I started masturbating when I was around sixteen. It began with me playing with myself in the bathtub. It wasn't really masturbation at first; I would pinch my foreskin closed, and piss into it, letting it balloon as much as I could before the pressure made my fingers slip... I've found not many men have a foreskin, so this was a rare pleasure, I suppose. Anyway, one day I started rubbing myself instead-- I was totally innocent, I had no idea what the compulsion stemmed from --and felt like I was racing ahead to some kind of accomplishment, and the next thing I knew I'd come. It took me a couple of seconds to realize what happened.
By then I'd been having nocturnal emissions, and I understood what those were in a detached, academic kind of way, like my sexuality was a phenomenon I was observing in the lab during science class. The incident in the bathtub revised their importance to me... but after a while I wasn't leaving myself full enough to have them anymore.
Sometimes I would slip a straw into the end of my urethra and blow into it and try to inflate myself. I used one of the cocktail straws from my grandmother's bar, the kind that came in a plastic cylinder. They're probably still in her bar now. I engaged in this quasi-masturbatory behavior for a few weeks, until I blew fairly hard and sent air into my bladder, producing a noise kind of like a duck call. I think it felt funny more than it hurt, but I was afraid of injuring myself at that point, so I quit blowing myself.
It didn't take long for me to figure out I could get a larger erection if I constricted the base of my penis, and eventually I wrapped a rubber band around it, flexing and flexing myself, filling with blood that had no way to escape. It felt pretty good, but after the second time I noticed pinpoint bruises scattered all over my cock, so I stopped doing that, too.
My mother had this thing called a 'Mark Eden Bust Developer,' which was basically a pink plastic clamshell with a spring in the middle. There was a lot of talk about blood flow and nutrient distribution in the booklet that came with it, but mostly it pumped up your pectoral muscles so you thought your tits were bigger. The booket had pictures of a girl with huge breasts demonstrating the device, and I would sneak this booket off into my room for the occasional wank session. I don't think my mother used the Mark Eden Bust Developer that often, but she was already pretty large up front, so I don't know what more she could have wanted.
The first piece of pornographic art I ever drew was necessarily amateurish, and torn up shortly after I'd masturbated to it, for fear of my mother finding it and possibly killing me. I wish I'd saved it... I'd wank to it right now if I had.
So far as I knew, my mother would rather sex not exist at all as far as I was concerned; although one time we were watching TV, and I held one of the throw pillows in my lap to cover up a spontaneous erection. During a commercial I flexed my cock and made the thing roll around. "What's making that move?" she asked calmly. "I am," I replied, grinning. "You are?" she said, in a weirdly salacious voice... then the show came back on. Maybe she thought I was doing a magic trick; I've often wondered if my mother was really expressing approval of the robustness of my erection.
When I was in college, this guy I'd met online sent me some rubber sex toys. He was really into stretching, so while I'm sure he thought he was sending a starter set, the smallest toy enclosed was a medium-sized butt plug. There was also a 9" rubber cock about as big around as a Coke bottle, and a butt plug which measured at least three inches at its thickest point. He also sent me some Polaroids of himself naked and trussed up in bondage gear.
I would start out with the medium plug to loosen myself up, and then slide either the dildo or the large plug in before finishing myself off. The problem was that these toys were so huge that I'd barely get them in before I came... I could barely breathe with them in. They would just crush my prostate and set me off. That was no fun. The medium plug was gentler but I couldn't really stroke with it. Instead I used the handle of a screwdriver wrapped in a condom. It didn't go deep enough, so after a while I switched to one of those slim spray cans of 'Designer Impostors' cologne my mother had gotten me the previous Christmas.