I had always been fascinated with women's clothing. As long as I can remember I've always loved the way it looked. And forever was I curious with the way it looked on a hot girl, the way it moved, how it stretched over every curve, and the way it must feel. I was mesmerized with the effect a beautiful woman had over every guy in a room. How could a pair of pretty eyes capture the gaze of every man within sight? Very soon, I was about to find out.
I suppose the first time that I ever gathered the courage to try on women's clothing was after school one day, when I was 18, during my senior year of high school. My parents never came home within four hours of school being out so finally I took advantage of my timely situation and that day my fears were overcome.
Opening the door to my parents bedroom I went straight for my mother's dresser. Upon opening the top drawer I found all her lingerie. Panties, nylons, bras, girdle's, you name it she had it. At forty years of age, she had the body that any woman would die for. My own body was rather small. At a little over 5'6 I weighed a measly 120 pounds. For a guy this was bad, but for a woman, this was ideal.
After stripping naked I pulled out a pair of black nylons and laid on my parents bed and becan to roll them on. I had already shaved what little hair I had on my body and the feeling of them stretching up my smooth calf and over my knee was too much, and I instantly became aroused. Once I had finished putting them on I followed with a pair of matching panties. A bulge was instantly noticeable which was fixed by folding my penis between my legs. After strapping the clips to the lacey top of my nylons I rummaged through her drawer some more. I stumbled upon a pair of latex bust enhancers in the back of the drawer. After putting them on inside a black bra, I put on a very thin black, low cut shirt which showed the bra and created the illusion that I had very nice C cup breasts.
I went into my parents bathroom and fumbled around with some of my mother's makeup. After toying around for around a half hour I managed to get one of her wavy jet black hair pieces on and applied a minimal amount of makeup. Looking into the mirror I was surprised with the result. I found a pretty young girl staring back at me and surprised I smiled at myself. I went to their closet and picked out the sexiest high heels I could find. After putting them on I walked around in from of their huge dresser mirror. I didn't have much when it came to curves, but I found that if I arched my legs and shifted my weight, it created the illusion that I had shapely hips. Lying on the bed looking at my self I couldn't help but notice how great I looked. My small feet fit nicely into the heels and going up I stared at the womanly long pair of beautifully toned and silky smooth legs.
Posing for my self for what seemed to be a short time I looked over at the clock and realized that either of my parents could be home at any minute. Thankfully I removed everything and got it all back to their original places before they got home.
Three years after this first attempt, I had come a long way. I had grown out my own hair which was black just like my mother's. My skin was no longer white but a nice tanned shade. My already high voice now sounded higher pitched and had a girly tone within it as I practiced talking and eventually I sounded just as any woman would. I had been on horomones which helped with my voice and my body had very nice curves and full breasts. My parents by now knew of what I was and were very supportive of my choice which was the biggest jump to hurdle. Over this time I had gotten very good with the makeup and hair and by the time I was done, I was no longer staring at a cute girl, but a beautiful, full breasted woman.
