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.