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.

Stuff 105: Brown Shoes

By J.J. Atwell

Ole, Lonesome George

In days of olde, well not that old for some of us, Johnny Carson was the host of The Tonight Show on TV. On one particular night in 1969, Johnny had quite a group of famous, glamorous movie stars, all of which were well-dressed. Then out comes George Gobel who looked over the group and quipped to Carson, “Did you ever get the feeling that the world was a tuxedo and you were a pair of brown shoes?” Of course the panel broke up in laughter. For the younger crowd or those with shorter memories, you can click here to view that episode on YouTube.

But that telltale joke revealed a tender spot. Something that I think many of us have. Do we sometimes feel like a brown shoe when en femme? Do we envy some of our sisters in how well they present? I’m asking about other CDs here, not GGs. I know when JJ goes out, she always strives for her best look, but like lonesome George, you can only do so much with what you have. 

Cope With Reality

So, here we are, a pair of brown shoes. So what? I know it’s disappointing not to measure up to your own high standards. Do we have unreasonable expectations? I think that’s true. I think that all the societal pressures that are put on women about how they should look and act have found their way into our Femulate world. How do we reconcile those ideals with the reality of who we are? Ideals that even GG’s struggle to meet. 

Too Philosophical?

I fear that I’ve let this edition of Stuff stray into some philosophical quicksand. At this point, many readers have turned to other things. Sorry about that. But for those who have stuck with me, I invite you to follow my current thinking. And to offer your own thoughts in the comments section. 

I deal with the reality of being a pair of brown shoes by acknowledging it and by taking it as a challenge. I know I can do better than what I do now. My girl self hasn’t reached her best presentation. Being reminded of that is a good thing. I think the worst thing that could happen in my femme world would be to just accept being a pair of brown shoes. Unless they go with your outfit of course. Apologies to those in the shoe business. 

Encourage Others

Let’s take the opportunity the next time we are with other CDs to encourage each other to continue down this fascinating path we have embarked upon. If you see a pair of brown shoes, maybe comment on how nicely they match the bag. Be positive. A few kind words cost you nothing and can mean much to the recipient. Support your femulating sisters. 

I’ll Be Back

As always, comments are welcome either here on the blog or by email to Jenn6nov at-sign gmail dot com. JJ is always looking for more stuff, so if there is something you would like to read about, please let me know!

Wearing A.L.C.

Jai Rodriguez femulating on television's Detroit 1-8-7.

Captions Calculated to Make You Cackle

Learning to Wait in a Skirt

During the Summer of Love, I was sixteen and endlessly raiding my mother’s and sister’s wardrobes whenever I had the house to myself. Always alert to the possibility that someone might walk through the door at any moment, I worked quickly: dress, makeup, a few stolen poses in the mirror—then everything undone just as fast.

I was as confused as a teenager could be, but I knew one thing for certain: I liked dressing up. I liked making up. I liked becoming a young woman, even if only for a few fleeting minutes. I treasured that secret girl-time alone, though I had no idea where it might eventually lead.

Then one day, I thought I’d found an answer.

It was in the August 11, 1967, issue of Life magazine. Buried in the news section was a short article titled “Now the Mini Has a Man in It.” According to the piece, “In a ‘spontaneous’ fashion happening, miniskirts for men have begun showing up in Paris, Munich, London, and Tokyo.” Accompanying the article were photographs of miniskirted men in Europe and Japan (see image above).

I was stunned and thrilled. Naively, I assumed the fad would spread. Surely it wouldn’t be long before boys in the United States would be wearing miniskirts too. And when that happened, I could finally step outside in the skirts and dresses I loved, in plain sight.

It didn’t happen.

I waited patiently, but the fad never caught on. Still, in time, I did go public wearing the skirts and dresses I loved, just the same.

C’est la vie.

Wearing L'Agence

Robert Woolsey and Bert Wheeler femulating in the 1933 film So This Is Africa.

Dressed to Thrill (Passing Optional)

I didn’t decide my legs were exceptional. Other people did that for me.

My mother was the first. She used to say I had beautiful legs and then, with a mix of admiration and regret, add, “You should have been a girl with legs like yours.” My wife has said the same more diplomatically. Other cisgender women have been less diplomatic, admitting outright that my legs are nicer than theirs.

At some point, you stop arguing with that kind of consensus.

