My first exposure to the concept of a guy "playing" with his penis occurred when I was twelve. There was an older boy up the street that had been babysitting me for a couple years. My parents thought they were being real cool about it because they did not use that word. Instead they said, Steven will be your friend tonight. Trying to make it sound more like he was not a babysitter. By now Steven (I called him Steve-O) was sixteen and recently got his driver's license.
To make a long story short, Steve-O stayed with me one night when my parents went to see about somebody that was sick. He was on a spare mattress on the floor by my bed. After we quit horsing around and were going to sleep, he began jacking off under his covers. I had no clue what was going on but knew I had to find out. I thought of a funny idea.
I jumped up with a yell and threw his covers back and yelled Peek A Boo! Well, there was his hand around his big hard dick and it was substantially embarrassing to me, and I'm sure to him also.
But he told me it was okay, and wanted to know if I'd ever seen anybody do this. He said it was something that big boys had to do every night and I could either cover him back up or watch if I wanted to
So he continued jacking off, telling me things while he masturbated. He said it made him feel good to know I wanted to watch him. He let me touch his dick and feel how hard it was. But he refused to touch me, saying it wouldn't be nice because he was older and taking care of me.
He told me that what he was doing made a guy really feel good and that it felt better and better while you did it. He had some paper towels, and in a minute he put them in front of his dick and told me to watch real good because this was the best part.
He told me several times that it was almost coming. I didn't know "what" was coming, but I was watching closely. And then he said “NOW!” and I saw some funny wet stuff shoot into the paper towels and Steve was also saying that it felt very good.
After that he said for me to go on to sleep and to forget about this until I was older.
That was the beginning of sex education and self exploration for me. I tried to jack off a lot of times before I was ready but finally got cum when I was a late thirteen. But I never told Steve-O about it because he never again hinted about what happened that night.
Maybe Steven and I might have been JO buddies if I had been closer to his age. As it was, I had a couple of JO buddies that would sleep over and we would have a simultaneous jack off together and my secret joke was when I would tell them it was coming, I was thinking about Steven telling that to me.