A Trip to the Pharmacy

3/20/2023

I have not had a proper outing in forever. I have been busy doing other things, I guess… I have been craving some time to dress pretty. (Sometimes I wear a dress as a guy.) Recently, I started feeling sick. I called my doctor’s office. I thought, “Do I have enough nerve and willingness to go to my doctor while dressed pretty?” They scheduled me for a remote appointment. I met with a medical person on a video call. I was wearing a black dress and a red cardigan. I also had on black flats.

I doubt she saw much more than the shoulders of my outfit for most of the call. She prescribed me some medicine. Later, I was notified that my prescription was ready. I thought, “Do I have enough nerve to go to my pharmacy while dressed pretty?” I went for it.

Grocery Shopping in a Dress

1/26/2023

I had a day off of work. My wife and kids were going to be out of the house all morning. I asked my wife to make a grocery list for me to do our shopping. She made the list the night before. On the morning of my day off, I showered and shaved, I packed a bag of men’s clothes, and I put on my new, long, black dress with a red cardigan. I wore black flats. I was going to go grocery shopping while dressed pretty! (I am a guy who likes to wear a dress sometimes.) I searched online for any events occurring in the town I like to go to when I am crossdressed. There was an LGBT group having a meeting at a coffee house. I do not feel like I am very LGBT, but I decided I would attend their get-together. I walked out of my door in my dress, carrying my bag of menswear. I pressed the button and then walked across the garage to my car while the garage door opened.

One Last Errand in a Dress

1/5/2023

I had tried to complete several errands while crossdressed. I did my part, but uncontrollable external reasons made me have to go back and try a second time. One errand still was not completed. So, I put on my black dress, black wedge heels, and my beige cardigan, and went on my final errand.

And I Felt Beautiful!

1/4/2023

I went on an outing to complete my recently failed errands. I wore a black skirt, my new black and white blouse, and my black wedge heels, and I felt beautiful! It was so nice. I went to the bank and I donated blood. I was a man in a skirt, and the world politely did not mind.

Dud Outing

1/2/2023

First post of 2023!

I had some time off for the New Year’s holiday. Since January 1st fell on a Sunday, today was the holiday from work. I tried to go run some errands and do some of it while dressed pretty. Several parts of it were not successful, but a dud while dressed pretty is better than not dressing pretty! I wore my new black dress, a new pair of my favorite brand of pantyhose, Shimera, black wedge heels, and a nude/taupe cardigan. As usual, I was presenting male otherwise.

Two Sightings in the Wild

12/27/2022

On two recent occasions, I was out in public, dressed in menswear, and I saw a transgender person. To my surprise, they were not “doing it” how I would have expected… So first, some background. I grew up in the 70’s/80’s. In those days, the only time you ever saw a man in womenswear was on television or a movie. It was always comedic. Crossdressing was an embarrassing secret. It was not normally done in public. When I was a teenager, there were two crossdressers who, once per month, would shop at the grocery store where I worked. That was very unusual. When I started going out in public, I felt like I had to pass as a woman in order to be allowed to wear their clothes. I think that the two crossdressers at the grocery store also felt that way. They would try to go all out with hair, makeup, dressy clothes, etc. In the early days of reading forums and chatting online with other people like me, I discovered that everyone felt like they had to be 100% passable, or they felt like they should not go outside.

These people I saw this week do not feel like they have to do that. I find that very interesting…

A Short Christmas Shopping Outing

12/22/2022

Every year, for many years, I have gone out dressed in women’s clothing while doing my Christmas shopping. In recent years, it has been harder to have the free time to do this. This year was particularly difficult to get my Christmas shopping done, regardless of my apparel! However, I did get to do a little shopping while dressed pretty. I started out in a khaki skirt, white top, and a red duster/cardigan with black flats. Later, I changed into a new black dress with the red cardigan and flats. I took my camera on this outing, but I forgot to take the battery off of the charger… Therefore, I have no pictures.

Love Your Neighbor

11/6/2022

This post is not about crossdressing. Instead, this is about something that I recently discovered about myself and how a guy I know made me a better man.

Crossdressed at the Dermatologist 4.0

10/17/2022

It was time for my fourth, and final, dermatologist appointment. It all started with a red spot on my face that would not go away. He froze the spot twice. This new appointment had two purposes: to check the spot, and to do a full-body exam. I crossdressed for all of my three previous appointments. I decided to wear my gray skirt, my black/white/gray printed top, black pantyhose, and my new shoes.

Road Trip In My Little Black Dress

10/16/2022

I went to a family event that required a two hour drive to attend. I packed some womenswear for the drive home. After the event, I changed into my black dress, black pantyhose, and my strappy black flats. While I was getting dressed, I realized that I forgot to bring a colorful cardigan. I did not like being so monochromatic. I decided that I needed to do something to change my outfit. I made several stops on my way home. In a small, rural town, I shopped in a pharmacy, a shoe store, and a thrift store. Later in my trip, I went to an outlet store and a gas station while dressed as a man in a dress.