Like Father, Like… Son?

Father's Crossdressing Shame Imposed on His Son

By Cathy Laura Peterson

Stana’s recent post, “Like Father Like Son?”, stirred up memories I hadn’t revisited in a long time—memories that go all the way back to the 1960s, when I first found myself dressed in feminine clothing alongside my three sisters.

It was my aunt who encouraged it. She treated it as harmless, even natural—just kids playing. My mother, on the other hand, seemed almost detached. Not disapproving, not approving… just indifferent. 

My father wasn’t around much. He left when I was very young—so young that I don’t remember him ever really living with us. But I do remember something else: my aunt’s old black-and-white photo albums. Tucked inside were a few striking images of my father, fully en femme, taken in the early 1940s before he went off to war. 

He was young, slim, and—there’s no other way to say it—convincing. Dresses, stockings, heels, even the suggestion of a bra and slip beneath it all. Later photos showed him again, after the war, dressed up at what looked like a costume party with my mother. 

My aunt didn’t dance around it.


“Your father liked to dress up,” she told me plainly. “He did it when we were kids, and again after you were born—but he never went out.” 

That knowledge didn’t quite fit with the man I would occasionally encounter as a child.

He would show up unannounced now and then. And twice—only twice, but vividly enough—he saw me dressed with my sisters. Dress, tights, shoes, bows, maybe a little lipstick. I remember the anger. Not just disapproval—real intensity. He got in my face, shouting, threatening to throw me outside for the neighbors to see, hurling the kind of language that was all too common in that era.

It frightened me. It frightened all of us.

And then… he was gone.

By the time I started kindergarten, he had moved out of state. We never heard from him again.

Years later, as adults, my sisters and I tried to make sense of it all. The contradiction was hard to ignore: the same man who had once dressed as a woman himself reacting with such anger and shame at seeing me do the same. 

In time, we came to a conclusion that felt right. His anger wasn’t really about me—it was about him. About whatever conflict, guilt, or fear he carried but couldn’t reconcile.

As for me, I moved in a different direction.

Those early experiences—playing dress-up with my sisters, encouraged by my aunt—were never strange or uncomfortable. Quite the opposite. They felt safe, affirming… even therapeutic. I loved it. The clothes, the textures, the ritual of it all. Slips, dresses, stockings—it was a world that felt welcoming rather than forbidden. 

And yes, I eventually ventured outside.

Halloween became my sanctioned opportunity—my annual “excuse” to be seen. Under the cover of costume, I could step out fully dressed and feel, for a few hours, completely at ease in the world.

By high school, I had gotten more inventive—improvising curves, styling my longer hair, making the most of the era’s fashion trends. It was the early ’70s, after all, and shoulder-length hair on boys made certain things… easier. 

Life moved on.

As adults, my sisters and I eventually discarded those old photos of our father. But the conversations about him lingered. They still do, in a way.

I’ve lived my entire life with this part of myself—not as a phase, not as a secret to be buried, but as something that brings genuine joy. There have been close calls, awkward moments, and the occasional anxiety—but the overriding emotion has always been a kind of quiet elation. 

My own family took a different path. My sons never showed any interest in dressing, and I never encouraged it. In fact, I’d be lying if I said I didn’t feel a flicker of anxiety at the thought that they might. It made me wonder: Was this something passed down? Or simply something uniquely mine?

Even now, there are boundaries I haven’t crossed. I’ve never appeared en femme in front of my sons, their wives, or my grandchildren. The thought still carries a weight of discomfort—maybe even a trace of that old word: embarrassment.

And yet…

I still dress. At home. Out in public. On business trips where I can spend days at a time fully as Cathy. I’ve learned how to navigate the risks, the “what ifs,” the chance encounters with someone who might recognize me. 

Because in the end, the equation is simple.

The joy outweighs the fear.

And after all these years—since the 1960s, really—that hasn’t changed.

I expect it never will.

Wearing Boston Proper

Peter Butterworth femulating in the 1966 British film Carry On Screaming.