Are You a Crossdresser or Trans Woman? 5 Questions That Might Help You Decide

Look, I'm going to be real with you right from the start: this question keeps me up at night sometimes. Not because I don't know my own answer anymore, I'm pretty solid on that these days, but because I get messages from people in our My Girl Life Podcast community every single week asking some version of this exact question.

"Maddie, how did you know?"

"Am I trans, or do I just love crossdressing?"

"What if I'm getting this all wrong?"

Here's the truth: there's no magic test. No blood work that comes back with your gender identity neatly printed on the results. But after thousands of conversations, hundreds of podcast episodes, and my own messy, beautiful journey, I've noticed some patterns. Some questions that, when you sit with them honestly, can help point you in the right direction.

So grab a cup of coffee (or wine, no judgment here), and let's walk through this together.

Question 1: When You Take Off the Dress, Do You Take Off "Her" Too?

When I first started exploring my feminine side, I thought it was just about the clothes. The thrill of slipping into a cute dress, doing my makeup, feeling pretty. And don't get me wrong, that part is absolutely magical.

But here's what I noticed over time: when I took off the dress at the end of the night, Maddie didn't go away...I still feel that side of me it's just not enough to want to be dressed all the time. When I come home at night I can't wait to take my female clothing off. I love being a man and do not have gender dysphoria, however, there's no internal conflict. The femininity is something I do, not something that I am. Maddie never really goes away in my mind...I just anticipate the next time I'm going to dress and go out or do a podcast episode.

For others, the feel like they are in a costume when they change back into their male clothing...they may indeed had gender dysphoria. Neither experience is better or more valid. They're just different. Ask yourself: When you're not dressed, do you still feel like a woman inside? Or does that feeling come alive specifically when you're expressing femininity outwardly?

Question 2: Is This About Pleasure, Identity, or Both?

Okay, let's talk about the elephant in the room wearing fabulous heels: arousal.

A lot of people who are exploring their gender get really freaked out if they experience sexual pleasure from crossdressing. They think it means they're "just" doing it for a fetish, and therefore they can't possibly be trans.

Here's what I've learned: it's way more nuanced than that.

Many crossdressers experience crossdressing as a sexual kink, and that's completely valid. It's a form of expression that brings joy and pleasure, and there's absolutely nothing wrong with that. For them, the arousal is a primary motivator, and the femininity is part of the fantasy.

For trans women, there's often arousal in the early stages too, what some researchers call "embodiment euphoria." Seeing yourself as you've always felt inside can be intensely validating, and yeah, sometimes that comes with sexual feelings. But the key difference? Trans women still want to be women when they're not turned on. At the grocery store. Doing taxes. Arguing with customer service.

I remember a conversation with a guest on the podcast who said, "When I'm dressed, I feel sexy. When I'm not dressed, I feel wrong." That "feeling wrong" part? That's the gender dysphoria talking, which brings us to...

Question 3: Do You Experience Persistent Discomfort with Your Birth-Assigned Gender?

Gender dysphoria is one of those clinical terms that sounds scarier than it needs to. Basically, it's ongoing distress about the mismatch between your internal identity and your body or how people see you.

Not every trans woman experiences dysphoria the same way. Some people have intense physical dysphoria about their body. Others have more social dysphoria, they hate being called "he" or "sir" or being put in the "men's" category.

Crossdressers typically don't experience this persistent discomfort. They're generally comfortable with their assigned gender; they just also enjoy expressing femininity. There's no constant internal battle.

Be honest with yourself: Is there a nagging feeling that doesn't go away when you're presenting as your assigned gender? Or is the discomfort more about not being able to express your feminine side as often as you'd like?

Question 4: How Do You Want the World to See You?

This question really cuts to the heart of it for me.

When you're out in the world, at Target, at a restaurant, walking down the street, do you want people to see you as a woman. Full stop. Not as "a man in a dress." Not as someone performing femininity?

Many crossdressers like myself don't have that same drive. When they're dressed, they love being treated as feminine, and it brings them joy. But they're not necessarily seeking that treatment in every aspect of their lives. They're not thinking about changing their legal documents or coming out at work or navigating the world full-time as women.

There's a difference between wanting to express femininity and wanting to be recognized as a woman in all contexts. Both are valid. Both deserve respect. But they point in different directions identity-wise.

Question 5: Can You Imagine Your Future Self?

Here's my favorite question, and honestly, the one that can provide some interesting insight.

Close your eyes and imagine yourself at 70 years old. Sitting on a porch, looking back at your life. Who is that person? What do they look like? What name do they go by? How do other people talk about them?

If you imagine your future and see yourself happily moving between masculine and feminine expression, maybe crossdressing on weekends, maybe in private, maybe with a partner, and that feels complete? That might point toward crossdressing as your truth.

If you imagine your future and can't see yourself NOT living as a woman? That's information too.

The Beautiful Messy Dual Persona vs Gender Dysphoria

Here's what I want you to know: you don't have to have this figured out right now. You really don't.

Some people are "trans curious" crossdressers who are still exploring. Some people identify as non-binary and reject the binary categories altogether. Some people flow between identities over time as they learn more about themselves.

I've had guests on My Girl Life Podcast who thought they were crossdressers for years before realizing they were trans women. I've had others who explored transition and realized crossdressing was actually their truth. Both journeys are valid. Both deserve celebration.

The most important thing? Give yourself permission to explore without judgment. Work with a gender-affirming therapist if you can. Connect with communities (like ours!) where you can ask questions and hear diverse perspectives. Try things on, literally and figuratively, and see what feels right.

Your identity is yours to discover, and there's no timeline you have to meet. Whether you're a crossdresser, a trans woman, something in between, or something entirely different, you deserve to express yourself authentically.

And hey, if you're still figuring it out? You're always welcome in our community. We've got wine, great conversations, and zero judgment.

Welcome to your journey, beautiful. However it unfolds, I'm rooting for you. 💕

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