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Crossdressed Grocery Shopping Inception

January 29, 2022


I have been taking the COVID-19 pandemic seriously. Therefore, I have not been going out in public very often. This has greatly reduced how much I get to crossdress. Other lifestyle changes have really reduced how many outings I have had as well. I really wanted to dress pretty and get out of the house, but I simply have not been able to for many weeks. I have had a few minor outings, but they were rather insignificant. Today, I had the day off from work and I arranged with my wife for me to go to the next town over and do our regular grocery shopping, while wearing a skirt. I wore my khaki skirt, and a black top. For shoes, I started with black wedge heels, and later, I changed into black flats. I was just a man in a skirt out in public. It was a good outing, but at some points, it felt like that movie, Inception.

Outlet Mall Inception

Before going to the grocery store, I went to an outlet mall. It was quite cold at the beginning of the day, requiring me to wear my men’s heavy coat. I visited several clothing stores. I started noticing that people were looking at me as they passed me. It was like that scene in Inception where the woman was walking around in an artificial environment and all of the artificial people were glaring at her as they walked by. No one glared at me, but their behavior seemed unusual. People used to be polite and either greet me or pretend not to see me. There was a considerable amount of time before someone did either of those.

Here are a few things that happened at the Outlet Mall:

I visited one large store. They had just opened. I was one of very few customers. I was in the shoe section. An employee was working at a shelf in the shoe section and I was looking for my size. She realized that she was not alone and said, “Hi, can I help you find something? –Oh.” I assume she thought I was a man in the ladies’ section needing help, and then saw that I was wearing a skirt and ladies’ shoes. She was professional after the awkward, “Oh.”

I passed a man going the other way on an aisle. He made eye contact but did not say hello. I walked a little farther and saw that I was heading into the menswear section. I turned around. I was about 10 meters behind the man. He saw his wife and called to her and made a hand motion to beckon her to him. They met at an intersection and I believe that he told her about me. They both looked up my way only to realize that I was facing them. They moved on.

When I walked through the open-air part of the mall, at least a dozen people would walk past me and look at me. In some stores, this also happened. It was rather unusual. One employee came to me and smiled and politely tried to help me. After over fifteen minutes, she was a welcome friend! I encountered more people who stared. I met a salesperson who must like to meet people as much as I do. She stood and talked to me for at least ten minutes. She only left me because another customer came into the store with a return-item in hand.

Hanesbrands Outlet

Years ago, there used to be a store called the “Leggs, Hanes, Bali Outlet”. Now, it is called the “Hanesbrands Outlet”. This store was where Leggs Pantyhose would sell their “slightly imperfect” pantyhose (sheer tights). You could buy a six-pack of pantyhose that were slightly imperfect for $15-20 instead of for $5 per pair. Slightly imperfect typically means that the waist band seam meets up 3mm off from perfect, or that the toe seam on one leg is 90 degrees off from the other toe seam, requiring you to have a twisted leg, if you want the seam to be under your toes. Normally, I cannot easily tell the difference between the imperfect and the perfect pantyhose.

If you are a woman or a young crossdresser, you may not care for pantyhose. However, for some reason, old guys like me who crossdress, we love to wear pantyhose. We are from the 1980’s when dresses and skirts always were accompanied by pantyhose-covered legs. I know I will sound like a caveman when I say this, but pantyhose are slightly shiny. I love that! They make the whole world feel like silk. They make my legs look pretty. They make me feel beautiful. I love the feel of my legs swishing when I walk and the feel of my legs when they are crossed. If you can find a style and size of pantyhose that works well for you, then they can be very pleasant to wear. Finding the right style and size is not necessarily easy.

I am of the opinion that the Leggs outlet and Victoria’s Secret are the two places to where all crossdressers from my era must take occasional pilgrimages. I don’t go to Victoria’s Secret these days, but I will go to a Hanesbrands store when I can. This particular store had moved. When I walked in, I was shocked to find that the store was SIGNIFICANTLY smaller than it used to be. I stood there in shock. They were selling undergarments and athletic wear, but I did not see a hosiery section in the entire store. This is like Apple Computers deciding to stop making computers. This is a big deal! I sure hope that Leggs pantyhose is not getting out of the pantyhose business!

I spoke with the employee and she said that they had a bin with packs of pantyhose in it that were $5 per pack. I went to the bin and looked. Their leftover stock of pantyhose had been put in a clearance bin. I searched for something good. There were few things in my size. I found a couple 3-packs of Hanes Silk Reflections pantyhose in my size and color and bought those. I confess that I am feeling sad. I do no think that I will ever have a reason to go back to a Hanesbrand store. 😦 I know that clothing stores are hardly carrying skirts any longer, since the pandemic lockdown started two years ago… Now this too…


I left the outlet mall and headed toward my car. I saw something was going on beside my car. A person was in the car next to mine, and a woman was outside of it, talking to the driver through the passenger-side window. She was standing next to my car’s driver-side door. When I was about 20 meters away, the car drove away. The woman looked toward me and started walking in my direction. She walked over a snowy area instead of walking around it. That seemed unusual.

The woman approached me and started asking for money. She did what many “panhandlers” do, she told me her story about why she needed help. She told me that she was homeless and someone had burned down her tent and sleeping bag. Her family would not help her… There was more, but I forget the bulk of it. The fact that I was crossdressed did not slow her down at all.

