I started playing with myself when I was about 7, I would rub my cock head onto the fabric of my Y-fronts.
When I was about 11, I had a pair of engineer boots which I was polishing, sitting on the floor, as I rubbed the boot, it ground into my crotch. It felt very strange, but pleasurable, I kept polishing more vigorously, suddenly there was the explosive type feeling and a wet mess in my jeans. (I thought I had broke something, but it felt very good too).
About two days later, I decided to see if that could be repeated, and made the same set up polishing my engineer boots. This time I went a bit slower to see if I could understand what was happening, and if I could stop before there was a mess. I pulled the boot around with toe digging into my cock. The more I moved it digging into my dick, the better it felt. Suddenly, I decided to see what could happen that way, and exploded before I could stop. I was hooked: boots and sex.