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One Last Errand in a Dress

January 12, 2023


I had tried to complete several errands while crossdressed. I did my part, but uncontrollable external reasons made me have to go back and try a second time. One errand still was not completed. So, I put on my black dress, black wedge heels, and my beige cardigan, and went on my final errand.

Clothing Store

I had bought a sweater for my wife for Christmas at a small, locally-owned shop in a small town. I was dressed in menswear when I bought it. I tried it on in the store to see if it might fit my wife. It was not too small on me, so I bought it. My wife, however, did not like it and asked me to return it. (Sigh…) I guess I should have bought diamonds…

I drove to the store in my black dress. The only parking was about a block away. No people were visible, so I felt safe enough to make the walk down the sidewalk to the store. However, it was uncomfortable. I felt so exposed. When I had almost reached the business, I noticed someone was sitting in their car, facing my direction. She was watching my approach. I walked into the business.

Inside, there was the employee that had served me when I bought the sweater. She was talking to a customer. When I walked in, the customer said, “Let me go so you can do your job,” and she left the store. The employee, who was actually the owner, remembered me and said, “You have a return.” She was happy and friendly. After she completed the return, I shopped around the store, looking for things for me. She talked with me some about the outfits and some options.

Eventually, I said, “You seem very casual about this. Do you have other male customers?” She said, “No, but I have one now!” We kept talking. Eventually she asked me about my wife and kids reactions. I told her that my kids did not know. She questioned whether they really did not know. I said (as a good engineer), “I have seen no evidence that they have any idea.”

Later, I mentioned that I have considered telling my mother about it. Again, she seemed doubtful and asked, “Do you think she does not already know?” Again, I told her that I could not tell that she knew anything about it. But then, I confessed a few incidents that should help her know something is going on: She found my hosiery stash when I was ~8, and she found my sister’s dress hanging in my bedroom when I was a teenager.

The store owner needed to work. I needed to go back to my job as well. We said good-bye. She welcomed me to come back. I thanked her and made another daring stroll down the sidewalk to my car.

From → True Stories

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