Crossdresser or Femboy?

I’ve Been Called Both and They Aren’t the Same

For most of my adult life, I thought I was a crossdresser.

That was the word available to me. It came with a script: secrecy, timing, discretion. You dressed when you could, not when you wanted. You folded everything back into drawers before anyone came home. You erased the evidence. You returned to being a man.

And for a long time, that fit. When I dressed, it was intentional. Deliberate. Almost ceremonial. I chose the clothes carefully. I became attentive to posture, movement, the sound of heels on a floor. But when the moment ended, so did the version of me who wore them. I didn’t want to be feminine all the time. I wanted to visit it.

Then one day, much later, I heard the word femboy. At first, I dismissed it. Too young. Too online. Too unserious. But the more I watched, the more unsettled I became, not because it felt wrong, but because it felt familiar in a way I hadn’t expected.

Femboys weren’t sneaking. They weren’t switching. They weren’t compartmentalizing. They were just… being. Feminine in daylight. Feminine without apology. Feminine without an exit strategy.

That difference matters more than people think. As a crossdresser, femininity was something I put on. As a femboy, femininity is something you live with. One is episodic. The other is ambient. One has a beginning and an end. The other just… continues.

I realized that what separated us wasn’t clothing—it was relationship. I always returned to masculinity like a home base. No matter how far I wandered, I knew where I was going back to. Femboys, by contrast, didn’t seem interested in returning. Masculinity wasn’t forbidden, it just wasn’t necessary.

There was a confidence in that I found both enviable and alien. I didn’t grow up with language for public softness. My femininity developed in private, under pressure, shaped by risk. Femboys grew up in a different climate. Online, at least, they had mirrors that reflected something back without shame. They didn’t have to choose between hiding and confessing. They could simply post.

That freedom creates a different posture in the world. I’ve noticed that crossdressers often want to pass. Femboys often want to play. Crossdressers study women. Femboys remix femininity. Crossdressers ask, “Do I look convincing?” Femboys ask, “Do I look cute?”

Neither question is better. They’re just not the same. And yet—there’s overlap.

I’ve seen young men who call themselves femboys but approach femininity with the same ritual seriousness I recognize. I’ve seen older crossdressers who gradually stop returning to masculinity as faithfully as they once did. The borders blur with time.

I know this because mine did. There were days I didn’t feel like “switching back.” Days when I resented how conditional my femininity was. Days when I wondered what it would feel like not to schedule it, to let it leak into the rest of my life.

That’s when I understood something important: Crossdresser and femboy aren’t stages on a ladder. They’re different strategies for surviving the same desire. One learned to hide. One learned to display. One adapted to scarcity. One adapted to abundance.

I don’t begrudge either.

If someone calls me a crossdresser, I understand what they mean. If someone calls me a femboy, I understand why they might think so. But the word I choose tells you how I relate to myself, not how I dress.

Labels don’t exist to trap us. They exist to explain us—briefly, imperfectly, and only when asked.

And if there’s one thing I’ve learned, it’s this: The clothes never mattered as much as the permission.

Wearing Ann Taylor

Kevin Kline (left) femulating in the 1999 film Wild Wild West.