My Halloween at Work En Femme

Every October, I thought about going to work crossdressed on Halloween. But thinking about it and actually doing it are two very different things.

Then one October, Human Resources announced that it would hold a costume contest on Halloween, with a major prize offered as an enticement. I didn’t need one. The opportunity to go to work en femme was enticement enough!

I already had everything necessary for an “office girl drag” costume. Actually, I had enough clothing for several office girl costumes, so all I had to do was decide which one to wear.

It never occurred to me to dress less than authentically so that the civilians wouldn’t become suspicious. On Halloween morning, I got up early and did my best to look like a genuine office girl. I wore a black-print, knee-length, short-sleeved sheath dress; tan pantyhose; a bra, waist cincher and panty girdle; black pointed-toe pumps with 3½-inch heels; an auburn wig; jewelry; full makeup; and a black handbag.

My wife looked me over, gave me a thumbs-up and sent me on my way.

When I arrived at work, I parked the car but hesitated before getting out. Finally, I put on my big-girl panties, stepped out of the car and entered the building.

Our receptionist and a woman from Human Resources greeted me in the lobby. Instead of buzzing old Stanley through the security door, the receptionist looked at me and asked, “May I help you?”

They didn’t recognize me until I revealed my identity. Then they began gushing over my costume!

I went upstairs to my cubicle. Because I had arrived early, few people were around to see me. One of my best friends at work was among the handful of employees who usually arrived before I did, so I went to her cubicle, stuck my head around the corner and said, “Trick or treat.”

She was floored!

After regaining her composure, she began calling me “Stella” and insisted on escorting me around to visit the other early birds. Our first stop was her boss, who had been with the company for about six months. I didn’t work directly with him, but his cubicle was only three spaces away from mine, and we crossed paths every day.

My friend pushed me into his cubicle, and he had no clue who I was. At first, he assumed I was a new female employee. Then my friend blew my cover.

“Don’t you recognize him?”

He didn’t—not until I explained that I was the guy who worked three cubicles away.

And that was the way it went all day.

In an office filled with Halloween costumes, my height was a clue. Most people read me as a man in drag, but they couldn’t figure out which man until I showed them the photograph on my security card. On the other hand, a surprising number of people didn’t read me at all—including some with whom I worked regularly.

By midmorning, word had spread that there was a guy in drag upstairs, and a procession of onlookers began marching to my cubicle to check me out. No other men appeared in drag. In fact, only a handful of men wore costumes of any kind. The women had much more Halloween spirit, with approximately 25 of them arriving in costume.

In general, the women loved my outfit. Some were amazed that I had shaved my legs and arms. Others complimented my makeup, and several asked, “Did your wife do your makeup?”

“No, I did it myself,” I replied, which caused even more amazement.

A few people suggested that I quit my job and become a professional female impersonator. One woman said I had made her day, then returned to my cubicle three times, bringing two or three new onlookers with her on each visit.

A pretty administrator remarked, “You look better than most women I know.”

That made my day!

A few women gave me knowing looks, as though they suspected I looked too good for this to be my first time. But I didn’t care.

Shortly after arriving at work, my pantyhose began running like crazy. I don’t know whether they were defective or I had been careless, but by 10 o’clock, I had three runs that were growing larger by the minute. I wanted to look my best, so I slipped out of the building and drove to a nearby CVS to buy another pair.

This was where the day became even more interesting.

I parked the car and walked into the store, passing several people who paid no attention to me. To avoid causing a commotion, I approached the first saleswoman I saw and explained that I had gotten a run in the pantyhose I was wearing with my Halloween costume and needed a replacement pair.

“Hosiery is in aisle eight, Ma’am,” she replied, apparently unfazed by my mention of a costume.

Evidently, I wasn’t going to cause a commotion.

I went to aisle eight, selected a pair—only $1.99—and returned to the register. The same saleswoman rang up my purchase without displaying the slightest suspicion.

Here is the remarkable part: I never used a feminine voice. I spoke in my normal voice, which is admittedly soft-spoken but definitely male. Apparently, the saleswoman’s eyes convinced her that I was a woman, regardless of what clues her ears might have been receiving.

I returned to the office, changed my pantyhose and waited for the results of the costume contest. Many people had told me they planned to vote for me, and I guess they did because I won.

I thought three or four costumes were better than mine, but perhaps having the nerve to wear what I wore provided the little something extra that pushed me over the top.

I had the time of my life. I wished the day would never end, but of course it did.

What remained were many wonderful memories of my first day at work en femme—and the knowledge that thinking about doing it had finally become actually doing it.

Wearing Boston Proper

Gary Busey femulating in the 1998 film Rough Draft.