. But... I still miss him. And I can't even say, since he's dating my friend now. I want them to be happy. Just that "what if" will haunt me for a long time I guess.

 

[Highway_Star]

About 16 years ago, two girls took me home from a pub.

Game on I thought.

Back at the home of one of them, they appeared to be more interested in each other than in me, so I upped and left. (I was quite drunk and it was like 4am).

I was recounting this story to my now wife, she reckons I was supposed to join in!

Doh!

 

[Cirac]

There were a few missed opportunities but two stood out. The first was when two of my male friends and I went to Club Med for a holiday (we were probably 20 years old). The two friends were assigned a room to share while I had my own room. On the first day, I was in their room chatting away with them and one of the guys asked if it’s okay that we chat on while he takes a shower. What we didn’t expect was that he essentially stripped off and showered with the door wide open and we saw everything. Was a little awkward but I got to perve. The next day - the other friend was out exploring and it was just me and the free showering guy in the room. He was lying on the bed while I laid on the pull out bed next to him. Conversation slowed and he was beginning to close his eyes but it was clear he was developing a bit of a bulge under his berm shorts. I was so tempted to reach out and grab it but I kept second guessing myself. I felt that he was posturing but I knew if I misread the signs - it’s going to put me big time. Till this day - I wondered if he was enticing me. He’s married with a few kids though.
The second incident was when I was in Sydney during the Mardi Gras event. Stayed in a backpackers - and went to the bathroom to brush my teeth etc. Next to the basins were the shower cubicles, with doors. One of the cubicles was occupied - door closed/latched and water running. Then the person inside opened the door - looked out - saw me (I was the only one there) and he left the shower door ajar. I looked across and he was still showering but it appeared to be quieter. He looked out again and disappeared behind the door, still ajar. I hesitated - and again, second guessed myself - and I just left the bathroom. He was quite good looking and fit - and till this day I wonder what that experience would have been like!

 

[Cooper72]

Not a gay or bi missed opportunity. The one that stands out to me the most is with a coworker at an ambulance service I used to work at. She is about 8 years older than me. Was always flirting but I was too naive to pick up on it. She called me one day and asked if I could come to her house to work on her computer. She lived about an hour away plus I was supervising that day and couldn’t just leave. A week or so later I asked her is she still needed me to come work on her computer and she said nothing is wrong with my computer. My husband was out of town and I was horny and wanted you to fuck me.

Several months later, maybe even a year or longer we were working together again and for whatever reason she decided to sleep in the bunk next to mine instead of in the other room. I decided what the hell and got in bed with her. Ran my hand down her pants and just inside her panties and we got dispatched on a call. I took that as a sign and never tried anything again. I left my job there not long afterwards. Looking back there was numerous times she would have fucked me but I just never picked up on the mostly subtle hints. I’ve heard from other coworkers that her oral skills were amazing.

Funny thing was this was pretty early in my first marriage. She was super jealous even though she hated sex. She accused me of having an affair with every female I ever worked with except this one. She liked her and never complained when we worked together.

 

[MilfBanger78]

With women, many many missed or passed chances. Lot of times I was too busy with other women. Later I learned to just take the opportunities when they arise.

As for the OP question.. Missed bisexual chances

-When I first moved to FL and got internet, I was 21. Met a bi couple in the ol' AOL chatrooms. They lived like 5 mins from me. I always had curiosity, and with the exposure of even more porn via internet, my curiosity grew. So this couple was tempting but I was still nervous. Attractive 40 yr old MILF... the hubby had a nice cock. We made plans Sunday morning to meet for coffee and then back to their place. I got in my car, drove over there, saw their car....got nervous and.....drove away lol. Kick myself for that one.

-2 yrs later I was 23, dating a 19yr old GF. we were fucking and watching porn, she picked out a bi scene and mentioned she liked seeing guys play around. I clammed up and didnt confess I was curious. Her and I had even gotten into swinging so we could have made the bi thing happen, but in the back of my mind I was like "What if we split up and then she tells our mutual friends about this etc". She was kind of a bitch but who knows. I do regret not taking that chance to pursue it though.

