I don't know when I started masturbating. It was at such a young age that it seems like I always did it. When I was little I did it a couple of ways. I can remember lying on my stomach on the couch in front of the TV with my hands in my PJs and rubbing into them until I got that great feeling. In bed I'd rub on the mattress or pillow.
When I was 11 I was doing little project in the garage making a wooden sword. When I got to the point where I was ready to sand it smooth, I struggled to hold it still while using the electric sander. One position I tried was putting the handle of the sword between my legs to hold it while I sanded the blade. That worked well, and as I sanded, the handle slid up toward my crotch, and suddenly made contact with my penis, which was hanging limply down a little in my boxers. I jumped at the sudden sensation, but realized that it felt good. So I did it some more. I got a little boner pretty quickly, and held it against the sword, and it felt better and better. I realized I was going to get the good feeling that way, so I pressed harder and all of a sudden I started spasming, holding myself hard against the sword as it vibrated from the sander.
I liked that. I liked it a lot. And of course I found the need to sand that sword several more times over the next couple of days. I finally realized the sword was just a middleman in all this, and it was cumbersome to hold both it and the sander in position at the same time, so I tried the sander alone. It was too powerful and hurt a little, so I got a good sized terrycloth rag and covered it up, and that worked fine. I just held the sander to the front of my pants and had a great time of it. I'd do that when I knew no one would be home for long enough for me to have the privacy I needed. I also discovered that it felt good to do it while not wearing underwear - the feeling of being loose in my pants helped to get me in the mood for a good session with my sander.
When I passed through puberty and started ejaculating, I had a new problem to deal with: The mess. I didn't like the mess in my pants, so I experimented with new techniques and settled on propping the sander against a board nailed to the workbench so I didn't have to hold it. Then I'd put the rag on top of it, unzip my pants and pull out my penis and hold it onto the rag-covered sander. That felt really good, and I found that being able to hold myself and move my hand on my penis allowed me to be more subtle in how I stimulated myself. If I pushed forward and back, it would pull my foreskin back and forth, and I found that at different stages of arousal the best position of my foreskin varied. Sometimes I'd keep it over the head for a more gentle vibration, and sometimes I'd pull it back for stronger stimulation. I found I could make it last a lot longer by doing that, and it felt better overall. And when I ejaculated the rag would catch the mess, so there was no appreciable cleanup. I kept the rag behind a box on a shelf in the garage. When it got too crusty, I'd just toss it into the washing machine.
I had a really funny experience when I was 14. I can laugh about it now, but sure didn't at the time. I was in the garage having a great time with my sander, and was very close to orgasm, when suddenly the garage door started to open. Mom was home! I was just about to shoot, and was past the point of no return. In a panic, all I could do was stuff my penis back into my shorts and zip up, and just as I did my orgasm let loose, and I shot everything I had into my shorts, just as the door reached the top and my mother was right there behind the windshield. Unfortunately, the buildup to orgasm when I used this technique for a good long session meant I shot larger than normal loads, and this is what happened this time. There was jet after jet of copious sperm unloading into my shorts. I tried to act as though nothing was happening, but the look on my face must have been a giveaway. As my mother got out of the car, she asked if anything was wrong. My penis was still pulsing in aftershocks as I squeaked out, 'No, the door just startled me.'
She walked into the garage with a bag of groceries and headed for the door to the kitchen. I pretended to be busy at the workbench, and could feel my sperm dripping down onto my thigh. There was a rivulet dribbling below my shorts, and a quick glance down showed not only was it visible all the way to my left knee, but also there was a nice wet spot that was forming on the front of my shorts. I quickly turned so the mess wasn't visible to my mother as she walked by. My face felt hot with embarrassment -- I must have looked really strange. The only good thing is that the shock of it all had made my erection deflate almost instantly after I finished ejaculating, so I wasn't sporting a tent in my pants.
My mother went on into the kitchen, and there I was, red faced, sperm dribbling down my leg, several blobs had dribbled onto the floor, a big wet spot was on the front of my shorts, and the garage door was wide open. If a friend or someone came I'd be busted, big time. I ran to the garage door button and closed it, then started to clean myself up. It was tricky because I couldn't just take my shorts off because my mother might come back. The best I could do was go into a corner with my rag and wipe up as much as I could through the fly of my shorts, then sneak to my room to finish cleaning up and to change into another pair of shorts. Sperm was all caked in my pubes, and I felt like I reeked of semen. The smell was probably not as strong as I imagined it, but I was paranoid by this time. I couldn't help but remember the times when I'd actually taken my pants off to do my thing in the garage. If I had done that this day my mother would have gotten quite a surprise when she opened the garage door!