The Fuck That Got Away

[Heir2012]

When I was a teenager, I had a teacher that I was obsessed with. He was beautiful. I think he was one of the men that started my DILF obsession. He wore tight pants which showed off a sizeable bulge and hugged his ass. I'd ask questions during tests just so he would walk over and stand at my desk, the desk's top at the perfect level to be eye-to-eye with his dick. I used to jerk off to his picture in the yearbook, plastering his face with cum. I've seen him since, but only a few times. I always wished something could have happened between us. He's married, but that doesn't stop my need to fuck him and have him fuck me back. 

Anyone else have someone from their past that they wish something could have happened with, then or even now if your paths crossed again? Who is he? What did you wish could have happened? 

[Rawhole-Danny]

I think part of the teacher thing is the position of authority. I remember I use to fantasise in my teens of being used by a groups of teachers and looking back some of them wasn’t even very good looking but very charismatic or very authoritative. Even if that’s imitation had arisen I would never of managed a gang bang in my teens lol 

 

I did have a fumble with one of my mates dads when I was about 18 or 19 and I wish I’d of took that further but i chose not to because I didn’t want my mate to find out. If I had that opportunity now I wouldn’t think twice haha 

[Hairypiglet]

It's not just about positions of authority.

 

My Phys.Ed. teacher in 8th was a gorgeous bull of a man, but also he cared about me. I was large and extremely hairy, I was a violinist built like a linebacker and hairier than most adults. They called me sasquatch. He used to stand by my locker, which happened to be right in front of his office, and just chat with me during changing. I rememberone afternoon he told me the other students were jealousthey hadn'tgone through puberty yet and I could already grow a beard. It wasn't authoritative at all, he made me feel safe. He was married, just genuinely a great man a good teacher.

In high school I had another Phys.Ed. teacher, Coach Nickerson, the football coach. He was tall, built like a freight train, no one challenged him. I'm sure he could have knocked anything out. The kind of man myths are written about. But again, he was soft with me. I was a giant too, but I've never been aggressive. He tried to get me on the team, but I'm just not wire that way. I remember when we had to do stretches over a box as part of our testing and I could not only reach my toes, but put my arms over the box and my entire hand folded down the back of it, he and the cheerleaders couldn't believe it. He wasn't as protective as my previous PE teacher, but I never felt vulnerable. A couple years later he was promoted to VP and I'm certain he had a part in helping me get through some issues where I was being threatened and harassed for being gay.

Then in my senior year, I had the opportunity to be a Psych TA for a gorgeous man. I hadn't been in his psych class. My psych teacher the previous year was actually the baseball and softball coach, who was actually a minor league player. He was handsome, but not my type. But I took his class and we got along. In my senior year I had extra credits, he wasn't teaching psych, so I got him to push me through and another teacher accepted me as assistant. I can't even remember his name, only that he wore thick-rimmed glasses, had a POW-MIA flag over his desk, and had a smile that could open your soul. I hated my life and was on a lot of drugs that year. He knew, but he always aided me. He didn't turn me in, he just gave me assignments that allowed me to hide in the staff room for extra hours or sent me to run exams through the scanner. I was always so high from pills I could have slept standing up. I remember his name was Matt, I think. My attraction to him had nothing to do with his authority. I had desired him for years, but was never lucky enoughto have him as a teacher. He was gorgeous. Perfectly sculpted slender nerd. I remember falling asleep at the back of class one day after grading papers for him. I felt a hand through my hair and when I looked up it was him smiling down at me. He told me to go make him some copies. Fuck, what was his name?

Laguna Creek High School '03

[Heir2012]

17 hours ago, Hairypiglet said:

My Phys.Ed. teacher in 8th was a gorgeous bull of a man, but also he cared about me.

A couple years later he was promoted to VP and I'm certain he had a part in helping me get through some issues where I was being threatened and harassed for being gay.

An emotional connection can definitely draw someone in.

For me, I didn't have that with my teacher. He was a bit of an asshole at times. It was a purely physical thing. I remember once there was a time when our school did a swimming class at the YMCA, and even though I knew how to swim, I went. He was there and I saw him shirtless for the first and only time. His chest was covered in hair with a trail going down beneath his swim trunks. I wish I remembered more. 

[Ieatcumholes]

An uncle of mine. I was probably 12 or 13 (I knew I was gay at 5), and he was living with us, probably after getting out of prison for something or other (so he was probably familiar with man on man sex even though he wasn't gay). I don't remember what I did, but I DO remember he was in nothing but boxers and probably had been shaving. He's holding me down on the carpet in the living room and complaining that I play too much! My mother (his sister) wasn't home. He must've been holding me by my shoulders because my memory is that I could easily have reached up into the gap of his boxers, but I stopped myself for some reason. (By that point, I had already played with two cousins, so us being related wouldn't have been the reason why.)

The cable guy in the mid-to-late 90's. Don't remember if this was when I first moved into the building or when I moved into the apartment next to the one I had been living in (inverse orientation from my original apartment). I remember overalls unbuttoned 3 or 4 buttons and a pelt of hair peeking through. 👅I probably had a Chippendales calendar in the living room (cause I didn't have a TV in the bedroom) and he mentioned something about liking pictures like that. But it didn't register until AFTER he left! 😖 That was back when I was a bottom and I would've given that man ANYthing he wanted as long as he got nekkid and I could explore his hairy body!

There have been others I wanted to have sex with and didn't for whatever reason, but, under torture, I couldn't even tell you who they were! The two above definitely count as ones that got away!

[YourNoLimitsBottom]

Back in my straight sex days, I went to a  small college party with a female friend. The party was hosted by a gay friend of hers. After it wound down, the host went to bed and only she and I and a gay couple were left hanging out in the living room. One of the guys asked if I wanted a blowjob, and I declined. The two guys ended up having sex on the couch which turned on my female friend and we ended up having sex on the living room floor.

To this day I still kick myself in the ass for turning down an opportunity which may have lead to a very hot sexual experience.

[PendragonSpirit]

Oh gosh, yes. Mine was also a teacher. Mr. Dvorak, our high school social studies/history teacher. Traditionally gorgeous from a Caucasian-centered perspective. Blond hair, blue eyes, and from what you could tell based on his wardrobe, built like a tank. Rumor was he used to be a stripper, and that was 100% believable. I "accidentally" came out to him hoping something would come of it, but... alas, life is not a porn video.