Cross-Dressing Brought First Orgasm
When I was young and both of my parents were working my mother would wake me up an hour or two before school and, since I was a responsible kid, would go to work leaving me at home. Well, I began to explore around the house and went into my parents bed room, I was always forbidden to go there at the time. In their walk-in closet I found a nice Lacy Teddy with matching stockings and a built in garter.
Being a young curious boy I decided to try on the piece of lingerie, at that time I was a little shorter then my mother. I quickly took off my own clothes and placed them by the door to the room and ran back to the closet. I took the teddy off of its hanger and examined it. After a few minutes of touching it and smelling it I wiggled into it. It had a peek-a-boo crotch so my small throbbing prick stuck straight out. I look to the stockings and hastily pulled them on, my whole body was quivering with excitement.
I ran to a full length mirror and looked at myself, I saw four small straps hanging down from the teddy and had no idea what to do with them at the time, luckily the stocking had some elastic on the top to hold themselves up. I stood there for maybe ten minutes just looking at myself and my cock pocking out from the middle of the fluffy lace that I was wearing. I went back to the closet and got a pair of my mothers high heels only two inches tall, but that was more then enough for me.
I went to the bathroom, right across from the closet, and put the heels on. They were a little big but comfortable. I pranced around on the hard floor making a clicking sound that all my teaches do when they walk down the hall. By this time my cock started to secrete some pre-cum which I have never seen before and got me really excited. I whipped it off with my finger and put it into my mouth, it tasted so good that I wanted some more. I started to rub my cock with one hand while I explored my body with the other. It felt so great when I rubbed my free hand over my legs in the stocking, the sensation was completely new to me.
After a few minutes of stroking my cock exploded a huge load that I caught in my hand. I devoured all of the cum while I continued to stroke harder then before. As I stroked I walked around in the heels on the hard floor with each step I began to beat harder and hard. Finally I exploded a second time, it was such a great orgasm that I nearly fell in the heels. The cum spilled all over the floor, onto the heels and my feet.
I was so exustated that I sat down where I was. I leened over and licked the cum off of the floor and spent a few minutes sucking on the heels and my feet to get the cum off of them. It tasted so good and I loved the feeling of the stockings on my tongue and feet as I liked them clean.
After a few peaceful minutes I erased all evidence of my session on that day and could not wait for tomorrow when my mother would leave me alone again. --Alan