Culturally, I was raised to believe that panhandlers lie to you. I was told that they are getting rich doing this. I was told that they will use the money for drugs. However, my father would always give to panhandlers. He would quote Jesus to me and say that “we should give to those who asked from us, hoping that they will not repay us.” (Dad’s interpretation of the last part may be unique.) Dad would always give. He was generous, even though it went against our culture. I had mixed views. I was not as generous as my father. Then, I had kids. Saying no to a poor beggar in front of my children made me very uncomfortable. I started giving money to people at traffic lights when I was in front of my children. Then, I said, “I do not want to be a different man in private than I am in public.” I started giving money to beggars in private, too. After George Floyd died, I learned a ton more about how imbalanced of a world I live in. I also started seeing that my culture more resembled the “goats” in Jesus’ parable of “The sheep and the goats”. More and more of my stingy walls came down.

It was slightly above freezing. This woman was wearing a shirt, leggings, and a medium coat. She was clean. She spoke like she might not have much education. I typically do not believe panhandler stories. I did not believe her story. Regardless of her story, this woman was poor and had more needs than I have. I saw past her words and saw her true needs. I still did not want to give her my money… But, I pulled out some money and gave it to her. I also gave her a “homeless bag” that my daughter had assembled and placed in my car. It contained socks, a mask, toiletries, towels, etc. She thanked me and walked on.

I am not generous enough, yet. I could have given her $100 and not missed it. The Lord has blessed me more than I have ever asked for or imagined. I look back and wonder if I should have given her much more money so that she could be done begging for the day. Then I could have sat down with her and had her tell me her whole story… I am trying to get better, y’all…


When I left the outlet mall, I was hungry. It was almost 1:00 PM. I needed to go to the restroom. I decided to go to a fast food restaurant and use their restroom and then get food to-go. I walked up to the door of a restaurant that sold good milkshakes and found the door was locked. The dining area was closed, presumably due to the big spike in the Omicron variant of COVID-19 infections that is going on. I used the drive through and got my lunch milkshake with the obligatory meal.

I still needed to go to the restroom. I ate in the car and drove until I got to the grocery store. I drove past it and went to the nearby big-box hardware store. I decided to use their restroom and maybe buy a tool that I have been wanting.

Hardware Store

I walked into the hardware store and felt so oppressed. No one did anything to me. Hardly anyone looked in my direction. It was simply busy and I felt like I should hide. I immediately went into an aisle where I could avoid people and navigated to the back. I went into the restroom and did the required excavating to remove the layers of spandex that I wear to compensate for my old-man-metabolism. I finished in the bathroom and returned to the store. I did not see the tools section. I eventually returned to the front of the store. I glanced around and saw that tools section was located far away from me. I also saw that the exit was very close to me. I left the store. No one had given me any reason to feel uncomfortable, but I had to get out of there.

Grocery Store

I arrived at the grocery store. I changed into my flats. I walked up to the shopping carts with my list in hand. A woman was there getting her cart. She was around five years older than me. Her hair was very pretty. It was blond and it had a lot of body. It was curled and was sticking out of the hood of her coat framing her face. I saw her and smiled and said, “You are having a good hair day today!” She responded, “Yes I am!” I think she did not mean to say something possibly arrogant. I think she was caught off guard and said what came to mind. She thanked me.

I started shopping in the store. I was trying to be efficient. I did not notice people staring at me. Some people would talk to me. Some people would not acknowledge me. One woman stood near me looking at the rack and said, “I do not remember why I am here.” Then she looked at me and joked, “Can I have your list?”

I tried something new. I set up my camera in my cart and set it to record video in order to get a few screenshots. Next time, I might try using the time lapse feature and just capture higher quality pictures.

I crossed paths with the woman with the pretty hair a few times. She and I would make eye contact but we did not speak. Eventually, she passed me again and leaned toward me and said, “I think that you made my day!” She smiled. I said, “Good. You are beautiful!” That was the last time I crossed paths with her.

I completed my shopping and checked out. Nothing very notable happened. While I shopped in that store, I may have encountered over 50 people. In total, I saw one woman wearing a dress and one woman wearing a long, black skirt with black tights and wedge heels. So, one in three people wearing a dress/skirt today was a dude.

Other Grocery Store

I went to a second grocery store for a few things I could not find. I shopped quickly without incident. I went to check out. A man was running the cash register. I started moving my groceries to the conveyor belt. First, a stack of frozen pizzas. The man said, “Pizza party!” Then, I moved several packages of sausage. (Please pardon my crudeness.) I said, “Don’t say that for these.” He looked and laughed gently, and then realized the joke and laughed heartily. Then, he went there. I said, “Oh no, you did it anyway.” He responded, “I had to.” We laughed. I loaded the rest of my groceries and he took my money. It was as if we neither cared that I was in a skirt… because, just maybe, we neither actually cared. I was just a man in his store and he was just my cashier. 🙂

From → True Stories

  1. Thanks for the story Joey! My first thought about your hardware store encounter was that you perhaps associate such a store more with masculinity, and as being frequented by the kind of guys that are less likely to appreciate you dressed pretty. In other words, you feel more comfortable in a traditionally female setting than a traditionally male one. That would certainly be true for me anyway…

    • I have had other experiences in hardware stores. The first time I went there, your evaluation definitely applies. Then, I discovered that hardware stores were just like everywhere else. People looked briefly and then stopped looking. People would be polite if I spoke to them. So, I don’t know if your explanation is fully applicable to this experience or not. (You’re probably right.) I have gone to this same store before and not felt this awkward. So something was different about me this day… I think I do feel like dressing pretty in a hardware store is like wearing a costume in public on some arbitrary day. I definitely feel awkward crossdressing around blue-collar/laboring class men. The hardware store has quite a few of those. I feel like such men are more likely to be rude to me, so I try to dodge them. However, I have only had a few uncomfortable experiences around such men.

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