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A Short Christmas Shopping Outing

December 24, 2022


Every year, for many years, I have gone out dressed in women’s clothing while doing my Christmas shopping. In recent years, it has been harder to have the free time to do this. This year was particularly difficult to get my Christmas shopping done, regardless of my apparel! However, I did get to do a little shopping while dressed pretty. I started out in a khaki skirt, white top, and a red duster/cardigan with black flats. Later, I changed into a new black dress with the red cardigan and flats. I took my camera on this outing, but I forgot to take the battery off of the charger… Therefore, I have no pictures.

Consignment Store

I went Christmas shopping yesterday near my home town. I was in men’s wear. During my shopping, I needed to drive to a nearby city to get some tickets to an event. I realized that I would be driving right by a consignment store where I love to shop. I think I have not visited this shop in a couple years. I say that the owner is my “big sister” when it comes to clothing. She is honest and never lets me buy something that looks bad on me.

I changed into a below-the-knee form-fitting khaki skirt, a white top, and a new red cardigan. I walked into the store. Two customers were near the door. They both looked at me. One opened her mouth, leaned back, and just slowly gazed down my outfit. They both greeted me. The owner of the shop was there and she happily welcomed me. She came around a rack of clothes and gave me a hug. At a couple points during my visit, these customers spoke to me as if I was a friend.

I shopped around in this store and tried on a few outfits. I bought a black and white top, and a black, knit dress. The dress does not have a waistline. This is good because I cannot normally wear a dress with a waistline because of how tall I am. This dress fit me well and I loved it! There were other customers in the store. They did not seem as comfortable around me. When I checked out at the cash register, these customers were behind me in line. We spoke and they were kind.

Box Office

I went to the box office where I wanted to buy tickets. They were closed.

Grocery Store

I needed to get some stuff for our upcoming Christmas festivities. I decided that I would go to a grocery store in the city and wear my dress while I was there. I changed into my dress and sat in my car in the parking lot, watching who was going in and out of the store. I finally got up my nerve and got out of my car. This store was busy. It was a higher-end (more expensive) grocery store. When I arrived at the entrance, there were several people coming and going. I did not see anyone notice my outfit.

I selected a shopping cart and entered the store. There were people everywhere. After a few minutes, I stopped feeling nervous and just did my shopping. I had a few pleasant encounters where an employee helped me, or a customer said “hello”. I had a lot of non-encounters where no one paid me any attention. I also had a couple encounters where people seemed unsure how to behave. No one was rude.

One man, who might have been 5-10 years older than me, crossed paths with me at one point. I saw him looking at my legs. It made me wonder if he was a guy like me. I saw him looking at the hosiery display in the grocery store at one point. So, maybe… He never spoke to me.

I finished my shopping and got in line to check out. I felt a bit exposed at this point. I was standing in a line that left me in the main aisle of the store where many people walked by. It was no big deal, I guess. Eventually, I was at the front of the line. The cashier was sweet and friendly. A woman bagged my groceries. She was nice, but not very engaging. She asked if I wanted help taking the groceries to my car. I declined.

I walked out to my car, put in my groceries, and then put up my shopping cart. A car was waiting for me to get into my car, because the parking lot was full.

After that, I changed back into menswear and did some more shopping near home.

From → True Stories

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