You Should Have Been a Girl

When I was young, I occasionally heard words that were probably intended as teasing, but sounded more like encouragement to me:

“You should have been a girl.”

Perhaps an aunt thought I was too pretty for a boy. Maybe someone admired my long eyelashes or commented that my legs were better shaped than most girls’ legs. At other times, it may have been my quiet voice, gentle disposition or mannerisms that were considered insufficiently masculine.

Whatever prompted the remark, it always caught my attention.

I suspect that many boys who grew up to become crossdressers heard something similar. In those days, children were expected to fit into clearly defined gender roles. Boys were supposed to be rough, loud and interested in sports. Girls were supposed to be pretty, graceful and well-mannered. Any boy who wandered a little too far into the feminine column risked being told that he should have been a girl.

Most boys probably regarded the comment as an insult. Some tried to prove it wrong by becoming more masculine. But for a budding femulator, the words could have a very different effect.

They might feel like a compliment.

A boy already fascinated by dresses, high heels, makeup or the women in his life might quietly wonder whether the adults had noticed something. Did they see the girl he sometimes imagined becoming? Was his femininity showing even when he was dressed as a boy?

Being told that you had pretty eyes or shapely legs could also provide a little hope. Perhaps femininity was not completely beyond your reach. If your face was pretty enough or your legs were good enough, maybe someday you really could look like a girl.

Of course, hearing those words did not make anyone a crossdresser. Plenty of pretty boys with shapely legs and gentle mannerisms grew up with no desire to wear women’s clothing. The remark merely had special meaning for those of us whose feminine interests were already waiting below the surface.

Years later, after we finally slipped into a dress, pulled hosiery over those supposedly shapely legs and applied lipstick to that supposedly pretty face, we may have remembered the old prediction.

“You should have been a girl.”

Perhaps they were not entirely correct. I did not necessarily want to stop being a boy forever. But I certainly wanted the opportunity to find out how convincingly—and how happily—I could become a girl for a while.

Looking back, I sometimes wonder whether the people who said it realized how closely I was listening. What they considered an offhand observation became something I stored away and treasured. During the years when I doubted my ability to look feminine, I could recall that someone once saw femininity in me without my wearing a dress, wig or makeup.

That was encouraging evidence.

And when I finally saw my feminine reflection looking back from the mirror, it seemed that the people who had teased me years earlier had been onto something.

Maybe I should have been a girl.

Or perhaps I was simply fortunate enough to discover that I could enjoy being both.

Wearing Walter Baker

Guymon (Oklahoma) High School womanless beauty pageant contestant (1966)

A Generation Apart

Crossdressers of my generation often have a very different relationship with dressing than millennials and the generations that followed us.

Baby boomers and those who came before us, grew up when the rules were unmistakable. Boys wore boys’ clothes, girls wore girls’ clothes, and anyone who crossed that line risked ridicule, punishment or worse. A boy interested in dresses, makeup or high heels quickly learned that such interests had to be hidden.

So we hid.

Many of us accumulated secret wardrobes, dressed only when nobody was home and became experts at covering our tracks. We invented excuses for buying women’s clothing and worried constantly about being discovered. Even when dressing brought us enormous happiness, it was often accompanied by guilt, fear and the nagging question, “What is wrong with me?”

Eventually, the word “crossdresser” gave many of us a useful identity. It told us that we were not alone and helped distinguish what we did from our sexual orientation or a desire to transition. Support groups, newsletters, conventions and later, the Internet allowed us to meet others like ourselves.

For many older crossdressers, presenting convincingly as a woman became the goal. We practiced walking, talking, applying makeup and coordinating outfits. Passing was not merely an accomplishment; it could also be protection. If the civilians saw us as women, we could go about our business without unwanted attention.

That background may also explain why many boomer crossdressers favor a very traditional presentation. Dresses, skirts, hosiery, heels, jewelry and carefully applied makeup represent the femininity we admired while growing up and were forbidden to experience.

Millennials entered a different world.

They grew up with looser dress codes, greater LGBTQ+ visibility and a much broader understanding of gender. Many younger people do not believe that clothing should be divided strictly between male and female. A young man might wear a skirt, makeup or nail polish without considering himself a crossdresser at all.

