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Crossdressed at the Grocery Store

June 30, 2021


I have not had an outing where I could dress pretty in a couple months. I needed to go to a dental appointment. I packed a khaki skirt, a gray and white striped top, a red cardigan, and black heels. I wore some skin-toned pantyhose under my menswear and went to my appointment. If you are new to my story, I am a guy who crossdresses, but presents male from the collar up.

Dental Appointment

I wore menswear for my dental appointment. I would like to go to a dentist appointment while dressed pretty one day. For now, however, these people know too many of my family members for me to do it in this office. There was about an inch of my hosed ankle showing between my blue jeans and my low-profile, athletic socks. I was not worried that they would notice it. I am pretty sure no one ever looked.

Grocery Store

After the dentist, I changed into my pretty outfit and drove to a grocery store that was rather far from home. It was not far enough from home to guarantee that I would not run into someone I know, but I did what I could. I only needed to get some milk. I progressed through the store cautiously. I looked to see if I saw anyone familiar. I chose a path that was not heavily traveled. The racks in this store were short enough that you could see into other aisles.

I made it to the back of the store safely. I selected two jugs of milk. A male customer was getting help from an employee while I got the milk. The employee looked my way, but the customer may not have seen me. I returned the way I came. I decided that it was safe here. So, I looked for a memory card for my camera. I did not see anything nearby and I did not want to tour the whole store looking for it. I was ready to go to the cash register when something unusual happened.

Someone called to me. I turned to see a woman who was older than me by over 20 years. She was pushing a shopping cart that contained one potted sunflower. She asked me if I wanted her cart. I told her, “No, I am about to go check out, but thank you.” Then I added, “Really… thank you very much.” I do not know if she was being friendly to me simply because of what I had in my hands, or if it was because she wanted to be kind to a man in a skirt. It was very kind in any case.

I got in line to pay for my groceries. The woman in front of me was tall. She was unloading her cart. I complimented her on her height, “I love how tall you are!” She smiled at me and thanked me. She never glanced at my outfit. A customer was ahead of her in line, so this left me standing in the front aisle of the store where anyone could see me. Another woman got in line behind me. An employee entered the aisle and saw us standing there. She looked at my lower half for only a moment and then invited us to come to her lane. She reopened her lane for us. The woman behind me told me to go first.

I went through the checkout with the employee. She never commented on my clothing, of course. We talked briefly and I moved on. It did not take long to purchase two jugs of milk. I returned to my car.

Shoe Store

I stopped in at a shoe store. I am still looking for some flats to replace my strappy black flats that are falling apart. I tried on some shoes. They had size 12 W and size 13 ladies’ shoes. These did not fit me comfortably though. An employee came over and talked to me. I asked the employee if she felt that a pair of shoes I tried on were “old lady shoes”. She said, “Those do look like shoes that a seasoned woman might wear.” I complimented her on her tact. We talked briefly. She advised me to buy shoes based on the comfort and not on the appearance. I think I will strive for both. 🙂 She called me ma’am at one point in our conversation. That never happens to me. I did not correct her. She moved on and worked elsewhere in the store.

Beauty Supply Store

Next, I went to a beauty supply store to get some Surgi Invisi Bleach. I ran out of this product and my leg hair is becoming visible under my pantyhose!! The employee was seated behind the counter. I did not see her. She stood up and asked if I needed help. I saw what I needed and declined any help.

I returned to the front to pay for my hair bleach. I started talking to the employee. I told her why I needed it and why I preferred it over competing products. (I am a fan of it.) Eventually, we moved on to talking about other things. She asked me what pronouns that I preferred. She mentioned that today was the last day of pride month and that she had changed her hair color a few times for it. Today, she was a bleached blonde. Then, she mentioned being trans. That is when I realized that I had been misgendering the employee. I asked, “What pronouns do you prefer?” The answer: “He, him, they, them.”

I apologized for calling him “ma’am.” We started talking about his story. He was wearing loose clothing, had short hair, and presented nothing feminine, except for a female-sounding voice. We had a pleasant conversation. I am so very ignorant about most things in the LGBTQ community… I know me and I am acquainted with a little about heterosexual trans women (men who are trans who are married to cis-women). Otherwise, I am rather unknowledgeable.

He did not know many trans people in our area. I spoke of the very few encounters that I have had in the area.

A customer came into the store and eventually came to the front in order to pay. I broke off our conversation so he could take the customer’s money. I said good-bye. He thanked me for talking and he asked me to come and visit again any time.


From → True Stories

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