Skip to content

Independence Day Grocery Shopping

July 11, 2022


I went on a crossdressed grocery shopping outing today! I had the day off for Independence Day. Independence Day, or “The Fourth of July”, is a United States holiday, celebrated on the day that the Declaration of Independence (from England) was signed. Americans typically wear festive colors from the American flag. I chose white and red. I wore a khaki skirt, a white top, and a red cardigan, with white sneakers.

Leaving the House

My wife took the kids to an event. I had the house to myself. I packed a bag of men’s clothes, and I got dressed and left the house. Instead of waiting until I was in the car to open the garage door, I opened door by pressing the button on the wall. Then, I walked across the garage to my car while the door was partially open. If a neighbor were in their yard, they might have been able to see me. They probably would not have noticed that I was wearing a skirt instead of shorts, though. I got in my car and realized that I did not have my key! I raced back inside, got my keys, and walked across the garage again. Of course, no one saw me.

Gas Station

There is a gas station that I like to stop at on my trips. It is out in the country. They sell old-fashioned candies. I stopped there to get some candy and some milk. I hesitated in order to see what type of men were around. Sometimes, there are a lot of laboring-class men at this place. I feel less comfortable being seen in a skirt and pantyhose around groups of “manly men”. It felt safe, so I went in. Inside, I went to the row of tables that contained the old fashioned candies. A woman was shopping on the other side of the tables. I selected some cinnamon red hots. She saw my selection and smiled. She was in a delightful mood. She started talking to me. I doubt she saw my outfit. I continued browsing the candy. Eventually, we were on the same side of the tables. While I was there, she started talking to me again. There I was, on full display, wearing a skirt as a man, and this woman continued happily talking to me.

Grocery Store

I drove about a half hour to a different town. I went to a grocery store that I had not been to before. Even though people were around, I did not hesitate to get out of my car. An older man happened to be walking toward the entrance at roughly the same time as me. A woman in the spot next to my car finished loading her groceries. She asked if one of us would take her cart back. He and I both stopped. I took the shopping cart. She thanked me and we went on.

Inside, a couple female employees were at a kiosk. They were facing the entrance. They looked at me as I pushed my cart into the store. I looked their direction a couple seconds later. They were looking at each other talking. I started shopping in the produce section. Eventually, I proceeded to the end of an aisle where an employee was working. I asked her, “Would you do me a favor?” She responded, “Yes.” I asked her to take my picture. She agreed and she took a few pictures. Then, she said that we should take some more pictures closer to one another so that the pictures would look better. I do not know if she had seen me before she turned toward me to receive my camera. I saw no signs that she was surprised to see a man in a skirt.

I shopped throughout the store like normal. One woman was wearing a nice looking outfit. I said, “You look very nice today!” She thanked me and said that she liked my festive, red top. I do not think that she had seen my skirt before complimenting me. We passed several more times as we continued shopping. We did not interact again. The store was busy. I never felt uncomfortable. Honestly, if felt like I was not doing anything unusual. I was not watching for people’s reactions, and they were not reacting to me. One time, however, a family with two kids walked past me. The ~12 year old daughter saw my outfit. As they passed by me, she kept her eyes on my lower half. Beyond that, I saw no reactions.

I went to the checkout area. I figured that I would have to wait in line for a long time. However, when I got to the cash registers, the lane closest to me had no wait. I got in line and started putting my groceries onto the conveyor belt. The cashier was a young woman. I complimented her on her hair. She was smiley and pleasant. Eventually, all of my groceries were out of my cart. I moved my cart to the end and took a selfie. I started putting my groceries into my cart. A woman came into line behind me.

The cashier asked if I had my customer loyalty card number. I typed in my phone number, but it did not come up. The customer behind me offered to scan hers instead. She helped a man in a skirt!

I left the store and put my groceries into my car. I pushed the cart back to the store, and returned to my car. When I sat down, I realized that I still had red hots left, but nothing to drink with them.

Drug Store

I drove to a nearby drug store and went in. An employee saw me and glanced down at my clothes. I went to the drinks area, but the only milk I found was chocolate milk. I gave up and headed for the exit. The same employee and I spoke briefly. Then, she and said good-bye. I headed home.

Returning Home

On my way home, I realized that I would arrive home close to the time for my wife and kids to also return. I decided that, even though I would very likely beat them home, I would not risk it. I pulled over in a parking lot and changed into men’s clothes and went home. I arrived before them. I went inside and put away my women’s clothes. Then, I heard them inside the house. I was home only a couple of minutes before they had arrived.

Later in the day, my wife asked me, “Where did you go to the store?” She knew that I probably was crossdressed since I went shopping while having time to myself. I love her. She knows I am a crossdresser, and she does not love it, but she still loves me!

From → True Stories

  1. Brave ⭐⭐⭐⭐⭐ There are time when dressed down I go out with woman’s apparel about feel naked with out the full assembly.

    • What I was wearing was my full assembly. I never present female. I’m just some old guy in a dress. 🙂

  2. Christina Cross permalink

    I love your khaki pencil skirt. A nice modest length too. I am tall like you and have a longer torso that I would like and I generally wear my skirts at my natural waist so I tend to like longer skirts that hit at the knee+ but I can still wear high on my waist. Can be a challenge to find skirts like that.

    I enjoy your stories and it is encouraging that people think nothing of a man in a skirt. Making progress!

Trackbacks & Pingbacks

  1. Wearing a Skirt Around My Wife and Having Zoom Calls | joeypress

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: