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Grocery Shopping in a Dress

January 30, 2023


I had a day off of work. My wife and kids were going to be out of the house all morning. I asked my wife to make a grocery list for me to do our shopping. She made the list the night before. On the morning of my day off, I showered and shaved, I packed a bag of men’s clothes, and I put on my new, long, black dress with a red cardigan. I wore black flats. I was going to go grocery shopping while dressed pretty! (I am a guy who likes to wear a dress sometimes.) I searched online for any events occurring in the town I like to go to when I am crossdressed. There was an LGBT group having a meeting at a coffee house. I do not feel like I am very LGBT, but I decided I would attend their get-together. I walked out of my door in my dress, carrying my bag of menswear. I pressed the button and then walked across the garage to my car while the garage door opened.

Coffee Shop

My GPS lead me to the coffee shop. It was in a building with numerous other businesses. After orbiting the parking lot a few times, I found a vacant parking space. There was an elderly woman wearing sunglasses sitting in the car parked in front of mine. She was facing me. I got out of my car, rather unconcerned about her. She was looking right at me. I waved, but she did not react. As I walked past her car, I saw that she was messing with her phone. She had never looked at me! HA!

I had to go inside the building and follow signs to get to the coffee shop. I walked through the door of the coffee shop and looked around. There were about a dozen customers in the room. No group was larger than two people. I did not know what to do. The people in line looked at me. I looked at them. I decided to get in line behind them.

While I was in line, I asked an employee who was returning to the counter from the tables, “Is there a group meeting here today?” She looked like she was 30 years old. She had bright, friendly eyes. She did not know about any groups. She said no one had called ahead to reserve tables. I was thirty minutes late, so the group should have already assembled. She asked another employee (who was wearing a rainbow bracelet on her wrist). That employee was not aware of any groups either. The customers in line went away to sit down. The employees continued talking to me while they worked.

A third employee, closer to 50 years old was standing down the counter looking my way. At one point, she said something. Then she said, “You look very nice today, by the way.” (Yay!) I finally said that it was an LGBT group that was meeting. The woman with the rainbow bracelet asked if it was a specific group that she named. I said no. She said that she followed the group some. I looked it up on my phone and found the event. None of them had ever heard of the group or the meeting. We talked about other things for a few minutes. Then I walked over to a couple men on a couch and asked, “Are you two here with the <group name> group?” They said no and almost seemed like they were going to invite me to join them. I thanked them and I returned to the counter. I thanked the women and I left.


I asked my phone where was a nearby Mexican restaurant. I followed my phone’s directions. I parked in a public parking. There was a sign that said pay at the kiosk. I walked around looking for a kiosk. Eventually, I asked a woman if she could tell me where it was. She said, “That’s what we are trying to find, too.” She pointed to a man at another location in the parking lot. I went into a business. The female employee came to me and offered to assist me. I asked her, “Where is the kiosk for the parking lot?” She said that it had been removed and that the parking was free. I went back out to discover that the other kiosk seekers were gone. During all of this, no one seemed to notice or care that I am walking around dressed pretty!

My phone gave me walking directions to get to the restaurant. It took me up to main street for the town. I walked down the street, looking around. I noticed that I was not paying attention to the people I was passing. I was at ease! I got to my destination and the restaurant was not there. I asked some people on the street if they knew about the restaurant. They said they saw a Mexican restaurant down the street on the other side, but it looked closed. They were not from here, I surmised. The woman that I had talked to from that group remarked, “Aren’t you cold?” It was a little too cold to not be wearing a coat. Yes, I was cold, but only up top. My dress is sleeveless, and the knit cardigan did not do enough to keep in my heat.

They went into a business. I followed them. I asked the employee about the restaurant. She had never heard of it. (The Internet used to be smarter than this…) I walked across the street and visited a few shops on my way to the other Mexican restaurant. It had gone out of business. As I walked down the street, I noticed a café ahead of me. A man walking in front of me was about to go into it. I asked the man about the café. He stood there talking to me about how good it was and what he likes there. My dress did not make him uncomfortable.

