Six Months… With a Fifteen-Year Head Start

People ask me all the time, "When did you start your transition?" I know what they mean. They want the Big Official Start Date. April 17, 2026. Go me! 🎉 Simple question. Simple answer.

But wait. What do you consider the start? And what exactly do you consider transition? Because there are people who would still consider me "pre-transition." After all, I still go to work as Him. I still spend a significant part of my life presenting as male. So have I transitioned? Am I transitioning? When did I actually start? And why does my brain insist on making a perfectly simple question so complicated? Well, because apparently that's what my brain does.

Here's the funny thing. When I meet people, my timeline usually comes up. And when I tell them I've been transitioning for five or six months, I sometimes get the most wonderful reactions. "Five YEARS?" "Ten years and five months?" Nope. Months. As in, you can count them on one hand and have a finger left over. Well, depending on which date we're talking about.

I'm not going to lie. Those reactions make me feel pretty darn good. But they also confuse the heck out of me. I've spent some time thinking about why people perceive me as someone who has been transitioning for years. And I've come up with three things.

First, HRT has been very good to me. A little genetics, a little estrogen, and apparently my body had some plans of its own. Second, I've put a LOT of work into makeup and presentation. I've practiced, experimented, made mistakes, learned what works, and developed a style that feels like me. Those two things make sense. A little genetics. A little elbow grease. A whole lot of glitter.

But the third? The way I carry myself. That's the one that got me thinking. Because when did that start? And after following that question backward through my life, I realized something. It started long before April 2026.

February 2011: A Beginning

In February 2011, my daughter and I went together to get our ears pierced. Her holes closed up years ago. Mine? Not a chance. I've worn earrings every single day since. You see, I'd wanted pierced ears since I was sixteen years old. I'd waited twenty-four years to finally get them. Twenty-four years! Those holes weren't going anywhere.

And those earrings weren't just jewelry. They were something feminine I could wear every day. Something that belonged to me. Something that made me happy every time I put them on. They were also wonderfully safe. Men can wear earrings, right? Of course they can. Plausible deniability. But I knew what they meant to me.

For a while, that was enough. I bought cute earrings. I matched them when I could. I enjoyed having that little bit of femininity with me everywhere I went. I didn't have to explain it to anyone. I could just enjoy it. And I did. For years.

July 2018: The Wardrobe Revolution

Then one day I looked at my closet. Gray. Blue. Green. Brown. More gray. Oh, look! A different shade of blue!

I was a teacher, surrounded by other teachers who were mostly women. And I started noticing something about their clothes. Colors! Patterns! Flowers! Characters! Personality! Their clothes were FUN. And I wanted that. Not necessarily dresses or skirts. Not yet. I wanted the freedom to express myself through what I wore.

So in July 2018, I bought three shirts. Three colorful, interesting shirts that actually reflected my personality. And then I bought a few more. Two or three a month for a while. And then a few more. Today, I own approximately 125 shirts. Yes. One hundred and twenty-five. Colors, characters, themes, holidays, aliens, Bigfoot... You name it, I probably have a shirt for it. And naturally, I started matching my earrings to my shirts as well as I could. Because if you're going to do something, you might as well do it properly.

But here's what I realized while thinking about all this. Those shirts weren't just about clothing. They were about freedom.

I'd always been a playful person. A little silly. Creative. Expressive. The kind of teacher who enjoys making people laugh. But I hadn't been expressing that personality quite as freely as I wanted. Once my wardrobe caught up, something changed. The colors, patterns, and characters on my shirts gave me another way to show people who I was. They matched my personality. And because they matched my personality, I felt more comfortable letting that personality out.

There was a feminine element to it, too. Absolutely. I knew that. But once again, I had plausible deniability. It was just a fun shirt. Just a pair of earrings. Just a teacher who liked colorful clothes. Nothing to see here, folks!

Except there was. There was a woman who had found another way to express herself without having to explain herself. And she was having a wonderful time doing it.

The Fifteen-Year Head Start

So now we come back to that third thing. The way I carry myself. People sometimes seem surprised by how comfortable I am presenting as a woman after only a few months. And honestly, I've been surprised by it myself. Because there are things about being Amber that feel remarkably natural.

Not everything, of course. I'm still learning. Still practicing. Still figuring out what works for me. But the confidence to be expressive? To be playful? To wear something because it makes me happy? I've been practicing that for years.

My earrings were a beginning. My shirts were another beginning. And each time I allowed myself a little more freedom, I got more comfortable with being seen. I wasn't consciously practicing how to walk or move like a woman back in 2018. But I was practicing something important. I was learning to let my outside match my inside. A little more every day. And every time I did, I discovered that I liked it. So I kept going.

We have been making improvements ever since. And that process didn't suddenly stop when I started HRT. It accelerated. Dramatically.

Now there are skirts. Dresses. Makeup. Wigs. Shoes. Handbags. More earrings. And glitter. Dear goddess, the glitter. But the person wearing all those things? She's not nearly as new as people think.

So When Did I Start Transitioning?

April 17, 2026, is my official date. That's when I started taking medical steps toward becoming the woman I wanted the world to see. And that date matters enormously to me. But it isn't the whole story.

Because transition isn't just hormones. It isn't just makeup or clothing. It isn't even necessarily about whether everyone in your life knows who you are. Sometimes transition begins with a tiny act of self-expression. A pair of earrings. A colorful shirt. A decision to stop hiding quite so much of your personality. And sometimes those little decisions add up over years, quietly preparing you for a much bigger change.

I spent a long time believing I couldn't be the woman I knew I was. But looking back, I can see that I was finding little ways to be her anyway. I couldn't have everything. So I found something. And then something else. And then something else. Until one day, I was finally ready to stop settling for little pieces. I wanted all of me.

And now, six months into my medical transition, I look in the mirror and increasingly see the woman I've wanted to see for most of my life. People meet me and think I've been doing this for years. In a way, they're right.

They just don't know about the earrings. Or the Bigfoot shirts. Or the twenty-four years I waited for those first little holes in my ears. They don't know about all those small beginnings that came before the Big Official Start. But I do. And I think I'm finally beginning to understand why some of this feels so natural.

I didn't become Amber overnight. I've been letting her out a little at a time for fifteen years. So the next time someone asks me how long I've been transitioning, I think I finally have my answer.

Six months... with a fifteen-year head start.

💜 -- Amber