Monday, April 15, 2024

Working Woman

If you have been following along, you know that I crossdressed at work for Halloween seven times. The first two times, the company had a costume contest and encouraged employees to come to work in costume. The last five times, the company was not sponsoring any Halloween events, but that did not stop me and I dressed in “office girl drag” five more Halloweens in a row. And I would have continued the tradition if the company had not offered me an excellent early retirement package in 2017.

Or would I?

During the last few years that I was employed, I was hemming and hawing about working en femme full-time. I had already come out to Human Resources and they were ready to support me whenever I decided to show up dressed as an office girl for real. My manager and her boss were on my side, too and I discovered later that almost everyone in the building was waiting for the other high heel shoe to drop. But I never pulled the trigger.

The main reason was that I thought that I could not sell the idea to my wife. In retrospect, I don’t think it would have come as a surprise to her. I already went out just about everywhere (except work) en femmeAnd the last few Halloweens, she wondered out loud if my co-workers suspected anything. I told her I had no idea what they thought only to learn later that that ship had already sailed.

If I had not taken early retirement and worked until I was 70, maybe I would have finally pulled the trigger and my Halloween dress-ups would only be quaint memories. Who knows! But I do regret not pulling the trigger when I could have.

(By the way, I was inspired to write this piece by the lady in today's Femulator slot below.)

Source: Ann Taylor
Wearing Ann Taylor

April Flowers runs her own business en femme with nine people reporting to her and nary a word about her gender from her clients.


  1. Question, how receptive is any of the wives to a husband being en femme all the time at home? Any friction? My wife said, if she wanted to be married to a woman, she would have married a woman.

    1. My observation is that about 5% of the wives are totally accepting, 55% DADT and the rest no way. ----Paula G

    2. When my wife was alive she did not mind my wearing dresses at home, and she also didn't mind when I went out alone en femme. But if we both went out together she insisted on my wearing men's clothes.


    3. I have the same response from my wife , she said if she wanted to be married to a woman she would.
      I have cross dressed for a long time my wife knew and she encouraged me to do so , it was until I decided to go out and hang out with other girls that some friction started . Never escalated to a fight but I can see a change in personality in her every time I go out which is more often.
      Now she thinks I’m gay. lol

  2. Stana, unfortunately, you didn’t work a few extra years, in case the sisters here at the Femulate don’t know. Stana and I work together for the same company and have been acquainted through this blog for many years. It wasn’t until the very end of her career that I put together some subtle hints that she mentioned about her workplace when I realized that we were working for the same corporation. I sent her an email from my mail account asking her if she knew Paula Gaikowski. Big smile, gosh, the two of us could’ve made the whole place abuzz. Paua G

  3. Stana, you didn't crossdress on Halloween. You crossdressed the other days. This is the real you.

  4. A few days ago, I wrote about my first Halloween at age fifteen where, with mom's help, I dressed up as a girl and had a wonderful time in spite of the teasing

    As a young adult my first job out of college was at a bank in Indiana. They encouraged costumes if Halloween was on a work day. One year some of the tellers came up with the idea of all of them coming as pageant girls. They asked me if I wanted to do it along with them.

    I feigned surprise and reluctance, but said I would do it. A couple of my female co-workers took me under their wing and helped me get ready for the big day. They borrowed an evening gown for me to wear and all the proper undergarments. They loved helping me. My dress was lavender chiffon and silk. Probably someone's old bridesmaid's dress, but I loved it.

    Each of the pageant girls wore sashes with cutesy names or slogans. Mine, which I didn't care for, read Miss Steak. (ha ha)

    It was a fun day at the bank and I got a lot of attention from the girls and customers. I have to admit that it was a long day in full make up, pantyhose, and heels. When I finally got home I was more than happy to become Michael again.


    1. You lucky dog! When I was young I would have loved it to have a chance like that. Even if it was for a Halloween party female attention would have been a dream fulfilled. My female supervisor had her husband wear one of her old prom dresses, heels and wig for a Halloween party. He was a short man, but average height for a woman. All the women in the office wanted to see pictures. When the "Walk-A-Mile-In Her Shoes" charity event was held in the downtown business area all the women flocked to the street to watch and try to figure out who was a cross-dresser; eying the ability to walk without stumbling in high heels. All that attention, but if a husband were to be a cross-dresser, when would that playful attention make a quick 180 degree turn?

  5. If I worked for a company that promoted crossdressing on Fridays, you can be sure there would be nothing casual about my outfit! Pencil skirt, crisp white blouse, stockings, stilettos, my best jewelry, hair, and makeup. It would be more like fabulous, formal, feminine Fridays!