Instead, younger people may identify as genderfluid, gender-nonconforming, nonbinary or queer. Some do not bother with a label. They simply wear what they like.

This can create an interesting generational divide.

An older crossdresser may spend hours trying to pass as a woman, while a younger person may wonder why passing is necessary. The older person may enjoy a complete transformation from male mode to female mode. The younger person may combine masculine and feminine elements in the same outfit without feeling any need to become one or the other.

Neither approach is wrong. They simply reflect different experiences.

We boomers learned that crossing the gender line was dangerous, so we tried to cross it as carefully and convincingly as possible. Younger generations are more likely to question why that line exists in the first place.

Of course, these are broad generalizations. Some boomers have enthusiastically embraced newer ideas about gender, while some millennials love nothing more than getting completely dolled up in a dress and heels. Younger people also continue to face rejection, discrimination and genuine concerns about personal safety.

Still, the central difference may be the question each generation learned to ask.

Older generations often asked, “What is wrong with me?”

Later generations are more likely to ask, “What feels right for me?”

That change did not happen by accident. Earlier crossdressers ventured out, organized support groups, shared their stories and gradually became visible. By leaving our closets, we helped make the world a little safer for those who followed.

Now younger generations are taking the next step. They are questioning whether clothing needs a gender and whether anyone should have to enter a closet in the first place.

Wearing Frame

Womanless beauty pageant contestant at Glen Oaks High School, Baton Rouge, Louisiana

Womanly Yours

A Full-Time Job

One of the attractions of crossdressing is the transformation. With the right clothes, makeup, wig and accessories, the fellow in the mirror disappears and a woman takes his place.

It is magical—but magic requires maintenance.

A civilian woman may put on lipstick without giving it a second thought. A crossdresser applies lipstick, checks the corners, blots it, checks her teeth, checks the mirror again and then wonders whether the shade looks different under fluorescent lighting.

Before leaving home, I conduct an inspection that would impress the Federal Aviation Administration:

• Wig secure?

• Earrings attached?

• Lipstick even?

• Stocking seams straight?

• Skirt behaving itself?

• Handbag packed?

• Male wallet removed from back pocket?

• Price tag removed from new dress?

That last item is especially important. Nothing spoils a sophisticated entrance like trailing a tag that reads “CLEARANCE—70% OFF.”

Once out in the civilian world, the maintenance continues. Lipstick disappears during lunch. Hosiery develops a run for no apparent reason. Earrings loosen. False eyelashes threaten to abandon ship. A wig that looked perfect at home suddenly seems crooked in every restroom mirror.

And then there is the beard.

You can shave close enough in the morning to remove the top layer of skin, apply enough foundation to resurface a driveway and still discover a hint of whiskers by midafternoon. At approximately 3:30, the face begins announcing, “He’s back!”

In a future when feminized men fill the offices, the men’s room may become a very busy place late in the afternoon. Instead of discussing baseball while standing at the urinals, the fellows will line up at the mirrors with electric razors, powder compacts and lipstick.

“May I borrow your concealer, Bob?”

“Certainly, Jim. And your skirt is caught in your pantyhose.”

“Thanks. I hate when that happens.”

Of course, handbags present their own problems. Men often joke that women carry everything in their purses. Crossdressers know why. We need lipstick, powder, a comb, tissues, spare hosiery, nail glue, breath mints, an emergency sewing kit and enough cosmetics to repair the transformation following a minor natural disaster.

The handbag grows heavier as the day progresses, although nothing is ever added to it. I suspect handbags manufacture additional contents when no one is looking.

High heels require maintenance, too—not mechanical maintenance, but personal maintenance. After several hours in four-inch pumps, my feet begin sending strongly worded complaints to management. Nevertheless, I keep smiling because beauty is pain and because the comfortable shoes are in the car, three blocks away.

Despite all the inspections, adjustments and emergency repairs, I would not trade the experience. The effort is part of the fun. Every successful outing feels like opening night, with yours truly serving as star, director, costume designer, makeup artist and stage crew.

Crossdressing is hard work, but I love my job.

Wearing Shein

Alan Hale (center) and other gents femulating in the 1943 film This Is The Army.
Click here to view this film on YouTube.

