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One Day Road Trip

January 30, 2019


I went on a long, one-day, round-trip drive yesterday to see a friend.  I took some pretty clothes to wear on the drive.  I changed into my beige skirt, black and white striped top, black cardigan, nude pantyhose, and black flats.  As usual, I presented male (no bra, wig, make-up, or padding).  I was just a man in a skirt.


Gas Station

On my way, I did something that took me back to my early days of crossdressing.  I had to stop for gasoline.  I remember reading about early crossdressers, during our frontier days, telling of their harrowing adventures of pumping gas en femme.  I remember that first, frightening time of doing it myself.  It was a non-event then, and it was a non-event now.

While I was pumping gas, I walked along the side of my car.  When I turned around, I realized that there was a man pumping gas on the other side of my pump.  I had forgotten myself!  I returned to the nozzle.  When he finished pumping, he came into view again.  I asked him if he was a fan of the sports team on his hat.  He was.  I asked him if that passion resulted in the color of his car.  He laughed and admitted it was.

I paid at the pump and kept on traveling.

Lunch at the Mall

I went to a mall during lunch time.  I wanted to get something to-go from the food court.  I mis-judged where the foot court would be.  I had to walk half-way down the mall.  It was not very early, but the mall was only partially opened.  This mall is open unusual hours on Sundays, apparently.  On my journey to the food court, I crossed paths with a few dozen people.  I was completely at ease.  I did not try to hide from people or dodge people.

I was under the impression that I received more surprised looks than usual.  Maybe I was simply paying more attention.  I was in a city.  I assumed that city people would be more used to uncommonly dressed individuals.  Many people looked at me like they were from way back in 2005.  Oh, well.

I was in a hurry.  I wanted to get my food to-go because I was trying to get to my destination on time.  I needed time to find my way to my destination, change clothes into menswear, and make it to my appointment.  There was nothing in the food court that I could eat to-go.  Chick-fil-a was closed.  I decided to eat Chinese food.  Two women were working in the restaurant.  They seemed a little unsure when they first spoke to me.  I spoke what little Mandarin that I could to the ladies.  The awkwardness melted as we tried to communicate.  I bought some sesame chicken and fried rice.

I sat at a table and ate my food quickly.

I walked out of the mall.  Again, I had the same reactions on my way out:

  1. The “wide-eyed look” where they follow my movements.
  2. The “take a look, and then never look back, no matter what”.
  3. The rather common “too busy to notice” look.

I suppose there should be something in the middle where they did not find it more interesting than a girl in a skirt.


At my destination, I wore menswear.

Shoe Store

On my return trip, I dressed pretty again.  I stopped in a shoe store that is known to carry shoes in my size.  I found a few things to try on, but I did not find any pretty, casual flats to replace my regular black shoes.  The employee spoke to me briefly.  A couple customers saw me, but did not pay much attention to me.  One customer and I exchanged greetings when she entered my aisle.  I did not buy anything.


On my return trip, I stopped for supper at a sit-down restaurant.  The parking lot was rather full, but the dining area was not.  The hostess never looked at my clothes.  I honestly do not know if she noticed what I was wearing.  She seated me.  There was only one couple near where I ate.  The server may not have seen what I was wearing.

I ate my meal.  I used the restroom.  I paid the bill at my table.  I left.


I physically needed to walk around.  Also, I did not want to take off my skirt with so little being out-and-about.  I found a store that was open and went inside.  I browsed the clothes primarily looking for tops.  I did not find anything that I wanted.  The most interesting thing to happen: a woman and I were browsing on opposite sides of the same rack.  Then, she came around it to my side.  We did not interact.  Then one of us walked away.  I forget whom.

I am not sure if she noticed my outfit.  I am not sure if anyone paid me any attention.  It was not a big event.

I spoke to an employee.  She answered my question.  She was polite and helpful.  She seemed unsurprised by me.  Later, I went back to the employee and asked her to take my picture.  She politely did.

Service Station

I stopped at a service station with a restaurant because I wanted a milkshake.  They did not have milkshakes.  While the woman at the restaurant told me this, she looked down at my skirt.  She was warm and friendly.  I think she enjoyed getting to speak to me.  She was nice.

So, I walked into the service station.  I found me an ice cream sandwich, a candy bar, and a drink.  I stood in line and paid.  I was completely at ease browsing the racks in a truck stop/gas station on the side of the interstate.  Random customers and various truck drivers came and went while I found my items.  I am impressed with myself.

I returned to my car and returned home safely.







From → True Stories

One Comment
  1. Pat Scales permalink

    It seems that you had a good day in all regards.
    I have been mostly dressing around the house. One of the benefits of being empty nesters.
    Saturday night, after I had prepared a nice meal while dressed in a black pleated skirt, gray top, hose and heels we realized we were out of wine. I offered to make a run to the local liquor store and I spruced up my makeup, put on a wig and blazer and made the wine run.
    That bottle ran out last night and I again offered to do a wine run. this time I put on a wine colored dress with my black blazer and beige hose, light makeup and wig. The lady in the liquor store seemed to recognize me from the prior evening and greeted me with a big smile. I guess I am becoming a regular.
    It is really nice to get out, even for a quick run, while dressed pretty.

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