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A Confession and a Shoe Store Outing

May 14, 2022


There is something that I have not talked about on my blog. I battle/live with anxiety. I worry and fret. I doubt myself in some large-scale ways. I was not always this way. I used to be confident about some parts of myself — to a fault. Now, I feel like I am inferior. I feel like a failure in many facets of my life. Intellectually, I know that I am not as bad as I feel. Unfortunately, intellectual ideas are not very strong against emotional ideas. For example, no one ever said, “I am convinced that the lion at the bottom of this tree is not hungry, so I will climb down.”

My anxiety has grown strong lately, due to work, I think. I started going to a counselor about it. She has been helping me to stop dwelling on the past, or the future, or the imagined. She is helping me to be mindful about here and now. I am getting better at it. I can pull myself out of anxiety pretty well these days. I have been seeing her for over 7 months. In my first session with her, I told her I was a crossdresser. On many of my visits with her, I have dressed pretty. A couple of times, I had a minor crossdressed outing before or after my meeting. I have not written about these outings to the counselor’s office because I wanted to keep that part of my life private. I was also trying to avoid saying, “I am a crossdresser and I have issues.”

With that background, I went to a meeting today, and I wore a khaki pencil skirt, a white top, and a black and gray striped cardigan with black wedge heels. I wore a pair of my favorite pantyhose that I recently discovered were for sale again, “Shimera everyday sheer pantyhose”. These were not in my ideal color, but they were still very pretty and comfortable.

On the Sidewalk

When I leave my meetings, I take a look to see if any cars are coming down the street before I step out of the building. The building is in a small town. The town is close enough to my home to warrant extra care to avoid being seen dressed pretty. The road was clear. I walked out of the building, down to the sidewalk. I started walking toward the adjacent parking area where my car was located. Suddenly, a fast-moving electric cart (like a golf cart) came around the corner. This cart is part of a public transit system in this town. This public transit removes the hassle of walking from the various parking lots to the businesses in town center. The driver stopped beside me and asked, “Do you need a ride?” I declined and said thank you. He drove on.

Shoe Store

I did not want my outing to end. I felt extra pretty in my new pantyhose. These hose are so nice. They look like they are not there. They have a gentle sheen. They are just beautiful. I felt beautiful. I did not want to change clothes and go home. I drove to a shoe store.

I parked in a side parking lot between two shopping centers. This parking lot is a little out of the way. I presume that the employees park here. I parked in this lot because people would be less likely to drive by me or see me walking. I could walk between the wall and parked cars. The entrance to the store is just around the corner. It felt safe enough. I have gone to this store before while dressed pretty.

The front area of the shoe store was filled with short shelves, and the back area had tall shelves. There was a man shopping in the men’s section. There was a mom and daughter in the kids’ section. There were three female employees. I think there was a shift-change occurring. One of the employees was in the short-shelf area, talking to a friend. Another one of the employees was at the cash register. She saw me, glanced at my outfit, and said, “Hello. Welcome…”

I went to the ladies’ section where they sell flats. I have large feet. This store had 12W, 13M, and even 13W and 14M. Normally, I wear either 12W(ide) or 13M(edium) in ladies’ shoes. I tried on several pairs of shoes. I heard someone enter the store. It was a man and woman. They started shopping near the front of the store, in the short shelves. I kept trying on shoes and test-walking in them. While I was seated, the man and woman unexpectedly came around the end of the shelf and entered my row. They never looked at me. They might have seen what I was wearing before I saw them, though. …and I WAS trying on shoes in the ladies’ section…

I stayed seated while I looked for shoes in my size. I had my knees pointed away from them, just in case they had not seen that I was a man in a skirt. At one point, the woman walked past me to go look at herself in a mirror. She spoke to me as she came back by. They kept shopping near me. I stopped being bashful and got up and did my shopping. They were shopping 1-2 meters to the right of where I was shopping. I found several pairs of shoes that I wanted to try on. Eventually, they made a selection and went away.

I continued shopping. I found that size 14 shoes fit me rather comfortably. However, I am concerned that they might be too loose. I am primarily seeking some black flats to replace my “strappy black flats”, that are wearing out. I found some shoes that were close to what I am looking for, but they had a decoration on them that did not please me. I probably would not wear them. I did not buy those. While I was still shopping, the man, alone, returned to my aisle. He had the box of shoes that the woman had selected. He returned them to the shelf and left. He did not look at me or speak to me. I assume he was awkwardly avoiding interaction with me.

I stopped shopping. I did not purchase any shoes. As I walked toward the exit, the employee who was talking to a friend was the only employee I could see. She was standing at the cash register. She and her friend had not stopped talking the whole time I was there. The employee, still talking, looked over at me. She glanced up and down at me. She finished what she was saying, and then told me, “Good-bye and thank you.” Her friend was talking at this point. As I was passing behind her, the friend started to turn to look toward me. By the time she was turned, she was behind me. She did not resume talking. I opened the door and glanced back. Neither were looking at me, but they were silently laughing together. That was rather crummy.

