I think I have always liked showing off my body, so if the watcher is excited and interested in what they see, it makes the experience all the better. When I was about 16 I noticed our paperboy that I thought was a real cutie. He was about 13 years old I would guess and while I knew his name was Jay, I really didn't know too much about him other than he was from another part of the town. I didn't see him much, except for once a day as he made his route delivering papers. He was about 5 feet tall and skinny with long blond hair. He would show up on our street each day at about four in the afternoon, coming down the hill on our side of the street delivering to the next door neighbour's and then cutting across the yards to my house. He had a gorgeous body and a killer smile.
Sometimes I would stand in my bedroom peeking out the window on the second floor, watching him come down the street as I stroked my dick. I let my imagination go wild, as I thought of him and me naked together. Then one day I got the idea that I could give him a little show, but I would be careful to make it look like I accidentally let him get a peek. The windowsill was low enough that if I stood in front of the window he would easily see my dick, as he cut through from the neighbour's house on the way to ours. I was trembling with excitement as I made my plan to give him a peek.
I stripped off my clothes and waited where I could peek out the window to see Jay approaching. Sure enough, he showed up right on schedule. As I saw him start his deliveries on our street I started to get a huge hard-on thinking about what I was doing. I had done plenty of mutual dick showing with other boys, but it was always something that was agreed to. When he started to leave the house next door I stood at the window and opened it. That made a little noise and sure enough he looked up at the window. I pretended that I was trying to get the window unstuck as I stretched up to push on the top of the window. I could tell immediately that he saw me and was interested in what he saw.
He paused for a moment and watched. He then put his paper bag down and pretended that he was sorting them or something, as he knelt there working with the papers and repeatedly taking quick peeks at me in the window. I then stood back from the window where I could see him, but he could not see me. It was fun to see him stall as he kept looking up at my window to see if he might see any more. Soon, he started up on his route again and as he went up the other side of the street, he paused to look back at my window to see if I was there. This got me so excited that I had to lie on my bed and give my dick a good stroking. It was a good one and I reached a wonderful orgasm that shot cum from my dick, as I thought about Jay watching me.
The next day I just watched Jay as he came by and sure enough, he checked out the window. In fact he did that every day, until about four days later I decided to give him another show. Like the first time, I stripped completely, waiting for him to show up. As he got to the point where I knew he would be checking out my window, I just slowly walked past the window giving him a good look. To my surprise he stopped and just stood there looking my way. Then he sat down on the hill coming down from the neighbour's next to some trees. He was out of sight from the street and the neighbour's view, but had a clear view of my window.
By now I was so horny that I decided to give him a good show and walked in front of my window once again. This time I looked at Jay as he looked at me. He knew I saw him and he smiled. I grabbed my dick in my hand and made a motion like I was jacking off. He loved the show and I loved doing it. It was only a few seconds and I was stroking my dick for real and getting very excited. What a turn on having this little cutie enjoying my show! I saw Jay rubbing his dick through his shorts, as he watched and it was then that I decided to shoot a load for the pleasure of us both. It didn't take long for me to feel the warm feeling growing in my dick. In all, it was maybe only a minute of stroking when I started to shoot my load, as I arched my body in ecstasy. As my cum shot from my dick, one spurt actually went out the window while the rest spewed out on to the windowsill.
My heart was pounding as I slowly stroked and squeezed out the last few remaining drops of cum, getting it all over my hand. After I shot he gave me a thumbs up. I quickly stood back from the window and he eventually got up to continue his deliveries. I never did that again, but for some time Jay would check out my window as he made his deliveries on our street. I dreamed about greeting him at the door with only a towel on when he came by to collect for the paper. I would then ask him in as I looked for the change he needed and would accidentally let the towel drop to the floor. Next I would imagine him getting excited and stroking me off. That never happened, but it was a nice dream.