Date: Fri, 30 Dec 2005 20:02:59 -0800 (PST) From: Lady Gurl Subject: How I Started Crossdressing How I got started crossdressing was when I was young my mother would leave here pantyhose to dry in the shower and for some reason one day when I got in the shower I decided to try them on. Once I had them on, they were way too big for my height so they came up over my nipples just under my arms. I remember how they were still damp and the material felt so wonderful against my skin. I had not hit puberty yet but had a total hard on. I even pranced around the bathroom acting like a girl and was totally hooked from that point on. It wasn't long after that when she left a pair of panties on the bathroom floor after her shower so I once again let curiosity get the best of me and put them on. They were a satin hip hugger style, still too big but I loved the feel of it as well, I especially remember how they rubbed my butt and felt so wonderful. It was these starts that got me going more and more into crossdressing into my teen years and beyond. Before ever trying on the pantyhose, I would often steal my sisters Barbies and undress them and wonder what it was to be a girl. I would take my clothes off and tuck my penis between my legs to make it disappear so I could be a girl. It was later in Jr, High I found the book "everything you wanted to know about sex but were afraid to ask" in my parents room. This book was amazing, it talked in detail about transvestites and crossdressing, homosexuality, anal masturbation and regular masturbation, It was after that when I started to dress more often every chance I could get, even stealing panties to wear under my clothes when my folks would be gone for the day. I was probably 14 when I did the whole thing, makeup, dress, etc. The folks were gone for a couple of days; my sister who is older was at work so I had the house to myself. I still at that point did not have any body hair so I still felt feminine, I had been experimenting with anal masturbation, having read about it, I took small hair brush handles put Vaseline on it and inserted it in my anus, I can still remember how it felt, long and pointy not big but loved the feel of it going in and out. So having got to that point, I stripped naked in front of their full length mirror, staring at my small penis (was not real big) bent over looked at my butt hole examined every inch of me. I then proceeded to put on the panties and hose and bra, I loved the look and feel and walked all thru the house a few times making up reasons to be about. Next I got mom's makeup out and put on the foundation, eyeliner, mascara, eye shadow, and then finally the lipstick. I did look very pretty and not a bad job for the first time, she had an old wig I put on, not anything sexy but I was amazed at how I could become a woman. Now it was time to find a dress, being older now than when I first tried her pantyhose on, I could wear her things more fitting. I chose a white color blouse and a black and grey checked knee length skirt. I had stuffed the bra with panty hose so that was a nice feel on my chest with the blouse and accentuated my figure. All the while I am tugging my dick trying not to full out jack off because I am so excited. I got down on my knees and dug around and found the perfect pair of high heels, that was the first time I had ever done that and it took me a few minutes to learn how to walk in them. Now the outfit was complete and I stood there admiring myself and making kissy faces and trying to look seductive. I was quite proud of myself and went strutting around the house, dusting, fixing myself lunch, playing my female self, pretending to talk to my imaginary boyfriend and acting like a tease. I had learned a lot from that sex book at too early an age I am sure. With my hard on pushing ever so harder against the outfit, I decided to do some anal play and finish jacking off. I went to the mirror again admiring myself and lifted my skirt above my waist and pulled my pantyhose and panties to just below my butt cheeks and penis to give some relief. It was then I decided to be a girl again and took the comb handle, put some Vaseline on my ass and slid it in and out, looking at myself in the mirror, on my knees chest to the floor ass up the comb portion sticking out my but cheeks with the handle inside, having the most powerful orgasm of my life to that date. That is how it all started and continues to get better each day.