August 23, 2026

On the road we travel, life can bring unforeseen turns and surprises as we stumble through our days. After you spend 10, 20, 30, or more years in the closet wearing your sisters’ or mothers’ clothes, little by little, every cross-dresser begins to find some degree of clarity. Whether that is a good or bad thing is different for each person.
Does being happy in the role of a girl’s life mean that we are girls, or should we be girls?
I can recall days in the closet where I thought I was going to suffocate to death. The few times that I did go out in public over the course of years — when I was in my 20’s and 30’s–– usually skulking around in the shadows of some town far from home, it was as though the air was suddenly plentiful and sweet.
Dressing up became compulsive, like a drug; we want to experience it again, despite the fear of being caught, the guilt, shame, and downright self-loathing of our actions. And yet, though all the ups and downs and the dress and purge, we’re left with a truth: that we feel helpless in its pull.
We come to understand the truest sense of the word secret. We can’t sidestep it; we can’t lie about it, manipulate its meaning, or pretend it didn’t occur – because there was no other party to it but ourselves.
Those were rough years, and certainly there was not only guilt, but also self-loathing, disdain, madness, and internal conflict that ripped at the fibers of our soul.
When I came out in 2000, I had had enough. I was tired of being “damaged goods,” a broken man. I was committed to getting concrete answers. I had decided that this thing, that I considered a compulsive, depraved behavior, interfered with my life, and I was tired of lying, hiding, and manipulating circumstances to protect it.
So I stepped out to explore “it” and myself without the fear of what I might find. Oddly, I didn’t approach it with the fear or anger that had gripped me for so many years. Brianna was pretty carefree and spontaneously happy in her travels. But I was sure some deep, dark secret caused this in my life. So my goal wasn’t to dress up and have fun; it was to get to the bottom of it, discover what it was, and extricate it from within me, so that once and for all I could cure myself and get on with my male life.
But then the twist: with every day that went by, I became more comfortable and content in this girls’ life I had created. The excitement and compulsion to dress in girls’ clothes had all but evaporated. It was the ‘being’ the girl that fulfilled me, not the clothes. I explored my interactions with other people, how they responded to this new presentation, and my internal feelings about it. I read and educated myself about transgenderism, transsexuality, transvestism, and cross-dressing, from which I gleaned new meanings as it related to me.
Without any effort, I eased into a girl’s life as though I had been one my whole life. I didn’t care if I passed or not, and had no problem with, or difficulty in, discussing any aspect of it with strangers – whether they were transgender, gay, or straight.
I was a bit cavalier, careless actually, and without much thought, found myself after years on herbal estrogen taking prescription Premarin – without the prescription. I don’t advocate hormones without a prescription: it’s stupid and dangerous.
You may be wondering about this guilt I first mentioned. Be patient, I’m getting there.
After several years as Brianna, at the height of my recognition — as founder of the Girls Club and a transgender magazine columnist for GIRL TALK, TG Community News, and a contributor to others — I found myself with body changes that were reaching the point of no return. In that moment, I was once again confronted with the questions that haunted me from my earliest childhood memories—what it would be like to be a girl; could I be a girl, and should I be a girl?
Yes, yes, and yes was my realization. All those years of pushing the envelope and expanding my girl experiences were, I now realized, just an exercise to find the answers to those questions. Finally I knew who I was. All that was left was to decide what to do about it.
I had reservations about transition: I’d no longer be a father, I was in my 40s, and the ability to finance all the surgeries. A new question appeared before me: with the new knowledge I had come to know about myself. I now knew what all that white noise in my head stemmed from for all those years; could I now live happily and content in the body I was born with?
And so the journey continues, which I will cover in the forthcoming book The Last Woman & Me.
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