I’m tall, so my legs are long. Maybe that length creates an optical illusion that elevates them beyond their actual merit. I honestly don’t know. What I do know is this: if people keep noticing, complimenting, and occasionally envying your legs, it would be foolish not to treat them like the asset they clearly are.

Which raises the obvious question: if you’ve got it, why hide it?

My answer has been skirts and dresses with short hemlines, sometimes unapologetically short (“Stana Short”) and heels ranging from two to four inches. Add four-inch heels to my six-foot frame and I don’t just enter a room; I announce myself. I top out at nearly six and a half feet, tall enough that strangers start inventing backstories. Some assume I’m an Amazon. Others think I played for the WNBA. A few decide I must be a man in drag.

They’re not entirely wrong but they’re missing the point.

There’s a well-worn rule in crossdressing circles: dress your age if you want to pass. If you’re an XX-year-old crossdresser, you should dress like an XX-year-old cisgender woman. At my age, that rule translates into longer skirts, lower heels or worse.

By “worse,” I mean this uncomfortable truth: many cisgender women my age now dress like cisgender men. Slacks, trousers, and flats dominate. Skirts, dresses, and heels have largely disappeared. Camouflage, masquerading as practicality.

I saw this vividly one night while dining with four other T-girls in downtown Hartford. The restaurant was packed with twenty- and thirty-somethings men and women. Want to guess how many people I saw wearing a skirt or dress? Two. One of the T-girls at our table and me. Not a single cisgender woman in the room was wearing one.

If I’d truly wanted to blend in, I should have worn slacks instead of the short black skirt I had on. And if I really wanted to pass, I should have committed fully: flats instead of high-heeled boots, socks instead of pantyhose, a plaid shirt instead of an animal-print top, boxers instead of a panty girdle, a T-shirt instead of a bra. Skip the makeup. Leave the wig, jewelry, and designer bag at home.

I would have passed effortlessly.

As a man.

That’s when I decided passing is wildly overrated.

If the choice is between dressing to pass and dressing to thrill, I’ll choose thrill every time. Dressing to pass is joyless. The clothes rarely make me happy, and the entire experience becomes an anxious audit: Do I pass? Did they clock me? What about now?

It’s exhausting. It drains all the pleasure out of being en femme.

When I dress to thrill, the opposite happens. I like what I see. I feel confident, expressive, alive. I’m not policing myself or monitoring strangers. I’m simply being me and here’s the delicious irony: that’s often when I pass anyway.

One of my favorite examples happened during outreach at Southern Connecticut State University. I started the day in three-and-a-half-inch stilettos but tossed a pair of flats into the car just in case. After shopping at the mall and visiting the first of two classes, the stilettos finally won. I headed back to the parking lot to change shoes.

That’s when I saw it: a university dump truck parked directly in front of my car. The driver was chatting with another university employee beside the truck.

Perfect. The classic nightmare scenario. Crossdresser versus Macho Guy, center stage.

Bracing myself, I made a beeline for the car and tried to disappear. Instead, the man standing beside the truck looked at me and said, warmly and unmistakably flirtatiously, “Good afternoon.” The driver smiled, lingered for a moment, and then drove off.

They flirted with me.

I wasn’t trying to pass. I was trying to get to my flats.

So now, when I go out en femme, I dress to thrill and show off my legs. If I pass, that’s fine. If I don’t, that’s fine too. Passing is optional.

Thrill is not.

Wearing Boston Proper

Wearing Boston Proper

Stuff 104: Carnegie Hall

By J.J. Atwell

How to Get There

You may be familiar with this story. A guy is hauling a violin case on the streets of New York, but gets lost. He asks a passerby how to get to Carnegie Hall. The stranger says, “Practice, practice, practice.”

Yes, it’s an old joke. But I think it applies to those of us who femulate as well.

Practice Your Presentation

As you might have guessed, that’s a lead in to today’s Stuff which is all about practicing so you make your best presentation. What do we need to practice? My list would certainly include:

• Doing makeup
• Dealing with long hair
• Walking in heels
• Having long fingernails
• Wearing a skirt
• Being conscious of your boobs 
• Mannerisms

Before actually talking about the individual items, I should be clear that my experience in dressing is actually somewhat limited. I’ve only been going out dressed for a bit more than three years. Before that I didn’t need to think about those things, but now that I get out in public, they have become important.

Let's Consider Some of Them 

My biggest need for practice is doing makeup. When you only dress about once a month that’s not really much practice. It’s easy to forget steps or remember what works best from past outings. 

