Halloween is “National Crossdresser’s Day,” so they say. I guess there is some truth in that because my first public crossdressed outing was on Halloween and I know many other crossdressers also poked their bewigged heads out of the closet for the first time on October 31. And over the years, I have continued to crossdress on Halloween to attend parties given by friends and COS. But, Halloween 2000 was different.
One week before Halloween, my company announced that they were sponsoring a day of Halloween events including a costume contest. In all my years of being gainfully employed, no employer of mine had ever sanctioned wearing costumes to work on Halloween. I know some of you have gone to work en femme on Halloween and I often considered it, but I never had the nerve to do it. However, this year, I could go to work en femme with the blessing of the boss! T’was a crossdresser’s dream-come-true.
There was no doubt that my costume would be en femme, but how en femme was the question. I considered my options and decided to dress appropriately for my workplace, which is an office. My costume would be “office girl drag.”
I had a plenty of outfits that qualified as office girl drag, so I went through my stash to decide what to wear. I narrowed my choices down to three outfits. To make the final decision, I slipped into my unmentionables and modeled each outfit. My wife and I agreed that the black print, short-sleeved, knee-length sheath looked best. To round out the ensemble, I chose tan pantyhose and a pair of black patent pumps with 3-1/2-inch spike heels.
The night before Halloween, I prepared for the next day. I depilated, combed out my wig and laid everything out so I could get ready as quickly as possible Halloween morning. I turned in early because I had set the alarm clock for 4:45 AM to give me enough time to depart for work at 7:15 fully made-up and dressed. However, turning in early did no good because I was so excited I had a hard time falling asleep. It was after 2 AM before I finally nodded off and I woke up 15 minutes before the alarm clock was set.
I got up, shaved, showered and applied my makeup. For a change, I made no makeup errors and was finished by 6:15. I put on my undies, dress, shoes and wig, then I checked myself out in a full-length mirror. Was that Nicole Kidman’s reflection in the mirror? Not quite, but when I squinted real hard, I thought I saw Nicole Kidman’s mother.
Last thing to do was my nails. I glued press-on nails to my pinky and ring fingers, then I had an incredibly hard time gluing the nails to my middle fingers. None of the press-ons fit quite right and the glue could not make up the difference. Time was running out, so I decided to forgo the nails. After removing the press-ons from my pinky and ring fingers, I grabbed my purse and hit the pavement.
The commute was uneventful and I arrived at work 15 minutes early. I exited my car and walked to the main entrance enjoying the feminine beat of my heels clicking on the sidewalk.
Inside, the first people I encountered were our receptionist and a woman from Human Resources, who were lining up pumpkins for the carved pumpkin contest. At first neither of them recognized me. Then, they both recognized me and started gushing over my costume. So far, so good.
I went upstairs to my cubicle. Since I was early, there was no one around to see me, so I went to the cubicle of one of my best friends at work (she is one of the few people who gets to work earlier than I). I stuck my head around the corner of her cubicle and said, “Trick or treat.” She was floored!
After she regained her composure, she began calling me “Stella” and insisted on escorting me to the cubicles where other early birds were already at work. Our first stop was her boss, who had been with the company about six months. I don’t work directly with him, but he is only three cubicles away from me and we cross each other’s paths each day. My friend pushed me into his cubicle and he had no clue. At first he thought I was a new female employee, but my friend blew my cover, “Don’t you recognize him?” He didn’t until I explained that I was the guy three cubicles away.
And that was the way it went all day long. A tall woman in a Halloween costume environment is a dead giveaway. As a result, the majority read me as a man in drag, but did not know which man until I showed them the mug shot on my security card. On the other hand, a minority did not read me at all including some folks that I work with on a regular basis.
By mid-morning, the word was out that there was a guy in drag upstairs and a procession of onlooker began marching up to my cubicle to check me out. (No other guys appeared in drag. In fact, only a handful of guys wore costumes at all. On the other hand, the woman had a lot more Halloween spirit and approximately 1 out of 4 women appeared in costume.)
In general, women loved my costume. Some were amazed that I shaved my legs and my arms. Others complimented me on my makeup and some asked, “Did your wife do your makeup?”
“No, I did it myself,” I responded, which caused further amazement.
A few remarked that I should quit my job and become a professional female impersonator! One woman said, “I made her day,” and she returned to my cubicle three times with two or three new onlookers in tow each time. A pretty administrator remarked, “You look better than most women I know.” That made my day!
I don’t think I fooled everyone. A few women gave me knowing looks… like they knew I looked too good to have only done this once. But, I didn’t mind.
On the male side, the majority appreciated my costume, but there were two or three who seemed to be phobic about it… typical macho twaddle, I guess.
Shortly after getting to work, my pantyhose began running like crazy! I don’t know if they were defective or I was careless, but by 10 AM, I had three runs that were getting bigger by the minute. I wanted to look my best, so I left the building for a few minutes and drove to a nearby CVS to buy a new pair.
Now, this is the scary part because the CVS was not having a Halloween costume contest. I parked the car and walked into the CVS passing a handful of people who paid me no mind. I entered the store and to avoid causing a commotion, I went to the first saleswoman I saw and explained that I ran the pantyhose of my Halloween costume and needed a new pair.
“Hosiery is in aisle eight, Ma’am,” she replied unfazed by my Halloween costume hint.
I guess I was not going to cause a commotion, so I went to aisle eight, picked out a pair (only $1.99), then I went to the register where the same saleswoman rang me up without a clue.
Now, here is the amazing part. I never used a femme voice. I spoke in my normal male voice, which is admittedly soft-spoken, but definitely male. I guess the saleswoman’s eyes convinced her that I was a woman no matter what clues her ears might be picking up. (I had read about this phenomenon, but did not believe it until I actually experienced it.)
I returned to my office and waited for the results of the costume contest. A lot of people said they would vote for me and I guess they did because I won. I thought there were three or four costumes that were better than mine, but I guess having the guts to wear the costume I wore was that little extra that pushed me over the top.
I felt a little guilty about that because it did not take any guts to do what I did. This was something I wanted to do for a very long time. I also felt like I cheated a little because this wasn’t a costume I put together overnight. I’ve had practice dressing like this for years.
I’ll admit that I did have some qualms about possibly losing the respect of some of my colleagues. But when I thought about it, if somebody lost respect for me because I crossdressed on Halloween, then I don’t want their respect. So, qualms be damned! Tighten that corset as tight as you can. Today you are a woman!
I made one fashion blunder… my choice of footwear. I had not worn that particular pair of high heels in such a long time that I had forgotten why I stopped wearing them. Because they hurt a lot in a very short time! I have other pumps with the same heel height and even higher that don’t hurt like that pair did. The only saving grace is that I did not have to get up and walk around too much. I could just sit at my desk and pose for my admirers whenever they showed up.
However, I regret that I did not wear more comfortable shoes because I wanted to go to the mall, have lunch at the food court and do some window-shopping. But by noon, my feet were so hobbled that walking around the mall would have been very ugly.
I also had a fashion revelation. Wearing a tight corset all day was quite painless. The corset did inhibit movement, but it did not cause any aches or pains (like my shoes and clip-on earrings), while improving my figure immeasurably.
I had the time of my life. I wished the day would never end, but it did and now I have a lot of wonderful memories about my first day at work en femme.
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| Wearing Shein |
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| Jordan Peele and Keegan-Michael Key femulating on television’s Key and Peele. |
