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Crossdressed at the Dermatologist

April 26, 2022


I have a spot on the skin of my jaw that has been there for a few months. I scheduled an appointment with a dermatologist just in case it is something bad. This office is across town from my home. As the appointment approached, I started getting the idea that I could dress up on this outing. Then, I got the idea that I could go to the dermatologist in a skirt. They probably would not document any lifestyle choices I make onto my chart. So, I did it! It was just fine.

At Home

I was alone at home when the time for my appointment came. I put on my black skirt, my black/white/gray patterned blouse, and my black flats. I had intended to wear my purple top, but I never feel as pretty in that top. I have also put on some belly fat, and I am self-conscious about it. I packed my bag of menswear and drove out of my garage dressed pretty!

Waiting room

I arrived at the doctor’s parking lot. There was a man walking to his vehicle. I pulled in the open parking space that was two cars away from him. I felt the urge to hesitate until he drove away. I ignored the urge and got out of my car. There were reflective windows at the front of the building. It was possible that people were looking at me as I walked past them. I looked away to hide my face. When I am this close to home, I feel so cautious. With that said, I was really not too nervous to be doing all of this.

I walked inside and found that there were only three people in the waiting room. Two were sitting down. I got in line behind the third person. The other two people never looked up from their phones. The ladies working at the counter glanced over at me, glanced down at my outfit, and then returned to their work. I checked in with one of the ladies and took a seat not very far from the man who was in front of me. He never looked up from his phone. Perhaps he looked at me when he sat down, but it is possible that no one in the waiting room knew that there was a man in a skirt among them.

I crossed my legs and waited. A woman entered with her ~9 year old son. She had him sit down while she went to the counter. He did not pay attention to me. Eventually, he looked over my way. We made eye contact and then I looked away. It is possible that even he did not notice my outfit. The mother took him to the restroom after she checked in. In the few minutes while they were away, the man, and later I, were called away.

Exam Room – Interview

The woman who called me out of the waiting room guided me down the hall to an exam room. I will call her Miss C. I started chatting with her on the way. She had me sit on a chair, and she started interviewing me as a new patient. I felt so unprepared. I could not remember the name of one of my medicines, etc. At the end of the interview, as Miss C was about to depart, I asked her to take my picture. She agreed. I could tell she thought it was odd. I told her that this was the first time I had ever gone to the doctor dressed like this.

Exam Room – With the Doctor and Nurse

In a few minutes, there was a knock at the door. The doctor came in and asked me to sit on the table. I saw the nurse take a short glance down. If the doctor did the same, I never saw it. I had assumed that this was going to be one of those visits where I would have to strip down to my underwear and lie under the infamous Napkin of Dermatology (a small, paper blanket). I had prepared by bringing a loose pair of athletic shorts to wear instead of underwear. I was wrong. He was only interested in the spot on my face.

He examined me while the nurse watched. I never noticed her look at my outfit any further. He looked at, touched, scratched, and photographed my spot. He was unsure of what it was, but was not highly concerned. Eventually, he ordered me a medicine to apply for a week. He gave me other instructions. Then he set up two future appointments. One to check my spot, and one for me to lay under the Napkin of Dermatology for a full-body scan.

The doctor politely said his farewell and left the room. The nurse stayed and gave me my further instructions. Then, as she was leaving, I asked her, “Do you get many guys who dress like me?” She said, “Not many, but I am new.” We said our good-byes and she left.


I walked out of the room behind her and started toward the checkout desk. There was another nurse in the hall talking to Miss C. I saw the other nurse glance down at my skirt and legs. She kept her train of thought and continued the conversation. Miss C smiled and waved. She said, “Bye!”

At the checkout desk, the employees probably did not see me below the rib cage. While I stood there, however, another patient got in line behind me. She was an older woman. The other woman at the counter called her forward. Then, another older woman arrived and got in line. (I was the only one in a skirt.)

After we were done, I entered my new appointments into the calendar on my phone. Then I walked out. I did not encounter anyone in the building. Just as I stepped outside, I realized three people were walking together toward the entrance. I considered that I should hold the door for them. I did not choose to do that. They were far enough away for chivalry not to win. I chickened out about the door, but I walked past them on the sidewalk as I went toward my car.

EDIT: Here is a link to my second trip to the dermatologist.

Clothing Store

There is a clothing store that I like to call the “Fashion Store” because they have beautiful clothes, and because the women who shop there are normally dressed quite fashionably. I walked in and scanned the room quickly to make sure it was safe and no one I know is there. Then I walked on in. I browsed the ladies’ tops, looking for something that would work. Other women were shopping nearby, but they ignored me. I eventually gave up and went to look at dresses. I found nothing there either. A couple of other customers saw me and kept shopping. Many women were in skirts and dresses. They were beautifully dressed.

I went to the shoe section. This store has size 13 shoes on the back wall of the shoe section. I found a young woman trying on a high-heeled shoe nearby at the smaller shoes. I walked past her to my section. I started browsing. I was looking for a pair of black flats, because mine are wearing out. Instead, I saw a pair of size 13, nude, pointy-toe, stilettoes. I kind of had to try them on. I am not fond of pointy-toe shoes, but these were not too bad. While I was seated, the young woman finished up and walked past me with a friend. I put on the shoes and walked around some. I did not realize that a woman was in one of the rows of shoes leading away from the back wall. She looked and said, “They look good! They match your color. They work.” I thanked her and said, “I came here for black flats.” She laughed and said, “Sometimes we get diverted and have to try things on.” She was friendly and she talked to me complimentary. How nice!

