Learning from a friend
Since the last time I'd seen my friend from middle school, I'd learned the about erections and girls and all that stuff, but I didn't have a clear idea on how to masturbate. Since I didn't have the technique down yet I was constantly a horny little boy, rubbing myself to frustration reading whatever erotica I could get my hands on, but never really finding a good way to cum. That's the context for our first sleep over together in a long time, ever since I'd started hanging out with different people.
I had never thought of my friend in 'that way' before, but that night he suggested that we sleep in just boxers, and it was all I could do not to reach for him whenever he shifted his weight and I caught of glimpse of his cock through the fly of his boxers. I thought about all the hypothetical, thinking what would happen if I just went for it, but I determined it was all in my hormone-filled head and that he'd probably just call me gay and kick me out of the house. We ended up play wrestling later in the night, and I dragged him so that his boxers stretched against the floor and I could catch even more glimpses of his cock, surrounded by short black pubes. All that fighting tired him out, so it was regretfully, and hiding a hard-on, that we went to bed.
We were aware enough of our changing roles that we didn't sleep next to each other in bed, but rather end to end. As a consequence my hands were only a few inches from his crotch, and I could feel the heat coming off of his cock. My heart beating as fast as it could, I tried to pretend to be asleep while at the same time reaching my fingertips inch by inch towards the warmth. I had moved aside his fly with an index finger and was nearly there. I still get off to this day on the feeling of his cock in my fingertips, growing harder and harder the longer I held it.
I thought I was done for when he shifted slightly, his hand batting away my own, and I prepared a number of probably worthless excuses, but to my surprise I began to hear a rhythmic noise and the sound of skin on skin that would become so familiar to me later on. Gingerly I moved my hand back, and felt the movement of his hand as it clenched up in a fist around his shaft, stroking back and forth. My heart was beating as hard as ever, but I tried to control my breathing so I could hear his fingers work and his breathing get shorter and faster. I put my hand over the top of his cock, brushing up against his knuckles with each stroke. When he finally came with a quiet grunt my fingers, already clammy with sweat, got most of his cum, but he shot so hard it ran down his knuckles and his shaft. I expected him to get up to wash up after that, but he just lay there, chest pumping as his breathing went back to normal and his hot cum cooled in my sticky hands.
He fell asleep soon after that, but the motions of his hands became acid etched in my memory, and when I woke up earlier than him on the narrow bed I tried to duplicate what he'd done, making much more noise than he had. He stirred, his stretching legs brushing against the sticky spot on my thighs were he had spilled, and asked in a sleepy voice,
'Are you playing with yourself?' I could only nod my assent as I kept it up under the covers, getting red in the face from the exertion as he stared at my hands moving under the covers. He had started rubbing himself before I got even close to finishing, but then again he'd been doing this longer than I had, and when I came all over the underside of his sheets he was right behind me.
We never really talked much about it, after that night, and we never did anything together. We both have girlfriends now, but I sometimes still think about that night when I'm right on the edge of orgasm, and it was that night that helped me learn the 'proper' technique, in that age before the internet.