Opportunities Missed

[+ imagooddog]

I feel sure most of us regret having missed an opportunity and wish we could somehow go back and

and act upon it for a different outcome.

When I was about 25 and in graduate school on an assistant ship, teaching 2 classes and taking 3 I lived

in a dorm with mostly underclassmen. I almost always studied in the room with the door to the hall open

and could see all who walked by. There was an 18 years old freshman, a really cute personable guy, black

hair, dark eyes, great smooth body who would stop by an talk occasionally. I think he admired me, being

older and more mature and in those days I was a good looking guy. One day (Tom) stopped by and in talking

said that he thought he had jock itch. I asked what it looked like and the said he could not see down there

himself. I told him that I had it years before and could take a look if he wanted and he said sure. So I told

him to go on down to his room and I would come down and take a look. So in a few minutes I went to his room, opened the door and he was standing there naked.

Now here is where I screwed up. Those were the days before "gay", you were queer and I was deep in the closet and I was very shy.

I got on my knees, face about 8 to 10 inches in front of his dick. And what did I do? I took a nearby pencil and moved his dick and balls about with it !! (He did not have jock itch or any sign of a rash).

I feel sure this 18 year old testosterone fueled good looking boy would have had a hard on in a minute it only I had used my fingers and hands while I carefully examined and moved around his dick and balls. That thing

could have been in my mouth then and maybe many times in the future. If only I had known than what

I know now.

[+ sniper]

When I was 35 a 19 year old of my acquaintance wanted to have sex with me one summer night in the city. I felt weird about it and backed out. (There were also some logistical challenges - due to us living in opposite directions each an hour away we would have needed to get a hotel room and I was too self-conscious to check in with someone so obviously younger for so obvious a reason).

 

12 years later he's hotter than ever but living across the country and I am still kicking myself.

[Racketjock]

I was 16, traveling with a student group in Germany. Was with a buddy at a beer garden, having already downed my first taste of German beer. My buddy couldn't handle his liquor even though he was two years older than me. We were all seated around long farm tables, elbow to elbow with other patrons who were friendly, singing songs, and having a good time. A particularly strapping blond haired, blue eyed hunk of a man close to my age seated slightly across from me kept giving me a wink and a beautiful smile as we clinked glasses amidst cheers. My bladder got the best of me and off to the bathroom I go, and lo and behold he follows and stands next to me at the piss trough, whipping out a beauty of an dick with curly blond pubes. I openly stared and I'm sure salivated. He beats his cock and asks me if I want to have some German fun. I have the good sense to bolster my courage and quickly shake my big and small heads both. My horrible luck bit me in the ass as one of the female bar maids pops her head into the bathroom to tell me my friend had fallen over, vomited, and needed to go. I had to slug the bastard back to the hotel and my opportunity for my first German cock was delayed another couple of years. Thankfully, my drunken friend and I were sharing a hotel room, different beds and he passed out promptly leaving me alone with my five fingered friend and a fond memory of the big German cock that got away.

[+ azdr0710]

quick intermission from the great stories!.....I post this classic occasionally, mostly because of her great voice and the great melody and lyrics in this one.....note the single camera pan used throughout the entire song with no change at all (there's a term for this I don't remember just now)......

 

Edited May 10, 2018 by azdr0710

[+ poolboy48220]

I think I've told this story in past threads about this topic...In my 30's, just a few years before I came out, on a ski trip with some friends from work. I drove up early with one guy I had a crush on, and he was very open about anticipating using the hot tub naked before everyone else got there. I was so tempted, but never made a move, nor did he.

[+ sniper]

did you see him naked in the hot tub at least?

[+ Charlie]

When I was 21, I was picked up on the street in Greenwich Village one evening by "Peter," a very handsome, powerfully built older man ("older man" to me in those days meant anyone over 35). He took me back to his apartment, and we were partially undressed and just getting into it when the doorbell rang. Friends of his, a straight couple, had just stopped by on their way home from dinner at a nearby restaurant. He let them in, although he was shirtless. I was still in the bedroom, but after a few minutes of waiting for him to return, I dressed completely and emerged. I could tell that the couple were surprised, and intrigued, and after about fifteen minutes of rather awkward conversation, they didn't seem at all inclined to leave us alone. I became fidgety, and finally said I had to leave. "Peter" was obviously irritated by the whole situation, but he let me go; however, he slipped me his number and I slipped him mine as I left. I went to a diner on Sheridan Square, where I was picked up by someone else, who then picked up a third party, and we all went to the third guy's place for some rather interesting sex (my first experience with poppers).

 

A few days later, I received a phone call from "Peter." He immediately went into a spiel which was as heavy as any paid phone sex you could imagine, and I came by hand during the call. But the things he said he wanted to do with me scared the shit out of me, even though I found it terribly exciting to hear. He insisted that I travel back to New York that Friday, because he was going to make me his complete sex slave for the weekend. He was so intense that I agreed to go, although I knew I wouldn't do it. Instead, as soon as I was off the phone, I wrote him a letter, explaining that although I was extremely attracted to him, I was not psychologically prepared for what he had in mind. I received a very short, gruff acknowledgment in reply, and never heard from him again.

