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Road Trip

July 25, 2017


I went on a day road trip.  I wore my new, blue and white striped, maxi skirt.  I also brought a white button up top, a white t-shirt, nude pantyhose, and white Keds canvas shoes.

I stopped at a restaurant that has a store attached to it in order to buy some candy.  I parked rather far from the door and walked in.  I was wearing sunglasses.  I do not know why that is important, but it was a different experience.  I walked up to the restaurant where a few people were sitting outside waiting.  One of the people looked like a 20-year-old girl.  She smiled, but she was not smiling politely at me.  I might be wrong, but it looked like she was containing her laughter.

Inside, I removed my sunglasses.  The staff was polite and professional.  The customers were also polite.  I found my candy and bought it.  I walked back out past the porch people and returned to my car.

Grocery Store
Next, I stopped at a store to get some milk to drink with my candy.  The store was rather busy, but I was not afraid.  I walked in with my head up.  I was impressed with myself.  I walked past a lot of people.  Many of the people never noticed me.

I selected a cashier who was smiling more happily than the others.  I got into her line.  She was dealing with another customer.  When it was my turn, she seemed very reserved.  I suppose I may have made her uncomfortable.

Clothing Store
I drove for about an hour in my skirt eating my candy.  It was very nice.  I stopped at a clothing store and shopped for a few minutes.  I noticed that all of the mannequins had either patterned tops and solid bottoms, or they had patterned bottoms and solid tops with necklaces.  Only one solid top did not have necklaces over it.  That top had ruffles that went diagonally across.

So, I received the message: I need to break up the plainness of a solid top.  I asked an employee how I could accent my solid-patterned tops without jewelry or scarves.  She gave me some options that were similar to what I already do: wear jackets, sweaters, or cardigans.

I changed back into trousers before getting to my destination.

Rest Area
A couple hours later, I was on my return trip.  I changed clothes back into my skirt and continued driving.  I stopped at a rest area and used the men’s room.  There were two options for which men’s room I could use.  I heard someone in one room.  I hesitated briefly and then went into the other men’s room.  I used the rest room in solitude.  I felt like I had acted cowardly.

Several Stores
Eventually, I stopped in a small town.  I shopped in a clothing store.  Then, I bought some gardening supplies at a hardware store.  Next, I went to a small grocery store for another small bottle of milk..  They did not have small bottles.  Nothing significant happened in these places.

Fast Food Restaurant
Next, I went to a fast food restaurant for a milkshake.   At this stop, things were somewhat uncomfortable.  I walked across the parking lot and approached the door.  A family was exiting the restaurant.  Through the glass, the teenage daughter in the family saw my outfit and started laughing.  Her mother and grandmother did not laugh.  They also did not tell her to stop being rude.  I held the door for the women.  The mother was providing a lot of physical support to the grandmother.  Both women thanked me politely as they slowly exited.  While they progressed past me, the girl, who was behind them, was using her hand to hold her face.  The teenager eventually gained her composure when she finally exited the door that I was still holding.  She straightened her posture, looked me in the eye, smiled at me and said, “Thank you.”  I replied.  I entered the restaurant and glanced back at the family.  The teenager was laughing again.  Her family members still were not laughing.  I was not affected by it.  It did not shake my confidence.  I just felt that she was young enough that she could not manage to respond to my outfit in a casual manner.

Let me add that more than half of the people did not react to me.  They seemed mostly disinterested in this anomaly of a man in a skirt.

I got in line behind two men.  Behind the counter, there was a cashier, a male employee, and a tall, female employee.  While I stood there, the tall employee noticed me and smiled and gave me a bright, “Hi there.”  She did not speak to the two customers in front of me.  I noticed some employees back in the kitchen area huddled close and looking at me.  A teenage employee looked like she was laughing.

I ended up ordering food and water to go with my milkshake.  I paid and walked over to the drink area.  A male customer was refilling his drink.  He walked away and sat by his female companion.  I heard him try to tell her about me in hushed tones.  When I walked past their table on my way to the exit, I looked their way.  The woman seemed uncomfortable.

I was not made significantly uncomfortable by their reactions to me.  I had a nice outing.

Shopping Center
Next, I drove to a different town.  I stopped at a shopping center.  I walked to a store that had a blue jean skirt in their display.  A male employee was at the entrance.  I felt awkward, perhaps he felt awkward as well.  We said hello and I walked on shopping.  Eventually, I walked over to him for help.  I could not find a knee-length denim skirt.  He started helping me like normal.  Eventually, he called in a female employee.

They did not have skirts as long as I was seeking.  The three of us continued speaking briefly.  I walked toward the exit.  The female employee walked away.  The man kept talking to me.  Eventually, the conversation ended and I exited.  I was surprised that he was slightly difficult to get away from.

Gas Station
My last stop was to a gas station.  I filled up my car.  No other cars were there.  I saw the woman working inside looking out the window at me.  I finished with the gas.  I went into the store and bought a small bottle of milk.  The employee was social with me.  Then, I went home.

My Impressions
As usual, many people either did not notice my outfit or they did not react beyond glancing down.  However, I perceived that the people in these small towns were not used to men dressed like me.  I do not know why anyone in my town would be more accustomed to such things.  The demeanor of the people I encountered seemed more surprised or uncomfortable than I usually observe at home.  Whatever it was, it was subtle.

When I first started going out in public wearing women’s wear, I normally felt like the people who saw me were shocked or uncomfortable.  However in the past few years, I have stopped noticing such reactions.  I concluded that one of two things were true: either I was not paying as much attention to peoples reactions, or the general public where I normally go out is less shocked than they used to be at seeing a man in a skirt.  After this experience, I think that the difference was not me.  I think people are more at ease with a crossdressed man.

When I typed up my experiences on this outing, I started noticing a pattern.  I wondered, “Were people laughing because my outfit was unusually silly looking?”  I had to reassure myself that I did in this outfit what I often do in a new outfit.  When I was being helped by sales people in the clothing stores, I asked, “How can I make this outfit better?”  With this outfit, I received higher compliments than I normally receive.  I do not recall any suggestions for improvement from the two women I asked.

Thank you for reading about my silly experiences.


From → True Stories

  1. rat permalink

    i enjoy reading about your outings. i dress at home but more in girl shorts and leggings or pj’s. i have yet to openly wear dresses or skirts around my wife. I don’t see myself out and about in openly feminine items although i do go stealth at times.

    I understand that photos make one vulnerable, but would like a visual added to the descriptions when possible. I am wondering if you’ve had anyone point a camera phone at you while you are out and how concerned you are that photos will be uploaded without your knowledge or consent.

    • I have caught a couple people with their phones pointed at me. I tried to cover my face. I search occasionally to see what I can find of me. So far, I have not found myself online dressed fabulous.

      I said to myself that I should at least place my outfits on the bed and take pictures of them for these recent posts. In the end, I did not bother to take the time and clicked “publish”. Sorry…

  2. I would wonder if the male in the clothing store was ‘one of us’ and was just wondering about your bravery and courage.
    I do think that the more frequently cross dressed males get out and about in the civilian society the more easily we become accepted as part of the every day life of people in general.

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