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2021 Christmas Shopping Outing

December 6, 2021


Every year, I go Christmas shopping while dressed pretty. “Dressed Pretty” == me, as a man, wearing a dress or some other women’s wear. I normally go to a town about an hour away. Last year, I went to a town that was slightly closer, but smaller. This year, I went to a new town because it had a better weather forecast. I wore a black dress, black pantyhose, black shoes, and a deep red cardigan. I have crossdressed in this town once before, when I bought my car. Today’s trip was not very pleasant. There were plenty of very pleasant experiences, but there were some negative ones that overshadowed the whole day. Probably, my attitude was what made it unpleasant, not the negative experiences…

Furniture Store

On my way, I saw a furniture store that I have always wanted to visit. I decided to go there in a dress! While I was browsing around, a man came over to help me. He behaved as if he never saw my outfit. He was very friendly. We chatted some and then he returned to his office while I finished browsing around.

Gas Station

On my way back to the highway, I saw a gas station. This chain of gas stations are clean. The employees seem like they are all college students. The employees are energetic and efficient. I have gone to one of these gas stations, before while dressed in “inconspicuous” women’s wear. I decided to go into the gas station. I bought some gum. The girl at the cash register was friendly, but she seemed a little apprehensive. It was another good experience that felt like an achievement.


I parked my car in a parking space on Main Street. A man in a truck parked beside me. I did not hesitate to get out of my car. We walked around our cars at the same time and wished one another good morning. I proceeded to walk down the sidewalk on Main Street.

I shopped in a small boutique. The owner was friendly and helpful. She tried to help me find my style. (I know, I was supposed to be Christmas shopping.) I ended up buying (OMITTED UNTIL AFTER CHRISTMAS) for my wife.

I walked past three men digging a hole in the sidewalk. I feel uncomfortable crossdressing around blue-collar (laboring class) men. In my head, they are more likely to feel the need to react rudely to me. One of the men saw me coming. I think he was in charge, because he was not working. He just looked at me, staring. Their truck was parked on the sidewalk. I walked by on the other side of their truck. He quietly told the other men about me. They all stopped working and looked at me when I emerged on the other side of the truck.

I passed where a three-story building was being built. It was still basically a skeleton of a building (no walls). A man on an upper story saw me. He told someone else about me. They both stared at me as I passed.

People have not behaved this way toward me in years. These days, people may see me, but they do not tell their partners. Normally, only the one person ever takes a look. This town felt like I had gone back in time.

I went to several other stores and had positive experiences until I met a rude woman at an intersection. I was walking down the sidewalk approaching a corner. A woman appeared as she was approaching from a perpendicular street. She saw me and stopped. She exclaimed, “Whoa!” A moment later she said, “Why are you wearing a dress?” I felt that she was being particularly rude. When she asked, I was crossing the street. I could not stop. I did not feel like she deserved much of my time. I replied, “I don’t know,” (that was all that I could think to say in the moment). She continued saying loud things, but I could not discern what she was saying. I continued walking.

I passed a group of men going to a restaurant. They all looked at me for a couple seconds. They made no comments, they did not laugh, but they stared. I made eye contact with one of the men and said, “Mornin'”. He responded appropriately, but did not do anything extra to be friendly.

I began to want to avoid people. I did not want to feel their stares. This feeling kind of ruined the rest of the outing. My attitude was bad. Attitude is everything!

Other Stores

I went to a few different stores and had positive experiences. In one consignment store, they had four pairs of shoes that were almost large enough for me. Some crossdresser had purged, I assumed. This store was busy with women. They did not stare. They looked, but they were polite. On one aisle, two 60+ year-old women appeared. They saw me and continued talking and shopping beside me at the rack as if I was normal and welcome. That was possibly the best moment of the outing. I appreciated them SO much.


OK, if I say that I was avoiding people, then this is a contradiction. I went to a buffet-style restaurant. If you have never seen one of these, then let me explain. There was a long counter with salad, vegetables, meats, other sides (mashed potatoes), a taco bar, and numerous deserts. You pay as you enter the restaurant. Then you go up to the counter, take a plate, get what you want, and go eat it. Then you go back and get more. It is an “all you can eat” restaurant.

The first time I went to a buffet-style restaurant while crossdressed was quite an achievement. However, I knew that this restaurant was different because it had no dividers separating the restaurant from the buffet. While I would be at the buffet, people in the restaurant could see me. Oh well, I went in anyway!

In the parking lot, a man and his wife were entering the restaurant at the same time as me. They paid and sat down. Then I paid and found a seat. I ended up in the same area as them. I went up to the buffet. I saw a restroom nearby. I diverted to the restroom. While I was washing my hands, the man from the previous couple came to the other sink beside me. I said, “We keep bumping into each other!” and I smiled. He responded politely, but awkwardly.

I got my salad at the buffet without fear. I sat down and started eating. A young couple entered and sat behind me. They had a small child. The guy was a good father. He seemed cool and confident. He had a tattoo on his neck. They were polite to me. An older man sat at the table in front of me. He was dressed professionally.

I got up and returned to the buffet for my main course. On that side of the restaurant, I saw a table of construction workers. One of the construction workers saw me approaching that area. While I was at the buffet, I looked over and saw that most of them were staring at me. When I looked their way, a couple of the men looked away. Some of the other men did not stop staring.

I got my food and returned to my seat. (Please forgive for including this man’s crude sentence.) The older man looked up with his eyes at me. He said, “At least you could have put on some titties for us to look at.” He was not loud enough to easily hear. I believe that he might have been saying that for the man and wife at the table beside him. They reacted by laughing gently. Perhaps they were laughing uncomfortably. I saw their reaction because I had turned to sit at my table and I was facing them.

