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All Day Outing In A Skirt

October 21, 2022


Monday was a national holiday. I took the day off from work. I had a load of errands to accomplish, so I did it in a skirt! I wore a black skirt, a gray sweater, black pantyhose, and black flats. I was just a man in a skirt for seven hours. I felt beautiful, and I felt welcome in public.

Side note: I was able to wear black pantyhose because I have started shaving my legs for the winter! I bleach my leg hair during the summer so that I have hair, but it does not show through my pantyhose, so I can wear skirts of any length all year. Unfortunately, the light-colored hair will poke out of black pantyhose and be visible. Therefore, I do not wear darker hosiery for most of the year.

Bloodwork at Doctor’s Office

I had to have a little blood drawn by my doctor’s office. I did this in menswear.

Thrift Store

I changed clothes and drove into the donation lane at a thrift store. As I stepped out of my car, a woman came out to receive my donation. I saw her take a glance down at what I was wearing. I donated a bulky Halloween costume that my son and I had made a few years ago. A man came out to help. They both loved the costume and we laughed and talked. They interacted with me politely and respectfully.

I parked my car and shopped inside the thrift store. An employee greeted me as I entered. I shopped around the whole store. There were about 25 other customers. I only saw one person look at me in a way that seemed disapproving. All others acted like they did not notice anything unusual about me. It was relaxing and uneventful.

Large Clothing Store

I shopped in a clothing store. I did not find anything to buy. I was around quite a few people. I noticed a couple of people glance down. Other than the few “glancers”, no one acted like they saw anything unusual.


For breakfast, I went to a restaurant that is significant for me. At least 13 years ago, I had to work late one evening. When I left work, I wore a skirt to this restaurant and ate supper. I think it was the first time that I ever went to a restaurant in a skirt. It was hard to do and it was scary. This is significant because, in those days, I tried to maintain control of every situation. In a restaurant, you cannot leave until you pay. You cannot easily hide. It was SO scary, and I felt SO stupid for for doing it. Afterward, it felt like an achievement because I had done something scary and survived.

This time, I casually got out of my car and walked across the sunlit parking lot into the busy restaurant. However, I asked the hostess to seat me in a not-so-conspicuous place so that I would not be on display. The hostess sat me in the booth she had already chosen, which was sufficient.

Three people were seated in the booth across the aisle to my right. They were a man and wife, and another man. They were all in their 70’s. They took several glances. They never tried to greet me or be friendly. I felt like my outfit made them uncomfortable. It did not bother me. I think they were mostly over it before they left.

After I finished eating, and after the people in the other booth had left, I asked the waitress (45 year old) if she had noticed my outfit. She responded that she liked my shoes. She commented on them several times in a row. I told her about my previous visit, and that this restaurant is significant for me. I asked her to take my picture. She continued to be a good waitress. She told me to come back when I am out dressed pretty.

Shoe Store

I drove to a shoe store. As I was driving in the parking lot, I saw a woman carrying something white and flowy on a hanger. When I got out of my car, I looked toward her. She was putting two white ghosts (Halloween decorations) into the trunk of her car. I remarked to her from across the parking lot, “When I first saw you, I thought you were carrying a wedding dress!” I laughed. She laughed back and spoke to me. I walked away wishing her a “Happy Halloween.”

I went into the shoe store where I have previously shopped for men’s shoes while wearing a skirt. This time, I was shopping for two pairs: some athletic shoes and some semi-dressy men’s shoes. I browsed around and tried on several pairs of shoes. I walked around in the shoes that I considered buying. These days, almost all men’s athletic shoes are dark colored, often charcoal gray. I ventured into the women’s section because they had shoes in brighter colors, but they did not have anything big enough for me.

I bought this pair.

No one paid me any significant attention. No employees offered me help. I bought two pairs of shoes. The young woman at the cash register was polite, but non-engaging.

I also bought this pair.

Expensive Clothing Store

For fun, I went to a store that sells very nice women’s clothing. I have shopped here before, but I seldom purchase anything because their clothes are rather expensive. I was approached by an employee promptly after entering. She glanced at my outfit, and then politely and professionally did her job. She asked me what I was shopping for. I told her that I need help making good outfits, and I also need tops. She said that I was in the petite section and that she would take me to someone who could help me.

