Dressing Up For The First TimeI was always interested in women's clothing. I don't know what it was but it just made me wonder what it was like to be a girl. When i was 15 i finally gave into my curiosity and wanted to browse my sisters clothes. I went into my sisters room when the house was empty and opened up her closet. I saw all of her nice shirts, blouses and dresses, i looked around pulling some stuff out and eventually made my way to her dresser and saw all the panties and bras. I wanted so badly to try on a whole outfit but i was terrified of getting caught. Then i got an idea. I picked out the clothes i wanted to try on (a purple tank top with short shorts and a padded purple bra with a lacy thong) and went to my room, locked the door then striped down and started to put on the thong and bra. It felt so good to be wearing them, it just felt right but something was off, i needed boobs. I stuffed the bra with socks and then it looked right. Then i put on the shorts witch were even shorter on me and the tank top. I looked in the mirror. My body looked good and my face need some work. I went back to my sisters room and grabbed her razor, shaving gel, and her make up bag. I went to my bathroom and took off everything and shaved off all hair below my neck. I never realized how good my legs and *** looked now that all the hair was gone. I put back on all the clothes witch felt even better now that my skin was silky smooth, then went to my mirror to apply the blush, eye liner, lipstick, eye shadow, and mascara. I went back to my sisters room and got her blonde wig and came back and put it on. I looked amazing, no one would be able to tell that i was a boy. I spent the rest of the day in the clothes. I started doing my nails, looking at clothes online and taking cute pictures of myself in the mirror. When it started to get near the time my parents got home i went back to my sisters room to put everything back. I was heartbroken that i had to take off everything, but i did and i put everything in the room back to the way it was. At least once a week i would dress up in different clothes, but the time after this was when i really discovered how fun it was to cross dress.
Part 2 of this story is up, go to my profile to read it
deleted 26-30 18 Responses 52 Oct 10, 2012