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Some Errands and a Church Service Part 1

April 5, 2018


  • Part 1 (You are here)
  • Part 2

I read a blog post by Hannah McKnight recently.  Hannah mentioned in the article that the Transgender Day of Visibility was coming on March 31st.  I do not call myself “transgender” because I do not cross genders.  I call myself a “crossdresser.”  I am just a guy who wears a skirt sometimes.  When I go out, I am a guy in a skirt doing boring guy things.  Regardless of the terminology mismatch, I decided that I should try to go out on Saturday, March 31st, and be visible and represent myself and my peers well.

I asked wife if I could go on an outing that day.  I would do our weekly grocery shopping.  She said yes without hesitation.  Normally, she expresses more discomfort about me going out in public.  I was pleasantly surprised.  I started planning.

I looked online at maps of a town sufficiently far from my home.  I looked to see what was near the grocery store.  On a whim, I searched for churches nearby.  I looked at each to see if they had a meeting of some sort that day that I might attend.  Then I discovered one that was having its regular worship service that day.  I thought, “Oh, I do not think I could do that.”  As in most things I do, I did not commit to go to church in a skirt.  Instead, I kept my options open.

The idea stayed with me.  I wanted to do it.  And I did do it.  AND, it was way better than I expected.

I first woke up at 3:00 AM.  I managed to fall back asleep.  I woke up again at 4:00 AM.  I was filled with anticipation.  No more sleep came.  At 4:30, I got up and started getting ready.

I wore my silky, green, maxi skirt with my new black sweater.  I brought two pairs of shoes, black flats and black one inch (2.5 cm) heels.

My first stop was a nice restaurant that had beautiful food — if the Internet was to be believed.  I put on my heels.  I wanted some practice in these shoes before I attempted to wear them to church.  I walked in.  One table had three men in their 50s sitting and talking.  I was feeling those jitters (fears) that always come at the beginning of an outing.  I did not want to draw attention to myself.  My shoes were making too much sound on the floor.

Two women were standing near the hostess station.  They were possibly cooks.  They did not greet me.  Instead they stood there and looked at me.  The hostess walked up and welcomed me.  She was happy and friendly.  She was dressed practically, yet very cutely.  She led me to a table and seated me.  My heels on the wood floor made more noise.  I was nervous and self conscious.

I sat down and waited.  My waitress was very friendly, and giggly.  She set me at ease.  I was concerned that my skirt was too casual for the heels.  I asked her, “If you do not mind, would you tell me do my shoes look OK with this skirt?”  She looked at them and said they were fine.  Then she added, “You look nice.”

Other customers came in.  I got at least one awkward sideways glance.  (Those looks make me feel like I should avoid the person who gave me the look.)


My breakfast was large, delicious, and beautiful.  I probably ate too much.  After my meal, the hostess was also my cashier.  I mentioned my feelings of awkwardness.  She responded with something like, “You are doing better than I would do.  I can only wear up to this high (and motioned a heel height with her fingers).  You are doing pretty well.”  She thought I was talking about feeling awkward walking in my heels on their wood floor.  Then, she complimented me on my outfit.

Grocery Store
I wore flats to the grocery store.  It was still very early.  The store was almost empty.  Normally, when I go grocery shopping, there are always a couple people who are making their way through the aisles at the same rate as me.  They are kind of like “shopping neighbors.”  They are always on the same aisle as me.  Not this time.

I shopped for about an hour.  I had almost no interaction with other people.  Infrequently, I passed people.  One pair of ladies said, “Excuse me,” as they passed.  They shopped on the aisle with me and then passed me again.  Some people never seemed to notice me.  My cashier and bag boy treated me normally.  It was a normal experience.


Here I am pretending to be interested in some decorative, green icing.

Gardening Store
Next, I went to a store that sells agricultural products.  I had very little interaction there as well.  Several employees offered to help me.  The cashier was a friendly woman of roughly 55 years.  She was happy and natural.  Near the end of my transaction, she complimented me on my sweater.  Women in public rarely compliment me on my outfits.  It has only happened two or three times in my many years of going out.  Today, I have received three, so far!

Go read Part 2!






From → True Stories

  1. Pat Scales permalink

    I can understand why you would get three compliments on your outfit. It is very pretty. I like the sweater and it goes well with that very feminine and comfortable looking skirt. The hose and shoes tie in nicely with the sweater. You present as someone who has gone to the effort of pulling yourself together.

Trackbacks & Pingbacks

  1. Some Errands and a Church Service Part 2 | joeypress
  2. First Time Crossdressing In Public | joeypress
  3. Church and a Event | joeypress

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