I suppose I should just go ahead and try doing makeup even when not going out dressed. I could do that but it takes time and time can be hard to find. It takes me probably an hour from shower to full face. Happy to do that when I’m going out, but if I’m staying in and will have to wash it right off, it seems like a lot of work. So I don’t. And hence, I fail at makeup. Sigh. 

Dealing with long hair is an interesting adjustment. As a guy, I have a typical guy haircut. When dressed, my hair depends on the wig. You probably read about my adventure buying a new wig in Stuff #98. The new wig (see photo above) is quite different from the previous one and took some amount of re-learning. Things I notice most are how I need to hold my head when eating so I don’t get some hair in my forkful of food. Yuck. I also find I need to pay more attention when driving as the longer hair affects my peripheral vision, requiring me to turn my head further when checking for cars on either side. Another annoyance is that I’m always fiddling with the bangs so they aren’t in my eyes (a bit more hair spray should take care of that). 

Walking in heels is kind of a fun adjustment for me. Of course it depends a bit on how high the heels are, how narrow the heel is and if there is a platform. So each pair of heels can feel different. But mostly, we need to concentrate on our walk when we wear heels or flats. Swinging the hips a bit as we walk but not over doing that sway is important. Fortunately it’s easy to find time to practice walking in heels. 

I’ll Be Back

I know I didn’t address all the items I listed. Watch for them in a future installment Stuff. As always, comments are welcome either here on the blog or by email to Jenn6nov at-sign gmail dot com. JJ is always looking for more stuff, so if there is something you would like to read about please let me know!

Wearing Ann Taylor

Matt Damon femulating in the film The Good Shepherd.

I Only Dress Like A Woman When I'm Awake

Dad Was a Female Impersonator During the War

I grew up believing my father was an ordinary man shaped by extraordinary times. He was quiet, precise in his habits, and careful with words. He ironed his shirts meticulously, polished his shoes even when no one would notice, and corrected my posture at the dinner table with a gentle tap on the shoulder. I assumed these were remnants of military discipline. I was only half right.

It wasn’t until after his death that I learned the fuller truth, one he had carried as carefully as he carried everything else.

During the war, my father had not carried a rifle. He had carried a mirror.

He was stationed far from the front lines, assigned to a morale and intelligence unit that traveled between bases and occupied cities. Officially, he was a clerk. Unofficially, he performed. The unit staged revues, musical evenings, and cabaret-style shows meant to soften fear, distract boredom, and, occasionally, gather information. Women were scarce. So my father became one.

He learned quickly. How to pad the hips just enough to suggest softness without parody. How to move with economy, letting suggestion do the work. How to lower his voice without forcing it, how to let silence linger after a joke. He performed under a name that was not his own, one that never appeared in any record I’ve been able to find.

There is a photograph I discovered in an envelope tucked inside a book of war medals. In it, a young woman smiles faintly at the camera. Her hair is waved, her lipstick carefully applied. She looks self-possessed, almost serene. It took me a long time to see my father in her eyes. Once I did, I couldn’t unsee it.

He never spoke about those years directly. But suddenly, things I had dismissed as quirks took on new meaning. His comfort in women’s spaces. His fluency in unspoken rules. His insistence that strength and hardness were not the same thing. When I cried as a child, he never told me to stop. He sat with me until the feeling passed, as if he had learned long ago that emotions, like performances, must be allowed to finish.

I imagine him backstage during those wartime nights, adjusting a stocking, steadying his breath, listening for the cue. I imagine the audience, soldiers hungry for distraction, for beauty, for something unreal enough to make the war briefly disappear. I imagine how dangerous it must have been to walk back to his bunk afterward, still carrying traces of that other self.

After the war, he came home and put on a different costume: husband, father, provider. He wore it well. But I think he understood better than most that identity is not a single uniform you are issued once and keep forever. It is something you learn to assemble, piece by piece, depending on what survival requires.

He did not pass this story down to me in words. He passed it down in attitude, in tolerance, in the quiet permission to be more than one thing. Only now do I understand that his greatest act of courage may not have been what he did during the war, but how completely he returned and how much of himself he chose to keep hidden, yet alive.

My father was a female impersonator during the war.

And because of that, he taught me that masculinity was never as rigid as the world pretended it was.

Nota Bene: This is a work of fiction.

Wearing Lafayette 148

Artur Chamski femulating Malgorzata Walewska on Polish television's Twoja Twarz Brzmi Znajomo. Click here to view this femulation on YouTube.