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Errands in a Skirt

January 30, 2021


I checked my blog recently and I saw that someone had left a comment 18 days before. I knew it had been a while since I had last logged on, but that was a bit of a surprise. That means it has been even longer than that since I last wore something pretty in public (or in private). I have been avoiding going out in public unnecessarily for so long that I have almost forgotten that I am a crossdresser!! I needed to run a few errands. I decided to do it while dressed pretty (at least for part of the time).

I packed my khaki skirt, a purple top, and a white cardigan with nude pantyhose and black flats. I also brought some men’s shorts.

Barber Shop

My first errand was to get my hair cut. The barber shop that I normally go to when I am dressed pretty was not open. I went to another shop where I have only once gone to while crossdressed. I was the only customer. The woman who was working was someone I have never met. She was similar in age as me. She welcomed me and seated me without giving any reaction to my outfit. Eventually, she casually asked about me wearing women’s clothes. Our conversation continued about other topics. Occasionally, she asked other questions about my family, whether they knew about my dressing, etc.

She had a Bible verse on the wall in Spanish. I asked her about several words in it. I asked her if she was a woman of faith. She was. I told her that I was too, but that it was difficult being a crossdresser and being a man of faith. She asked me why. She went on to suggest that she thought my mode of dress was not important.

She was so friendly! We had such a fun conversation about lots of things. She washed my hair after the hair cut. We talked, we laughed. We stood around talking afterward. At the end, I told her how nice it was to meet her, and she responded likewise.

Clothing Store

Since I was rather close to home, I changed back into my men’s clothes in order to go to a clothing store. Except, I put on shorts over my pantyhose instead of long pants. I knew that it was daring, but most people do not see nude pantyhose. I walked in and made my way to the womenswear section. They had a sale on a lot of their winter items. I selected a red sweater and approached a salesperson. She was 5-10 years older than me. I asked her, “If you were to wear a red sweater like this with a black skirt, what would you wear with it?” She answered with some perspectives. She talked about what “she” would wear with it. She asked me how tall my wife was. I answered her and tried not to give any hints that I was shopping for myself.

I returned to shopping. As I walked away from her, she said, “You are brave!” I correctly assumed that she meant, “because you are shopping for a woman.” I put the red sweater back on the shelf. I visited several parts of the store. I returned to the women’s section. I browsed a rack that I had previously avoided because a woman had been shopping there. I found a green sweater.

I returned to where I had found the red sweater. The salesperson saw me. “Are you still floundering?” We started speaking again. She asked, “How old is she?” I paused… I walked toward her and said in a low tone, “I am shopping for me.” She furled her brow and said, “Well, why didn’t you say so?!?” She started trying to help me shop.

Let me pause and explain why I was shopping. I looked over to my wife’s side of the closet recently. It was full of many different colors. I looked at my side of the closet and I saw predominantly black, white, and beige clothing. The purple shirt that I was wearing on this outing is one of my few colorful tops. I explained this to the salesperson and she started browsing the clothes with me, trying to find a top.

She suggested lots of things. I felt like I was saying no to all of them. I always found something to dislike. Too low cut, too open in the back, too see-through, etc.

She asked me some of the usual questions: “Are you married?”, “Does she know”, “Do you have kids?”…

She mentioned that she noticed that my legs were shaved when I came up to her. I asked her, “You saw my legs were shaved, and that I was shopping for women’s clothes, but you did not assume that I might be shopping for me?” Nope. It sounded like she did not see my pantyhose (Leggs Sheer Energy, Light Support, Nude). I decided not to mention my pantyhose.

Eventually, I bought the green sweater from her. I was not able to try it on due to COVID-19 restrictions. She said that I could return it if it did not fit. While I was standing at her cash register, a woman got in line behind me. She was standing 8-10 feet behind me. I felt exposed, but did not worry. I asked the sales woman, “Did you notice anything else about me?” She said, “I saw that you had on a wedding band.”

I debated mentioning my pantyhose. I did not. When she handed me my change, I gave in and said to her, “You did not see that I am wearing pantyhose?” She said no. I stepped to the right and she saw around the register. She said, “I did think that is unfair that men can have such nice looking legs.” I thanked her for her help and said good-bye. She warmly wished me well.

Grocery Store

I went to a nearby grocery store in my shorts. I had only a few items on my shopping list. I found all of my items. Interestingly, I was not the only person who decided to wear a khaki skirt and pantyhose today. There was a woman shopping who was also dressed up. However, I think she was doing it for religious reasons. I may have seen her before. This woman’s skirt went down to her shins.

