My Sophomore Sweetheart

The Gym Teacher

Back when I was sixteen and in high school, I had started to really explore my sexuality. I had liked girls back in middle school and before that, but I never really thought any more intimately than that until I reached high school. I thought some girls looked nice before but that was as far as it went. I was that awkward boy who only hung out with guys and feared the pressure of talking to girls. It stayed that way for most of high school as there weren’t many attractive girls. High school was memorable. It was a time for new experiences and friends. It was a time where I could be a bit more independent and hang out with people outside of school. It was also a time when my hormones really started coming in and giving me an urge and drive for sex. I had experimented on my own body before, but this is when I really started wanting the real thing.

I’d get super horny really easily on some days. Particularly when I was in the eleventh grade, I’d masturbate up to twice a day. It felt like there was some warm urge in my groin that would not go away until I rubbed one out. But that urge came a lot. I’d feel it at home and especially in the classroom. It was so satisfying letting my cum out of my smallish tube. Seeing the foreskin go back and forth until my glistening head turned purple and shot out my white, warm juices was so hot. My cock would flex multiple times as I orgasmed. The semen would shoot out in shots and get all over the place. Sometimes I would moan a bit when I had a stronger ejaculation. Those ones felt the best, especially when there was loads of boy juice spewing out of the slit. Then my penis would retract and return to its small, one-inch size. It was so hot seeing this, sometimes I’d film my own orgasms and jack off to them later.

It wasn’t until the year of grade eleven that I started to find my body very sexy. I had gained ten pounds in the first year of high school and I was no longer a lanky Asian boy. I wasn’t chubby, but I had a bit of a dad bod. I had developed some meat around the hips and a small belly. I also had very subtle tits. Although my cock was only three inches when erect, what the best feature that I developed was my ass. All the fat went down there and procured two thick and spankable buns. They were so soft and round. They would spread so nicely, like butter, exposing my wrinkly sphincter. Other guys would talk about girls with ‘bubble butts’, and I would smile, knowing that I had developed one myself. It was nice to know that they found big butts attractive and made me all the prouder and hornier. I’d practice twerking them and spreading them wide open in the mirror so you could see my pink wrinkly hole. There were a few hairs there bit I’d shave them off. I admired my body and butt so much I really didn’t want it to go to waste. I wanted to show it off and have people be in awe of it. I knew a lot of men liked twinks with big butts and I felt inclined to be one. I was a proud bubble butt bottom boy. The problem was I was so nervous about showing my heteroflexibility to others. It felt weird to come out as a sissy to other boys my age. There was lots of judgement and stigma towards people like that in my age group.

So, because I felt so insecure about my orientation, I kept it a big secret and expressed it in other ways. I’d pleasure myself since I had no one to do it for me. I started using my middle finger to shove up my anus and it felt so good. The first time I did it, I couldn’t help but reaching for my cock to stroke at the same time. The same, horny feeling I always felt in my groin came back. It made the entire masturbation experience so much better. There was something about feeling my finger pounding my tight hole that was so pleasuring. Almost like I was being used by someone. This made me feel even sexier as I’d film myself riding my fingers. I also really liked spanking myself. That pain and crisp noise was so hot. I’d leave my bum cheeks bright red by the end of it as my widened hole was getting trained. The ejaculation from the combined fingering and spanking was so strong, my cute little cock would spurt out so much juice. I’d watch the milky liquid come out as my cock flexed back, as if it were telling me that it was enjoying it. My anus would pulse as it opened and closed from the pleasure. I later started using the back end of my toothbrush to penetrate my hole since it felt more like an actual man’s cock. And oh, that felt twice as good. It was a super tight fit at first, but as my body got warmer and I massaged my hole, it started accepting the plastic stick easier. My pink hole would suck in the stick as it impaled it and I would pull it out and stick it back in again. This was how I started masturbating every time at this point. This was the best way to masturbate for me as it gave me the most pleasure. I started riding my toothbrush while jerking off my cock and imagining a fantasy at the same time. My favorite fantasy was the one where I was being humiliated in front of several guys. I’d be tied down while I was forced to ride one of their cocks. I had to suck one of their cocks at the same time and when I came, the guy came inside me. I always imagined what it was like to have another guys’ hot semen inside me. It would probably feel like diarrhea and I would have to push it out. My hole would fart and sing at the same time as the semen leaked out. This fantasy was so hot, I really wished that it became a reality but that was super unrealistic. I started fantasizing more that same year. I imagined different scenarios from that gang bang, to masturbating in public, to making love to a much older man. It was such a turn on to think of being used by another man and being able to please his cock. There was something about it that made me feel so sexy and feminine. I even started exploring cross-dressing. I’d go to the store and secretly pick out some one-piece lingerie sets and try them on. Seeing how the tightness of the lingerie contoured my curvy butt and bulging balls looked so nice. I really wanted to buy some lingerie and bikinis, but I was way too nervous that someone would discover my cross-dressing secret.

The scenario that turned me on the most was me being used and toyed by someone older. I had always found older white men so hot, especially those in their fifties to sixties. The age difference between me and them was what made it so naughty, sexy, and exciting. It was taboo for people of that age gap to be together, and it made it all the better, and made me all the hornier. Knowing that that man was almost triple my age and shouldn’t be with me felt so hot. It was a secret fantasy that I had for a while and I was dying to be able to experience it. I wanted to let a much older man finally give me the pleasuring that I was always craving. I had been doing it to myself and enjoying my own body, that it was time to share it with someone else. It was time to let someone else appreciate my big ass and sexy curves. I wanted to be fondled and jerked. I wanted someone to caress my smooth and hairless skin while they explored me. Maybe taste my tits, then my cock. I wanted my ass to be groped, spanked, and fingered. Then I wanted my hole to finally be drilled as that man jerked me off and made out with me at the same time. It was a lot to ask for as I wanted the full-on experience of man to man sex. But I had no one to go to. Many older men were careful not to break any rules. I read about how older men were with much younger guys and got called out on it, but I didn’t care. That taboo factor really just turned me on even more. I wished that I could have just gone to the gym and seduced an older man in the locker room. I really just wanted to take all my clothes off in the middle of the room and have everyone come and get a piece of it. My cock was erect in so many of my classes when I thought about doing that. I’d have to try and hide the bulge that was sticking out of my jeans. When others walked by, I’d have to put my hand over that private area.

To be continued...