Missed Opportunities

[Whippoorwill]

I am sure we all have missed opportunities...or at least missed fantasies. I have scores, some of which I still beat off about. Let's hear yours. I will start off with the fantasy of what should have happened, and follow up with what really happened: 

Fantasy: Tony.

When I was a sophomore in college, I was in a dorm with sophomores and freshman. In these ancient times, I was just starting to deal with the reality I was into guys not girls. Just starting to deal, I say, because I was jerking off to the fantasy of girls, but starting to have wet dreams about guys. In those days, I was also a Catholic, having been brought up as such, but not really having thought about it much. I was smart enough to "graduate" from a catholic high school to a secular college, but was still going to Sunday Mass on campus. Somehow, I got myself into the role of waking up the other Catholics on the floor for Sunday morning mass. So come spring, sophomore year, when we are all horny with morning wood ever day, I made my early morning Sunday rounds with the Catholic boys. Prime among these was Tony, a Long Island Italian boy, with an 18-year old's hairy Italian body to beat the band. His roommate was Joe, and equally hot anglo boy, with a reddish hairy body. 

I softly knocked on their door, and went in to wake up Tony for mass. I was wearing my boxer shorts (gleep). Tony was asleep in bed, totally naked, with a massive hard on, that I could fully see as he was only covered in a sheet. I woke him up, and told him it was time to go to mass. 

All the while, I was of course fixating on his gorgeous hard-on...big, curved, raring to go. In my fantasy, we talked about how horny we each were; how we needed to cum; how Tony invited me to get up on his bed and suck him off; and now while we were doing this, Joe woke up, got behind me, and started fucking me while I was sucking off Tony. 

Over the decades, I have beat off countless times thinking of me sucking off Tony whey Joe fucked me silly. It should have happened. It probably could have happened, 

The reality:

I told Tony it was time to get up for Mass. We talked for a minute or so. He went back to sleep. Joe never work up. I left and went to mass. Boring. 

The upshot:

I have been jerking off for decades since then, thinking about what could have been. 

What are your slutty missed opportunities? 

[+ azdr0710]

thanks....very much.....for this story!.....I'm going to sleep like a baby tonight!

[+ poolboy48220]

Getting a new refrigerator, two guys got it inside the house and plugged in.  The door worked better opening the other way, so one guy went back to the truck while the other guy (more my type) stayed inside to flip the door. At one point, he & I were holding the door up and I'd swear he was grinding his crotch against my hand. I was much more timid in those days, so...missed opportunity. 

[Whippoorwill]

Fantasy: Benji Alejandro.

Any city I travel to I want to see it from above, to understand its structure and overall image. Before GoogleEarth, one had to do this, by, literally, going to a high place and looking down. One city where there are many opportunities to do this is Florencia, Florence, that wonderful medieval/early renaissance City of Flowers located in Tuscany. Wonderful at least if you are not there in the height of summer when it is overrun with American tourists from Kansas on package bus tours. The obvious place to view Florence from is the Piazzale Michangelo, built for just this purpose. The problem with that is, it is built with tour bus parking, and you probably want to avoid it like the plague (which last hit Florence in the mid-14th c.). Better viewpoints are can be had from Santa Maria del Fiore. the cathedral of St Mary of the Flowers. There are two routes "up" here...one is to the top of the dome, that great structure, still the largest masonry vault in the world, that ushered in the Renaissance. And I certainly recommend ascent to the top, for any of us still able to, as the essentially 35 stories take you through the bowels of the construction of the dome, with views both into the church below and the city beyond. 

But I digress. This fantasy revolves about what happened when I last climbed to the top of the Campanile, the bell tower, of the cathedral. Not for the faint of heart, at some 25 stories tall, the stairs have risers higher than the width of the treads, as only the Europeans do. But when you reach the top, such magnificence. You look down on the medieval city of red clay tile roofs, and beyond to the agricultural countryside, unspoiled by 20th c. high rises. And happily, the tour bus crowd never makes it up here. I arrived on a beautiful May day, with blue cloudless sky forever, but early enough in the year to be an enjoyable 70 degrees. While several dozen people can fit on the narrow balcony that encircles the tower, there were perhaps only a dozen tourists rotating through at any one time. As I was intently studying the city from this viewpoint, I remained here for some amount of time, photographing and reflecting. I soon noticed a comely young man who also remained as others came and went. I don't know who made the first advance, but we soon were talking. I learned he was from Columbia, product of an American father who ran a large American factory there, and a Columbian mother. His name was Benjamin Alejandro ___________. long before Madonna made Alejandro a hot name to have. He went by Benji as a nod to his father, but he secretly preferred Alejandro and his hispanic side. He had just finished his freshman year in college, and his parents sent him on a European summer vacation. We talked about life in Columbia, life in California, his schooling (he was a Business major), his hopes and dreams, and so on. At some point, I asked if I could take his picture. This was in the days of big heavy 35mm through-the-lens reflex cameras, with no possibility of texting him the photo. (so why did he possibly think I wanted to take his picture?). He said "Yes, but let me take my shirt off". Holy shit. I had hit the jackpot. He removed his shirt, and I took a series of photos of him, his face, his torso, his profile. At some point, I said, "would you like to come back to my hotel?" 

