Skip to content

Shopping While Crossdressed

October 24, 2019


I had a gift card for a department store at the mall.  I had visited the store a couple times in menswear looking for something to buy.  I decided to go back there dressed pretty so that the clerk could help me with some understanding.  I arrived just as they opened to avoid the crowds.  I wore my black skirt, my purple blouse, and my black cardigan.


Entering the Store

I arrived a few minutes early.  The store was not open yet.  I stayed in my car.  I realized that around six cars also had people waiting in them.  The woman in a nearby car got out of her car, and went toward the building.  I decided that it was about time.  I got out too.

It started sprinkling on me while I walked.  I quickened my pace.  The woman was standing by the doors.  They were still locked.  I started doubting whether I should have gotten out of my car.  When I approached the building, the woman smiled and spoke to me.  Inside, a clerk inside was walking toward the doors to unlock them.  She started running when she saw the increasing rain.  She let us in.  There were a few of us waiting by the door by then.

I walked into the store and walked down the main aisle toward the ladies’ wear section where I had shopped before.  Several clerks greeted me on my way.


The clerk who helped me previously was there.  I was happy to have her back.  Eventually, while I was browsing, she approached me carrying several items for me to consider.  We discussed some options.  Eventually, I went into the dressing room to try them on.  I wore several of the combinations out for her to see.  She gave her opinions.  At one point, she was busy and a couple other employees, who were stocking shelves, offered to help me.  One of the women was a young, pretty, and fashionable.  She gave me very helpful insights.  I really appreciated it.  She acted like it was an every day experience helping a guy like me.

At one point, I stepped out of my dressing room to look at my outfit in the three-way mirror.  A woman in her 70’s came in and walked behind me.  She started to enter my dressing room.  I could not stay invisible.  I said, “That’s my booth.”  She looked at me and said, “Oh, it’s yours?” and proceeded on to the next booth.  She seemed unconcerned.

During my shopping, I walked past a customer who was browsing in the same area.  She was in her 30’s, pretty, in a lively colored outfit, with cork wedge sandals with green straps.  She looked at me and saw what I was wearing.  I said, “Hello” and then her expression changed into a lovely smile.  I think I had caught her unexpectedly, but she was kind.  Later, when I stepped out of the dressing room, and the clerk and another employee were giving me feedback, The woman who smiled was looking on and expressed some approval of the outfit with her facial expression and a slight nod.

Checking Out

When I finished shopping, I got into line.  My clerk was at the register.  There were several customers in line as well.  A woman and her husband were in front of me.  The clerk tried to talk them into getting a new credit card.  The man said that they had put a block on their credit because of some recent data breach somewhere else.  I made some comment or asked a question.  I forget which.  The man started talking to me.  He was at least 60 years old.  Perhaps he was retired already.  There we were, two men, standing in the aisle in the ladies’ wear section, talking about credit cards.  My skirt was of no importance.

Eventually, my clerk checked me out and she bagged my purchases.  I bought a top and a long cardigan.  I had some money left over on my gift card.  I decided to visit the hosiery section and possibly buy some Spanx brand pantyhose.

Hosiery Section

I started browsing the hosiery selection.  Two female employees were working nearby.  I asked for advice on the brands.  I was curious about the brands that I had never tried.  The dressier of the two clerks confessed that she only ever buys pantyhose from the grocery store (Leggs or Hanes).

During our conversation, a customer who was close to my age was shopping around us.  I kept moving to get out of her way.  Eventually, she made her selection and moved on.

I settled on buying some Spanx.  They were pricey, but I had a gift card and felt freer with my money than I would if it was going to be paid with cash.  I asked about size advice for the Spanx pantyhose.  The dressier clerk asked the other clerk who was close to 6 feet (1.8 meters) tall.  The tall woman said that she always goes one size larger when she wears Spanx.

I then spent forever trying to decide which color to get, and trying to find it in my size.

During this time, another customer in her 60’s or 70’s started browsing the pantyhose.  She noticed me and my outfit.  We made eye contact.  She seemed pleasant.  When I finally made my selection, I started to walk away.  She looked at me.  We made eye contact.  I said, “Good luck!”  She smiled at me and responded.

The two female clerks who advised me were being helped by two younger clerks, a male and a female.  They were trying to move some shelving that was attached to the wall.  I am rather tall.  I walked over and held up one side of the shelf.  The young woman was supporting the other side.  The man was moving the brackets that supported the shelf.  It was such a complete non-event that I was there and helping.  No one seemed interested.  No one seemed put off.  My clothes were irrelevant.

Roughly, that was how the whole event was.

From → True Stories

  1. donlan1 permalink

    I do enjoy reading about your outings. Its enlightening to see the positive or virtually no reactions you get when you wear your pretty clothes.
    Its seems we have a similar taste in dresses and skirts….. however I need the security of wearing a wig and makeup.
    Keep up the outings…I absolutely love them

    • Hello. Thank you for writing! I love to read comments from readers!
      I don’t think you have ever commented before. I am glad to meet you.
      I used to feel like I couldn’t go out in public in girls’ clothes unless I looked like a girl. So, one time I wore a hooded coat with a scarf and sunglasses. Several other times I went out at night where no one would see me up close. Infrequently, I would wear pantyhose (sheer tights) with men’s shorts. A few times, I wore ladies’ shoes, khaki pants, and a white top in public. No one noticed that at all, of course. One day, however, I was on a morning walk in a skirt. I did not expect to see anyone. I was out in a skirt as a man, and I felt so afraid that I would be seen. I may have been driven by the rush of the risk/fear. I don’t know. I did come upon someone and they did not react. I don’t remember how many mornings I did this before I realized that I did not have to be a girl to wear a skirt. That gave me such freedom!
      OK. I should say that I recognize that some people crossdress because they feel like they are a woman inside. I am not that way, personally. Dressing pretty pushes all of my buttons that want pushing. For the cis-man who feels that they are a woman, the wig and makeup are probably the most important thing to do. The clothing would be accessories for them.
      Again, thank you for your comment.

  2. Hank permalink

    Hello Joey,

    I have been following your blog for sometime and I really enjoy your posts, sometimes I also wear woman’s clothes as a man, I wear just a skirt and heels and a man’s aloha shirt ( I live in Hawaii ) some times a dress and heels with no makeup or wig, I’m not sure what state you live in, but in Hawaii I get zero reactions from being out in public, I have many shopping experience and lunch and dinners out and I never had a negative response, well some times I do catch someone giggling, but I guess I would giggle also seeing a man in a dress and heels. Please post often if you can.


  3. Pat permalink

    Another excellent post and a good response to the comment.

    Your being able to get out while dressed pretty is becoming the new normal.

    “My skirt was of no importance”…”It was a complete non event. No one seemed interested. No one was put off. My clothes were irrelevant”.

    These are all excellent observations and excellent developments as the world becomes more conditioned to accepting those of us who prefer to wear woman’s clothing.

    Unlike you, when I do get out I do like to wear a wig and makeup but that is, in part to make sure I am not recognized.

Trackbacks & Pingbacks

  1. Haircut and Other Errands | 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 )

Google photo

You are commenting using your Google 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: