Debra's Story
IN THE BEGINNING
My family lived in a small, beautiful Georgian town in England called Cheltenham. It's located in central western England near the river Severn and in the region known as the Cotswolds. The second of five children, I arrived in 1952 and enjoyed a happy and relatively uneventful early childhood. We lived in what was called "council housing" in a new estate on the southwest edge of town and I took the bus to school every day. My very first recollections of any feelings of femininity date to around 1961; I was about 9 years old. I remember looking at one of my mother's clothing catalogs and being intrigued by pictures of lingerie and pretty dresses. Later than year, I took that first step so common to many transgendered people--I tried on stockings, garter belt, and a bra that lay invitingly on top of a dresser. Even today I can remember that first experience! The cool, silky touch of the nylons and the intense feeling of sheer joy that ran through my body as I looked in the mirror and fantasized about being a pretty young girl all dressed up for a walk in the park completely enthralled me.
My interest in the feminine developed more as curiosity initially, although I didn't have many opportunities to explore during the next year or so as in 1962 our family packed up all of its belongings and emmigrated to Perth in Australia. In retrospect, I don't think I suffered much internal conflict or guilt at the time, although growing up in a fairly strict Catholic household certainly helped to repress the feelings and desire to explore this evolving side of me. In fact, there was a little bit of a thrill attached to secreting a piece of female clothing and trying it on without getting caught!
It's that childhood notion of knowing that you're doing something "naughty" but you want to do it anyway and you're willing to take the risk. My elder sister had a blue frilly, lacy party dress with which I became very enamoured. I would sneak it into my bed at night and slip into the dress before falling asleep, dreaming of becoming a girl and spending my days clothed in pretty dresses and skirts. Unfortunately, one night I pulled one of the seams as I was pulling the dress on and had a real panic attack. I didn't dress up again for nearly six months after that, not because my sister went ballistic when she found the rip in the dress (she had no idea how it happened, fortunately!), but because I really was afraid of getting caught, going to hell, and burning in agony for ever. Ah, that Catholic guilt....
EXPLORATION
As a teenager, I suffered from the normal agony of confusion over my sexual identity and from the struggle to understand why I loved dressing up as a girl. My family moved back to England, to a beautiful medieval town called Shrewsbury in the Midlands. I became involved in rock and roll, playing the drums for a group that enjoyed local success during the late 1960s and had the opportunity to meet lots of women, although I remained sexually naive with the opposite sex. However, I did learn lots of fashion tips and I regularly practiced being feminine at home when the house was deserted. I almost always wore something sexy to bed at night, most often a black corset that I had purchased "as a gift for my sister." How many retailers have heard that line?? Many nights I would cry myself to sleep, desperately wishing that if a god did exist, she would turn me into a female by morning. Of course, I always woke up in the same state as I had gone to sleep but, nonetheless, I continued to ask, beg, plead, and cajole for several years.
My early sexual experiences were, of course, driven by the thrill of wearing lingerie, dresses, and make-up. Many times, simply the act of putting on lingerie would bring me to orgasm.
Later, I discovered the joy of masturbation while dressed. My lingerie collection grew to several bras, stockings, a red garter belt, and that oh-so-sexy black corset. Then, one day all hell broke loose! My mother found my stash of girls' clothing and demanded an explanation. Was I gay? How long had I been "doing" this. She gave me a booklet printed by the Catholic Church about the "evils" of masturbation and how I needed forgiveness for my sins. I eventually concocted a story about "collecting" things and that was about it. My parents were not too good about having frank discussions about these types of issues. I solved the problem within the following year by leaving home just a few days after my 18th birthday and migrating back to Australia by myself.
Now I could be free to explore myself without having to answer to anyone. Or so I thought!
STRANGE GIRL IN A STRANGE LAND
Finally living on my own and renting my own apartment in Sydney, Australia, gave me the freedom to explore my gender identity. I found mail-order catalogs and set out to build a modest wardrobe. Most of my early purchases were often too big or too small and the wrong color; an expensive learning experience but useful in hindsight.
What I really loved most, of course, was lingerie--the lacier, the sexier, the tighter, the better. I couldn't have been any happier coming home from work and slipping into something slinky and sexy. The first year of my new life in Sydney was crossdressing heaven, with an overabundance of self-pleasuring stimulated by an orgy of lingerie-wearing.
Transgendered lifestyles were not very well understood in Australia during the 1970s, especially in a very male-oriented culture where any hint of "non-normal" behavior provoked vitriolic and sometimes violent responses. Drag shows were a popular form of entertainment and there were a couple of fledgling transgendered organizations. But for a young crossdresser still trying to understand his/her desires, it was a lonely time. I did join the Seahorse Society in Sydney and got to meet a couple of very nice girls. But, in general, I stayed in or very close to the closet at home. About once every six months I ventured a drive around the area and even went for a walk in downtown Sydney one night, which scared the hell out of me!
I developed a relationship with a local (real) girl that lasted quite a number of years. At first, I didn't mention anything about my feminine desires. She found out the embarrassing way. One day she had gone to work and I had transformed into Debra, with full makeup, and was happily doing little chores around the house. She came home unexpectedly for lunch and I didn't hear the car come up the driveway. She walked in on me and gasped, "what are you up to? Why are you dressed as a girl?" Of course, I had to explain the entire situation to her, which took forever because she wasn't all that receptive. Anyway, we managed to reach an agreement that she wouldn't bother me about my crossdressing if I kept my feminine side away from her. She never wanted to see me dressed in women's clothes again! For the next several years, Debra didn't have many opportunities for expressing herself due to constant travel obligations, work, and a non-accepting partner. By the end of the 1970s I had decided it was time to move on, so I decided to move back to England in early 1980. I hoped that I could find a new career and a fresh opportunity to express my feminine persona.
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Last updated on 3/2/03
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