 

Even after all these years, I still sometimes wonder if my life would have taken a different course if I had gone to see him that weekend.

Edited May 11, 2018 by Charlie

[+ sniper]

Never know, you might have done got yourself killed. You don't know he knew what he was doing.

[cany10011]

When I was 21, I was picked up on the street in Greenwich Village one evening by "Peter," a very handsome, powerfully built older man ("older man" to me in those days meant anyone over 35). He took me back to his apartment, and we were partially undressed and just getting into it when the doorbell rang. Friends of his, a straight couple, had just stopped by on their way home from dinner at a nearby restaurant. He let them in, although he was shirtless. I was still in the bedroom, but after a few minutes I dressed completely and emerged. I could tell that they were surprised, and intrigued, and after about fifteen minutes of rather awkward conversation, they didn't seem at all inclined to leave us alone. I became fidgety, and finally said I had to leave. "Peter" was obviously irritated by the whole situation, but he let me go; however, he slipped me his number and I slipped him mine as I left. I went to a diner on Sheridan Square, where I was picked up by someone else, who then picked up a third party, and we all went to the third guy's place for some rather interesting sex (my first experience with poppers).

 

A few days later, I received a phone call from "Peter." He immediately went into a spiel which was as heavy as any paid phone sex you could imagine, and I came by hand during the call. But the things he said he wanted to do with me scared the shit out of me, even though I found it terribly exciting to hear. He insisted that I travel back to New York that Friday, because he was going to make me his complete sex slave for the weekend. He was so intense that I agreed to go, although I knew I wouldn't do it. Instead, as soon as I was off the phone, I wrote him a letter, explaining that although I was extremely attracted to him, I was not psychologically prepared for what he had in mind. I received a very short, gruff acknowledgment in reply, and never heard from him again.

 

Even after all these years, I still sometimes wonder if my life would have taken a different course if I had gone to see him that weekend.

 

 

I loved your bit about the hand written letter. So charming! The closest thing i had to a missed adventure was during my residency at Penn when a hot visiting german scientist (MD, DDS) who i was working with kept on asking me out over the course of my rotation. We bonded over classical music, german literature and the opera. At that time, i was not out yet and though i would have liked to, i demured and just made up stupid excuses. I wish I hadn't...Maybe things would have been different .... Though I am happy with how things have turned out, one always wonders what if....

 

I'm often reminded of a lovely poem by Robert Herrick when i think about things that might have slipped by....

https://www.poets.org/poetsorg/poem/virgins-make-much-time

[+ sniper]

Oh, I forgot, when I was in my late 20s a pair of 40ish doctors in Manhattan hit me up on gay.com telling me they were looking for a third in a houseboy/poly kind of situation. They were quite attractive too. I felt my profile pic at the time was probably the best picture I have ever taken in terms of how attractive I was and I didn't feel like I live up to it, plus I sort of felt like I had gone to too good a college to wind up as a houseboy, so I demurred.

Eh, I'd probably have gotten hooked on drugs and OD'ed(one was a pain specialist and I have significant back issues).

[+ sniper]

Actually I just looked the one who emailed me up, he wasn't even 40, he was less than 10 years older than me.

[+ poolboy48220]

did you see him naked in the hot tub at least?

I did. I'd also seen him naked in the locker room at the gym.

[NJMMZ]

I used to get my haircut by a guy maybe 10 years older than me. He would come to my house and cut my hair or I would go to his house. He was always touching my shoulders and chest but I never gave it a second thought. But he always had a bugle in his tight pants. But I was so young and naive I just didn’t realize what was happening. Anyway onectime he was asking me about girlfriends I may have had and sex became a topic. At that point he pulled down his pants revealing the biggest most beautiful cock I had ever seen. I simply froze. Wasn’t sure what to do. I was only in my early 20’s. Was very naive. Anyway I’m sure it would have been a fun experience if I acted. But it planted a seed in my head that I was actually attracted to men. I jerked off many times thinking of what might have been. Took another 30 years before I sucked a cock.

[+ Charlie]

I loved your bit about the hand written letter. So charming! The closest thing i had to a missed adventure was during my residency at Penn when a hot visiting german scientist (MD, DDS) who i was working with kept on asking me out over the course of my rotation. We bonded over classical music, german literature and the opera. At that time, i was not out yet and though i would have liked to, i demured and just made up stupid excuses. I wish I hadn't...Maybe things would have been different .... Though I am happy with how things have turned out, one always wonders what if....

 

I'm often reminded of a lovely poem by Robert Herrick when i think about things that might have slipped by....

https://www.poets.org/poetsorg/poem/virgins-make-much-time

When I was 21, a hand written letter was the most convenient way to communicate with someone in another city; there was no email. Even a phone call from Philly to NYC (landline, of course) was a long distance call that cost extra money.

 

I know the Herrick poem by heart, but I didn't think the weekend activities would include rosebuds.