A Boarding School Story
When I was thirteen, I was horny all the time. I usually jerked off every day. It was fantastic! Because I had my own bedroom, I could jerk off every night before going to sleep. The handkerchief in the nightstand received my cum instead of the bed sheets. One day the handkerchief disappeared from the nightstand and I realized that my mother had discovered my nightly habit! I replaced it with a fresh handkerchief and continued my merry way.
At fourteen, my parents sent me away to boarding school. That meant two boys to a bedroom. I was too embarrassed to let my roommate know what I did under the sheets, so I had to find a different place for my solo performance. Usually, the place was a little used toilet in the basement of the schoolhouse. This arrangement was not very satisfactory and I also started yearning for some variety. The answer came with John.
John was a classmate who was the same age. I can't remember how we got started into mutual masturbation, but it just seemed a natural a thing to do. Usually, I would be in my room some afternoon studying and John would stop by to visit. We would discuss school topics, but we both knew why he was there. I knew the attic in my dormitory was unused, and I had secured a key to the attic door. I would show John the key and, saying nothing to each other, we would quietly walk up the stairs to the attic, go into the room and lock the door behind us.
The routine between us varied but usually started by disrobing. Sometimes I would start by feeling John's crotch outside of his trousers. As usual, his crotch bulged with his fully erect penis. We would then disrobe completely and start rubbing penis against penis. John had the most wonderful looking prick - it was a dream; long, thick and fully erect! It was difficult for me to keep my mouth off of it! Its head glistened inviting me to put my lips around it.
But first we had to select our routine. We started first with mutual masturbation. Standing facing each other, we would grasp each other's penis and jerk the other off until we shot cum all over the floor. There was a small bench stored in the attic with a removable cushion. Sometimes, we would put the cushion on the floor, lay down 69 and slowly suck off each other. There was no rush as we had the whole afternoon and no one was going to bother us up there! We became very proficient doing this and many times we would cum at the same time! Sometimes I would sit on the bench, John would straddle me on his knees, facing me, and I would suck him off cradling his testicles in my hand. I liked to do him a lot! He tasted so good!
We finally evolved to anal intercourse. Now this is something you have to perform carefully. It requires some experience but the results are fantastic. With the cushion on the floor, John would get down on his knees and elbows. I would apply lubricant liberally to his anus and to my penis. I would then slowly insert my penis into his anus. John learned to relax his sphincter muscle, which let me achieve an easy insertion. I then stroked his penis with my hand while simultaneously pumping his ass. Shortly we both experienced incredible orgasms. John came all over the cushion and my hand. I, in turn, pumped my cum into his rectum. After we recovered, I suggested we reverse roles. John said 'Next time when I'm not so empty!'
We continued these meetings in the attic often until the day we graduated. I never saw John again after graduation.