Boarding School Lesson
My earliest masturbation memory is not my own. I was at an all boys boarding school in England from 12 - 18. I developed fairly late and was fascinated by all of the talk amongst the other boys about sex, erections, orgasms, sperm (or spunk as we called it) and everything related.
One day, one of the older boys decided to introduce me to masturbation, by persuading me to masturbate him. We went to a dark place (a loft if I remember right) and he proceeded to instruct me in the technique he liked. He liked my hand to be dry, and for my dry hand to slide lightly up and down his large hairy cock. He controlled the tempo by asking me to slow down, or speed up as his urgency arose. Eventually he would announce that he was going to cum, and that I was to keep my hand away from the "knob" when he came because it was too intense. That first time that his spunk spurted was so thrilling to me. I could hardly wait for my own abilities.
While at school we would have mutual masturbation cliques, but we soon grew out of them. Since then, I have not been with another man, and have had sex with several female partners. However, for me the best sex is still masturbation.
When I am out of town, I like to take the lotion that the hotel provides, turn on one of the soft core movies on the hotel TV (harder core in Canada and Europe), and commence to stroking. My right hand (the stroking hand) is suitably slippery from, the lotion. I position myself so that I can slide a finger from my other hand into my ass, and locate my prostate. So, I lubricate that finger in preparation. Then with a slight twisting/turning motion I slide my right hand up and down my cock. From the base of the shaft off the tip and back down again. Long slow sweet strokes just as I was taught. I start to tremble as I feel the orgasm building, until I can hold it no longer. I make sure the finger from my left hand is well inserted, and I locate my prostate, and push gently. As I push on that, I stroke harder until suddenly there is this fantastic release. My cum shoots and lands on my chest. My ass tightens down so hard on my finger that I can't remove it, and yet I can feel the waves and ripples of contractions.
If anyone would like to see this process, please email me at