My Descent

This is the first time I've told my story publicly. I wrote this maybe 3
years ago, and have shared it with one person.

I used to cross dress in my hotel room while away on business trips. I'm a
fat bald 46 year-old who looks ridiculous dressed up in ladies underwear.
When you're obsessed, though, appearances don't necessarily stop you from
doing something. I'm married, but my wife doesn't know about my hobby. I
never do it at home. It was something I only did when traveling.
Fortunately, as a sales manager, I spent a lot of time on the road. But
with airport security these days, it has become way too risky to carry a
suitcase full of ladies undies and a dildo for pleasuring myself.

Even as a nine or ten-year old, I was the one who volunteered to play the
girl role when we played games. Thinking back, it's funny how sexual some
of our play was even though we did nothing overt, and didn't really know
what we were actually doing.

I don't know how I got the idea to do it, but in high school, I began to
dress up in my sister's or my mom's underwear and walk around in front of
an open window. Then I would jack off. I don't think anyone ever noticed
me. If anyone did, I never found out about it. My sister had a garter
belt and my mom had this fabulous pink and black lace highly boned corset
that I liked to wear. This was at the end of the girdle era. I carried on
with this even into college, when visiting home for the summer. I stopped
cross-dressing when I was caught by my father. I pleaded mental illness
and he didn't punish me but he didn't try to do anything to help me either.

I saw my first picture of a transsexual sometime while in college. There
was a spread in Hustler of a shemale. That wasn't revealed until the last
photo of the spread, of course. I was absolutely fascinated. Yet men held
no attraction for me whatsoever.

I had a roommate for the first year of college, during which my sex life
revolved around masturbating to girlie magazines. Then I got my own
apartment, and I made one of the great discoveries of my life. My anus.