I returned to the parking lot. I was walking between the cars and the building. On the other side of the cars was a young woman in her early 20s. She was dressed as young women currently do: stretchy pants, athletic shoes, and a casual top. She and I were walking in parallel. My heels were making high-heel sounds on the asphalt. She was not paying me any attention. When we arrived at our cars, it became apparent that we were parked side-by-side. Our cars were oriented such that the driver-side doors were toward each other. She paused and I proceeded to get in my car. We never made eye contact. As I was lowering down onto my car seat, she said, “I love your shoes!” I looked at her and she had a big, friendly smile on her face. I said, “Thank you!” Then, *I* had a big smile on MY face. That was NOT crummy!

From → True Stories

  1. Great interaction. Realize that any trip out dressed causes stress in itself. We all suffer from that, and you know that. I suffered terribly, until I realized logically that the only person who could help me is myself. Then it took a while to actually internalize that. Now I handle it much better. However, that being said, you are still much brave than I, and I admire you for it.

  2. Hi Joey – thanks for sharing your struggles with anxiety – this echoes my own experiences. I’ve often wondered if my desire to crossdress is rooted in my own feelings of inadequacy… something like, deep inside, ‘if I had been born a girl I would be a better/happier person’ whilst also recognising that I wasn’t, I am a man.

    I enjoy your stories and given that you do find yourself interacting with and ‘meeting’ various people, I think it must only be a matter of time before someone comes up to you and discloses that they are also a cross dresser. That would be an interesting story to hear… 🙂

    • Steve, I have been going out in a skirt openly for perhaps 10 years. I have done it more frequently in recent years. I have never had a man speak to me about his crossdressing.
      I have experienced one man awkwardly compliment me my saying, “Um, I like your dress.” On another occasion, a man said to me, without making eye-contact, “Nice dress,” as he and another man passed me outside of a restaurant. Once, a man asked to join me at my table at an ice cream restaurant while I was dressed. He asked me, “How do you identify?” and later told me that he was homosexual. Yet another time, a man, whom I think was homosexual, was shopping in a shoe store at the same time as me. He was wearing women’s shorts and open-toe shoes with toenail polish and shaved legs. He approached me in a secluded place in the store and invited me to a club in town (I was on vacation) that caters to “alternative people.”
      I have been told by (perhaps) five employees in women’s clothing stores that they knew one or more crossdressers. One adult, female employee told me that her son wore his sister’s skirt to his friend’s house. She did not mind. She later said that her husband was uncomfortable with it. She said that her husband felt it was bad if boys kiss each other. So, I conclude her son might have been gay.
      Finally, I have been in the presence of two crossdressers in recent years. The first one was in line in front of me at a restaurant. we were waiting to pay. He, or she, was dressed like a REAL woman, in blue jeans, tennis shoes, and a casual top. I did not realize what was going on until it was too late to speak. Another time, I saw a man in a skirt. He had on a denim skirt, a white top with small blue flowers, and flip flops. I was going to make eye contact and say, “Me too.” However, he was nervous, and I may have looked like an unwelcoming bully, because he nervously only looked at his phone as we passed. I was nervous too. Perhaps men do not tell me that they are crossdressers because I look uncomfortable around men. I often avoid men when I am crossdressed.
      That’s all that I can think of (except for when I went to a crossdresser party). All of these stories are in my blog somewhere. 🙂
      Thank you for your kind words, Steve.

  3. Paul P permalink

    I think the anxiety causes you to overthink what you percieve others are thinking or saying about you and your style of dress. Talking about “Dressing Pretty” reinforces the taboo in your mind, just say you were dressed as YOU feel like, in a skirt / dress etc. There’s no shame if you are dressed well, but try to carry yourself with some confidence.

    Being in fear of seeing colleagues or friends will only add to the stress, and fearing every car that passes or group of un familiar men will make each journey worse.

    What is the worse that will happen? Put a skirt on first thing in the morning, nice shoes etc and stay in it the whole day. Your wife knows of your hobby, it will soon become commonplace amongst workmates, some may praise you for coming out, some may say nothing, all have a choice. After a few days you will wonder what all the fuss is about.

    The anxiety vibes are picked up by people, which may change their interaction with you. Regardless of what’s worn even in regular guy clothes,not everyone may like us.

    I love that skirt, and am looking for one like it 🙂 I enjoy your blog 🙂

Trackbacks & Pingbacks

  1. Man in a Green Skirt | joeypress
  2. Me in a Couple of Skirt Outfits | joeypress

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