St. Charles' Place

I finished my Biography with a promise to tell about the first time I masturbated with someone else. I didn't think it would take me so long to get around to it, but here it is -- finally!

When I was in 7th grade one of my best friends used to hang out at my house after school, and I would hang out at his place. One day when we were at my house he suggested we ride our bikes to a "neat place" he knew about. We started on the street but he soon veered into the woods. It wasn't so bad on the path, but when he took off into a thicker part of the woods it was hard going on a bicycle. I kept asking him how much further it was. Finally, in a small clearing he stopped. I looked around and didn't see anything special about the place and couldn't understand why he wanted to come here. When I looked back at him to ask him what was so neat about a bunch of trees, he had his erect penis sticking out of his pants.

His penis was huge compared to mine, and he had much more pubic hair. What stands out in my memory more than anything is the shape of the head of his penis. It seemed disproportionately large compared to the rest of his penis. And it seemed rounder than the head of my own penis. His penis bobbed up and down a couple of times, and I finally found my voice and asked him what he was doing. I was scared someone would come by, even in this remote spot. He said that if I wouldn't join him I couldn't watch him, and he covered his penis with his shirt tail. I really wanted to see his penis again, so after a quick look around to make sure we were really alone, I took mine out, too. I was embarrassed because his was so much bigger, but he didn't seem to mind. He asked me if I ever masturbated, and I said, "Sometimes." Ha! If 3 or 4 times a day means "sometimes," then I was telling the truth. He said it was even better when someone else did it for you and started playing with his penis. He asked me to touch it, but again I was too afraid. He got mad and we biked back to his house.

When we got there he asked me if I wanted to play Monopoly, and I agreed. He said we wouldn't use the money but would play "Strip Monopoly": every time we owed money, we had to remove an article of clothing. I felt much safer in his locked bedroom and didn't even hesitate. Both of us were buying property like mad, just to have an excuse to remove another piece of clothing. Soon he was just in his socks and underwear. His penis was erect again, and I couldn't take my eyes off the tent it made in his underwear, and the little wet spot that was starting to form at the top of the tent.

I'll never forget the property that finally led to some action. He landed on St. Charles' Place, which I owned. He stood up and said that since it was his last piece of clothing (socks don't count?) I had to take it off for him. When I slid the underwear past his penis it caused it to snap up. Without asking permission, I just reached out and grabbed it. It was weird, partly because it was bigger than I was used to, and partly because of the way I had to hold it, since I was in front of him. I stroked him a few times and he said it was better if we were side by side. I took off my shorts and underwear, and we sat next to each other on his bed. He grabbed my penis and would give a few strokes, then play with my scrotum, then a few more strokes. This was WAY better than doing it to myself! He had to remind me to do him, too, which I did without further encouragement. I was still fascinated with the ball-shaped head of his penis and loved the way it felt when my stroke pulled his skin over it.

It didn't take long for either of us to ejaculate. I again felt inferior because he ejaculated not only more semen than me, but it SHOT out, whereas mine only dribbled. But he rubbed it over my penis as he continued to stroke me. Without even losing my erection I had another orgasm, though there wasn't much of an ejaculation this time, and my testicles hurt a little for about a half hour afterward. I figured it was because I ejaculated too soon without "recharging."

In high school it was a completely different environment. Anything even remotely gay was taboo, so I never found another partner to take his place -- until I joined the navy, that is. But for pure intensity, nothing has ever matched that first time playing strip Monopoly.