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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.

black_skirt_black_and_white_striped_top.JPGBlack and white striped shirt and black skirt.

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.

  3. rat permalink

    i’ve been following your posts on occasion but finally got a chance to sit and read several this morning. i dress at home and have a tolerant/accepting loving wife. i haven’t ventured out in anything that could be tagged as definite women’s wear, but i do have a few stealth items that i enjoy wearing out on errands.

    as far as the demeanor of the hostess, it’s impossible to know the reason for any change. the hardest part of the effects of my taste on my marriage is that i tend to overthink her ‘moods’. she may just be tired or distracted and i tend to need reassurance that she’s not at a point of overload with my taste.

    by nature, cd’ers are one of most vulnerable groups in society and as such, we are always on the lookout for ‘danger’ signals. assumptions are made by others and assumptions are made by us cd’ers as to the assumptions of others.

    i don’t know the source for this thought, and i am paraphrasing but… “there’s what we think of ourselves, what others think of us, and “what we think” others think of us. the third factor can be the most damaging to our egos and the most inaccurate.”

    while reading your posts i always wonder if your wife knows about or reads your blog.

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  1. Shorts and Pantyhose at Lunch | joeypress

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