Finally at 27 I hooked up with a guy, from online, was great. Hung older guy, lived very close. But still I regret not having started sooner

 

[techpump]

more than I care to admit to! In college I think I had...10 or so missed opportunities. Easy ones, I just didn't time things right. There have been more through the years and of those I do not want to admit them publicly

 

[Kingsrocker]

At our HS graduation. We're performing our graduation song at the stage when one of my classmate (Marlon) starts groping my ass and doing weird hand gestures. Luckily we are placed at the back of the choir . I'm really nervous at that time , I literally bolted running to my seat after finishing our performance.
Sadly, thats the last time I've seen him personally since he went and studied abroad.

He's now already married with beautiful daughter.

I'm still thinking now. I should have accepted his advances.

 

[MrTMT]

I've had 2 missed opportunities with 2 different girls.

One summer after my freshman year in college. I stayed on campus as I took summer courses there. There was a girl that was also taking summer courses, but she commuted each day for her classes. I'd ran into her multiple times during lunch in the school cafeteria. I've found her to be easy to talk to, but I didn't realized she had somethings for me. The first few times when I met her, I've provided her my dorm room # and have extended inviting her to stop by my room whenever she got free time while on campus, as I didn't have roommate during summer semester.

Long and behold, she took my offer. I've not even thought I've meant it or was serious about it. One day just after lunch, around 2PM, I heard a knock on my door and I opened the door, it was her as she marched right into the room with her face was really a few inches my mine. She mentioned that she thought over and decided to take my offer and come over to "see" me, her way of saying and her body started to press closer to my body, she walked forward as I walked backward into the middle of my dorm room. At that time, I knew she was horny and wanted to have sex.

For some reasons, on that day, I wasn't horny at all, I may have already jerked off the night before or whatever, as she was so forwarded in a semi-aggressive manner, it freaked me out a little bit as I wasn't prepared. I've not seen her behaved like that.

I made up an excuse that I've to go somewhere for an appointment, she seemed disappointed but decided to leave. I've not seen her anymore after that. Looking back if I knew a possibility that I can have sex with her, I would have prepared and would have had sex with here right there in my dorm room.

The other one was at the end of my junior year, there was an end of year dinner and dancing party. I didn't have a steady girlfriend to go with, a buddy of mine knew of an exchanged Japanese student and connected me with her, since she's was available and would enjoy attending even like that.

So I asked her and she accepted to go with me. Near the end of the party, there was a slow dance which she and I was on the floor dancing, while both of us were in a hugging position for this dance, her legs and body wrapping my body in a such way that was much more intimate and kind of signaling that she wanted to have sex with me later on.

At that time, she was staying in a dorm, but her roommate went home for the weekend so she had the room all for herself. I wanted to have sex with her there, but the idea as she knew my buddy. I just felt like I don't think it was a good thing to fuck her that night. Even thought she and my buddy aren't really committed, they're just friends at that time.

 

[Motion-of-the-Ocean]

For a missed bi opportunity, yes. But since it was not 18+, I can't go into details.

However there was one with a female friend of the family whom I've known since we were kids. Though I always thought her good looking and had the occasional sexual thought; I still considered her more of a friend and I was very clueless and awkward with women back then at any rate. Several years later after I was already married I attended her wedding, where in a conversation she admitted to me that both her and her family somehow always thought the two of us would have hooked up and she sometimes wondered what would have happened had we. I was surprised since I figured she had zero interest in me beyond friendship and never had those same thoughts about wanting more like she seemed to.

However since that seed was planted, I still do every now and then wonder how different things would have been for both of us had we took advantage of that opportunity long ago. However it is a merely "what if" game, since I don't regret for a minute the life I've built with my wife and can't imagine a life without her. While I still see this friend once or twice a year, we've never spoken about this again as she's obviously accepted her choices and satisfied with them as well.

