First Story. Based on some reality and fantasy mixed for what I hope is fun reading.
My name is Ted. Back when I was in high school I used to hang around a couple of senior guys name Tim and Mark. They were cool to me because we all grew up on the same street and had always played pick up games of football, baseball or whatever. Once high school started I started riding to school with them instead of the bus or having my mom drive me.
As the school year progressed we used to have some interesting conversations on the rides to and from school. Tim, especially, used to like teasing me and asking me about girls. He would ask me if I'd had sex yet, or how far I'd gotten with any girl, etc. Mark used to laugh but never asked anything himself. Eventually, I'd get all embarrassed and Mark would tell Tim to knock it off.
One day Tim was teasing me. 'So, how's the sex life of a freshman?' He asked with his usual sly grin. I just gave him the finger. 'Ah, so you're still just jerking off in the bathroom?' Tim joked.
Little did he know I WAS jerking off in the bathroom.
I had the perfect alone time after gym because I went straight to study hall and the gym teacher was in charge of both classes so he didn't really care if we were late. I used to just hang around in a stall until everyone left and take care of myself. Something about the girls in gym class and their tight shorts and t-shirts made my six inch cock hard as a rock.
In the stall I would drop my shorts and underwear to my ankles, take off my shirt and stroke away while fantasizing about the girls in the class. What made me even hornier is if you were quiet enough you could hear the girls giggling in their locker room while changing because only a concrete wall with a vent at the top separated the two rooms. I could never really make out too much conversation but it helped me envision them in their bras and panties. Who knows, maybe they even liked to play like me. The thoughts of them rubbing their pussies and pinching their newly developing breasts was so intense to fantasize. I only needed a few minutes. My hand squeezing my cock as it went up and down I would orgasm, blowing my cum into my free hand.
I really was getting good at masturbation by then. In my favorite stall I enjoyed tugging my balls while I stroked. Soon I began to get more daring. I'd take off all my clothes except my gym shoes. It felt so dirty to just leave my shoes on. I began to experiment with pinching my nipples. I also liked to rub my ass and soon realized my asshole was a huge source of pleasure. One time while stroking my cock I began to gently push my finger into my asshole. The first time I don't think I got more than my fingertip in. It felt so naughty I exploded instantly. No catching my cum this time, I just let it fly all over my legs and the toilet.
From then on my asshole was regularly fingered. I eventually would get my full finger in. I loved the feeling and these feelings started changing my fantasies in a new, exciting way. It always felt so taboo having my finger in my asshole and I began to wonder what else could go in there! Topped with the fantasy of some sexy freshman girl encouraging us to jerk off while she was naked playing with herself always made me cum hard.
...more to come.