I tried on a couple more pairs of shoes, but none of their flats were right for me. Most of the flat shoes in my size were too casual. …and I do not need dressy stiletto shoes. I used to have a pair of similar shoes with an open toe, but I almost never wore them, and I eventually parted with them. (They did not fit me very well.)

I decided to look at the tops in the clearance section. I ended up shopping by the woman who spoke to me previously. She was in the small section. I was in the extra large section. When I was done, I said to her, “I am clearly shopping in the wrong section and held up a lime-green half-sweater that would not have reached to the bottom of my rib cage. She agreed thoroughly and talked about how so many of these outfits are not for her age either! I thanked her for her kind words earlier and said, “and also, thank you for talking to me. Most people ignore me.”

I, with forlorn hope, went to the accessories section to see if they had any pantyhose. Years ago, I found Shimera pantyhose here. They became my favorite pantyhose. They are almost invisible. One of their shades matches my skin very well. Everything about them is perfect, except that the sparkly, golden panty section does not grip and stay put as well as I would like. Almost immediately after I discovered these pantyhose, the store stopped carrying them. I had to see if… just if… they had my brand again. They DID!!! They did not have my preferred color, but they did have my hose! I bought all three pairs that they had in my size. The color was a little darker, but I think it will work.

My preferred color of Shimera Pantyhose on me long ago.


As I was driving home, I saw a store called Torrid. Torrid is a plus-size store. I thought, “They might have shoes my size.” I stopped and went in. The employee, who had green hair that matched her glasses, greeted me from across the room. She saw me walking across the room and looked at my outfit. I found shoes in the back above some clothing racks. There were only a few and they were not my size. I looked at tops afterward. The employee came into the same area as me and asked if she could help. I asked her if she had any other shoes. She did. There was a rack that I had overlooked. She said that she might have some shoes in the back that were returned from Internet purchases. She went to the back, and I went to the rack.

A ~25 year old woman and her mother were shopping nearby. The younger woman was sitting near the shoes. I walked around her to look at the flats. I said, “I am going to look at these shoes. Please pardon me for crowding near you.” She kindly spoke to me. She said, “It is fine! I just finished up here.” I forget what else was said as she got up, but it was warm and friendly.

I found some several pairs of shoes that were 12WW in size. Some fit me rather well. I think that the black flats that they had were a little short and would eventually make my toenails hurt. They also cost over $50, which is more than I want to pay for some shoes that are not quite what I was looking for. The employee brought me some size 13 shoes from the back. They were actually size 13WW (wide width or possibly wide-wide). In any case, they were much too big, and they were taupe, not black.

Before I left, I went to the cashier area in order to give her back the shoes she had brought to me. I asked her if she has many guys who dress like me. She said some. She said most were trans-women. Then she added that she was married to a trans-woman. That is when I knew I needed to stop and ask questions. “Does she have a long torso like me? Where does she buy dresses?” We spoke briefly. Her answer was a web site that I had never heard of. I thanked her and I started to leave, but I had a thought and I turned back. I asked, “Was she a trans-woman when you started dating?” She told me that she transitioned about a year ago. This woman had been with a man for over a decade, and then he expressed that he was a woman and needed to live as one. She stuck with him as he became a woman. She, the cashier, now has a wife and still is in love. I do not know how many women could tolerate something like that in their marriage. It is impressive.

Ice Cream Shop

I went to an ice cream shop as my last stop. I go to this shop occasionally in either menswear or womenswear. I got in line. Two women were in line ahead of me. It took a while. Another family got in line behind me. I think they were a ~40-year-old woman, her daughter, and her ~3-4-year-old grand-daughter. We all waited. The two women apparently ordered a single sundae to share. I asked one of them, “Are you going to share that? I got in trouble for trying to share ice cream with my wife.” She laughed and responded, “She (her friend) gave me a dirty look when I ordered it.”

One of the employees, who is normally there when I visit, saw me and greeted me. She said that she had missed seeing me. It has been a while since my last visit.

The child behind me started declaring that she wanted “one of those”, pointing at waffle cones that had been dipped in chocolate and rolled in Oreos. I started laughing. My kids used to be little, and I know that the ice cream would be on the floor if someone that young was given a waffle cone. The grandmother and I spoke briefly, smiling.

Finally, I placed my order and sat outside in the lovely sunlight and ate my treat. Then, I went home. As I write this a day later, I still feel warm inside from the great experience!


From → True Stories

  1. picklejuicesoda permalink

    It’s all so exciting! I’m envious, I want to dress openly but I’m so worried. Especially living in a small town and seemingly not so open minded. I have fully dressed when Covid first hit and I was masked up with a wig. It felt wonderful searching for clothes and trying on shoes. Walking past mirrors in the store and seeing myself in a nice black dress with hose and heels. I eventually threw it all away in a moment of guilt and fear my kids may find them. Thank you for your story. I will read more when I have time!

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  1. Dermatologist Trip 2.0 | joeypress

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