From time to time I’d take a stand: I’d throw away my entire stash of clothing, and vow to “go straight”. But my only real weapons in the fight were a vague instinct that cross-dressing must be “wrong”, and the associated feelings of guilt. They were too easily rationalized away. Why should I feel guilty? Who was I hurting? Why was it wrong?

I think I always had the desire to cross-dress. Some of my very earliest memories are of a dress-up box that my brother and I played with. It was probably filled with pirate outfits and funny hats, but there were also a couple of old dresses. I only dimly remember wearing them, but I more clearly remember the disappointment of finding that they’d been removed one day—presumably by my concerned parents.

That was that, until my early teens. Along with the usual bewildering chemical processes came the less usual and more bewildering urge to try on a bra. With no real clue why I was doing it, I fished one out of the dirty laundry basket and tried it on. I don’t remember feeling any particular joy or wonder; I thought I was simply satisfying some odd curiosity, and that would be the end of it. But it wasn’t. The desire returned a day or two later, and this time it wanted more than just a bra.

And that became the pattern. I was a happy, well-behaved teenager, but privately I was at the mercy of this inexplicable desire. My efforts to resist it always ended in failure; my efforts to fulfil it just made it hungrier. I graduated from rifling through the laundry basket to rifling through the local thrift store, always needing fresh fuel for the fire, but constantly terrified that I’d be spotted.

A lonely struggle

I didn’t want to be a woman; in the early days I think, above all, I just wanted to be normal. Even as the hiding places in my bedroom filled up with second-hand lingerie, I clung to the hope that one day I’d be “cured”—that the urge would disappear completely, or that the sense of disgust I felt whenever I yielded would prove strong enough to stop me yielding the next time. Failing that, I longed for the definition of normal to change—to learn that cross-dressing was actually something perfectly natural and wholesome, something everyone did. I wanted the struggle to end—either in victory, or in acceptance.

But victory seemed impossible. From time to time I’d take a stand: I’d throw away my entire stash of clothing, and vow to “go straight”. But my only real weapons in the fight were a vague instinct that cross-dressing must be “wrong”, and the associated feelings of guilt. They were too easily rationalized away. Why should I feel guilty? Who was I hurting? Why was it wrong? I went to church at the time, but my own personal brand of Christianity provided no more help: I believed in a God who had made me this way; I didn’t believe in a God who would want me to struggle against it. So I struggled, but with no conviction, and defeat was a foregone conclusion. I held out for an entire year once, but it was never sustainable, and the end result was always worse than the start. I began to accept the simple truth that I was a transvestite. It wasn’t a phase, it wasn’t going away, I couldn’t fight it: it was my identity.

“I began to accept the simple truth that I was a transvestite. I couldn’t fight it: it was my identity.”

As for acceptance, well, I wasn’t an idiot. Society was telling me that I should be true to myself, but in society’s eyes cross-dressers were either drag queens or perverts. Unlike today, when gender issues are a hot topic, very few people seemed to have heard of transvestitism. There were no famous transvestites in the news, except Eddie Izzard, and no one really seemed to understand much about it. I couldn’t understand it myself, so I had very little reason to expect anyone else to. Aside from one or two very close friends, the whole thing remained deeply secret. I craved acceptance—the freedom to live as God had made me—but I had no desire to get my head kicked in, which seemed to me to be the most likely result of attempting to go out in public.

So I lived alone, with the curtains constantly closed. I was sociable, and had friends, but what I thought of as my “true self” was confined to a few small rooms, denied all interaction with the rest of the world. I desperately longed to go outdoors: to learn what it’s like when your dress moves in the breeze, or gets wet in the rain—to try cycling in a skirt—or simply to feel the sun, to see what all these clothes actually looked like in the daylight. And I longed for conversation—for someone to show my new purchases to, to say, “Oh, that’s pretty, where did you get that?”, or even, “Ugh, that’s hideous”—just to have another observer, someone to give my “real” life an existence outside of my own private experience. But that too seemed impossible.

Read More