Missed opportunity stories

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Have you ever had a guy flirting with you or wanting something more and you were completely oblivious to it?
 
I wasn't oblivious, but afraid. I was in a fraternity, and a handsome fit fraternity brother who suspected I was gay (I never displayed any interest in women, but I wasn't out and was respectful of my situation) asked me to his room. He closed and locked the door - told me how much he loved his girlfriend - which he did - but said he would love to find someone to suck his cock. I should have dropped to my knees but I was afraid.
 
When I was in college, another guy in my dorm came by my room to hang out. Some thought he was a little feminine, but he was tall, had very thick hair, a trimmed mustache, and he was an attractive dude. Anyway, somehow we started wrestling on the floor and my cock started to get hard. I don't know if he noticed, but as we were rolling around on the floor, he cautioned me to "be careful what you start." I didn't really think it was I who started anything, but I got embarrassed and was actually a little scared of my feelings and we stopped wrestling. I've always wondered what might have happened if we had kept it up.
 
Yes. I used to work with a guy who was openly gay. I wasn’t out, but I think he knew I was gay. We both had training for work out of town once, and while texting about it I jokingly said we should have just shared a room. And he agreed and said he could have used someone to cuddle with at night. I brushed it off because I was afraid and inexperienced. A few days later back at home we were texting one night and he asked if I wanted to come over for a night swim, just him and I. Again, I was nervous and scared because I wasn’t out and had never been with a guy at the time. So I didn’t accept the invite. He continued to try and hang out with me and I always turned him down until he eventually just gave up and he got another job and I never saw him again. To this day I regret not pursuing it, because I know he wanted me. I would have happily given up my virginity to him.
 
I had recently left home to go to university when I met up with a mate from school and over a beer he told me that he was into sex with guys. I must have looked confused because he explained how he got started, a gloryhole in the science library. Next day, I was curious enough to check out the bathroom he had mentioned after my final lecture. Sure enough, there was a neat hole in the partitions between two of the three cubicles, and the third cubicle was occupied. I heard the outside door open and without thinking closed the door of the cubicle I was checking out, I didn’t want to be seen to be loitering. The guy entered the neighbouring cubicle, shut the door and almost immediately put his hard cock through the hole. I wasn’t sure what to do after gingerly touching the hard flesh so I fled, but my cock was rock hard.
Looking back, I missed a good chance to explore; I often wonder what might have been if I had explored that cock further and if it would have short-cut years of confusion.
 
There was a guy in my fraternity that I think wanted to mess around. I sure did. He ran out into the hall to greet me back from Thanksgiving or something. First time I ever noticed a guy holding on just a second too long. I thought, “hmmm. Is this what I think it is?” I always failed to trust myself to evaluate the situation. I kept thinking, “this can’t be what I think it is.”

Another time, we were watching TV on a couch. He was sitting and I was laying down at the other end. At one point, I stretched out my leg and accidentally brushed is uber hairy chest. I "jokingly” started to run my foot all over the thick hair on his chest. I expected he to say something, but he didn’t say anything at all. I think we had other opportunities (walking around the dunes at Ft. Walton Beach), but it seemed like neither of us had any idea how to start off or make the first move. So it didn’t happen. Thinking back, he had a single room in the house. I think I was just too afraid to be “that guy.” I was a slow learner and didn’t realize how many “straight” guys would fool around with some dick given the opportunity. Fuckin’ regret missing that opportunity so bad many years later.
 
Mr. Oblivious here. I have too many stories but the best one is when I lived in an apartment complex one of my neighbors was this attractive tall athletic guy with a swimmers build and short brown hair. We were about the same age. He lived upstairs and a few doors down from me. Our cars were always parked near each other so we would say hello and exchange some brief words when our paths crossed. I noticed he had a hot ‘friend’ who would come and go from his apartment a lot. One Saturday afternoon as I was parking and getting out of my car, I noticed my neighbor and his friend were getting out of their car. His friend went up to the apartment but my neighbor kind of lingered around his car. When I got out of my car, we said hello to each other and made some small talk then my neighbor said something like there is nothing going on for the weekend so he and his buddy would just be hanging out and I should come up and have a beer. I said something like ‘I don’t like beer. So no thanks.’ Then I went on my merry way. Later that night I was thinking about what had happened and then it hit me, ‘Heeeeeeey, wait a minute. I think that guy was coming on to me.’ Damn it!
 
