Transvestia
interest started before I was 8 years old, but the following story is the earliest that I can remember of getting dressed up as a girl.
I pulled out my mother's dresser drawer, and saw all of her clothes laying there. I thought, here is my chance to try on some of her clothes, after all there was nobody around the house, and they wouldn't see me dressed up as a girl, or so I thought. So I stripped down to my shorts. I first put on one of my mother's brassieres, and stuffed my socks inside to make me look like I had a woman's bosom. Next I put on a girdle, which was very tight, nylon stockings, and a slip. I then tried on a pair of my mother's shoes, but my feet were too big. Finally I put on one of her dresses, it was a black satin short sleeve dress, with buttons down the front from the neck to the bottom. I put this dress on and it was a bit big for me, but that didn't stop me from doing up all the buttons on it. I then looked at myself in my mother's full length mirror. I was surprised to see staring back at me a woman from the neck down, for I didn't have any make-up on. I was just going to put on a pair of her earrings when I heard the downstairs door open. I quickly started to undo the buttons, but I couldn't undo them fast enough as my fingers seemed to be all thumbs. The footsteps started to come upstairs, and the buttons started to come undone and I finally got all the clothes off, and let them fall on the floor. I decided that I had better hide mother's clothes, so I quickly put them all into my parent's closet and I also hid in the closet. My dad was just coming into the room, and the first thing that he did was to open the closet door, and found me standing there in just my shorts with all of mother's clothes on the floor.
He said, "What are you doing in our room, and what are Mom's clothes doing on the floor?" I tried to think quickly of an excuse to tell him, but before I got a chance to explain, he asked me straight out. "Were you wearing her clothes?" I couldn't think of an excuse quick enough and finally told him the truth.
"Yes, I was."
"Why would you want to wear these clothes?" he asked me.
"I lied when I said, "I have seen some comedians wearing girl's clothes, and I just wondered what it would feel like to wear women's clothes."
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