When I was 11, my little brother,lets call him Steve, was 7. We were very athletic and would skate or ride scooters or bicycles down the street.
Our house was on a T-shaped cross between two streets. When you went down the base of the T and around the corner to a dead-end street, there was a little clump of bushes that formed a clubhouse-like area. We would go down there and have picnics and stuff in our 'clubhouse'. Eventually we got bored just eatin' and stuff so we would play 'Truth or Dare' without the 'truth'.
It would be innocent at first until I would dare him to show me his 'wee wee'. In turn he would dare me to show him my 'private area' and so on and so forth.
This sort of thing has happened on several occasions. As we got older, we got a little more daring (I'll let you touch mine if you'll let me touch yours, etc.). Not until recently have I learned how to masturbate, and since I begun masturbating (I knew that boys must do it too and had an good idea how) and I had been waiting to try it on my little brother.
The chance finally arose to try my experiment. He came over to spend the night. He was to sleep in my room on the floor. Dare eventually came up. Flash me. Leave your pants off, etc. Until I got him to let me masturbate him. As he was only nine he didn't know what it was.
He laid down on the floor and pulled his pants and underwear to his ankles and spread his legs (under my direction) and I reached over and grasped his very small, one and one-half inch penis. He was very white and had no pubic hair at all, but it was kind of wide for being so small.
I slowly started to rub up and down as he moaned softly. I couldn't help but giggle. I asked him if it felt good and he said it did. I kept going, rubbing faster and faster, until he said, 'stop' in a hushed, but sharp voice.
I asked him to tell me when he was ready for me to do it again, and I climbed in my bed and started masturbating myself. I was much disappointed when he told me he was ready before I was done masturbating.
I jacked him off two more times that night and once the next. The next night he said he didn't like it and didn't want me to do it anymore which I assumed was because of guilt.
Well, more stories to come. Hope you enjoyed this one.