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Working Woman

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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.

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