By age 12 I had been masturbating for about two years, and wondered if other boys did the same. I figured they did, but didn't know how to find out until a new boy moved into the neighborhood and we experimented with each other.
A new kid moved onto our street a couple of months after I first started ejaculating. That experience made me even more curious about whether other boys masturbated, and I wondered about the new kid. We got to be good friends very quickly, since he was very outgoing and there were no other boys our age in the immediate neighborhood. He was really good looking, and liked to wear loose fitting shorts that hung low on his hips, and no shirt. His shorts were sometimes so low on his hips that I could see the 'V' of his stomach muscles descending into his crotch. Sometimes his boxers would show, but other times I don't think he was wearing any underwear, since often nothing showed when his shorts were down low.
Not long after he moved in we had a sleepover at my house. I have a large bed, so we were both in it, and both of us went to bed in our boxers. We talked for a while, and during the conversation he made several oblique references to masturbation, like calling a kid in his old neighborhood a real 'Jackoff,' 'Monkey spanking time,' etc. He was good at weaving such terms into the conversation, and I wondered if he was hinting around, so I started saying similar things. Anyone listening would have thought we were nuts, as the conversation became less and less coherent as we both looked for ways to refer to masturbation without saying it outright.
After that went on for a long time, I felt his hand sliding toward my crotch. We were laying on our sides facing each other, but I could feel the pressure of the sheet begin to lessen, and could see the outline of his hand moving toward me. I didn't say or do anything, and then suddenly his fingers brushed my penis through my boxers. He held still, and so did I, and he did it again. I had already had a semi-boner, but now it stood out hard and straight (all three or four inches of it), and he felt that. He got a sly smile on his face, and reached into my fly and held onto my penis skin on skin. Oh, man, that felt good, and I sighed softly.
He played with it for a little bit, and I slowly reached out to find his penis. When I did, I was surprised to find he didn't have his boxers on -- sometime between then and when we first hopped into bed he had shucked them without me noticing.
It felt neat to feel his hard shaft, and I played with his balls a bit, then held onto his penis softly, not quite knowing what to do. Then he started to push back and forth, basically rubbing his penis in my gripping fingers; he was humping my hand. I held on firmly while he did that, and I knew he was masturbating himself with my hand. It was a new, and neat, experience. I watched his face carefully, and could see him concentrating. After a while he closed his eyes in concentration, and I gripped a little harder. Then suddenly he stopped, and I felt a pulse in his penis, followed by a pause, then several quick jerks, and my hand was suddenly all wet. I caught it all in my hand, and he spasmed and started breathing hard. I just held on as he relaxed.
It took a minute for him to go soft, and I pulled my hand out and we both laughed at the mess on my fingers and in my palm. I rolled back and wiped it off on the sheet, and he said, 'Now its your turn.' He sat up and maneuvered between my legs, with his legs spread and under mine, so he had good access to my crotch. He pulled my boxers off and I spread my legs as he scrunched forward, and he took hold of my penis and began playing with it. Soon he was jerking me off gently, and I loved the sensation of someone else's hand on me. He got hard again while doing me, and I could feel his penis poking me in the crotch just below my balls, and it felt good. It didn't take long for me to cum, and I writhed and squirted several small jets onto my stomach, as he watched carefully.
After I settled down and cleaned up, we both just lay there reveling in what we'd just done. I asked if he'd ever done that with someone before, and he said no, and he asked me, and of course I said no. We agreed it was really neat, and we'd both like to do it again. We stayed naked and slept well, and did it again in the morning, and very often after that. We'd frequently get together after school and do each other in our rooms; we'd use whichever house had no one else home for a while. And in the summer we'd do it out in the yard behind the shed, which was a nice, private place.