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Skirt to the Grocery Store Again

November 19, 2016

A few days ago, I wore women’s shorts and pantyhose, etc. to a store in order to eat lunch in a cafe in the store.  I went back the next day in a skirt, dark pantyhose, etc.  I decided to go back again.

I wore a multi colored, knee-length skirt, off-black pantyhose, black flats, and a black top that has a faux cardigan built into it.  Sometimes I feel like this skirt is too girly for me.  I try to dress in feminine clothes without losing my masculinity.  However, I think this skirt makes a very cute outfit.  So, I wear it and wonder if it is a mistake.

I found a parking spot and built up my courage to get out of the car.  It does not take nearly the same amount of courage that it used to take to let the sun shine on me.  The hesitation is still there.

I walked across the parking lot to the store.  I peeked in the front of the store to make sure that no one I knew was in line.  I went around the corner to the door as a woman with a baby was coming out.  She looked me up and down and smiled politely at me.  I went in.

No one in the area around the cash registers noticed me.  I walked into the produce section and no one there paid me any attention.  I was blending in.

There were several men in the aisle at the back of the store.  One of them looked at me and I felt awkward.  I turned and went down an aisle.  I heard him turn and go down an adjacent aisle.  In the milliseconds that followed, a series of ridiculous thoughts went through my brain.  I feared he was following me so he could get another look.  I thought, maybe he is a crossdresser too and wanted another look.  He did not look like he was offended at me and wanted to confront me.  Then, after enough time had passed, I realized that he must have wanted something on that aisle.  He did not show up on the other end of the aisle.  He was not attempting to get a better look.  I never saw him again.  I mentioned this event in order to communicate the crazy stuff that goes on in my head in small amount of time.

I had relaxed a good bit by this point.  I walked to the end of my aisle and turned right.  I was walking across the front aisle of the store.  I was walking past the cash register area.  I looked down one of the aisles to my right.  I saw an employee walking toward me.  She was young and rather pretty.  I nodded gave a slight wave and a smile.  She smiled very prettily and said, “Hello,” out loud.  I walked toward the cafe area but turned when I got there.  I was not ready to stop walking around the store.

I turned into an area with short shelves where skin care products, etc. are sold.  I noticed the pretty employee walked into the same general area and stopped.  She started talking to another woman.  I would either have to walk past them or turn around.  I hesitated.  I would have to walk within two feet of two women while I am dressed in a skirt.  Although I considered stopping, I went for it.  I walked past the two women and said, “Hi there,” as I went by.  They both smiled and greeted me as I went by.  The pretty smile returned.

I finally made my way to the cafe.  I looked into the dining area to decide if I had the nerve to sit in a skirt and eat there.  If I were farther from home and work, I would have.  However, this store is close to my work and I did not want to be sitting there in pretty=wear when a co-worker walked in.  I got a to-go box.

I think the main reason I wore a skirt back to this store was to get a chance to interact with a specific employee.  There is a person who works in the cafe that I perceive to be a person who is female-to-male transgender.  On my previous visit to this store, I asked an employee that I spoke with if the cafe worker was only androgynous or was full transgender.  I was told that the person was transgender.  So, now I know whether to say “Sir” or “Ma’am”.

Here is a side note:

I have previously thought that crossdressing women have it better.  A woman can wear anything and it does not seem weird.  A woman can openly say she is wearing men’s pants, etc. and it is not perceived to be an alternative lifestyle choice.  This was the day I realized that this truth cuts in the other direction.  When a woman is transgender and dresses as a man and has a short hair cut, she still is perceived as a woman, unless she has facial hair.  If a dude shows up in a dress with make-up on.  Everyone knows what he is doing.  Polite people know what pronouns to use, etc.

