It's only fair that I tell my story, since I've enjoyed everyone else's.
I became aware of my evolving sexuality at age 12, in the seventh grade. I had a major crush on a classmate I'll call 'L.' I'd lie in bed at night and think about her titties (the word we all used then!) and my cock'd get soooo hard! And I'd hold it in both fists, and...nothing happened. I didn't know I was supposed to pump my fists up and down and make myself come that way (and my fellow Boy Scouts, guilty Catholic boys one and all, were no help).
My first orgasm was in my sleep, a classic 'wet dream' like they described in my Boy Scout Handbook. I was dreaming of women who were wearing baby-doll lingerie with no panties. I remember they were hairy and wet down there. Lying there at their feet looking at them felt good, and I woke up with the inside of my briefs wet with a thick sticky fluid that smelled like bleach. They went right under my mattress until the big round wet spot was dry!
I had more wet dreams, but didn't think much of it until about six months later. That night I was lying on my bed, home alone and watching a rerun. I imagined what the actress looked like naked. My jeans and shorts were halfway down my thighs, my cock was hard as a rock and I was massaging it and rubbing my balls, pretending she was doing it for me.
It felt really good, and the feeling just got better and better, centering itself where I was rubbing, and then all of a sudden something exploded inside! My cock jumped and throbbed, and I shot four long thick ropes of that sticky fluid all over my bedsheets, open-mouthed and gasping with the awe and pleasure. And then it was over. I was still hard as I stared at what I'd done, then said, 'Wow, I shot semen!' (Yeah, no kidding. And don't think I don't appreciate the irony of this actress 'coming out' as a lesbian over a decade ago.)
Anyway, that first conscious, self-induced orgasm created a come-monster. I'd jerk off in the morning in bed when I woke up, make time to do it before and after dinner, and do it just before I fell asleep, fantasizing about the girls in school with the biggest titties.
One morning during my freshman year of high school, Mom sent me into my ten-year-old sister's room to wake her for school. She'd started developing by then, and she was sleeping naked because it was hot. Her sheets were down around her waist and her titties were right there for me to see and savor. I was late for school that day, because I ran right back up to my room after I woke her, dropped my pants and briefs right in the middle of my floor, jerked off twice and shot all over my floor!
Once I found my dad's porno book stash, my fantasies and I really took off. But the single best orgasms I ever had by myself were after a freshman mixer at my university. At the mixer, I ran into a friend from classes I'll call 'B.' she was black too, light skined, had a big brown Afro and big braless titties with thick, constantly hard nipples. We sipped wine, chatted, danced a few dances. She had me harder than tax time for most of the night, but she was a resident student with a nerdy roomie. And I was a commuter student who had to catch the last train home.
Home I went, thinking about her big titties and thick nipples and the way they'd felt as we slow-danced in the dark auditorium. Upstairs in my room, I left my clothes in a pile on the floor, locked the door of my room, and jumped into bed. My cock was so hard and hot in my hand as I gently stroked up and down it, teasing the head and the sensitive ridge at the bottom of it. I hovered, in a near-dream state as I visualized 'B' doing it for me... The pent-up excitement of the night built itself bigger and bigger and then I cried out into my pillow, pumping my hips into my fist and shooting off on my sheets again and again.
I was still hard when the spasms stopped, and 'B' became my fantasy audience, rubbing her pussy and watching as I stroked myself to another orgasm. I was still hard after I came that time, and the puddle of come on the sheet was bigger than before. I imagined that 'B' kept rubbing herself, coming along with me. Next, I imagined sexing up my sister's best friend. I came all over the sheets, visualizing my come splashing all over her tiny, perky titties.
That was it for me; I fell into full sleep, finally satisfied, hugging one of my pillows. I woke in the morning to a sore cock and a half-dried puddle of come next to my loins that was literally as big as my head.
The only thing better than finally telling this would be 'B' reading it...just as long as my wife doesn't find out! =:)