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.

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.

Crossdresser Superstore

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?



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    Chuck Lund
    2 months ago

    That’s so awesome I go to work everyday in makeup but not my girl clothes except on Friday I have this shirt that has a lot of straps and shows my shoulders I do wear that on casual Friday

    Penny Farthing
    2 months ago

    Congratulations! Doesn’t it feel wonderful? I took the big plunge a few weeks ago and have been dressing at work about every other day. I think today will be my 8th or 9th time. My confidence level has gone up about 3000%!

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