I was 16 years old in the late 70's and I used to walk to work everyday after school. One day, a classmate of mine (Tim) offered to give me a ride in his VW Beetle. On the way to work Tim asked if we could pull over for a few minutes because he needed to talk with someone about a personal problem he was having. I agreed and we parked in a vacant lot very near where I worked. He started crying and told me he was ashamed of the size of his penis and because of its size he thought he would never get a girl friend. We talked for a few minutes and then he asked me if I would show him mine so he could compare sizes. At first I didn't know whether to get out and run or just show him my dick. I choose to pull my pants down and show it to him. At that age I was about 4' soft and 7-1/2 hard. Tim told me I had a big and good looking penis and said he wishes his was as big as mine. As he sat there and described my penis I started to really enjoy the fact that this guy was looking at my dick. I started to get hard so I moved to pull up my pants and he told me to stop. Tim then offered me $10 if I would jack-off in front of him. I told him to give me $20 and it's a deal. He agreed and I grabbed my erection and began stroking away. As I was beating off, Tim began describing how big, hard and fat my dick was. He seemed to be really enjoying watching me masturbate. I too was also enjoying it, but I also got a thrill out of him watching me. Within a few minutes I reached my climax and I exploded my wad all over his dashboard. I then collected my $20 and got out and walked to work.
Tim and I repeated this ride to work several times. He decided to join me on the second time and he was right in admitting that he had a small penis. It was fun getting paid to jack-off and a couple of times I let Tim do all the work.