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Lunch, Haircut, Shopping in April

April 14, 2017


I dressed pretty and went for a hair cut again.  This time was different in a few ways.  I received some cold reactions from some people,  a mysterious comment from a man that was either a compliment or an insult, and some direct, friendly engagement from complete strangers.

Sandwich Shop
I dressed in an orange maxi skirt; a zebra print, stretchy, knit top; nude pantyhose; and flats, and went out for a haircut and lunch.  As usual, I was a man in a skirt.  First, I went to a sandwich shop I have frequented in a skirt.  The time of day was shortly before noon.  I normally avoid the lunch crowd by going out on skirted outings earlier than this.  As I drove into the parking lot of the restaurant, I tried to see into the restaurant.  I thought I saw a few men inside.  I normally feel less comfortable being dressed pretty around men.  I was not sure if I wanted to go in.

I parked deep in the parking lot.  I walked up to the entrance.  I would not be able to see inside the dining area until I got to the door.  When I arrived at the door, I found two men eating lunch outside.  I immediately decided to go into the restaurant no matter what.  I walked in to find three men eating at different tables.  The only women in the restaurant were the workers.

I went up to the counter to place my order.  I noticed one of the men look over at me for a few seconds.  He was possibly 55 years old.  Let’s call him “the looker”.  I placed my order like usual.  Two female workers talked to me.  One of the women is slightly older than me and she has spoken to me on most of my visits to this restaurant.  I paid my bill, filled my drink, and found a seat near the door.  It is humorous now that I think back about it.  All four men in the restaurant were evenly distributed.  Just like how men space themselves in the men’s room.

At one point during lunch, I made eye contact with “the looker”.  We both greeted each other as is common where I live.  Other customers came and left with their to-go orders.  Once, a man who works in the restaurant came near where I was sitting.  He noticed me and greeted me like normal.  “The looker” finished his meal.  He walked past me to the trash cans.  On his way by, we made eye contact again.  Again we greeted as is common.  But this time he smiled — or perhaps I should say he smirked.  He said , “I like your dress.”  I could not tell if he was complimenting me or making fun of me.  His unusual smile, and the very nature of being complimented by a man made it feel ambiguous.

“The looker” left the trash cans, walked over to the drink machine, back to his seat, and back to the drink machines for a straw.  All this time, he avoided looking at me.  I could not tell if he was feeling awkward for complimenting me or awkward for mocking me.  I honestly could not figure out how to receive his words.  Eventually, he walked past me to the door.  We made eye contact one last time and told each other “good-bye” and “have a nice day”.

I eventually finished my meal, filled my cup, and left the restaurant.

Hair Salon
I walked into the hair salon I have recently started going to.  I believe the workers in this establishment are particularly conservative, morally.  I walked up to the counter.  One employee was putting a permanent curl into a customer’s hair.  Both she and her customer could easily see all of me.  The employee looked at me with no expression.  The customer appeared to be shocked and possibly disapproving.

The woman who has previously cut my hair was not visible.  Only one other employee was in the room.  Let’s call her “smiley”.  I asked if my regular person was available.  “Smiley” invited me to her seat.  She greeted me and introduced herself when I was close enough to shake hands.  “Smiley” is the woman who had said, “Please come back,” when I first visited this salon.  She is a happy person who laughs and smiles a lot.  We had a pleasant time talking and laughing during the hair cut.

At one point, the woman who normally cuts my hair appeared.  She was in the back working with another customer.  She greeted me nicely.  The customer also gave me a look, but it did not seem to be as disapproving as the first one.  She did not speak to me.

At one point, I asked my hair cutter if my outfit was too wild.  I am not normally a person who wears “prints”.  I primarily wear solid colors.  When I wear women’s wear, I often look very plain.  This zebra print top is a very bold change for me.  I felt like “smiley” was made a little uncomfortable with my question.  I think she was being nice to me, but still disapproved of how I was dressed.  I may have put her into a situation where she had to either compliment me or say she did not like it.  I clarified  my question when she hesitated.  “Is this shirt too wild?”  She told me she thought it was not too wild.

