By Jenn der Bentson

There’s a quiet, at least internal, rebellion that happens when a guy gets to slip into the feminine clothes he truly wants to wear. At least some times.

For many crossdressers, the desire to do so is not just personal. It also comes with social aspects and potentially even ramifications.. Our world has a long history of policing desire, and if you are a crossdresser who has ever felt guilt, fear, or shame simply for enjoying the way a skirt hugs your hips or how a pair of heels makes you walk taller, you’re not alone. That feeling isn’t a flaw in you—it’s a symptom of a society that exercises some degree of control over what is accepted. And unfortunately, crossdressing isn’t as accepted as many of us wish it was.

The Policing of Desire: A Societal Habit

Let’s start by naming what we’re up against. From a young age, most of us are taught what’s “acceptable” to want. Boys are supposed to want girls (and only girls), supposed to want power, toughness, sports, cars, careers. Girls are supposed to want boys, nurturing roles, softness, service, and sacrifice. And of course, your clothing should match the script. Veer from this path, and suddenly your desires become suspicious. Crossdressing, then, becomes more than a style choice—it becomes an act that calls attention to nonconformity, to desire that can’t be neatly categorized.

The discomfort many people have with crossdressing isn’t really about the clothes. It’s about what the clothes symbolize: freedom, fluidity, pleasure, and, yes, sometimes sexuality. Crossdressing dares to say, “I want this,” without permission. And that scares people.

Society has created an elaborate system to keep people in line—through shame, laws, mockery, even violence. This policing of desire serves to maintain rigid gender roles and control who gets to feel good, expressive, and whole. But here’s the good news: this system is built on fear, not truth. It only works if you believe the lie that your desires are wrong.

Unpacking Internalized Shame

If you’re like many crossdressers, you’ve probably absorbed some of this social policing. You probably even do it to yourself in some ways, requiring society to nothing specifically, because you do it to yourself out of what you think the rest of society might think or do.

Maybe you’ve hidden your clothes, purged your wardrobe after a particularly intense moment of self-doubt, or promised yourself you’d stop “giving in.” Maybe you’ve wrestled with whether you’re “normal,” or whether anyone could love you if they knew.

Let me say this clearly: you are not broken. You are not dirty. You are not shameful.

What you enjoy—whether it’s the silky feel of a camisole, the act of embodying femininity, or the thrill of transformation—is deeply personal and deeply valid. The shame is not yours. It was handed to you by a society that teaches us to fear difference, to distrust our own joy, and to silence the parts of ourselves that don’t fit the mold.

Reclaiming your crossdressing—however it looks for you—is an act of self-respect. It’s a declaration that your inner life matters. It’s saying, “I refuse to apologize for what brings me happiness.”

Desire Is Not a Crime

One of the trickiest things about crossdressing in a society that polices desire is how quickly pleasure gets painted as deviance. There’s often an unspoken (or very loudly spoken) assumption that if you enjoy crossdressing, especially if it’s in any way erotic or sensual, it must be perverse or fetishistic in a negative way.

But desire isn’t dirty just because it doesn’t look mainstream. You’re not harming anyone by feeling good in your body. You’re not hurting anyone by embracing a version of yourself that turns you on, excites you, or fills you with confidence.

Let’s stop pretending that there’s only one acceptable way to experience pleasure or to explore gender. Whether crossdressing is a source of sexual expression, comfort, identity, creativity, or all of the above—it’s yours. It doesn’t have to justify itself to anyone else.

You don’t owe the world a sanitized, “pure” version of yourself to be worthy of respect.

Taking Back Your Power

So how do we begin to push back against the policing of desire in our everyday lives? It doesn’t have to mean waving a flag in public (though more power to you if you do). Sometimes the most powerful resistance is quiet and consistent.

• Dress for yourself. You don’t need a reason beyond “because I want to.” Whether it’s underdressing with a secret pair of panties or going full glam on a night in, let your own pleasure be enough. 
• Find community. Whether online or in person, connecting with others who understand the complexities of crossdressing can be life-changing. It reminds you that you’re not alone and helps dissolve the shame that thrives in isolation. 
• Tell your own story. Even if it’s just to yourself in a journal, start exploring your own narrative. What do you love about dressing? What does it unlock for you? What false beliefs have you been carrying, and how can you let them go? 
• Set your own standards. The world will always have opinions, but you get to decide what feels right for you. Maybe that means shaving your legs. Maybe it means rocking stubble with lipstick. You don’t have to fit anyone’s idea of “feminine” or “masculine.” You get to write your own rules. 
• Be kind to yourself. Some days you’ll feel bold and radiant. Other days, doubt will creep in. That’s okay. Give yourself the same patience you would offer a friend. You’re on a journey, not a performance schedule.

Pleasure as Resistance

In a society that wants to regulate what you wear, how you look, and what you feel—it is an act of courage to say, “I like this.” To find joy in your expression. To let yourself feel good.

Pleasure isn’t weakness. It’s power.

And when you claim that pleasure, when you stop waiting for permission to enjoy yourself, you take back something the world has tried to steal from you: your freedom. Your right to feel beautiful. You’re right to feel sexy. Your right to feel you.

You are not a mistake. You are not an aberration. You are not something to be fixed. You are a living, breathing expression of what it means to break the mold—and that is something to be proud of.

So next time you look in the mirror and smile at the reflection staring back—whether it’s in jeans or a dress, sneakers or stilettos—know that that smile is a quiet revolution. And you don’t owe anyone an explanation for it.