 

[canadian_guy486]

I’ve had many missed opportunities, mainly due to my own fault. I was closeted for the majority of my life until my early 30s, so I never pursued anyone or tried to meet people etc for anything. I worked with a guy who was openly gay, and it was pretty apparent to me that he had a crush on me. We would chat all the time through IM and he would always invite me over to his house for a night swim etc and I always declined, due to my own insecurities and internal shame for thinking me being gay was wrong etc (a whole bunch of different issues that need their own thread lol). There was even a time where we both had training for work out of town, and he suggested we share a hotel room and again I declined. Eventually he stopped giving me these invites and then he moved branches and lost touch. I have a few stories like that where I didn’t let myself get close with any guys due to my own issues. Because of this, I didn’t have my first sexual encounter until I was in my 30s, and even now, I’ve only been with 3 men my entire life. I never got to experience that period of time in life where you meet different people and are figuring out who you are and what you want and who you are attracted to. I’m now in a long term relationship with a wonderful guy, but I can’t help but always think about those missed opportunities, and how those could have helped shape me into a more well rounded, more experienced person. And that maybe I settled down too soon. There’s no sense dwelling on the past, but I can’t help but always think “if only….”

 

[bravesoldier]

Ever since I was old enough to know what gay was I knew I was. But the thing was, I never wanted to be gay. I had a girl, fell in love and marred her. I was quite proud of the huge transition I made in life because I knew in my heart I was truly gay and not bisexual. My marriage ended at age 32 (not because of my sexuality) and I didn't date much or have sex until about 10 years later. At the latter of the 10 year period I gave in to being gay as the lust and attraction was too much to handle, just as it would have been if I were straight and craving women. I had sex with a man the first time at age 41-42. I have had several buddies over the years and have a steady BF now which I have an open relationship with. I have learned deepthroat and love it. I have learned I love the taste of sperm and the thought of it in my belly. I have fucked tight asshole and been fucked by long slender cock and cock with a 6.5 in girth. By the way, the 6.5 girth in me was more wonderful than I can describe. I have also discovered the indescribable pleasure of feeling the silky, smooth, slick as wet glass feeling of an uncut cock head in my mouth. Have had the pleasure of being sucked to completion and my load eagerly swallowed.

I say all of that to say I would like to have know the opportunities I may have had earlier and the mind blowing sex I might have had in the earlier years. Especially the hot football player who propositioned me to suck his dick when we were in high school. That would have been hot I know, which is a story I have shared before. Sometimes I wonder how pre-adolescent sex may have been too. I was a horny as fuck kid and I know there were other boys like me out there. One in particular proved to me his interest in comparing cocks when we were just kids. We did that many times and I could tell he loved it as he asked to do it nearly every time we were together. Have shared that story at length before too. I can see and feel some guys interest at work, but who are too afraid to do anything because of societal pressure and being married.

The potential of missed opportunities does make you wonder.

 

[latinsian]

When I was in my 20s I used to work in one of those banks that was located in a grocery store. We had a Disney style queue that used to snake in front of the bank. At least once a week we had a customer who used to come in and he always wore those spandex biking shorts. The guy had the biggest thickest piece of flaccid meat jammed into those shorts and he never wore underwear. I never missed an opportunity to stare at his crotch whenever I saw him. He was attractive, average height, had a good build and was in his mid 30s. Sometimes he would come in with his girlfriend. One day I had to take a piss and ran upstairs to use the employee restroom we shared with the grocery store. When I came out of the stall the big dick customer was standing next to the sinks in those biking shorts and said he had question about his loan. I thought that was a bit strange because 1) he had make a significant effort to locate me in the employee restroom which was upstairs in the back of the store and 2) it wasn’t a question I could answer in a restroom. I was so surprise to see him there I immediately said we should go back to the bank so I could answer his question. I regret that i didn’t take the opportunity to drop to my knees and pull that big dick out of his shorts.

