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Two Sightings in the Wild

December 28, 2022


On two recent occasions, I was out in public, dressed in menswear, and I saw a transgender person. To my surprise, they were not “doing it” how I would have expected… So first, some background. I grew up in the 70’s/80’s. In those days, the only time you ever saw a man in womenswear was on television or a movie. It was always comedic. Crossdressing was an embarrassing secret. It was not normally done in public. When I was a teenager, there were two crossdressers who, once per month, would shop at the grocery store where I worked. That was very unusual. When I started going out in public, I felt like I had to pass as a woman in order to be allowed to wear their clothes. I think that the two crossdressers at the grocery store also felt that way. They would try to go all out with hair, makeup, dressy clothes, etc. In the early days of reading forums and chatting online with other people like me, I discovered that everyone felt like they had to be 100% passable, or they felt like they should not go outside.

These people I saw this week do not feel like they have to do that. I find that very interesting…

First Sighting (at Chick-fil-a)

I walked into a Chick-fil-a (in menswear) and saw two women waiting for their order to be filled. One woman was unusually tall. She was wearing “a boot” (medical device on her foot), an old tennis shoe on the other foot, loose fitting denim pants, a tunic-length wrapped sweater top, and had long hair in a pony tail. When I walked into the line, I looked again at the tall woman and saw that she was wearing a wig that was pulled way down in the front. Being pulled into the pony tail made the front look very wig-like. The person had three days growth of whiskers, and no makeup. On her chest, she was wearing a silicone chest plate and had breasts (B cup or larger).

I placed my order and then walked over to where these women were and waited as well. I spoke and we started a conversation. The cis-woman did not speak to me. We did not speak about gender things. She was wearing a hospital bracelet. Perhaps she had just gotten out of the hospital. The conversation was short and polite. She used her normal masculine voice. She had no female mannerisms. Her chest plate had the color of a white Barbie doll’s skin. The silicone from the chest plate stopped at her whiskered neck. Then, an employee called out, “Order for <guy name>.” She took her order, said good-bye to me, and left.

It was also intriguing to see the people in the restaurant giving her glances and how they tried to be polite, but in unsure ways. It was neat to be the “fly on the wall.” Once upon a time, I would have been VERY self-conscious about being seen with someone like her. Old age has really chilled out my vanity!

Second Sighting (at a book store)

Yesterday, I went to a bookstore. I was out in public (in menswear) and I needed a charging cord for my phone. My battery was dying. I walked across the front of the store to where I thought they might have phone cords. I looked over at the cashier and saw a woman with a manly figure, and with breasts. I think she saw me look at her.

I shopped and found the cable I needed. I got in line. While waiting in line, I was able to observer the cashier. She had naturally wavy hair that came down to below her chin. I have seen guys with a similar hair cut before. She was not wearing makeup and she had a “shadow” on her face from whisker growth. She was wearing a V-neck women’s top. Her top exposed a patch of what I perceived to be unhappy skin. It kind of looked like a patch of pimples or something. She was using her natural guy voice.

Then, it was my turn… I walked up and saw that the patch on her chest was a circular patch of seemingly never-shaved chest hair.

Her: “Did you find everything you were looking for?”
Me: “Yes, I’m needing an emergency cable because my phone is dying.”
Her: (Some insignificant response.)
Me: (quietly) “What pronouns do you prefer?”
Her: “She and her. Thank you for asking.” (She smiled.)
Me: “It is good to meet you, ma’am.”
(We completed the transaction. She gave me the price… I paid… change was given… etc.)
Her: “Good-bye.”
Me: (I leaned in and spoke quietly) “Me too.”

I could not tell if she heard me say, “Me too.” I left the store.


  1. People have asked on “What would you do if you ever encountered a crossdresser in public.” I had predicted that I would not reveal that I could tell she was a crossdresser, and would try to say “ma’am” to her at some point in the conversation. I did not do quite what I had assumed I would do.
  2. Both of these transwomen were not nervous. Neither showed any awkwardness about being out in public. Both had achieved comfort in low-maintenance public transgender living.
  3. We used to say, use the pronouns that match how the person presents. If it were not for them wearing breasts, how would I have known what they were presenting? I go out in public with no makeup, no breasts, and wearing women’s clothes, but I am a man. No one has ever used female pronouns for me. I have been asked, “…, sir — or should I have said ma’am?” I have also been called by store employee who said, “Excuse me!” to get my attention (they did not use a gender-specific way to get my attention).
  4. Other than the fact that some people in the Chick-fil-a were unsure if they should treat the transwoman like any other customer, no one said or did anything different around these people.

From → True Stories

  1. I have been going out dressed at least twice a week for the last four years and spent two months dressed every day this summer. For the first two years I had a full beard. I always have a bra filled with bags of water to simulate breasts. So from the back I can be assumed to be female but not from the front. Even now that I am clean shaven and wearing lipstick I don’t expect anyone to think I’m female.

    But guess what, I have been treated with courtesy everywhere I go in eight different countries, in all styles of dress from winter furs to skimpy summer dresses.

    I think the idea that we must pass is a pernicious one and should be relegated to history. It causes many men to hide away in misery, unable to express their true selves for fear of not being perfect.

    Nina Lanyon

  2. This was a lovely observation

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