Also, while I was shopping, I saw a woman who was wearing a red sweater. Her sweater was just like my new green sweater. I looked at how hers fit. I determined what my sweater should look like when I try it on.

I finished my shopping and I returned to my car.

Clothing Store Again

When I got to my car, I had an idea. I could try on the green sweater and return it immediately if it did not fit! I tried on the sweater and it fit me well, just like the woman’s sweater in the grocery store. Yay! Then… I got another idea.

I put on my skirt and ladies’ shoes with my sweater, and I went back into the clothing store. I am too close to home to be taking chances like this, but I did it. I walked into the store and turned immediately into the clothing racks. No one at the counters at the front were looking my way. Eventually my path passed near a customer. I decided to walk past her and hope for the best. She did not look my way.

While walking through the store, I could feel my legs swishing. I did not feel that when I went to the barber shop because it was such a short walk from my car. Feeling my legs swish while I was successfully out in a skirt so close to home inspired my heart! I got to where my salesperson was and she was gone. ” Oh no!” I thought she might be in a back room that was near her cash register. I called out to her and said, “Jo, are you still here?” She responded and came out. I said, “I realized that I could try on the sweater in my car. It fits!”

She came out and saw my sweater on me and said, “Well, it DOES fit you well.” She had doubts that the size:large sweater was going to fit me. She came around the small counter and saw all of me. That was when she first saw my skirt. She said, “You make a nice looking lady.” I did not debate the “lady” thing. I had walked freely in pretty clothes through a store near home and I was having an emotional event. It felt about as exciting as the first time I ever went out in public in a skirt! I almost welled up with tears.

These are our feet when I was telling her how to use my camera. I do not know why, but this picture makes me happy. I guess it is because we are together in the image, sort of. 🙂

We talked for a few minutes. I thanked her several times and told her to consider herself hugged. She told me that she could tell that it meant a lot. While we were talking, a customer walked past us. I could not tell if she paid me any attention, but she did look our way. Later, another employee came nearby and looked over at us. She did some things at the small counter near us.

You can really see the fish-eye distortion that my new camera produces.

Eventually, I walked away from her and walked deeper into the store. I eventually, upgraded to walking down the main aisle. I turned and went toward the exit. I was not near many people. I walked between the two counters at the front. The employees at the counter had their backs turned toward me. I proceeded out the exit, victorious.

From → True Stories

  1. Victory!! At least one of us is having a good time.

  2. Great outfits, love the green on you.
    Seems you had such a great day out.

  3. Jamie permalink

    Nice story and photos. The shoes photo is great! Shows interaction, I think. That is sorely lacking in the age of the ‘rona. I’m sure that you made the saleslady’s day. She sounds like a sweetheart.

  4. mpc844 permalink

    Lovely story, thanks for sharing it, and you look great! Why are you more nervous ‘close to home’? (I think I know the answer… and share the excitement/concern… but I’d like to hear your take on it cos you didn’t explain that in the post.) Take care, S.

    • You’re right. I should explain myself more often! Some things that I say on my blog come up so often that I just wrongly assume everyone already knows. My wife is not comfortable with my crossdressing. She and I do not want our children to know about it. Both of us also do not want our friends and family to know about it. Therefore, I avoid being close to home while dressed pretty. However, I have gotten quite risky in the last few years…

      • mpc844 permalink

        Ah, ok, that makes sense. I have days where I imagine bumping into friends in a store and try to imagine how they would react. I suspect they’d be surprised, curious, and then ‘well, it’s not my thing, but if that’s your thing…’. And then on other days the thought fills me with horror. When I read about your trips, I start to feel emboldened and think ‘hell, yeah, why not!’. For my part, my wife is supportive, relaxed, not enthused. My late-teen age kids think it’s the coolest thing ever and actively encourage it… but then as Gen Z’ers they’ve grown up in a world that encourages diversity and self-expression, and their 50 year old Dad has ‘suddenly’ become a lot less ‘boring’. Lol. Thanks for taking the time to engage, keep up the good blog.

  5. Robert Doss permalink

    Yes you can tell that the camera is one of the cheaper cameras. Most of those are setup to get as much in the frame as they can without detracting to much from the quality of the shot. Usually this means using a wide angle lens instead of a lens that produces a 1 to 1 ratio in the photo. The example that comes to mind is that a 35mm camera uses a 50mm lens to achieve the normal 1 to 1 perspective. Anything under that focal length is known as a wide angle. This photo looks like it has what would be about a 35mm focal length if it was a 35mm camera.

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