Mr. Oblivious here. I have too many stories but the best one is when I lived in an apartment complex one of my neighbors was this attractive tall athletic guy with a swimmers build and short brown hair. We were about the same age. He lived upstairs and a few doors down from me. Our cars were always parked near each other so we would say hello and exchange some brief words when our paths crossed. I noticed he had a hot ‘friend’ who would come and go from his apartment a lot. One Saturday afternoon as I was parking and getting out of my car, I noticed my neighbor and his friend were getting out of their car. His friend went up to the apartment but my neighbor kind of lingered around his car. When I got out of my car, we said hello to each other and made some small talk then my neighbor said something like there is nothing going on for the weekend so he and his buddy would just be hanging out and I should come up and have a beer. I said something like ‘I don’t like beer. So no thanks.’ Then I went on my merry way. Later that night I was thinking about what had happened and then it hit me, ‘Heeeeeeey, wait a minute. I think that guy was coming on to me.’ Damn it!
Oh wow, you should be jailed for that.
 
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I was in a club one night, got chatting to a curious straight guy on Grindr... we were both in the same club so when the night was over we had arranged to go somewhere private nearby so we could suck each other off. His cock was still to this day the biggest I have seen in person, even soft he was huge! But midway through sucking him, his pal phoned him to ask where he was, the taxi was almost there etc. so he had to leave. Still to this day I wish I had just invited him back to my student flat
 
I was in a club one night, got chatting to a curious straight guy on Grindr... we were both in the same club so when the night was over we had arranged to go somewhere private nearby so we could suck each other off. His cock was still to this day the biggest I have seen in person, even soft he was huge! But midway through sucking him, his pal phoned him to ask where he was, the taxi was almost there etc. so he had to leave. Still to this day I wish I had just invited him back to my student flat
Oh wow, such a shame it ended so abruptly.
 
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During my college years at a large university, I made it a point to regularly visit the gym and became accustomed to the spacious communal showers. Following a consistent workout routine, I often found myself sharing the showers with the same group of men after our sessions. One particular individual frequently initiated conversations with me during our shower time, often asking to borrow my body wash. This interaction left me feeling somewhat uneasy, as he was significantly larger and in remarkable shape. I stood at 5'9" and weighed around 165 lbs, while he towered over me at approximately 230 to 240 lbs, showcasing the classic athletic build I admired. The showers were designed for football teams, providing ample space for him to use his own pole shower and showerhead. At that time, I was quite self-conscious about my body. Looking back, I sensed he might have been trying to flirt with me, complimenting my muscle gains, and he did not shy away as I did when he was washing his chest and impressive endowment. However, at that time I still felt uncomfortable being naked around other men and likely misread his intentions. Back then, I would never have considered complimenting another man on his physique while we were both exposed.
 
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There was a straight guy in college I had a huge crush on. I really wanted to be his friend and I really turned on the charm to make it happen. After a year we became really close friends.

He had a stunning body and a large flawless uncut cock that I would have to pretend meant nothing to me in the gym locker room.

We were both single so we shared a room while on holiday together with a group of friends. One night we were drunk wresting in the room after a night out. There was a moment where I could have gone for it and made a move. He gave me the impression that he was open but wasn't going to make a move himself.

I was too scared of the consequences of outing myself to him because I didn't want to risk losing him as a friend. He meant too much to me.

In hindsight, I regret not taking that chance because I do think he would have let me blow him. He's married with 3 kids now so that door is closed now. A sliding doors moment.
 
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I lived in a very small town and was very afraid of people knowing that I was into boys, despite all the gossips and bullying because I was a little feminine. There was this specific buddy that I knew talked shit behind my back, but he used to be my type. We sat close in class, and I used all my charisma and "straghtness" to convince him to go to my house after school to see porn.

I was so naive my goal was to hide and spy he take his cock out and masturbate (OMG, shame).

When he accepted, we were alone at home, he asked if I had a comdom. I said no. Left him watching the video alone while spying. He went away furious and never came back to my house again, despite my insistence. He still provoked me after this, but never gave me an opportunity again.

Sometimes I remember this story and want to slap myself in the face. Hard.