Nothing i’ll share. But my stupid brain won’t let me forget it.

Too many to count, in all honesty. I was what you might call precocious. I started fairly young, and stayed steadily active from early puberty until adulthood.

I think the most entertaining story from my actual teenage years was likely to do with my first foray into interacting with a couple

I made a friend in high school that was dating a particularly feminine boy, or so I thought. Turned out that said boy was what would later be called trans, and thus had female body parts. Friendship with the actual girl of the couple turned into a mutual attraction.

During that process, I also became friends with the boy. It was rather convenient since now they both had someone that they could take to family functions as a quasi boyfriend. Because of the friendship with the guy, when the girl discussed her attraction to me, he agreed to open their relationship up to allow sex with her.

While he was not at all interested in me sexually, he did partake in some of the foreplay, including “warming up” the young lady.

There were, however, some emotional issues with being present for the rest, so this wasn’t a three way thing, unless you count the minor degree of teasing he would do to me, and I don’t. Things like running ice cubes down my spine, or the rare times he would have a surge where his curiosity about cis male anatomy would rise up and lead to some teasing of my scrotum or brief touches of my penis. It was a tad confusing at times then, but looking back I can better understand his conflicting emotions and curiosity.

But when things progressed past a point, he would leave us to it.

We also could do our thing when he was at work, or otherwise not present.

That’s where the meat of the story is, if you’re looking for something more directly sexual.

She was not my first overall. But she was the first person to suck me. One afternoon, early in things, she and I had teased each other to a state where we were frantic and hungry. We made out, drawing that tension higher until she broke it and said she had to suck my cock. And the way she said it, with desperation and need was an instant kick to my already throbbing libido.

And gods, she sucked me. It’s fair to say that at that age, I likely would have thought any head was amazing, but this girl was beyond skilled. She sucked my dick like magic would come out of it and change the world. She worshipped my cock.

That is a very powerful experience, particularly combined with her obvious joy at it, the skill she showed, and the newness of it to me.

She sucked my cock on the couch, on the floor, on the table, across the floor and against a wall. We weren’t getting up and moving, it was me scrabbling at the carpet in delirium and bucking my hips as she took the root of me deep into her mouth, licked and sucked and screamed around me with her occasional orgasm.

She would pause now and then to stroke me with her hands until beads of pre-cum would start flowing, only to lick the line of it as it dripped down me, then swallow me whole again. I rode the edge of my own orgasm for an hour or more, and towards the end had my first orgasm without ejaculation. A wave of pleasure so intense I could only scream and babble incoherently hit me, and She cupped my balls, squeezing them gently. She thought I was ejaculating, but didn’t stop.

As the shocks and jolts of the orgasm faded, I was seeing motes of light and my ears were ringing, but she didn’t stop.

I screamed until my throat was raw, and that wave crashed into me again, and it was like my soul was pumping down my spine and out of my cock. I pulsed and shook as she drained me, still not stopping. The more I screamed, my arms flailing, she would slow slightly, back off until just the tip of me was embraced by her lips, then surge down my shaft to pull another scream from me.

Until I begged for mercy. I could barely speak, but I managed to get something said that made sense, and she began slowing, easing up the pressure until I exploded a second time. After that, she kissed her way up my body, the skin of her breasts eventually caressing my still hard and almost painful cock.

She lay on me for a while before either of us could move.

When we finally found the ability to move, the curtains were yanked from the wall, the coffee table was empty, with things strewn around the room. Her panties were ripped and hanging off of a plant. The room was demolished

That was back in 1989. I have still never had head better than that. It has been rare for anyone to even equal it. There was a span of time I would turn down head because how in the hell could anyone match it? It would just be disappointing in comparison.

Just remembering it makes my balls ache and crave the intensity again.

Nothing that exciting. I was curious about girls and I knew porn was commercialized trash, so I hit my father’s Encyclopedia Britannica set. Then went to the library and read books on anatomy. Then gynecology. I think by 15 I knew more about the internal workings of my female peers than they knew about themselves — but back then, girls were not taught a lot about their bodies.

I was (still am) a nerd — how the female reproductive system worked was far more interesting to me than what the external female genitalia looked like (or what it all smelled, tasted, and felt like). I figured that was relatively simple information. See a few, you’ve seen most of the data set. Plus, I’d rather get to know a person than reduce them, in my mind, to mere meat. I’m no saint or anything — I may be demisexual. But I’m just me — labels are a poor way to define people since they imply limitations more so than potential.

Like I said, not very exciting.

As for why I’m not a doctor today, 31 years later — money. Or rather, a lack of. Education in things like medicine and law take money. Had the smarts for it though, the aptitude. Still do, just not the training, the practice — or the degree.

When I was a teenager, some magazines were sold with a CD-ROM containing various uninteresting shareware programs and soft porn images encrypted with the software on the CD-ROM. You had to call a premium rate number to obtain the decryption keys for each image.

Not to brag, but the keys were in a separate text file with a simple substitution cipher :3

I remember “comparing” dicks. Something that guys did with other guy friends. You were just starting to understand jacking off and ejaculating. You never considered this gay, though some may disagree, but you would get naked with your friend and examine the other guy’s cock. That would move onto to jerking each other off. It’s the first time you experience cumming through the actions of another person.