In my fantasy, he immediately said yes. Our hard-ons were apparent as we climbed down the 500 stairs, and headed off to my hotel in a former Renaissance palace. We barely got to my room before we tore each others clothes off, and spent the rest of the day fucking our eyeballs out. 

The reality:

Benji indeed did take his shirt off and pose seductively. But when I asked him to come back to my hotel, he said no. But why ever did he offer to take his shirt off? He surely knew my game and was cock-teasing me. He probably was on the verge of coming out...we've all been there...but wasn't quite ready to pull the trigger. We parted ways. I went back to my 3-star tourist hotel and jerked off until I was totally spent. 

The upshot: 

Every once in a while I summon up memories of Benji for a jerk off. I had kept his photos until a few years ago when I cleaned house in a Covid clearing out jag. But my hope for him is that he found himself and is now bedding down every night with the man of his dreams, and fucking each other silly. 

[mtaabq]

2012 ... and I still think about it ... shirtless hitchhiker on University Dr in Tempe ... on a hot Sunday morning ... walking west ... I had the balls to follow him into a convenience store (he had put the shirt back on), ask him if he needed a ride, told him to get a bottle of water or a soda or whatever, then told him to wait by my car "and lose the shirt". I walk out, he is indeed shirtless (lean, brown, sweaty, sexy) and he gratefully gets in my air conditioned car. Tells me his name is "Ricardo" but to call him "Dick". Oh, jeez. Ask him where he's going, tell him I'll give him a ride, and he makes it very clear that he wants to play. (Understand that I was then and am now a fat guy and hot lean young men do not usually want to play. Unless they were paid. Which I was prepared to do.) But I chicken out, wuss that I am, drop him where he asks, give him twenty bucks ... and I saw him last in my rearview mirror. 

stupid, Stupid, STUPID!

[ShortCutie7]

I love this thread!  Let’s call mine “Greg.”
 

I met Greg in Junior High- we were both selected to go to represent our school at some sort of conference/ceremony.  We rode in a limo together with my mom chaperoning from and back to school- my mom insisted Greg call her “mom”, which he got a kick out of.  I got along great with Greg but only got to see him in passing since we weren’t in any of the same classes.

A few months later, I went to a new (to me) summer camp, as the one I had previously attended had shut down.  Who just happened to be in my camp group?  Greg!  Greg was the star of the camp, and I was his second-in-command.  Greg and I had a strong bond as we were both fat kids and could probably sense we would both end up being gay.  We both went back to the same camp the following year, but lost touch afterwards as we went to different high schools. 

My freshman year of college, I created a Facebook account and got an immediate friend request from Greg.  Greg was now tall, lean, and stunningly handsome.  We didn’t interact much and I didn’t really think about or keep track of him.  A few months later, I went into the city near my college and went into an establishment.  Who was working in that establishment?  Greg!  We didn’t get to spend a lot of time together since he was working but he was quite flirtatious.

My fantasy: I waited for Greg’s shift to finish and asked him out.  One thing led to another and we played (I had some incredibly graphic fantasies about him), dated, and for married, and he ended calling my mom “mom” for real.

The reality: I left the establishment to get back to campus, and Greg ended up transferring to a college that was not near mine a few months later so I never got to see him again.

The upshot: Greg is now incredibly successful and is married to a man who is fairly similar-looking to me (so even though I would typically think him to be out of my league, I do think he would have been interested).  I have actually seen nude photos of Greg and his body and cock are quite impressive.  I still often fantasize about Greg.

[+ poolboy48220]

Another one I remember. A group of friends did a yearly ski trip, staying at a big condo with multiple bedrooms and a huge hot tub inside. One year Frank and I went up early on the first day, the rest of the group wasn't arriving until after dinner. He mentioned several times we'd be able to use the hot tub naked, in a tone that made it obvious he was looking forward to that. There'd been other subtle signs that he was open to some play. Come hot tub time, I was too shy to initiate anything - not even some foot grazing in the tub which was my go-to move at the gym. A few years later I hung out at his place one night, we both put on our lycra shorts and laid on his bed watching a movie; and that's all. I kept in sporadic touch with him for years after that, just recently noticed that he'd removed me from his Facebook friend list. 

[ShortCutie7]

Here’s another one… let’s call him Chuck.

I met Chuck on my first day of grad school, as we were in several of the same classes.  I noticed Chuck immediately- his gleaming eyes and smile lit up the room.  He wasn’t really my “type”, but I thought he was very handsome.  We became fast friends and worked together on several projects.  About a month into our friendship, we had lunch with a (female) classmate to brainstorm a project.  That lunch led to Chuck and our classmate talking about dating.  Chuck revealed that he was a “Kinsey 5” and was mostly gay but did have a serious girlfriend at one point.  Chuck then turned to me and asked if I was seeing anybody.  I then told them that I had never dated/been in a relationship because I was gay but not out… that was the first times I had ever told anyone that!