I decided to move on. I went to a restaurant that I had eaten at once before. I went inside and had a Philly Cheese Steak sandwich. It was very good. No one seemed to pay my outfit any attention. Crossdressing has gotten so much easier these days.

Grocery Store 1

I went to the grocery store. A woman had just deposited a shopping cart when I walked up. I asked her if it was a good one. She said it was and I took it. I walked in and started shopping. A pineapple was on my shopping list. A Hispanic woman, her mother, and three children were at the pineapples. She was examining the pineapples and selecting several. I asked in Spanish for advice on how to select a good one. She told me what to look for and selected a pineapple for me. (Later, my wife said it was more green than she wanted… shrug.) While I was talking to the mother, her daughter looked at my cardigan, my dress, my pantyhose, my shoes, she looked me all over.

I asked another woman for advice about selecting avocados. She was older than me. She was eager and helpful. She offered to let me feel her avocado for comparison.

Later, while I was shopping, a woman complimented my outfit. When I finished shopping, I got in line behind the Hispanic family. The kids did not look at me this time. The mom talked to me and complimented my Spanish. When it was my turn, I set my camera on the conveyor belt and filmed while I checked out. The cashier was very friendly.

(Later, when I watched the video from the camera, I saw the cashier notice my outfit. My back was turned to her. I was loading my groceries onto the conveyor belt. She had stood up to adjust her clothes. She looked over at me and paused and glanced up and down a couple times. Then she sat back down and returned to work. She was all smiles when it was time to talk to me. When my back was turned, her face did not reveal any pleasure or disgust. This may be the only time I have ever been able to watch someone’s full reaction to me.)

I bagged my groceries near another customer. I spoke to her briefly. I ended up having an extra bag and I offered it to another customer who was bagging on my other side. I took my groceries to my car. The woman who took my bag held up the empty bag as she and her husband walked by. She thanked me for it. (I would have thought that she would have left the unneeded bag for the next needy customer.)

When I walked up to return my shopping cart, a woman to whom I had spoken earlier was also returning her cart. She looked like she was going to get there slightly ahead of me. She looked over at me. I looked at her. I started walking conspicuously faster. A man near the carts said, “It’s a race!” We had our laugh, I returned my cart, and I left.

Grocery Store 2

I needed a few more things that the first store did not provide. I went to a large, name-brand grocery store. I have also shopped here before while dressed pretty. I did not pay any attention to people as I walked in. I did not feel like I was on display. If people looked at me, it was not very noticeable. I did make eye contact and say hello to people. A few times, I found myself shopping with the same customer for several rows. We would end up talking. Everyone was friendly.

At one point, I was looking at the shelf for something. I had walked past an employee who was squatted, looking at the shelf in front of her. When she finished, she stood up and walked past me. She looked at me for the first time. She said something and then proclaimed, “I really like that skirt!” That was my third compliment in one outing. Unusual!

There was a woman pushing a cart while being followed by her husband. I passed them several times. Each time, he glanced at my feet/legs. Again, that made me wonder, “Is he a crossdresser like me?”

I shopped near a woman in a pretty white sweater with bright colored stripes. She had pretty curly hair. She was very well put together. Her style was modest. Her outfit and her demeanor made me think that she could have been an elementary school teacher. She was close to me in age. She and I spoke at least twice. When I was done shopping, I turned on my camera to record a video. I was walking across the back of the store toward the middle. I saw the woman in the striped sweater at the end of an aisle. I said, “I am finished!” and I held up my fist in triumph. She smiled and spoke to me. She talked back and forth to me a few sentences. My camera only caught a quarter second of her during our conversation. I captured her talking to me with a big friendly smile on her face.

I finished up my shopping and got in line. The cashier was friendly, but subdued. A woman was in line behind me. This was such a non-event that I did not worry or feel uptight. My watch said that I had exercised for thirty minutes on this outing, so I was at least somewhat uptight. I do not think I exerted myself enough to have actually earned exercise minutes. 🙂

After that, I left the store, put my groceries into my car, and walked across the parking lot to return my shopping cart. Then, I changed into my menswear, and returned home.

From → True Stories

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