This is a summary of my experiences
I first started masturbating around eight or nine when I would my rub my dick between the legs of one of my bigger teddy bears. I don't remember much sensation, though it must have been there. Soon it got uncomfortable, and I moved on to humping my pillow, I continued doing this for many years. I would have dry orgasms, fantasising about girls at school before I fell asleep.
I first came in a wet dream, it was a bit of a shock, but I changed my pyjamas and went back to sleep. I soon started cumming during humping my pillow, not realising the stains this created until I saw the pillow while I was changing my bed sheets one day!
When I turned 15, I had my first girlfriend. We would ride in to the woods near our homes after school. We would kiss and hug; we got really close and once went out in the pouring rain to be with each other. It was really romantic and she told me she loved me. Ironically, it was the last time we went out as a couple because we were both grounded for not telling our parents where we were going!
My second and third girlfriends where more of the same-we went out for a month or so and then split up.
I currently jack off to orgasm about 10 times a week, sometimes more, sometimes less. There are other times when I will get hard and play, but not actually cum, those times can still be nice though.
I have two main ways of doing it, the first is surfing the Internet reading sex stories, Solo Touch (great site by the way!) or watching porn vids. I'll use my right hand for the mouse and the heal of my left hand on my cock. I'm circumcised but I don't feel it makes a difference because I've never known different. The orgasms usually aren't great and it's more just a release of sexual tension.
My second way is just an improvement of humping my pillow. I do it when I have a specific girl in my fantasies. I'll try and go as long as possible and that really gets me going!
I would like to thank ALL of Solo Touch for contributing; this is my attempt at paying you back!