From Suits to Skirts: The Double Life of a Crossdressing Man

  The first time I came across the word crossdresser, something clicked. It gave me a label I could grab onto at a time when I felt very alone. I was young, curious, and fascinated by the way certain clothes could make me feel different—more like myself, actually. But even back then, I realized the word carried baggage. To most people, it meant kink or something secretive. For me, it was simpler, gentler. I just wanted the freedom to slip into a dress, lounge around in a silky robe, or paint my nails without that experience being sexualized.

  As the years passed, that single word felt too small for what was happening inside me. I started questioning why clothing was ever assigned a gender in the first place. Why was a skirt “for women” and jeans “for men”? The more I thought about it, the more I saw how arbitrary it all was. And as I explored makeup, wigs, and even practicing a femme walk, it became clear that I wasn’t just playing dress-up—I was discovering another version of myself.

  Eventually, I found language that resonated more deeply: bi-gender. It captures the reality that both sides of me exist fully. I can thrive in a sharp suit at work and glow in a cocktail dress at dinner. One identity doesn’t cancel out the other. I don’t think of it as switching masks, but more like stepping into different rooms of the same house. Each room has its own atmosphere, its own circle of friends, its own responsibilities—and yet they’re all mine.

  Of course, living between worlds has challenges. Safety is always in the back of my mind. A trip to the mall becomes a subtle calculation: who’s nearby, how do I carry myself, will I draw attention? Even on “boy days” I’m careful about small details—panties peeking above a waistband, a bra strap shifting under a shirt. It’s a balancing act between expression and protection.

  But the beauty outweighs the difficulty. Clothes aren’t shallow; they are my compass. They mark my moods, my confidence, my connection to both identities. A soft nightgown at bedtime, lipstick on a daring afternoon, or sneakers that make me feel powerful—each choice affirms me. And when I look back, I see not just a man who liked to wear women’s clothes, but someone who slowly built a life that could hold both sides of themselves without apology.

  I don’t know if everyone will understand. Maybe that’s not the point. What matters is that I understand—and that I feel whole.

Hannah