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Doing Manly Errands in a Skirt

October 29, 2021


I have not had a significant outing in quite a while! Today, I had a reason to drive across town. While I was out, I was determined that I was going to dress pretty and do something — anything! Where I live, in the autumn months, the weather gets significantly cooler. This causes the leaves to change colors and fall. It is a beautiful time of year. Women (and some men) dress in more “autumn colors” including orange, and various browns. I selected an orange blouse that is very autumn-appropriate with a denim skirt, white Keds sneakers, and a white cardigan sweater. While I was out, I got more and more daring.


I had the house to myself, so I got dressed at home and left house in my skirt. Let me say that this is a very special thing. I rarely get to do this. It feels so right! I had a backpack with the menswear that I would wear when I got to my primary destination. For some reason, it is harder to remember what to pack when I am packing my menswear than when I am packing my womenswear. After it was all ready, I left the house and headed for the bank. I realized recently that I needed to cover up when I am stopped at a traffic light near home, just in case someone I know sees me. The outfit I wore today, however, was not conspicuously feminine on top.

I had a handful of checks from the previous two months that I needed to deposit. The bank parking lot seemed rather full. A woman was in the vehicle to my left. I had to get out of my car and walk past the front of her vehicle. That caused me to hesitate. I finally built up my nerve and got out of my car. I walked into the bank and saw several of the ladies that I know from this branch. We all waved hello.

There were two men in the bank. A man was in the lobby area, talking on his phone. Another man was at one of the tellers. In this bank, to reduce human contact, they have a set of terminals with vacuum tubes, similar to the drive thru, that all walk-in customers are required to use. I walked past the man at the first position and went to the last position. By the time I completed my transaction, both men were gone.

On my way out of the building, I spoke to the employee that talked to me last time (her office is by the exit). She took my picture.

Barber Shop

For my next stop, I went to a barber shop that I have not gone to in a long time. The lady who spoke to me had short hair the last time I saw her. Now, she had beautiful, shoulder-length hair. We talked for a few minutes. Unfortunately, every barber/stylist had an appointment scheduled, and I could not get a haircut soon. She talked to me until her client with the appointment arrived. He entered and started standing several feet to my right. He even joined the conversation. I saw him take one look down at my outfit. Otherwise, he did not react to the man in a skirt.

Mexican Restaurant

I went to a Mexican restaurant that I frequent in menswear. I have gone here a couple times in a skirt to get carry-out food. I was determined to sit at a table, if it was not crowded. By now, it was after 1:30 PM and there were only a few customers. I hesitated for a long time in the lobby. The employee, who was taking a customer’s money told me that I could go on in and select a table. I was looking around the room to make sure there were no people who know me present. The employee started asking me questions about whether I was looking for a particular server, etc. I stepped away from her counter to let her see my outfit and said that I was just a little nervous.

I finally committed and walked in. I turned the first corner and sat at the first table. I was too nervous to walk through the room. Two men were at a table to my right and a woman was by herself was at the next table. She saw me. I am not sure whether the men ever looked at me. I doubt that the server, a man, ever saw my outfit. I ate my meal and enjoyed it.

When I was almost finished, a female employee approached my area to clean off the table next to mine. We started talking. She was very engaging. She asked me lots of questions and was quite friendly. I doubt she saw my clothes. I asked her to take my picture. We talked some more. Eventually, I got up to leave. This was when I think she first saw my outfit.

I said good-bye to the woman at the front desk as I was leaving. She complimented my outfit.

Other Stores

I did not want my crossdressed outing to end. I went to a couple other stores and shopped around. In one store, a female employee approached me to offer help. Immediately, another, younger employee joined her. Both of them were talking to me and answering my questions. I think they both saw me before approaching me. The first woman seemed like she was doing her job, but the second girl seemed like she was there because she wanted to be there. They broke off and I continued shopping. Later, the first woman helped me some more.

At another store, I just browsed around and left. A man was sitting at the cash register. He welcomed me, and then glanced down at my outfit. After that, he never looked my way again that I could see.

At a third store, I was the most nervous. It was a larger store and it was busier. I did not want to be seen by anyone who might know me, so I remained in the racks of clothes most of the time. I went to an area where I had met an employee last year and sort-of made friends. I asked an employee about her and I was told that my friend no longer worked there. The employee and I talked briefly. I asked her to take my picture.

Blood Bank

I gave blood a week ago. I looked at my online account and saw a surprising test result concerning my blood. I decided to go to the blood bank and ask about the result to make sure I understood what it meant. I walked in without any fear. The woman at the front desk was helping another woman. Eventually, we spoke and she answered my question. Then I left.

Car Dealership

We are considering replacing one of our cars. I had gone to this car lot recently (dressed in menswear) and sat in several cars. I wanted to try sitting in a couple specific models, and to take notes about them. I am rather tall, and some cars are not a good fit for me. The last time, there were not many customers. When I arrived, it was starting to get dark. I could see in the building. There were quite a few customers in the building that I was going to need to walk through.

I got out of my car and walked up to the entrance. Two women were waiting outside the entrance, talking. They saw me, but kept on talking. I looked inside at each customer. I saw no one who knew me. I walked in. I headed straight through the room to the door that leads to the cars. I noticed only a couple people look in my direction. Everyone inside was talking to an employee.

I went outside and sat in a couple cars. One car, however, had a dead battery. Therefore, the electric seat would not adjust for me. I went back to the entrance and spoke to a young, female employee, who was wearing a young, cute, knee-length skirt. I was so happy not to be the only one in a skirt! She was quite friendly. She confessed that she was not on the sales staff. She went in and got another employee to help me. This woman brought a device for jumping a car with a dead battery. She connected the car and I was able to adjust the seat. Afterward, we talked for several minutes. Mostly, we talked about life. She was very kind.

After about ten minutes of talking, I asked her to take my picture. Then, we walked back toward the building. She just kept on talking to me. I told her that when I went in, that I was probably going to walk rather fast toward the exit. She understood. But, when we got in the room, she kept talking to me. I paused briefly, but said good-bye and proceeded through the building. I did not see anyone pay me any attention this time.

After that, I went home.


From → True Stories

  1. Chris D'Orso permalink

    Yes! That sounds like a fantastic day. I’ve been doing the same thing for almost a year now, and honestly, I haven’t had a single bad experience. Overwhelmingly neutral – just folks going about their days too – but a surprising number of positive experiences that make it all worth it. We’re moving the needle, just a little bit.

  2. What a packed day jjjohane. Sounds like so much fun to be out. The outfit looks fabulous.
    I so enjoy your adventures.

  3. Glad to see you “out and about”. I notice you being braver and closer to home. It is interesting how people accept you when you are clean, nicely dressed and polite. I wore a pretty, Fall colored long sleeve blouse to get a “to go” pizza the other day and no one even looked twice.

  4. Alvie permalink

    You be you!

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