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.