She gave me to another salesperson who was slightly older than me. I will call this sales person “Francis”. She told Francis that I needed help with building outfits and finding tops. Francis went right to work asking me questions about what I was interested in and what I was trying to accomplish. She walked me around the store, showing me options. She asked more questions. I asked about combining things to make good looking outfits. She tried her hardest to be a big help.

Eventually, she asked me some questions that were more social than professional. She apologized if her questions were inappropriate. I was her first encounter with a crossdresser. She was interested in how my wife and kids feel about it. She complimented my current outfit. She became apologetic that she had not helped me more. I told her that the best advice that she gave me was, “When I see something that I like, I think, ‘How can I build that from things I already have in my closet?’, and then I might buy something to complete the outfit/ensemble.”

I ultimately did not buy anything because everything was over $40 and some things were more than $100. That is very expensive clothing for me! As I left, I told the manager that Francis was very helpful to me.

Stylish Clothing Store

I went to another clothing store that is not as expensive, and is more fashionable than average. I shopped around. There were a lot of customers. Few people ever looked at me. I went to the shoe section because they often have shoes in my size, but so far, they never have flats, which I need. There was a pair of [ridiculous] red pumps in my size. I tried them on… I left without buying anything.

Why do the only shoes they have that fit me have to be so unreasonable? 🙂

Appliance Store

I went to a large appliance store. I was shopping for a clothes dryer. I found my way past the furniture and televisions to the right section of the store. The large furniture, televisions, and appliances obstructed anyone from seeing me. I was invisible. I shopped around for a few minutes and found what I wanted. I went to a salesman behind a counter. I started talking to him. I doubt he could see my outfit from behind the counter. He came out to help me.

When he came to where he could see me, I saw no evidence that he even noticed my outfit. It turns out that Amana appliances have lost their good reputation. He said that most clothes dryers only last 5-7 years. He recommended a couple of other brands that do have a reputation for lasting 15-25 years. I decided not to buy anything until I could do more research.

Blood Bank

Next, I went to the blood bank to donate blood. Their system had started texting me, asking me to donate. When I walked in, there were three women working at the counter and one customer. They looked me up in the computer, but something was not working. They had to get a young man from the back to explain why the computer would not let me donate. It was too soon. I will have to go back next week. By this point, I had almost forgotten that I was crossdressed. I asked if I could use their restroom. When I came out, the woman on the end watched me walk toward her. She was smiling. I thanked them and I left.

Barber Shop

I went to a barbershop I have frequented in a skirt. My barber asked me to wait a few minutes. I sat in the lobby. A customer was facing me while getting her hair cut. My barber eventually came into the lobby and welcomed me. While she cut my hair, we talked about the appliance I was purchasing. She told me that another barber had purchased the brand that the salesman had recommended.

The helpful, big-haired barber is in the background. If you look carefully, you will see her large dog that she brings to work. She’s a country girl.

After my haircut, I spoke with the other barber about it. She was a country farm-girl. She had big hair, significant make-up, and a country accent. I think she may have been the shop owner. She never looked at my outfit. She gave me her positive review and recommended it. I went to my car and searched for other reviews online. I went back in and asked her some more questions. She answered those, and I left.

Appliance Store Part 2

I returned to the appliance store. I stood near a woman. She was listening to a salesman who was talking about the product I was considering. I listened in. A different salesman approached me. I told him who the salesman was who had been helping me. Soon, my salesman came around the corner. I asked a few questions and selected the model I wanted. We went to his window and I sat in the tall chair and crossed my legs. Still, he gave no sign of noticing that I was dressed differently. While we were there, I noticed that his arms were hairless. I purchased the dryer, scheduled delivery, and I left.

Visited a Friend

Long ago, I went to a store where the person previously complimented me for wearing pantyhose. I returned to visit a couple other times. This time, we talked for ten minutes and it was nice.

Consignment Stores

I visited two consignment stores where I have shopped previously. Both consignment stores were closed. They are both closed on Mondays.

Late Lunch

Around 3:00 PM, I had finished all of my errands and fun excursions. I had not eaten lunch. I went to a restaurant. It was so late, the restaurant was empty. The waitress was young and never acknowledged my outfit. I ate, she took my picture, and then I changed back into menswear and did one last errand close to home.

From → True Stories

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