Back to the story:

I got my food and walked up to the cafe cash register.  The transgender employee was there.  I wanted to say something to acknowledge his gender.  I thought I could say, “No, sir,” or something similar at some point.  Apparently, I am not that talented.  I do not think he noticed my outfit.  After I paid, he turned to walk away.  I asked a question about a multipurpose room in the cafe dining area that I have seen people occasionally use.  At this moment, the pretty smiling employee walked up beside me.  She and the transgender employee started answering my question.

The three of us talked for a minute or two and then I turned and walked away.  I did not exit the store through the cafe dining area.  I turned my back to the cafe worker and headed toward the cashiers.  I noticed that he did not turn and go where he previously had intended to go.  Maybe my “first contact” with a fellow crossdressing person was a success.

When I walked to the exit door, an adult employee was walking in.  She gave me the standard glance down and back up.  She looked me in the eye and thanked me for shopping there.  It felt very welcoming and authentic.

There was a nearby store that sells “home accents”.  I did not know what they sold, but I did not want to change clothes and go back to work.  I drove to it and walked in.  This store was filled with fancy things one would use to decorate a home.  A woman looked at me when I came in.  She seemed apprehensive and possibly shocked.  I said hello and she responded.  I walked around the store and looked at what they had for sale.

The store was filled with women in stylish, cute outfits.  They were shopping for stylish (and possibly pointless) things.  They were wearing scarves, flowy dresses with booties,  and plenty of accessories.  It was fun to be there but I had a nagging feeling that my manly attempt at feminine style was being cattily judged.  If anyone paid me any attention, it was shrouded in indifference.  Any negativity that I detected in that room was generated in my head.

I did not see anything I was interested in purchasing.  When I had finished my lap around this fancy store, I looked over my shoulder before walking out.  The wide-eyed woman was at the counter.  She was an employee.  She made eye contact with me and told me good-bye and welcomed me back.

I drove to a secluded area in a parking lot where I could change back into my work clothes.  After I was dressed as a man again, I opened my door.  I looked and saw a woman walking through the parking lot.  She was very tall.  I asked her, “Ma’am, how tall are you?”  She said, 6 foot 4 inches (1.93m).  I asked her where does she buy ladies’ tops.

She started telling me about how she layers her tops in order to wear pretty things and still ensure that she is sufficiently covered.  She asked me if I had a tall daughter.  I said, “No.  I am a crossdresser.”  She said, “Oh,” and then started bombarding me with the names of stores and the sales they will have where she can buy $300 dresses for $30.

This woman was completely not put off by the fact I was asking on my own behalf.  At some point in this five minute conversation, she asked me if I performed somewhere.  I said no.  I told her I just go out as a man in a skirt.  She was surprised.  She mentioned the crossdressers she knows.  I remarked that it was amazing that she knows several.  We are a rather secretive community!  She is from a larger city and is just visiting the area.  We spoke a little more.  She repeated several store names to make sure I knew where to shop.  I thanked her.  I told her my name, she told me hers.  I told her that she was beautiful (and she was/is).  She thanked me warmly.  She turned and headed onward to the store I had previously skirted through.

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From → True Stories

2 Comments
  1. Wesley permalink

    You mention of off the wall comments and conversations is of interest. While shopping at Goodwill, I have had two different black ladies spontaniously engage me in conversation while shopping in the womens section. Once dressed in skirt, ballet flats and blouse, and the other with womens jeans, flats and solid color mens tee shirts. .

    Both proved to be interesting conversations about many things including clothing. Both were totally accepting and friendly. .

    Also had several conversations with every spector of woman, if you will. . .

    I do notice a few oddball sidewise glances in more upscale clothing establishments though. . .

    • Where I live, African American people are apparently more comfortable speaking to me while I am crossdressed than white people are. Most of the strangers who have initiated conversations with me while I was out dressed pretty were black. I do not know if this is a regional cultural phenomenon or if it is nation-wide. I am white. My experiences that are similar to yours inspire me to be more expressive when I am in unusual situations. I do not have to pretend like nothing is unusual. (I have not mastered this, by the way.)

      Thank you for visiting and commenting. Few people comment on blogs these days!

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