Graduation was usually blow jobs. Having your friend suck your cock and then cumming in his mouth just turned your brain into jelly. And you would return the favor. It didn’t seem like a big deal having a guy shoot his load into your mouth and swallow it.

At this point, in my opinion, you start to define your sexuality. If you are straight you are done with your guy friend and sex. You are now consumed with the desire to fuck a girl. To feel your cock in a pussy.

If you are gay you are motivated to move onto anal with your guy friend.

I was a very early bloomer, so my stories start earlier than you asked. Girls never had cooties in my book; I wanted to kiss girls since kindergarten. And I was (am) intractably horny. If sex addiction were a thing, I could be the poster boy for high-functioning addiction.

My female cousin was my next door neighbor, and she is two years older than I. She taught me how to masturbate one xmas morning. Best xmas gift ever! Every single opportunity for privacy, we were naked and all over each other, trying to find ways to feel good. My parents divorced when I was 6, and I moved away with my mother. My cousin and I would have definitely taken the play as far as we could had we stayed in proximity. We talked about our sexual journeys and adventures well into adulthood until we fell out of touch after she married. Having that open conversation, free of shame with a trusted sounding board, was an immense boon to my adolescent journey.

Up until about 10, I had a string of babysitters. The first one had an early teen daughter who frequently wanted to do naked playtimes, which I loved. She would climb on top of me and rub her naked crotch on mine until she was done. I was very disappointed when my mother got a new job and we moved away.

My next babysitter was the buddy of my mother’s friend. He and I would sit on the couch watching TV. It wasn’t long before he started groping my crotch. Despite knowing this was “wrong,” and not being into boys at all, it still felt great. After a few nights of him groping me, I worked up the nerve to unzip my pants and encouraged him to go further. Things got really assertive, and before long he was jerking off in my mouth. His glans just barely fit in my face, but I was having fun.

After maybe a week of that, he started fucking my ass. Goddamn, that hurt and felt great at the same time! I loved the feeling of when he would cum in me and lay on top of me while he caught his breath. I didn’t understand the cumming part at the time, but I enjoyed the slippery feeling when he was done. I would be antsy all day at class, looking forward to going to my babysitter after school got out. I got in “trouble” at least a few times by going straight to his room, pulling down my pants, and getting face down with a pillow under me. I wanted to do the bedroom stuff all the time. I absolutely welcomed everything that happened and still reflect fondly on my adventures in exploring my sexuality with him. I was very sad when his job relocated him. There weren’t any babysitter adventures after that, and my mother decided I was old enough to be a latchkey kid.

When I was 14, I got my first “real” job. My boss was gay and always flirting with me. That was when I discovered top vs bottom. And he was very much a bottom. There was an elevated counter towards the back of the store. People couldn’t really see what was going on there, but we could see everything. He would blow me and let me fuck him any time work was slow. I still wasn’t into dudes, but any port in a storm, right sailor? :D Work has never been as fun as that. It was a lot of fun to quench my adolescent libido with another person, even if it wasn’t with my preferred gender. I also fully realized that I’m very much a top/Dom and I had a drive to spank and slap sexual partners. Moreover, I realized there were people who enjoyed getting spanked and slapped during sex play.

Things actually got mostly tamer from there. I moved out on my own when I was 16. I was oddly protective about my townhouse and was very wary of letting anyone visit except my besties. Because of the self-imposed domestic solitude, I came up with all kinds of ways to jerk off. My favorite was using a long, skinny balloon (like used for balloon animals), twisted in the shape of a vagina. I would lube it up with K-Y and spend a whole day fucking my balloon pussy. :D It was always tragic when I ran out of balloons.

Things got a little unhinged for a brief stretch. One of my good friend’s GF was seriously into me. She was very assertive about it, and who am I to turn down sex with a hot girl? Turns out he was into that and knew everything. She and I would make out in the elevator. We’d fuck at my place after school. She and her family moved out-of-state about four months after we started fucking, and we were both really bummed.

And my last teenage hurrah: at 17, my best friend at the time was (still is) a lesbian. One night while hanging out, she blurted out that she was really horny and asked if I would be willing to engage in a mutually beneficial arrangement. Absolutely, “but… you’re a lesbian!” There was some deep conversation: I couldn’t use her mouth or pussy, so it was anal-only. She introduced me to anal sex with girls/women, and that kink is solidly with me almost 40 years later.

The sexual portion of our friendship was a lot of free use, a term which I didn’t know at the time. Most of the time, it was just one of us getting off. We explicitly coordinated available times, breaks between classes, etc. all to assure that we could be there for each other’s needs. When time ran short, we would alternate days on who got to come. On weekdays, she would drop by after class and have me go down on her before she had to rush home, and the next day I would get to use her ass. On her days, sometimes she would have me fuck her while she masturbated, but because our time was limited, she was done once she came. I never did learn how to cum quickly. :D She would come over on weekends, and we’d would fuck around all day. She also taught me how give head to women which has paid massive dividends all through life.