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A Trip to the Pharmacy

March 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.

Departing the House

First, I considered leaving the house with no emergency clothes. Then I decided that if I am uncomfortable, I could wear some shorts and a top with my pantyhose and flats and go into the pharmacy. I have started letting my leg hair grow out for shorts season. I bleach my leg hair so that I look shaven when I wear pantyhose. I packed some shorts and a top. Then, I broke down and brought some guy clothes in case my family surprises me and comes home, or if I have a car wreck, etc.

I left the house dressed in my black dress and cardigan.

Parking Lot

I arrived at the pharmacy. The parking lot had ~12 cars that were probably all customer cars. I sat in my car. There were several pick-up trucks that arrived. For some reason, I have more fear when truck-guys are about. I do not have any experiences to suggest that they will treat me any differently than the other people. I waited…

Finally, I chickened out and went to the drive-through pharmacy window.

Drive Through

After a long wait, I was the next customer at the drive through. A woman was attending the window. She probably did not notice my outfit. I definitely saw no recognition. I got my prescription. I asked her if I could buy an over-the-counter medicine through the window. She said that she could not, but she could set it aside for me. I told her not to bother… We went back and forth. Finally, I admitted to her, “I am a crossdresser. I wore a dress today, but I chickened out on coming inside.” Her response was, “Oh. I see.” No negative or positive expression. Just a sort of “OK”.

I Went In

I thanked her and I drove away. I turned back toward the parking lot. I pulled in and sat for a few moments. I finally got up my nerve and prepared to go in. I put on a mask (I am sick), and I turned on my camera to get a picture of myself while I was in the store. It said my battery was dead. Oh well. I left the camera in the car and I got out. I was very nervous. This pharmacy is close to my home. I turned my face toward the building as I walked toward the entrance. I was keeping my face hidden from cars on the road or in the parking lot.

Inside, there was no one nearby. I saw an employee near the check-out area. She was not looking my way. I turned and went down the aisle by the wall. I looked around to see if anyone I knew was there. I saw almost no customers. I stayed near the wall for a brief time. I saw at the pharmacy counter that there was a man who was shaven bald and wearing camouflage. I guess the camouflage was not working (rimshot). I did not want to go near him. I waited.

While I was waiting, a woman on another aisle asked me if I worked there.

Eventually, my impatience led me to near where he was. I did not like lurking along the wall. An older couple saw me. She was dressed like me. That was nice. The bald man was still at the counter. The woman from the drive through was serving him. I stepped to the right so that she could see me in the distance. I waved with my hand to the side. She waved back. No smile, just an acknowledgement.

In Line

Before he went away, an older man and a woman my age approached and got in line. The bald man went away. I just committed and got in line behind the other two. I kept paying attention to be aware of any other people in the store. The older man went down to the “consultation” window. The woman in front of me seemingly changed her mind and walked away. The woman at the counter had already gotten my medicine for me.

I said, “I built up my nerve and came in.” She responded, “You were brave to come in here.” We completed the transaction like normal. If anyone else in the pharmacy area saw me, I did not notice. No one got in line behind me. I said, “Well… I did it!” She said something, “…, and you are fine.” This was the first time she smiled at me. Up until this moment, she had a very matter-of-fact, non-expression. She just seemed tired and ready for lunch. In that last moment, she encouraged me through kindness.


I started toward the exit by walking down the aisle along the wall on the other side of the store. On my way, I passed the woman who was in front of me in line. She looked like she was sick, like me. She started asking me a question about the store, but interrupted herself and asked, “Do you work here?” I said I did not. Then I remarked, “I should not have worn red.” She quickly took a look down and up at me with a sideways glance. I moved on.

There were people near the front on the side I was traversing. They were talking. It was the employee and an older woman. I decided to exit down the middle aisle. However, the older couple, that included the woman dressed like me, were slowly walking down the center aisle toward the exit. I browsed the aisles while I waited.

I thought, I should buy some Easter candy. I went to the candy aisle. I selected some candy and I went to the front. The older woman was waiting for something. The friendly employee, who has helped me previously, went to the cash register. The sick-acting woman was at the register. I waited in line. The older woman was behind me where she could see me. Another man with lots of tattoos came in and stood near the older woman.

Checking Out

The employee started ringing up my purchase. She was friendly and smiley, just like last time I was here (but in menswear). I complimented her on her textured, blue cardigan. She thanked me. She gave me my change. Then, while I put my change away, I said, “It was tough, but I did it!” She smiled at me warmly and told me good-bye.

I went back out to my car and got in saying, “I did it.” I think I said that ten times before I left the parking lot.

Then, I drove home and walked back into my house wearing my dress. I left home and returned while dressed pretty. That rarely ever happens!


The reason this is a big deal: I was at a store close to my home. There was a risk that I might have come upon someone who knows me. Someone who knows me could have walked into the store. Someone who was in the store could turn out to be someone I know later in life. Those are all undesirable things for me at the present moment. So, the obvious conclusion is that I should not have gone there dressed pretty. But… where else and when else am I going to go on an outing? I am planning on donating blood while dressed pretty, if I ever get over this illness. I suppose that will be my next outing.

I confess that I have had a couple other very minor outings. I was around no one on one of the outings. On the other outing, I was just wearing pantyhose with men’s shorts while exercising. No one noticed.


From → True Stories

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  1. Crossdressed at the Blood Bank | joeypress

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