 

[shldlop]

I've had a missed opportunity in college. There was this very popular guy in campus, attractive and excelled in sports as well as academics. His girlfriend was pretty, been a couple since high school. One day, I was in the shower alone after a swim in the pool when he walked in. He gave that longing glance at me, he was semi, and asked whether I would be interested in spending the weekend at his room as his roomie and gf were out of town. My heart leaped. But instantly, I hesitated. I had come out a year back, my sexuality was known to all. I wasn't sure what the deal was with him, whether he was curious or in the closet. I didn't want to risk the heartburn and complications that could have followed. So I said no citing some term paper deadline. We graduated some months later and I moved across the country for my dream job. Flash forward to 2020: I ran into one of his teammates in college who broke the news that the guy had come out two years back and in a relationship. Since then, I've been wondering what could have been.

 

[deleted3782]

Several years ago I met a guy online. He was much younger, super smart, very charming, great body, and a killer smile. We chatted quite a bit before agreeing to meet over dinner at a Thai restaurant very near my house. We met, sat down, ordered, and as we were waiting he started talking about his internship at a vet clinic. He was in the final days of his internship before starting school in Philadelphia. He asked if I wanted to see some of the cases he worked on. Not really...but he insisted and opened his photos to show pictures of dogs with one eye and cats with weird lesions, oh, and his massive dick. He stammered and grinned and looked at me to catch my reaction. Being a seasoned LPSG member, I played unimpressed and looked out the window. He was emboldened, scrolled back to more dick pics and said "Oh yeah, sorry about that...but...what do you think?" I affirmed "...yeah its a big one." He said it was nine inches. It very well could have been. Thick as an baby's arm, ect, etc. Then dinner arrived. We talked about relationships, his new life in Philly, and we moved on to Starbucks for coffee. He kept pushing... "we should have some fun" and I was not interested. He was much younger and was leaving the area in days. He kept pushing "...come on, it will be fun." The more he pushed, the higher my wall grew. Finally, my dad happened to call me on my phone, and I told the guy my dad was elderly and needed my help (a true statement, but dad did not need me at that moment). He followed me out to my car, and dad called back. I said "sorry, he really needs me" answered the phone while jumping in my car and left. We never chatted again.

There are lots of layers here to unpack. My avoidance, self isolation, relationship exhaustion, lack of confidence, mistrust, my dad, and delicious Pad Thai...but I still don't regret my reluctance to have a fling. I've had too many short term relationships, and in so many ways I think I'm a better person (and the world a better place) with me being solo. So...missed opportunity? Probably. Regrets? Don't think so. After all, I have a billion missed opportunity stories.

 

[Lemlucifer8888]

I had a huge crush on this guy. Swimmer. An immaculately sculpted lean body and a Devine mind. He studied philosophy and despite his lack of attraction to me I wanted him so badly for his beauty and intellect. But of course he was straight. His name was Evante Asa Lih’Leni. In this story he will be Asa - as that name captures him well - better than is bros that called him “Ev”.


Asa and I were mutuals on Instagram. And I was happy to see the timid photos of his body, his hard earned reward from hours dedicated to the pool.

I was extremely lucky that Asa seemed to tolerate me, even when he knew that I liked him too. He told me in longer, more thoughtful words, conveying a sense of contemplation about his own sexuality - that he was Ace. His words were : “I’m not attracted to bodies”. I was extremely unlucky it seemed, that bodies he did attract to were unfortunately all female. Maybe he was just being young and too sweet and too kind to tell me that, as he may have said around his hot swimmer buddies “I really only go for pussy”. He contained multitudes, I suspect.


However, I got lucky again my sophomore year when I ended up on floor full of testy athletes, which included the humble and pensive Asa. I got to see him, clad in a towel in the community style bathroom. I’d oggle his copper colored flesh in admiration and lust. I scanned his olive toned abs, arms, and pecs in their swimmer made perfection. We only ever said “Hi”.

The climax and homoeroticism comes when he and I entered a male pageant for charity. We got to share a dressing room. I still ogled at him, wishing I had the courage to tell him he looked amazing. But someone else did.


“Bro Ev’s got like uh 32 pack”



I smiled internally, glad that the conversation shifted to something I was an expert in. Asa, Ev to his bros, seemed humble and smiled meekly, perhaps awkwardly. I thought it was cute that he shy about his ripped college swimmer body and astonishing number and definition of his cinnamon colored abdominals. Then it happened.



