The Beginning

I wonder if I was born a transvestite like gay people are born gay or if it really was the environment I grew up in that shaped my secret life? Probably, a little of both. Skipping over a large part of those formative years I’ll tell you about the first time I remember getting a thrill form wearing women’s garments.

It was in the basement, right after Halloween when I was in the eighth grade that my secret sexuality blossomed. My memory might be smoky but it’s good enough to set the order of things so they’ll lead to where I am today. Where am I today? I guess I’ll use some common labels to identify myself and keep you interested in reading further. I am a bisexual transvestite. But let’s get back to the basement and see where things went form there.

It was right after Halloween, my best friend and another of his close friends had actually started hanging out with girls after school. I was younger than them and too shy to even talk to girls. At that age I was tall and skinny, gap-toothed, I wore glasses and had a bad haircut.

Anyway, my friend and Jim had gone out trick or treating that year with Jim’s girlfriend and her close friend. My friend told me that Jim and he had dressed up as girls, for the life of me I don’t remember what the girl’s costumes might have been nor did I care.

When my friend told me about his adventure I felt cheated and jealous for several reasons, One, being that they hadn’t included me and another being that they were actually hanging out with girls. But something must have been lurking within my psyche because I was jealous for another reason as well, I remember suddenly feeling like I had been struck like a bell or that a light bulb had suddenly flashed over my head. Boys could dress up like girls.

I suppose it may have occurred to me before that boys could dress up like girls. I’m sure I’d witnessed it campily done on television at some point. But, this was someone that I actually knew, someone close to me. I remember quizzing my friend for all the details about what he wore but he wasn’t so forth coming. So, at some point I decided I had to try dressing up as a girl for myself. But when you’re an awkward adolescent where do you find the clothes?

For me it was the basement, one side of our basement was devoted to my father’s workshop and the laundry, where our families clothes hung in two rows suspended from the ceiling. It was there that I sought out an article of clothing that might fulfill this new desire to dress up like a girl.

The back rack of clothing was where off-season or out of style items were relegated to. It was here that I found a flowered sundress to suit my needs. Safely hidden in the pantry, away from prying eyes I tried the dress on, hmm, nothing. Admittedly, the dress wasn’t fashionable like the mini-skirts the girls at school were wearing nor did my bony body even come close to filling out my mothers more ample size. It hung on me like the proverbial potato sack and didn’t make me feel like a girl one bit. Besides that, there was something missing. Actually, there was a lot missing, a woman’s shape and hair, makeup, shoes and stockings… it must have been at this point that I had a minor epiphany. Mom kept her pantyhose rolled up into flesh colored balls of nylon in the bathroom closet! I could borrow a pair and try them on with the dress and see if it worked better, see if that made me feel girlier.

I snuck a pair of Mom’s hose into my pants and then down into the basement, I carefully slipped them on and then the dress, it was then that I discovered that accessories were everything. Standing there in the purloined pantyhose and dress I felt a rush of excitement, this is what I had been hoping for. A moment when dressed as a girl (in a fashion) I felt beautiful. I’m rather glad there was no mirror in the pantry because I imagine the sight of me didn’t match the image I had in my head and might have discouraged me from ever trying this again.

As it was, I could only feel beautiful, it would be many years before I felt comfortable enough in my own cross dressing wardrobe to actually feel confidant that I could actually look beautiful.