A few months later (during finals), I got into an accident and Chuck basically saved my life.  I ended up living on campus the following semester while I was recovering from my injury, and Chuck was living in another dorm down the block!  I spent lots of time with Chuck that semester, and we would often go to gay bars and spaces.  He is incredibly outgoing and I am pretty introverted, and he got lots of attention from men.  We would also frequently go on his balcony and “guy watch.”  We were basically each others’ only gay friend, so we talked about a lot of things we had not been able to with others.  After that semester, I moved back off campus and Chuck graduated.

Chuck comes to visit my city every so often and is serially monogamous- he has introduced me to a different boyfriend each of his visits.  A few years ago, he sent me a drunken message that he regrets not making out and jerking each other off while “guy watching” on his balcony.  I had no idea he would have been game for that 😭

[Whippoorwill]

Fantasy: Discovering Porn 

I attended a private high school in the southern suburbs of a midwest rustbelt city, although our family lived in the northern suburbs, as did my buddy, Frank. Frank wasn't conventionally good-looking...he had a large hook nose, for which he was sometimes mocked as cruel teenagers do. But we got along great. He also had a nicely developing muscley body, unlike me who still had my baby fat. And this was in the era when guys walked around the locker room naked, which had gang showers. I can still see his 18-year old's developing pecs. I so wanted to feel them. Frank was also hung...he had a cock that came straight horizontally out of his pubis, and then maybe three inches out, turned down 90 degrees, as if it were too heavy to continue to stand out. I really liked to look at his cock, a lot. And today I still get turned on by guys with big hook noses...ever since Frank, I associate a big hook nose with a big cock. Some people judge by a big adam's apple; others by big hands or big feet. Me, it's the nose. 

To make this daily school treck took a two bus rides, transferring in downtown (this was the early 1960s before the era when high school students had cars and drove to school). There was a large magazine emporium near the bus transfer point where we often would hang out in the afternoon between busses. In the spring of our senior year we each turned 18, which meant we could finally go into the "adults only" section of the magazine store. Being horny teenagers in need of some sex education, we went exploring the adults section in detail. Soon Frank came to me with a different kind of stroke book, one of those early magazines with exotically oiled up body builders in posing straps, perhaps Phyisque Pictorial or some other of the ilk. All quite tame by today's standards, with no overt sexual acts but screaming sexuality to a gay boy in training like me. "Look what I found. Do you suppose these are made for girls, or for queers?" he said. As I eagerly devoured the pictures with him I noticed Frank had a huge boner, as we called them. I will never forget the sight...he was wearing really ugly very baggy brown tweed wool pants (private school was a suit and tie affair) that showed off his monster cock beautifully. "I don't know" I said, "but it sure gave you a boner." Frank looked down at his manhood, and looked back up at me and smiled. We cobbled the money together for the magazine, and got the bus home. We sat in the rear bench seat of the bus, hidden from others by the seats ahead. We took the mag out of the paper bag, and raced from photo to photo looking at guys in exotic poses wearing only posing straps; tight jeans; a lace bikini; two guys in posing straps straps horsing around with interlocking bodies; and a sailor boy in various states of uniform or not.

We were't five minutes down the road (it was a 45 minute bus ride) when Frank unzipped his pants, reached into the fly of his jockey shorts, and pulled out his monster. I thought I was going to cum in my dress pants in a second, so I followed suit, and pulled out my best friend. Frank spit in his hand, and started stroking. I had the presence of mind to pull my handkerchief out of my pants pocket. I came first, with a gusher in the handkerchief. I handed it to Frank, who added his load. Then unbelievably he took the handkerchief to his nose and took a good whiff. I still do that today...the smell of cum is an intoxicating drug for me. Frank took the magazine home the first night; fair enough, I had the handkerchief. We traded off the magazine every other night until it was dog-earned and pages sticking together with cum. But it would be a while before we hit the bed together...a story for a future time. 

The reality:

Frank indeed came to me with the stroke book and said "Look what I found. Do you suppose these are made for girls, or for queers?" he said. I only dared to glance at a couple of photos. I also noticed Frank had a huge boner, as we called them. I will never forget the sight...he was wearing really ugly very baggy brown tweed wool pants (private school was a suit and tie affair) that showed off his monster cock beautifully. But I pretended not to notice, and said "I don't know, probably for girls." He wandered off and eventually we went to our bus, and talked about the day's schoolwork on our way home.

The upshot: 

I've beat off scores of times remembering this and other times with Frank and fondly thinking of what might have been. We never overtly pursued anything with each other. Decades later, I did read in the matrimonial column of the local newspaper (remember matrimonial columns? remember newspapers?) that Frank married a woman in his mid-40s...a little late in life, perhaps? An internet search shows them living in a dreary prefab suburb in the Florida swamplands. No mention of children. But I still lust after guys with big noses. 

[+ poolboy48220]

I've had the same association with nose & cock size since I read it in "The Happy Hooker", sneaked from my parents' bedstand, in my pre-teen years. Gym classes in high school validated that to some extent. 

[ShortCutie7]

Sometimes these fantasies get triggered and it makes my day… “Greg” posted this sexy pic (cropped for privacy) today…