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Haircut and Other Errands

November 7, 2019


I took a long lunch break and completed of a list of errands.  I decided to wear some heels for this outing.  I also wanted to wear my new cardigan.  I wore my black dress, my new brown and black cardigan, my new Spanx pantyhose, and my bootie heels that I bought for a party.  I have only worn these shoes a few times.  I feel a little bit ridiculous in them because of how high they are.  I am a tall man in flats!  Well, this man in a dress and heels went on a marathon of outings in this outfit.


Apparently, I was the only one who felt like my shoes were silly.  Everyone else thought they were fabulous.

Department Store

Recently, I bought a blouse.  After I bought it, I asked a friend for her opinion of the top.  She said that she thought that the style of it was too elderly for me.  I asked her because I had started to have suspicions about the top, myself.  I decided to return the top.

When I entered the department store, I came upon a lady who was seated at a table at the entrance.  She tried to solicit some money from me for a store charity.  Other than taking a look at my outfit, she behaved completely nonchalantly.

When I left her, I walked among the racks in order to be invisible.  There were a lot of people in the store.  I felt a little silly in my high heels too.

The woman who sold me the blouse was not working this day.  There was only one employee in that part of the store.  She was checking out a small, much older woman.  I waited in line for five to ten minutes.  The cashier station was situated by the aisle of the store.  Waiting customers had to stand in the aisle.  I was embarrassed, so I stood in the racks across the aisle and waited.  Another older customer arrived to get in line.  She looked at me and figured out that I was in line.  My outfit was not significant.   She was only interested if she could get into line.

I returned the blouse.  Then I shopped briefly.  While shopping, I spoke to one other employee.  I wanted to be fast because I had a lot to do.  I gave up on shopping.  I had collected some confidence and I exited the store by walking out via the center aisle.

I waved good-bye to the charity employee.

I walked through the parking lot.  I passed two women in the parking lot.  One smiled and waved as we crossed paths.

Spanx Friend

Back in April of this year, while I was on an outing, a woman who owned a shop that I visited spoke with me.  She recommended that I try Spanx brand pantyhose.  I determined that I would return to her store while wearing them if I ever bought any.  In my previous outing, I bought some Spanx pantyhose, and I was wearing them today.

I walked into her store.  I was not sure if I would recognize her.  She saw me, she recognized me, and she remembered my name.  She pleasantly came over and spoke with me.  We were talking when a customer joined us.  The customer was interested in my shoes.  The three of us talked briefly.  Both ladies really liked my shoes.


I returned to the barber shop where I got my most recent haircut.  Apparently, I did not bother to write about that hair cut.  I cannot find a post about it.

A different woman cut my hair.  She was a young woman.  During our conversation, she told me that she has crossdressing cousins.  I asked for her opinion about my cardigan.  She said that she thought it was too elderly for me.  She loved my shoes, however.

After that, I was feeling unsure about the cardigan.

I visited a nearby business out of curiosity.  Two employees were chatting at the counter.  They both greeted me.  We spoke briefly.  They both commented on my shoes.  The shoes are a hit!


Lunch at a Grocery Store

For lunch, I returned to a grocery store where I had recently eaten.  Last time, an employee took my picture.  On a lark, I looked for an employee to take my picture this time.  I found the same girl as last time stocking the same shelf.  I joked with her, “Wow, are you still stocking that same shelf?!?”  We had a short, happy conversation.


It was close to noon and the store was busier than usual.  In the food area, I saw at least five people filling plates.  I selected some pizza.  No one was at the cash register in the dining area.  A woman who was perhaps ten years older than me was waiting.  We started talking about whether we should go to the checkout lines.  It was a completely normal conversation.  By now, I had started to forget that I was dressed oddly.

I walked across the front of the store to the checkout lines to pay.  A man was my cashier.  It was a complete non-event.  I walked back to the dining area and found a seat.  I ate my pizza.  I saw one man glance at me.  He never looked again.

I put away my dishes and trash.  An employee (in her 50’s) was nearby.  I noticed her look at me.  As I walked past her, she said with some embarrassment, “I love those shoes.  They are beautiful!”  I touched my chest with my palm and said, “Thank you!  You made me feel good.”


I went to my bank to cash some checks.  A male clerk was staffing the counter.  He was business only.  I think he is not a very social person.  The other employees there are very out-going.

One young female clerk was in one of the offices.  She saw me and smiled at me.  She raised her hand to wave at me.  She could not see my outfit due to the counter.

Later, another clerk, who was in another office, saw me.  She could see my whole outfit.  She said, “Hi,” and then did a little “Go ahead” dance to communicate that she thought I was looking good (I think).

Two separate customers came in.  First clerk came into the main room to help.  She was wearing a long cardigan as well.  Her cardigan was gray, with gray vertical stripes and red horizontal stripes.  She was wearing a black top and black slacks.  It looked great.  She had to walk away at one point while helping the other customer.  She peeked around the counter to see my outfit.  She complimented my cardigan.  She is young, pretty, extroverted, and fashionable.  That restored my confidence in the cardigan.

Ice Cream

As is becoming my habit, I finished my outing at an ice cream parlor for some dessert.  It was a complete non-event.  There were no other customers.  The clerk behaved normally.  When the second clerk entered the room, I said, “Hey,” and waved.  She waved back and responded.

Then, I *had* to change clothes and go back to work.

From → True Stories

  1. Pat permalink

    A totally wonderful day and I agree that the shoes are a hit. I like the rest of the outfit as well and I am so please to see and hear about all of your positive mid day interactions. I really think that while woman’s clothes matter greatly to us for the rest of the world there is nothing to fear from a skirt and high heels..

    • So Pat, what do you think when you see the picture of me seated? I have concerns that the dress doesn’t pass the sit-down test. I love how the dress fits me and how it is made. But, It has awkward moments when I sit down or bend over. Is it too short?

      • Gabrielle Dee permalink

        The length of the dress is just perfect. In being a woman one has to be conscious in sitting and bending.

  2. Gabrielle Dee permalink

    Hi Joey – I love reading your adventures. If it weren’t for your post and others I may still be in a closet.
    I started going out about 3 yrs ago and took a lot of baby steps. On my first outing I followed your style – no makeup or wig. Totally presented as a male in a dress or skirt. Lots of guts. Eventually I became very comfortable with it. Like what you said time and time again – most people don’t care. FYI- I venture out 20-40 mins away from home for my adventures and I’d be going out 1-2 times a week.
    One day the light came on and I questioned myself – what if someone I know recognizes me. In the past, dressed as a male I have bumped into friends and family 20-40 miles away from home. Between my wife and I we socialize a lot. I am not prepared to answer a question like that. From then I had to disguise myself with glasses, makeup and wig.
    I’m starting to develop my own style of dressing up en-femme however I still like your style of going out presented as a male. It takes so much tIme to be a woman although it is also fun.

    I like your outfit in this adventure of yours.

    Best Regards

    • Hello Gabrielle! Thank you for your comments. I don’t meet a lot of people who go out dressed pretty while presenting male.

  3. Pat Scales permalink

    I agree that the dress and the rest of the outfit work very well for you.
    I think that when folks like you and I sit while dressed that the hem tends to ride up a bit higher than if we were women. As men we just cannot cross our legs with the same ease as women do. Stuff tends to get in the way.
    Like I said it is a great dress and it works well with the shoes. Another inch or so of length would be OK but I think you can get by in it.

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