This happened when I was just learning to masturbate.
I discovered masturbation as a young boy. Once I found out the pleasure that I could give myself simply by playing with my penis, I was hooked for life. Starting out as a novice masturbator I quickly got to where I had to do it daily. The problem was the only way I knew how to do it was by laying in my bed at night and rubbing my penis head against the sheet above me. I had not learned any other way to provide the friction needed to cause me to cum. I even tried rubbing it against a car fender once with no success. (Don't laugh, I was desperate). It was kind of frustrating too since I'd often get a hardon during the day and being a beginner at it I wouldn't be able to do anything to relieve myself, at least not until bed time.
Then one day the next door neighbor kid and I were out foraging around in a patch of woods behind our house. David Lawson, who was not much older than me, had been my best friend for some time. I think we were sitting on an old log at the time when out of the blue David asked me if I played with myself. Of course I did but I was too embarrassed to admit it to him. So I lied and said no. He then told me that he did it and that I should try it because it really felt good. I asked him curiously how he did it hoping that he may know another way. That's when to my enlightenment he described his method and the method that I use to this day. He said that he cupped his hand over the end of his penis placing his fingers and thumb along the shaft. Then he pulled up on it causing his foreskin to envelope his penis head. Then he pushed down again with the friction from his fingers and the rubbing of his cock head against his palm causing a good sensation. (He made hand motions as he described it to me). He said he just kept repeating it until he 'shot his wad'. Apparently I wasn't the only one who was already ejaculating at the time.
Just listening to my best friend describe how he masturbated caused my own cock to stir. So I sheepishly told him that I didn't understand what he was trying to describe to me (whether it was true or not). Then I told him that if he didn't mind doing so, that it would really help if he actually showed me how he did it. At that point I wasn't sure if David would go through with it or not. But being the good friend he was, he answered my request by unfastening his pants and letting them drop. Then he pulled his underwear down. To my surprise his penis, which was also already erect, sprang out and pointed upward with a slight curve. It was about three or four inches long and slender. I noticed that David already had a sparse patch of hair at the base of his dick.
'Come on Dean' he said 'you gotta show me yours now.' I was still somewhat embarrassed about a guy seeing my hardon, but not enough to not go through with it and so I dropped my pants too. So there I was with my stiff little dick pointing upwards just like David's. The only difference I could see between his and mine was mine may have been a little bit thicker. I too had a sparse patch of pubic hair.
I noticed that David was staring at my erection. That made it quiver slightly. I'd never shown it to anybody before and quite honestly, I was enjoying it. My hard penis had never had it so good.
Then as I had requested, David started into a demonstration of how he masturbated. He placed his hand over the end of his dick and started pulling and pushing on it. I watched as the head of it kept popping up hitting against his bare palm as he settled into a steady rhythm. Now I was the one who couldn't quit staring. I was transfixed on watching David masturbate. I had never thought about doing it like he was showing me. If perhaps it worked as well for me as it did him, I would be free to masturbate anywhere and any time I wanted to do it.
As I watched David's moves intently, I reached down and started fumbling with my own penis and tried to imitate what he was doing with his. Whether purposely or not, I seemed to be inept at it and told David that I couldn't quite get the 'grasp' of it. Then I asked him if he wouldn't mind showing me how to do it by doing it on mine. Being the good buddy he was, David agreed with no problem. He then let go of his own penis, which bobbed up and down as it stood there angled out from his belly, and placed his hand over the end of mine and took up where he had left off with his. The pulling and pushing motion up and down on my penis shaft felt really good. So much so that every time my penis head bumped into his palm I nearly shivered. On top of that, this method felt every bit as good as doing it under the sheets and maybe even better. This way I wouldn't be rubbing my penis head raw as I had done in the past. This method definitely had promises!
I could tell that David was really getting into helping me out. I noticed his cock was every bit as hard as it was when he started. Then as if in answer to my observation he reached down with his free hand and started working on himself again while at the same time working on me. He had a double jerk going on.
I could feel the tension building up in my balls as David manipulated my penis. I knew that soon I would be coming if he kept it up. I looked down and watched what he was doing, confident that with a little practice I could do the same thing later on. Watching him made me that much more horny. Sure enough in a matter of moments I was cumming. Boy did it feel great!! That was the first time ever having someone else get me off, and I liked it!
David kept pumping my cock until he knew that I had cummed all I was going to be able to. Then he switched his hand from my penis to his and finished getting himself off. You can say that on that day my good buddy David performed above and beyond the call of duty of a best friend. After we had both gotten off we returned to just messing around. However, we both knew our friendship had taken on a new meaning.
Later that evening when I was alone in my bed I recalled David's performance earlier that day and especially the sight of his hard cock bobbing up and down and I masturbated. This time however I was able to do it without the aid of my bed sheet. It wasn't difficult to master his technique either. I just kept trying to mimic what I saw him doing until I found the right way that make me feel good. To this day as I said, that's the way I masturbate.
And by the way, I was to return the favor for David jerking me off at a later date. But that's another story.