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Happy to See Me?

September 10, 2020


Where I used to work, there was a nearby Mexican restaurant that was my favorite. I went there once or twice per week (in menswear) and I always ordered the same thing. All of the staff grew to recognize me. They would greet me when appropriate. One time, I heard a waitress (let’s call her “Miss B”) tell another staffer that “Un taco suave” was here. They knew me.

Eventually, I became willing to crossdress closer to where I worked. One day, I decided to wear nude pantyhose with ladies’ shorts to this restaurant. It seemed like no one noticed. On another occasion, I wore ladies’ slacks with black pantyhose and ladies’ flats to the restaurant. The male server noticed.

Eventually, about a year later, I wore a skirt to this restaurant. I tried it again, and again, and again. In several of these visits, I saw Miss B. Normally, regardless of my outfit, she is rather quiet and withdrawn. On at least one of these outings, Miss B was more social toward me. It was nothing inappropriate.

This may sound like a lot of visits while crossdressed, but I literally visit this restaurant 50-100 times per year. I have a problem…. These few outings occurred over the course of a few years.

Fast forward to the present. I am working somewhere new. I started going to a new Mexican restaurant. One evening, I visited the restaurant near my new work. Miss B was working there. That concerned me. I like to keep my crossdressing isolated from my menswear life, when possible. I saw Miss B there on other evening occasions.

One day, when I wanted to wear a skirt to lunch, I went back to the old restaurant. When I did this, Miss B served me. She was working the old restaurants in the days and the new restaurant in the evenings. She behaved like she knew me, and she behaved like the my outfit was no surprise. She took my order and brought me my bag of to-go food.

A few days ago, I went to the new restaurant to get lunch to-go (in menswear). I was waiting in the lobby and Miss B walked up to me. She started talking to me. I learned that she now only works at the new restaurant. She was so happy and friendly. She was happy to see me and was very talkative. I have spoken to her so little about non-food topics that I did not realize that she is weak at English. We managed to communicate sufficiently.

It really surprised me that this woman, who has seen me crossdressed on at least five occasions, wanted to come to talk to me for a couple minutes. She was happy to see me. She was proud to know me. It was so encouraging!


UPDATE: I returned to this restaurant. Miss B was behind the counter talking to the manager. They stopped talking and said hi to me. Miss B smiled like she was happy to see me. I placed my to-go order with the manager. I sat down and they returned to talking. They walked into the back together.

Moments later, Miss B came back out, all smiles. She leaned forward, placed her elbows on the counter, and started talking to me. I was sitting on the other side of the small lobby. There was no big topic that we discussed. I do not understand it. I do not think that she was flirting. (I’m pretty sure Miss B is “Mrs. B” to someone.) I have never done anything around her to make me seem very fun. I don’t think that I am all that good of a tipper…. I don’t get it. I told my wife about it.

From → True Stories

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