After my hair cut, I was taken to the back to wash my hair.  Then I finished up.  I said good-bye to “smiley”, then to both the woman who cut my hair last time and the customer she was working with.  The customer responded appropriately.

Grocery Store
My intent was to go to my friend’s consignment store next.  However, I did not want to stop being out in public yet.  I drove to a grocery store.  I decided to get some milk and some candy.  I am nervous about going to the store because it is a big room and I never know if an acquaintance is nearby.  The parking lot was not very full.  It gave me confidence.

I walked into the store and no one was near.  I walked through the store.  A few people saw me.  However, no one stared or spoke.  It is SO refreshing to go to the grocery store crossdressed!

I made my selections and walked the checkout lines.  I stopped and debated over which candy bar to buy.  The cashier said playfully, “It’s a hard choice.”  We talked while she checked me out.  She was friendly.  She did not seem uncomfortable.  I would describe her as possibly being unsure how to behave, but willing to be nice.

I think I love going to grocery stores in skirts!

Consignment Store
I finally went to my friend’s consignment store.  I shopped around and selected a few items.  There was a gray haired woman shopping.  She had a lot of personality and one lock of purple hair.  While I was shopping a few feet away from her, she started talking to the employees.  She was debating buying one dress.  They said that it was a short dress.  They said she could either wear it with leggings as a top, or as a dress if she was bold.  The woman said, “I am bold.”

She tried on the dress.  She came out wearing it with her pants and they discussed it.  She decided to buy the dress.  She walked by me after purchasing it and said, “If you wanted this top, you can’t have it.”  I assured her it was OK if she bought it and told her to enjoy it.  It made me happy that she spoke to me, a man in a skirt, when she did not have any reason to.  She exited the store.

Another female customer entered the store.  We spoke our hellos.  I picked out a couple unlikely items to try on.  I tried on a black dress.  It was too big and was too “grandmotherly”.  The woman expressed some interest in a dress I was wearing.  I returned to the dressing room and took it off.  I told the woman the size of the dress and she declined it.  My friend suggested a better dress for me to try on.  It was orange with white stripes.  I thought it was rather bold for me.  I tried it on.

A third customer came in.  I came out of the dressing room.  The third customer and my friend complimented the orange dress I had on.  I asked the employee if it was too bunched under the belt.  The customer immediately responded.  Then, the customer came over to me and started adjusting how the dress was bunched under the belt.  Now people…  Can I stop and ask just what planet am I on where women ask to try on a dress I am currently wearing and other complete strangers come up to me to help adjust my ladies’ clothes?!? Also, what planet am I on that I took all of this in stride as though it was normal?!?

I have this no-floral-patterns rule that I tend to obey.  I am not interested in being dainty or girly.  I just like wearing women’s clothes and staying masculine.  The top of this orange and white dress has what I perceived to be floral silhouettes across the upper chest and shoulders.  So, in spite of all of their compliments, I did not buy the orange and white dress.

…However, I am still thinking about it…


From → True Stories

  1. This seems like another great outing. I would not be totally against prints and floral patterns. It is clear that you are in ladies clothes so going away from basic solids is not a big move.

  2. rat permalink

    I check by your site on a regular basis looking for the latest adventure. I’ve missed this post for over a week because the title was so close to the last. That’s not a complaint, just an observation.

    I dress the way i like in private but have not been out. I consider myself to be sort of a ‘boy tomboy’ as there’s not really a reciprocal to ‘tomboy’ for men other than something derogatory.

    I’m a straight, monogamous older guy who’s been jealous of the things women get to wear for decades, but has only been enjoying it for myself, in private for a decade or so.

    in reading your post the thought that comes to mind about the ‘looker’ is that there’s a plausible likelihood that he’s closeted or at least sympathetic and wants to ‘go on record’ even if he is somewhat uncomfortable and awkward in his approach.

    • I imagined several scenarios for what it means and that was one of them. Maybe you are right. I doubt I would be able to say or do anything better than what he did if I was around a man in women’s clothes who was presenting male… 🙂

Trackbacks & Pingbacks

  1. May Haircut and Lunch | joeypress
  2. My First Halloween As A Girl – Part 2 – Dressing With My Wife | joeypress

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