At this point, I could have felt so embarrassed that I could have left the room and gone home and purged my crossdressing stuff. I could have had a lot of victim-like reactions. BUT, I did not. I had a reaction of, “What a jerk.” I have toughened up over the years!

I finished eating my main course. I waited a long time before going back to the buffet. I wanted to wait for those construction workers to leave. (So, maybe I am not so tough.) The older man left too. I went to the buffet and got some dessert and ate it without feeling harassed or stared at.


I went to the shopping mall. First I went to an expensive anchor store. I was looking for a nice, white blouse that I could wear when I want to look business-like. I wanted to replace one I purged years ago. A sales person started helping me. She was slightly older than me. She was relaxed and helpful. She took me to numerous places in the store where blouses were for sale. She was determined to help me find the blouse. Eventually, I said, “Do you get a lot of guys like me?” She said, “Some. It’s fun.”

We found a blouse that met my expectations. However, it was $150. She asked if I wanted to try it on. I told her that I could not afford it. I would have to save up if I was going to buy it. She stood there with me and talked about life and clothing. She was completely comfortable hanging out with me.

I visited various other stores in the mall. Some people saw me and told their partners and they all looked at me. Some people were polite and did not stare. Some people were uncomfortable, but polite. One particular shop worker was so very kind and loving toward me.

Hobby Store

My last stop was at a hobby store. This was a large store. I had to go to the very back to find some jewelry-making materials for my daughter. I asked a store clerk for help. She was experienced in jewelry-making. She helped me a ton! Eventually, I asked her if she would take my picture.

I got in line to pay. A woman was in front of me. I complimented her on her bright, beautifully colored shirt. She started talking to me. She confidently talked to me for a few minutes while we waited. A woman got in line behind me. When it was my turn to check out, the cashier was friendly and talkative.


I had a very nice day, but I also had an unpleasant day. The unpleasantness was highly uncommon. It had cast a shadow over the whole day. When my outing was complete, I did not feel fulfilled. I think my attitude was not great before the outing began. I felt unprepared, and the inability to go to my normal destination due to the weather was off-putting as well. My attitude had a negative impact on my day. My experiences during the day helped to sustain my bad attitude. Clearly, I need to do it again and do it better next time! πŸ™‚

From → True Stories

  1. Marissa in Ohio permalink

    Hello Joey, Your blog posts are always interesting and inflected with your own distinctive way of exploring the world as a crossdresser. The distinction that you bring to this activity (as I understand your approach) is that you boldly go out, ‘pretty’ as you put it, but with full male face and hair. I certainly can understand why you take this approach, rather than being in full ‘en femme’ or ‘disguise’ mode. There is a kind of reality, or openness, to your approach that says “I am doing what I want to in a way that I want to and it does not hurt (and should bother) anyone at all.” This post presents your experiences in what I believe must be a typical small to mid-size American town. The negative experiences you describe in this outing are exactly why I do not venture out of my house in my own small mid-western town. I just do not think I could stand the invasion, the assault, that such negative experiences must feel like. I am confident that for most of us, our dressing is something that is such an enjoyable and harmless activity that being confronted with the small minded, prejudicial, and crude attitudes and reactions like those you experienced, would totally spoil the day. At least I think it would for me. I would say that your feeling bad about what you experienced is entirely reasonable, but whatever happened that was ‘bad’ was not a statement about the fundamental human need to be happy and expressive of that happiness, it was about those people who are just plain mean. Keep doing what you enjoy, but do be cautious when it is called for. Best wishes for a good winter holiday.

    • I wrote about my experience in less detail on as well. I have heard several people say that this is why they never go out of the house crossdressed. I fear that I am doing damage telling about this experience!
      I have been in a dark place recently. Crossdressing is one aspect of my life that I feel “confident” in. I have had lots of self doubts, worries, etc. in my life in general lately. This negative experience has been partially driven by me being in this dark place, I think. For the most part, this was a lovely outing. Most people were nice to me in this town.
      Let me be more honest. This city was, to my knowledge, “Trump country.” Where I normally go, is more Bohemian and left leaning. Maybe that explains it. However, I have gone all over. I have crossdressed in left-leaning and right-leaning areas. I have even gone out crossdressing in the midwest (in Indiana). I have not had this kind of experience anywhere (at least for a LONG time). Maybe I was on the receiving end of the recent cultural shift to where it “has been made OK” for people to say horrible things. Maybe I was just in a place that is culturally rude. Maybe, I was just unlucky and bumped into the rudest people in town.
      I WILL say that the negative experience of this trip was not so bad that it made me regret going out. I experienced nothing so bad that I would want to stop dressing pretty and living life.
      So, if you choose not to go out in public, please don’t let it be because I had a bad experience this one time. I have lots of posts here where you can see that I get nothing more than surprised looks from some people to go along with the kind acceptance and appreciation of other people.


  2. Thanks for the story Joey. You should definitely have told it, I for one appreciate it. My first thoughts were that however bad you felt, you were absolutely right to do your thing and be yourself. Yes, others (including me) fear going out because of these kinds of reactions. But unless you go out, things will never change. For every person who saw you and stared, that’s one more person who has seen a guy dressed ‘pretty’. In time it will cease to be something so unusual as to be stared at. And for that progress, you are doing us all a service.
    Finally – do you know what brand (and size) your shoes are? I would really like to get a pair of those… πŸ™‚

    • Thank you Cantera! I bought my black strappy flats at Pay Less Shoes many years ago. Inside, I see “NO CALL” written on the sole. The “O” in “NO” has a slash through it. They are just ballet flats with four strips of black elastic across them. I suppose, if you are industrious, you could manufacture something similar.

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