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.

Join Our Community-cdh

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

View all articles by Sarah Kanter
The following two tabs change content below.

Sarah Kanter

I’m Sarah, and I’m a newbie. I’ve tried things on sporadically (and secretly) over the years, but only last year decided to jump into dressing up “for real.” I finally bought some clothing of my own and a wig and ventured out for a walk around the campus where I work at night. I don’t have to tell you all how much fun it was. Soon after, I was going regularly to the office (in the evening) and grocery shopping en femme. For those of you worried about going out for the first time, if you dress up with a little bit of class, no one seems to care. It’s almost disappointing how little people actually notice. I’m an endurance athlete though, so I pass pretty well as a tall, strong woman. My spouse is great, but not a fan. We talked about my desire to dress as soon as we were married, but she wasn’t keen on the idea. My first real outing came while she was travelling for a few weeks, and I talked openly about it with her when she came back. I don’t think you should ever hide things from your spouse. She wasn’t thrilled about it, so I told her I’d keep it to myself. A bit more about me: I’m 38 years old and I’ve always been interested in women’s clothing. As a little kid at the pool I thought one piece swimming suits looked way more fun than baggy shorts and I’ve always liked dresses. While dresses and swimsuits are my favorite I look best in skirts and blouses. I am definitely not transgender. I like being a guy and I view dressing up as just another interest among many. It’s certainly different than skiing or fishing or my love of old 4×4’s, but it isn’t any more important to my identity. I think I like cross dressing because I like women. Women are beautiful and it’s fun to look pretty (my artistic side comes into play here). The deviance also makes it fun. I think if it was normal for guys to wear evening gowns, I wouldn’t be that interested in them. There’s an element of disguise that’s intriguing too. Like when a super hero in a comic book puts on their mask, something special happens. Knowing you have this other, secret side adds something. All the best,

Latest posts by Sarah Kanter (see all)

5 3 votes
Article Rating
Inline Feedbacks
View all comments
Chuck Lund
2 years 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 years 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%!

Would love your thoughts, please comment.x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

Forgot your details?