It started about four weeks ago. I got up and started getting ready for work, just as I do every morning. Now, normally, I dress in normal “boy clothes” for work, and then change into my “girl clothes” when I got home. This day was no different. I got up, ate breakfast, checked my email and social media feeds for the day, then went to get a shower. Then I went in the closet to start getting dressed.

But suddenly, something changed. I thought, you know, I really want to wear a dress today. Of course I’d thought that many times before, but this time I decided that I was finally going to do something about it. I decided to shut off the part of my brain that kept telling me all the reasons why I shouldn’t, and just go ahead and do it. I pulled on one of my favorite dresses. It was a cold day, so I put on some cute leggings. Then since I already had the dress on, I figured I might as well put on some makeup – so next thing I knew I had a full face of makeup.

Now was the time to make a decision – head out the door, or change back into boy clothes? For some reason I can’t explain, I decided to stay as I was. I pulled on some of my favorite knee-high boots, kissed my wife goodbye, grabbed my purse, and headed for the door.

Now, to be fair, this wasn’t exactly a secret to my coworkers. I have worn makeup to the office before. I’ve also worn “girl shoes” with my slacks and shirt. I even wore a whole girly outfit to the office Christmas party in 2019. Many of my coworkers knew that I cross-dressed. But there were still many mental obstacles to overcome. I work in a large building on a military base. If I went to work dressed, I wouldn’t just be seen by my normal coworkers, I would be seen by everyone. The guards at the front desk. The military folks in uniform in the halls. Everyone.

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But for some reason I made it. I’ve been doing a lot of mindfulness meditation lately, and I’m sure that helped. I just focused on the workday ahead of me. I think the crucial decision I made in my head was, “I’m not going to worry about it. If anyone else wants to worry about it, that’s their decision, but I’m just going to be myself and do my job.” And it worked! I drove in, got out of the car without hesitation, and walked into the building, and the rest is history. No one, and I mean no one, said a word, or even barely gave me a second glance. I did catch a few covert double-takes out of the corner of my eye, but the only comments I got were “hey, love that skirt!” from a few of the women in the office.

So, that was a few weeks ago. Since then I’ve dressed to the office about 8 or 9 times, and my confidence has grown tremendously. It has been so affirming! I love the way I feel in a dress, even though I don’t make any effort to pass as a woman. I can now walk the halls in complete confidence. I admit that I still feel some trepidation when going to the bathroom, but I’m sure that will pass with time. (I have decided to continue using the men’s room since I identify as male.)

My only regret in all this is that I didn’t think to take a picture, so I can’t show you my outfit. Maybe I’ll do that soon.

So, if I can do it on a military base, you can too! Remember, most people don’t care what you look like, and a surprising number will be happy for you. At least, that’s been my experience.

  • Have you ever done what I did and just said to yourself, “The heck with it, I’m a cross dresser and I’m just gonna wear a dress with some knee high boots to work today!” And then just did it?
  • When you dress en femme, do you use the ladies restroom or the men’s restroom? And how did the reaction go in either restroom if you met up with someone at the mirror?
  • Have you ever had a full time job where you were allowed to dress up as a girl every day when you went to work? If so, what kind of job was it and how did your coworkers react to you?

Thanks girls for taking the time to read my article. Please feel free to send in any comments in response to either my article or to one or more of the questions I’ve posed to you above!

Sincerely, Penny



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    Penny Farthing

    Musician, computer programmer, amateur genealogist, science fiction and fantasy nerd, and lover of cute skirts and sexy boots.

    Latest posts by Penny Farthing (see all)

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    Alexandra Love
    Active Member
    2 years ago

    I don’t work in an office but I do the grocery shopping and it has gotten to the point that I won’t go to the store without being fully dressed! Oh and I do use the ladies room. It is completely natural and has never raised an eyebrow!

    Amy Myers
    Noble Member
    2 years ago

    Well, I don’t work anymore but am not nearly as concerned about being out and about dressed as I once was, either people don’t care or notice and the ones that do don’t seem to mind. I’ve actually had many positive comments, either about my clothes or about me being myself. When I did work I believe I could have gone to work en femme as I worked quite a lot with the local arts community, and there were a number of other staff who lived some kind of an alt lifestyle. It was great to read of your positive… Read more »

    Active Member
    2 years ago

    I work as a chemical engineer doing emission monitoring at big boilers and industrial air filters for customers like municipal heat plants, steel manufacturers and paper mills among other industries and do wear at least some clothes that are regarded women’s apparel most every day for work both in the office and out at the customer’s sites. Usually l will go in skin tight stretch jeans and a blouse or feminine top, often with some flower print or embroidery. I also have side zipped slacks and leather look stretch pants. Wearing both bra with inserts, a padded girdle and a… Read more »

    Last edited 2 years ago by Marianne
    Peta Mari
    2 years ago

    Great story. Kudos for courage.

    We own our farm. I’m often enfemme driving the tractor, fixing fences, hunting, gardening etc.

    Dawn Judson
    Active Member
    2 years ago

    I am a performer. I have performed some events, en femme, but to be honest, they were Halloween parties or CD/TG events. I would love to “Just do it" for all my other performances, but my wife says she wants no one to know about this other side of me.

    When I go out, en femme, I try to avoid having to use a restroom, but when I do, since I appear to be a woman, I always use the women’s restroom. I’ve never had an issue.

    Sherri Remington
    Active Member
    2 years ago

    I am in complete envy of you, I hear you when you say nobody really noticed but my fear is in the small setting where I live it wouldn’t go well if I was. When I work on away jobs I do take full advantage and go public in what I think is in femme, a blouse, tight jeans, of course bra and panties and wearing flats and since I have long hair I make certain that it’s fashioned in a feminine way, and I feel great. I really like when I’m shopping and the sales person comes up behind… Read more »

    2 years ago

    Great, well done Penny I have never done gone the whole way at work as you did but to answer a couple of your questions : regarding the restrooms, yes, I always use the ladies when out en femme, with no qualms on my side and no reaction whatsoever from the ‘lady’ users. This is probably because I ‘pass’ reasonably well … although not completely under scrutiny. In outside life, not work, I do not hestitate at all to be myself, ie en femme, whether for meetings in the block where I used to live, going to the doctors, the… Read more »

    Tammy Rogers
    2 years ago

    That’s a great story I’m so pleased for you in my case I ware makeup and womens clothes to work but not heels or skirts but I really want to ty for sharing it might just help me ty again

    Trishia Snyder
    2 years ago

    About a year ago I had gotten a new primary physician and updated my med. profile there were more options one being transgender (why all of a sudden I did it I have no idea) so I checked transwoman, boy did that open more forms but it felt good to finally share it with someone. The CNA told me via e mail to feel free to come in dressed in what ever I am comfortable in I am referred to with a female name and pronouns . The Dr. asked if I wanted this in my chart and that anyone… Read more »

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