Another guy, perhaps another man who drooled at, admired and even more likely envied Asa’s copper washboard stomach , who knew the whims of straight bros, reached over and rubbed Asa’s abs barely hidden by or perhaps not even hidden by the shirt he pulled over them.

I was in awe. I was extremely turned on by this display of eroticism that seemed so casual. I wish I could have hit pause, my mind to be a video camera. To rewind, hit pause… play… rewind. Because I cannot remember his face. The face of the other bros.



I hope his face conveyed excitement. But mild of course. Perhaps an eyebrow raised. Intrigue but moderate delight. Surprise then calm as he enjoyed the rare feeling of male to male contact. For me, I instantly wished Asa or one of his bro’s, perhaps the bro feeling him up had said “Yo Cart, man come feel Ev’s abs”

I can play straight. I can pretend. I spent my life pretending. 19 years. If you’re straight know that sometimes the way you praise your buddy is erotic to us. But keep it up. Men accept such few ways to compliment each other in the way that women seem to do naturally.

However, don’t feel wrong for turning to the quiet gay guy… the out gay guy who is comfortable and asking him to join in “Hey, Cart you like what you see?”



Fuck yeah I do, Asa.

If you’re like Asa (or you think you might be Asa) message me.

 

[curtdude]

I was in the school elevator with Peter he wore tight pants with a very pronounced bulge pants so tight I could see he was circumcised. he caught me staring at his bulge as I looked up at his face he winked and smiled at me I jammed out of the elevator as the doors opened.

 

[artboyd]

Recently, I had golden missed opportunity, who knows.

An empty profile messaged me on one of those famous dating apps one day. After going back and forth for a few days without showing our faces, I felt like an encounter was going nowhere. I'm the type who speaks my mind: I will praise you if I find you attractive but that doesn't mean I am desperate. I believe in the saying that you will never know if you don't ask. So I ask but I also tell. Anyways, I was like... "yeah, nice body pic but I'm not in a hurry". At the end I agreed to meet but didn't have too much enthusiasm.

Finally, I arrive late at night in his neighborhood and meet on the side walk. The guy very young, looks no older than 25. We talked and walked around the neighborhood for a bit and he appreciated the fact I was "normal" according to his words. In the meantime, he would behave as if I was too much.. shivering, shaking, breathing heavily... wanting to touch me discreetly while walking through darker parts of the town. He manages to convince me to go inside a discreet bathroom and I couldn't believe my eyes. The body is WOW, the dick is WOW, maybe 50% longer and fatter than mines, the ass... I mean, I couldn't process so much beauty. His body so lean and perfect. Flawless skin and just the right pattern amount of hair and a tanned skin. It looks like this guy is doing lots of rock climbing or calisthenics. I can pinpoint to a LPSG member lookalike if you guys want me to.

Never had anyone reacting so intense to my presence. He kept saying I was a "Bull" and a "Real Man"... etc etc. He would say he had bad thoughts, and wanted me to fuck him hard but then acted as if he feared me so he would stop me if I tried to actually do something at the same time. His dick was hard and leaking.

My initial reaction was to hug him, trying to calm him down. Telling him everything was alright but then I felt there was something else and I started fearing myself. I got scared. I'm thinking maybe he's gonna call the police, maybe he's a Karen or this is a stunt or whatever. Since it was my first time in this situation, I didn't know better, I decided it was time to end the encounter.

After the fact, he did not blocked me on the app but his responses to my messages where rather dismissive so I stopped messaging him.

Many days and months after the event, people I have talked about it have mentioned that there is some sort of fetish from younger guys to feel raped or something about domination, or used by older guys from what appears to be a "realm man look" which is apparently what I had... didn't know there ware fake men. I know there are fake muscles haha... but maybe my cultural background is so naive to these things that made me miss that amazing opportunity.

The guy doesn't know I know who he is and what he does. I wish I could have met him in better terms because WOW.... Besides his body and his desires, he is an amazing human being that I would love to be friends with.

Do you think it was a missed opportunity?