I suppose I started masturbating when I was about twelve. I always remember sitting on the toilet and rubbing my penis, but cant remember if I came or not. Some pretty great things happened between then and when my story takes place, but I would like to tell you about what happened when I was about 15...
I guess it was about the begining of 10th grade for me. I was in advanced classes, and working alot, but that didn't mean I had no time to jerk off! I would get in a nice long session every day after school alone in my room. Sometimes I liked to put a few pillows on top of eachother and a paper towel tube stuffed with wet cotton between it and fuck away, but usually I would just rub my shaft and head until I came all over.
About the same time, I was good freinds with the kid next door. He was in the same grade as me, but a little younger, and had two very hot sisters. I know I am not gay or bi, but seeing him in the showerat school made me get a big boner. I always wondered what it would be like to jerk off with him.
One holiday weekend, think it was winter break, I stayed the night at his house. We were talking, about just things in general, when we got on the topic of masturbation. I eventually found out that he did masturbate though not often. We talked for a while about how we did it, what we though of and such, when we began showing eachother our cocks.
His was about 8 inches, only half an inch more than mine, but mine was thicker. We were horny and started to jerk off with each other, but just then his sisters came bursting through the back door.
At first they seemed horrified, but then they decided to play... They promised not to tell anyone if we promised to do everything they said, and of course we promised.
First they commanded us to jerk eachother off. It was weird at first but then became great. His big cock felt warm in my hands. Just before we were about to come, they told us to stop. It was clear they were wet. They began to masturbate and look at our cocks.
They then commanded us to 69. We were unsure, but after a while got into it.We came in eachothers mouths, and though he spit my cum out, I swallowed his. It felt warm all the way down my throat.
Their final command was that he do anal to me, and I let him for a second, but it hurt so we just stopped, and jerked off on his sisters chests.
After that night my masturbation took a whole new demension. My anus. I was interested after having a dick halfway up my ass. I started with small markers, and after a while, began searching my mother's room for dildos and such.
I was never sucessful, till I one day found a vibrator, about 3 inches thick, and 9 inches long. I rinsed it off (just in case) and when I was alone, I lubed up my asshole, and slowly put the tip up to my back entrance. I massaged my anus, and slowly pushed the vibrator in. it really stretched my anus, but finally felt good. at the same time I began to jerk off, and I came quickly and very very hard. It was the first timeI ever screamed from an orgasm.
I'll write with more soon, but till then happy jerkin!