Date: Fri, 30 Dec 2005 20:02:59 -0800 (PST)
From: Lady Gurl <i12bagurl@yahoo.com>
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.