A Time and Place

I encourage crossdressers to leave the closet and experience the world as women. After spending too many years hiding, I learned that most of my fears about going out were far worse than anything I actually encountered.

Nevertheless, there is a time and a place for everything, even femulating.

The mere presence of a crossdresser does not make a place or event inappropriate. If you regularly live as a woman, you should be able to attend most places and events as yourself. The important questions are whether your clothing suits the occasion and whether your appearance will unintentionally make someone else’s moment all about you.

For example, a wedding is not the ideal occasion for your public debut unless the couple knows and approves. A wedding belongs to the bride and groom. Showing up en femme for the first time might attract attention that should be directed toward them.

The same consideration applies to funerals and memorial services. These occasions call for quiet respect, conservative clothing and as little distraction as possible. If the deceased’s family knows you as a woman, attending en femme may be perfectly appropriate. If they do not, that may not be the best time to introduce them to your feminine side. However, if you knew only the deceased and are unacquainted with the family and other mourners, attending as a conservatively dressed woman may be acceptable because no one would know you otherwise.

Religious ceremonies, graduations, award presentations and important family celebrations also require good judgment. Again, crossdressing is not inherently disrespectful. Turning someone else’s meaningful occasion into your personal coming-out party may be.

Court appearances, official government business and situations involving identification or security can require additional thought. Your appearance should reasonably resemble the photograph on your identification, and you should be prepared to respond calmly if questions arise. Confidence is helpful; confrontation is not.

Some places may be physically unsuitable rather than socially inappropriate. A construction site, hiking trail or muddy outdoor festival probably calls for practical footwear and clothing. Four-inch pumps may look wonderful at the mall, but they are not safety equipment.

There are also events where crossdressing is encouraged, but presenting as an ordinary woman might still be misunderstood. At a costume party, for example, people may assume that your carefully coordinated outfit is merely a joke. That never stopped me on Halloween, but it is something to anticipate.

The simplest rule is the same one most women follow: dress appropriately for the place, the weather and the occasion. Do not wear a cocktail dress to a picnic, a miniskirt to a funeral or stilettos to tour a factory.

And do not use someone else’s special day to test your passing meter.

Going out en femme should be enjoyable, natural and respectful. If your presence will not endanger anyone, violate a legitimate rule or steal attention from the person being honored, there are very few places where it is truly inappropriate.

Usually, it is not crossdressing that is inappropriate.

It is simply wearing the wrong thing at the wrong time—and women have been dealing with that question forever.

Wearing Boston Proper

Alan Hale, Jr., Jim Backus and Russell-Johnson femulating on television’s Gilligan's Island (1967).
Click here to view this femulation on YouTube.

Found Couldn't Find A Thing To Wear

Sunday evening, I was browsing videos on YouTube when I came across this YouTube Short.

Wow! It looked very familiar. I was sure I had created an image illustrating the same joke, so I searched through my collection and found the original, which I had created in December 2024.

The video is a near-perfect animation of my image, using the exact same words, background,  dresses, etc.!

I have to admit, I was impressed. I just wish whoever animated my image had let me know. I would have enjoyed seeing what they had done—and would have appreciated being given credit for the original.

Soldier femulating during the "Ladies of the Chorus" musical number in the 1943 film This Is The Army.

Wearing JustFab

Firsts

One day last week, the disc jockey on a local FM oldies station asked listeners to call in and name the first record, LP or 45, they ever purchased.

Listening to their responses was a trip down memory lane. Many of their “firsts” were records that I had also purchased.

For the record, the first 45 I ever bought was “Quarter to Three” by Gary U.S. Bonds.

My first LP purchase was “Beach Boys Concert.”

That got me thinking about some of the other firsts in my life—like my first car, a 1972 Buick Opel 1900.

And my crossdressing firsts—like the first dress that I actually purchased rather than borrowed.

Or my first wig, which came from Frederick’s of Hollywood instead of my sister’s closet. 

Those were just a few of my firsts.

And so it goes.

Wearing Boston Proper

Cary Grant considering a wardrobe change in the 1940 film My Favorite Wife.

Handbag Ha-Ha’s