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Lunch Outing

January 20, 2018


There is a restaurant that I frequently go to in my normal mens’ wear.  About a year ago, I started occasionally wearing womens’ wear to eat there.  I started in womens’ slacks and a sweater.  Several months later, I ate there in ladies’ shorts and a top.  Eventually I wore a skirt on two occasions to this restaurant.  However, I normally wear mens’ clothing to this business.

On my last mens’ wear visit, I was feeling down.  The hostess was very happy and smiled broadly.  She greeted me warmly.  Previously, she has seated me while I was crossdressed.  I felt touched at how nice this woman was treating weird, old me.  It helped me feel a little less down.  The way she made me feel welcome on that day might have inspired me to wear a skirt to her restaurant today.


I wore a new, black and white striped pull over top, a black business skirt, off black pantyhose, and black flats.  I arrived early in order to avoid the large lunch crowd.  I walked into the lobby.  The friendly hostess was there again.  She was not as bright and happy.  She smiled, but her voice and demeanor seemed stifled.  She seated me.  I perceived her to be uncomfortable.

At this point, I wondered if she forgot that I was a crossdresser, or if she somehow never noticed before.  She has seated me at least once while I was in a skirt… I think.  Anyhow, I think she has been around me in a skirt twice before this.

I sat in my booth with my lower half out of site.  A new male waiter served me.  I ate my food.  I received my bill.  I walked up to the counter to pay it.  The hostess and a female server were both there.  The server came to the cash register to take my money.  She seemed friendlier than usual.  At least she was not being uncomfortable with me.

Then the hostess spoke to me about the weather.  She was her usual, jovial self.  She must have not realized that I was a crossdresser.  The surprise of seeing me walk in wearing a skirt must has shaken her briefly.  At this point, both ladies were at least as friendly as usual, if not more friendly.

Another male server arrived in the lobby.  He served me once before.  We said, “Hello,” to each other.  As I left, they all said good-bye to me.

After that, I went to a small pharmacy for an item.  Nothing very interesting happened there.


UPDATE: I went back to the restaurant in men’s clothes.  The hostess seemed similarly calm.  She was friendly, though.  When I was paying, I told her thank you.  She looked me in the eyes and smiled while she said that it was her pleasure.


From → True Stories

  1. Pat Scales permalink

    Everyone’s mood and demeanor changes constantly throughout the day. Some times I am jovial and other times more dour. I would say on balance that by the end of your meal that everyone was comfortable with your skirt, hose and heels. I would chalk this up to another successful cross dressed outing.

  2. gndiaz100 permalink

    All your baby steps in the past has built up a your self confidence. I’m trying to follow your path but I’m miles away from you. My hats off to you.

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