I knew a lot for my age, I just didn't know how to work it out
When I was 14, I learned a lot about sex from tv actually. I used to love staying up late and watch those Real Sex specials on HBO, I learned everything there was to know about having sex, although I didn't know what masturbation was though, so every time I went to bed, I went to bed with a incredibly bad erection.
Fast forward about a month or two into my escapades, after another wonderful episode of Real Sex, I snuck upstairs and slid quietly into my bed. I slid out of my PJs and was only in my briefs and a T-shirt because it was making my little erection hurt (it was about four or five inches long at the time) I slid out of the briefs soon afterwards and looked down, wondering what the hell to do with my little problem, I soon got an idea of simulating what a vagina feels like to see the stimulation. I quietly took the two pillows I laid on and put them next to me, I sandwiched my dick in between them and began to thrust, thankfully I had very smooth sheets, because I loved every second of thrusting my little fella in between them.
About five minutes later I started to feel like I was going to go pee, after learning so much, I thought this was the orgasm, I kept thrusting and felt it peak, I panicked, not knowing what to do and quickly slid my underwear back up over me, a euphoric wave of pleasure overtook me as I quietly moaned, my dick spasmed hard, filling my drawers with my first cum shot. I was too afraid to move, but I felt so relaxed from the relief of it, I soon dozed off.
Naturally as soon as I woke up in the morning I changed my now crusty underwear and went on with my day feeling fantastic. Although that wasn't the actual time I figured out how to do it constantly, that sure relieved my tension for the first of many many times. I will tell the story about how I learned to use my hand, but that's for another time.