How I found freedom from gender confusion (Part 1)

To mark the release of Transgender by Vaughan Roberts, one crossdresser shares his story of how meeting Jesus Christ changed everything. The author has chosen to remain anonymous.

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.

The intoxicating scent of acceptance

And then, in my late twenties, I moved to London to study music, and, suddenly, it looked like an end might be in sight after all. Not victory—by this point I’d abandoned all hope of that. But among my musician friends I finally began to smell the intoxicating scent of acceptance. College was a pretty liberal place—my private activities were positively tame compared to what went on in the opera department, as far as I could tell. What had been a crushing secret battle for so many years was simply a non-issue to my friends. I had two wonderful female housemates who didn’t care what I wore to relax; one of them went so far as to lend me some clothes. I even began to experience a little of the outside world. Slowly, tentatively, my exile was ending. It seemed as though I could finally stop struggling. I was home. I was at peace.

Never enough

Except… I just needed to do something about my leg hair—it was spoiling the effect of the stockings. And the armpit hair had to go. (Pro tip: don’t ever try to wax your own armpits.) And the chest hair too. So much hair to remove! And now I needed some makeup to cover my stubble. And a few more bras. And some fake boobs, to put in them. And some padded pants, to give a bit of shape to my backside. And how was I going to give myself a waist? And I never had enough dresses, and they never looked good enough on me, and somehow I was struggling more than ever. The holy grail of acceptance had simply led me deeper into a trap. I’d embraced my desire, but it remained as unfulfillable as ever, and its demands were getting bigger every day.

"I’d embraced my desire, but it remained as unfulfillable as ever, and its demands were getting bigger every day."

It seems so obvious with hindsight. For years I’d been lying and hiding the truth, pretending to be what I wasn’t, and I thought that once I could be open about my transvestitism all of that would end. But I’d missed the simple fact that cross-dressing is, fundamentally, all about lying and hiding. I was donning a disguise, choosing the most feminine clothes I could find in an effort to pretend there was a woman’s body underneath them, hiding my real physical gender as best I could. And this was what it meant to “be myself”? I dread to think where things would have ended. I couldn’t be truly happy as long as everything was still an act of deception. The idea of surgery horrifies me, but I can easily imagine reaching a point when I would have welcomed it, believing it to be the next step towards freedom. In fact, looking back, I can’t see what would have stopped me.

But something did stop me. Because something amazing happened. Somehow, incredibly, my half-hearted loyalty to a soft version of Christianity brought me into contact with a church that taught the real thing…

Read part two of this story here. Ready to start thinking through how Christians can love and respond to trans people? Transgender by Vaughan Roberts is available now.