Today was a big step for me.

I went to work all dressed up. In the day time. While other people were at the office. I’ve gone into work after hours before, but I decided to go all the way today.

As most of you can relate, crossdressing brings with it a wide variety of emotions. Sometimes you feel it’s wrong, and other times it seems right. Sometimes there’s guilt and shame and other times its exultation. You’re scared, you’re excited, you can’t wait to get out the door, and you feel like you need to get somewhere safe.

Some of this is certainly from crossdressing itself, but I expect a lot of this comes with the feminine territory. I expect GG’s feel this all the time. The pressure on them to look a certain way tends to be much stronger than it is for men. As a guy, you can get ready in a couple of minutes. Women have to spend more time. Women experience more danger than men. As a young man, nobody ever taught me how to walk safely to my car through a dark parking lot at night. Young women face this all the time.

En Femme Style

One evening after a late class I was teaching I headed to my car and came up on one of my students going to her car. I could tell by her body language she was nervous. I thought about offering to walk her to her car to help her feel safe, but as she realized there was someone walking behind her (not close), she hurried to the safety of her car. I have so much more empathy for this as Sarah.

Anyway, back to today’s adventure.

I got up this morning and really wanted to go to work dressed up. I wouldn’t have hesitated so much, but my wife isn’t a fan of my alternative wardrobe so I usually only dress when she’s gone. She was planning to be home all day. She asked me if something was bothering me, and I told her what I wanted to do. She said, “Go ahead, it’s okay.” She said that since she knows I dress up anyway; it’s all the same and that maybe it would help her get used to the idea. I was super excited.

Until I had to shave.

I haven’t dressed in a while, so this wasn’t quick. Probably all of us have that feeling of hesitation and doubt as we’re getting ready. It can be easier to deal with nerves when you just jump in and go for something, but you can’t shave a hairy chest and legs in a rush, so there’s lots of time to reconsider and back out. I was nervous as I got ready, but I never cut myself (life goal accomplished). I’m the type who thinks you should do what you say you’re going to do and stick with things, so the fact that I had made the decision to go got me through the nerves.

The closer I got to being ready, the better I felt. Once I left the bathroom and headed for the heels, I was feeling really confident. My wife was surprised at how good I looked (white professional blouse, red pencil/midi skirt, beige high heels, long black down puffer). I was a bit wobbly on the heels at first but once I remembered to walk a bit slower it all came back. I grabbed my puffer and headed out. I felt so comfortable. All the nerves were gone as I drove to the office. I parked further away than normal so I’d have an excuse to take a bit longer getting to my building. Absolute confidence and ease. It was so much fun.

Actually, it still is. I’m writing this from the office and feeling quite at peace. My office is fairly private, and nobody has really seen me yet. We’re all weirdos here. I’m sure no one will care. I’m kind of hoping someone will come in or that the department chair will call me in to discuss something. It would be nice to get asked to lunch (not as a date, just as colleagues.)

Maybe I should go check my mail box in the main office?



More Articles by Sarah Kanter

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    Samantha Joan
    Active Member
    1 year ago

    Hey Sarah

    Hope this reply finds you well.

    What a brilliant article, thank you for sharing. I am sure the occasion will come around for a meeting or a colleague catch up soon, would love to know how that went.

    For me, my office was my safe place. I would be dressed at least twice a week. I do remember that first time and how nervous I was but that soon drifted off and I became more confident.


    Samantha x x x

    Trisha Lilly Hibbert
    Active Member

    Hi Sarah, your story resonates with me. My first public outing was at work. I still remember the reaction I got when I showed my colleagues Trisha. Then I went shopping after my shift. It felt like I was walking on air.

    Layla Jones
    Layla Jones
    1 year ago

    Well done you sounds like a dreamy day and a lovely read thanks layla x

    Deborah Sullivan
    Trusted Member
    1 year ago

    I know what a wonderful experience can feel like and hope more girls here get to share that feeling too

    Lucinda Hawkns
    Trusted Member
    1 year ago

    thank you sharing your journey, it must of been really nice to have your wife tell you go ahead and dress up and giving you a complement. too bad no one sees you dressed up at work! it would be a really good thing to have other employee’s see you dressed up and maybe give you a complement. wish my wife would let me dress up and be in same room as her when no other child is home, she lets me dress up but no help or see me dressed up, but she has seen me getting dressed up… Read more »

    Jane Don
    Active Member
    1 year ago
    Reply to  Lucinda Hawkns

    Yup-Society is Strange–Women are no longer required to Look really pretty & or Feminine-They can be as masculine or ambiguous as they choose–but “Men” are Supposed to present as Masculine no matter what–Women Dressing like men- are accepted — Even with children around —

    Samantha Jo
    1 year ago

    Hi Sarah
    What a lovely experience it must have been for you, I am in the process of building up to the time when I can leave the house as Samantha and your story has given me that little bit more confidence to do it.
    Thank you

    Jane Don
    Active Member
    1 year ago

    WoW-I’m sure I’m not the only Gurl who envy’s you–Good going-

    RJ Cole
    1 year ago

    That’s fantastic to read, well done!

    Bobbi Watt
    Active Member
    1 year ago

    Thank you Sarah we need to be seen .

    Would love your thoughts, please comment.x
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