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Road Trip In My Little Black Dress

October 26, 2022


I went to a family event that required a two hour drive to attend. I packed some womenswear for the drive home. After the event, I changed into my black dress, black pantyhose, and my strappy black flats. While I was getting dressed, I realized that I forgot to bring a colorful cardigan. I did not like being so monochromatic. I decided that I needed to do something to change my outfit. I made several stops on my way home. In a small, rural town, I shopped in a pharmacy, a shoe store, and a thrift store. Later in my trip, I went to an outlet store and a gas station while dressed as a man in a dress.


My first thought was to go to a pharmacy and purchase some skin-toned pantyhose so that I was not in all black. I went in dressed in menswear, found the pantyhose in the store and looked at what my options were. Under my dress pants, I was wearing Leggs Sheer Energy pantyhose in Jet Black color in size Queen. I do not remember what weight they were (Light vs. Medium support). Instead of purchasing skin-toned pantyhose, I bought some Queen+ sized jet black Sheer Energy pantyhose in medium support.

I have felt like my more sheer black hose do not look as pretty as they should look. I thought that these thicker, larger pantyhose might give me a richer color on my legs (I liked their color better, but I am not satisfied). I went to the front of the store to purchase them, and had to use the self-checkout machine because no employees were there. When I got to my car, I realized that I still only had black clothes to wear. I changed into my dress. I do not remember when I changed into the darker pantyhose, but I eventually did it. They looked better than the lighter-weight hose, but I still did not feel beautiful in them. At this point, I still needed to go shop for a cardigan or something to give my outfit more color.

Shoe store

I drove to a nearby shopping center. I walked from my car to the shoe store in my little black dress. A nail salon was nearby. a woman was sitting out in front of her store. She watched me cross the parking lot. I noticed her early on my walk. I decided to look at her and smile. She waved and smiled back.

I have been shopping for several months for some new ladies’ flats that I can replace my strappy flats with. My strappy flats are coming apart. In this shoe store, I encountered several people shopping. Since I was so far from home, I did not care about the people. I found the aisle that had ladies’ flats, and started shopping. A 20-year-old female employee came over to help me. I spoke to her briefly. Since I did not need a lot of help, and someone else did, she left me to help them.

At one point, a couple shopped in the handbags that were hanging nearby me. They saw me there in my dress. She looked at me with a look that I will describe as non-judgmental, but unfamiliar. Then, she did not care, and only shopped for a handbag and ignored me.

Later, a mother and teenage daughter came past me and shopped on my aisle. They went to the far end of my aisle, where the more casual shoes were located. I saw the daughter looking at me at one point. They shopped for ten minutes, but she only looked at me for fifteen seconds.

The employee came back. I had selected a pair of black shoes, but I was undecided whether I should purchase them. The shoes were not as dressy as what I wanted. They were OK, but I feared they were more “grandmother shoes” than fashionable shoes. The employee said they were “cute” and that she would wear them. I put them on and walked in them. The teenager was in line while her mother was paying for the shoes they bought. I asked the teenager for her opinion. She gave them a 4 of 10 for being grandmother shoes. She said she might wear them. I bought them and wore them out of the store.

Thrift Store

A thrift store was nearby the shoe store. I decided to go there. I walked to my car to deposit my bag containing my old strappy flats. When I walked back toward the thrift store, I looked over. There were now two women sitting outside of the nail salon. They both smiled at me.

I went into the thrift store and shopped for a cardigan. The only employee was in her 20’s and she was pretty with excellent hair. She was dressed casually. She was steadily working, putting clothes on the racks. We spoke occasionally while I was shopping in the aisles. She was completely unaffected by me wearing womenswear.

While I was shopping, I saw a woman who was close to my age. She was wearing a pretty, burgundy top, and she was standing at the end of my aisle looking at the rack near me. I said, “Come on, I don’t bite,” and I smiled. She said that she has not bitten since she was three, but she did not come down the aisle.

I found a long red cardigan (or perhaps it is a duster). It was a pretty red color and the fabric was soft. It was not very loose on my arms. I walked over to the employee and asked if it was too small for me. The burgundy woman was nearby. She turned around to see. She answered first and gave her advice. The employee joined in. Both of them kept trading off expressing perspectives.

I decided to buy the cardigan. I ended up in line behind the burgundy woman at the cash register. I thanked her for her help. After I paid, I put on the cardigan. Good, now I am not in all black. I stepped back and asked the employee if my shoes were old-lady shoes. She gently said yes. Great… (I would value your opinions. Please comment on what you think about them. In any case, I have shoes that are not worn out.)

Outlet Store

I drove for a while and then I went shopping at an outlet store. There were plenty of people in this store. (I thought I had a picture from a crowded moment in the store, but it must have been bad and deleted.) I shopped near people several times. A few times, I received uncomfortable glances. Mostly, I was hardly noticed. I found a lot of pretty things. Everything was marked down to roughly $40 at this outlet. That was more money than I had in my pocket.

While I was browsing the dress section, a ~25 year old girl, who stood 6 foot 2 inches tall started shopping nearby. I told her, “I love how tall you are!” Later, we were near each other again and I asked her a few questions. She gladly helped me. I asked about buying clothes for tall bodies and shoes for larger feet. We commiserated about how difficult it is to find clothes that we feel good in. I asked her about my shoes and she said they were “cute”, but agreed that they were not as young. She said she would wear them.

I know I took more pictures on this outing, but the do not exist…

I shopped all over that store. When I walked, I walked down the main aisles. Some people looked at me longer than other people, but no one acted like it was unusual for a man to walk around in a dress.

Gas Station

I stopped at a gas station. I got out and put gasoline into my car. I was pumping my gas among the other people pumping gas. When I was finished, I went inside and bought some candy. The man at the cash register was polite and respectful.

After that, I changed clothes and returned home.

From → True Stories

  1. MAZARS JOEL permalink

    C’est bien mais quel est l’intérêt de porter des robes pour un homme? Les femmes se sont battues corps et âmes pour avoir le droit de porter le pantalon, aujourd’hui rare sont les femmes en robe, pour moi une robe est un symbole de soumission, c’est pour cela que pendant longtemps le port du pantalon était interdit aux femmes. Mais je ne vous critique pas, d’après vos commentaires qui je l’espère ne sont pas des fantasmes vous vous promenez , vous faites vos courses, votre épouse est au courant, alors pourquoi floutez vous votre visage?

    • J’aime porter des vêtements féminins. Je suis content.
      La plupart de ma famille et de mes amis ne le savent pas. Jusqu’à ce que je veuille leur dire, je flouterai mon visage. Je ne veux pas qu’un logiciel de reconnaissance faciale relie mon travestissement à ma vie de tous les jours. C’est à moi de le faire quand je serai prêt. 🙂

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