Wednesday, October 21, 2020

Third Time’s a Charm

Over the years, I went to work en femme on Halloween seven times. The first two times, my company invited us to wear costumes to celebrate the holiday and participate in costume contests. 

The third time, there was no invitation. I simply decided to show up at work in “office girl drag” and enjoy the day at work as a woman. And that third time was probably my best Halloween en femme at work experience because no one was expecting it and I fooled most of my co-workers with my femulation.

For example, when my boss arrived at work that day, I made a bee-line to her cubicle, saying “Happy Halloween” as I entered.

She looked up with a confused expression and it took about a half minute before she recognized me. She was ecstatic. She checked me out and gushed over my appearance.

“He shaved his legs.”

“He even did his nails.”

“I hate him – he looks better than me.”

She took my photo and e-mailed it to some of our colleagues in our other facility. And throughout the morning, she brought people to my cubicle to show me off.

I never saw her act like this before. She was enjoying my femulation as much as I was.

My boss also suggested I play a trick on our president’s administrative assistant, so when she showed up, I went into her office and said, “I am the new receptionist and you are supposed to train me.”

She was completely fooled. She said that no one had informed her of my training, but she was ready to have at it.

I felt a little sorry forever her, so before it went any farther, I asked, “Do you know who I am?”

She shook her head “no,” so I confessed and she was absolutely floored! She confessed that she really had no idea who I was nor that I was a male.

Returning to my cubicle, I heard the voice of a female co-worker who I had known for 16 years, so I paid her a visit.

“Happy Halloween,” I said as she looked up without any sign of recognition, then she recognized me. After she stopped gushing over me, she said that when she first saw me, she thought I was a former co-worker woman. She said the resemblance was striking.

At 10 AM, I had to attend a meeting (a “gemba”) concerning a new product. I walked into the middle of ten engineers standing in a circular fashion for the gemba, said “Happy Halloween” and they all smiled and took my appearance in stride. A couple of the guys admitted afterword that until they heard my voice, they had no idea who I was.

Another friend asked if he could take my photo sitting in his cubicle. I gladly agreed, he took it with his smart phoneand sent it to his wife claiming I was his new administrator.

After his wife learned the truth, she replied, “OMG!!!!!!! That is soooooo funny! He looks really good as a woman. I don't want her sitting in your cubicle.”

Five co-workers took my photo throughout the day and graciously e-mailed me copies. One co-worker said he was “speechless,” then added, “You missed your calling... you should have been a female impersonator.”

During lunch, I drove to the nearby Lowe’s home improvement store to get a replacement part for a piece of plumbing that failed after the storm the day before. I had no trepidation about going to Lowe’s and I found my trip very revealing.

Whenever I go to Lowe’s or Home Depot in male mode, I have to find and ask a store employee when I need help. Today, I had a male Lowe’s employee practically at my beck and call. When he saw me looking lost in the plumbing department, he asked what I needed and directed me to the exact location where the part was displayed. After I found what I needed, he came over and compared it to the old part I had brought along to make sure I got the right part.

That’s the power of a short skirt and high heels!   

Speaking of high heels, I wore them all day long (over 9 hours) and my feet felt fine. I guess sitting about two-thirds of the day helped. I did bring flats just in case, but I only put them on when I drove home.

I returned to work, ate lunch and felt tired; the 4:15 AM wakeup was beginning to take its toll.

I visited the two women in Human Resources who knew that I am transgender. The HR woman, who is approximately my age, was enthusiastic and said I looked “great,” while the 30-something HR woman acted as if nothing was unusual and said nothing about my appearance.

Another female co-worker I have known forever stopped by my cubicle in the afternoon and said I looked “sparkling.” She also commented that I looked better than she ever did even when she went to the prom. She wondered if anyone at work had busted “my chops” and I happily admitted that no one had.

Except for folks stopping by to look and/or take photos, the afternoon was quieter than the morning. Overall, I had a great day at work en femme. Not a discouraging word was heard; instead, I received a lot of compliments.

Next morning, my boss saw me and remarked, “Thank, God, you're dressed normal today.”

I responded, “What's normal?”

So, what’s your Halloween story? I’d love to read it and share it with my readers. And don’t forget to send along a photo or two from your holiday in heels.     

A very professional-looking ensemble from Venus for boys who work in an office.
A very professional-looking ensemble from Venus for boys who work in an office.

Ms. Ross Erin and Mr. Patrick Holbert posing for their wedding invitation.
You can read all about it here.


  1. I posted about my experience in my old blog.
    I came in and the receptionist asked if she could help me. I smiled, held up my badge and she started laughing. She was still laughing when I went through the secure door to the side where I worked.

    I walked up to a couple of coworkers who were yapping and stood there quietly until the female one looked at me and said something like "yes?" and I identified myself and she proceeded to take me around the building, making up a different name and story for each one ("this is Stephanie. She's the new marketing assistant" or "this is Janet. She's from our Cambridge office").

  2. Stana, I'm not trans but I call your outings to Home Depot/Lowes "playing girl" and do something of the same. As a woman who builds houses for a hobby letting the guys demonstrate their knowledge always adds to mine.
    Theresa in Tucson

  3. Hi Miss Stana I thought you might enjoy this Vintage Hanes proportioned fit image for a future photoshop :)

  4. the way your Halloween coworkers (female)were so positive jives with my contacts with gals. wonder why they are so enthusiastic-what do you think?

    1. In general, I think that women are happy to see enlightened men join their team. Exceptions are certain religious fanatics and the some spouses of those men.