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Shopping for Menswear While Crossdressed

April 7, 2016


I wanted to go on another outing.  I also needed to buy some men’s dress clothes.  I decided to do both at once.

I put on my orange skirt, nude high heels, a white top with a navy cardigan over it.  As always, I presented male otherwise.  (Apparently it does not matter, but I have a beard.)

I was nervous as I prepared to exit my car.  The parking lot at the clothing store was rather full.  All of the cars slowly driving past the front of the store gave me pause.  I am not at ease walking in these heels, but I wore them anyway because they are so beautiful.  Since I was so uneasy about so many things, I hesitated to enter the store.  I ended up stopped between two cars where passing cars could not see me.  Apparently, one woman in car saw me and they stopped and blocked traffic so she could turn far around and try to see me out of her window.  She did not realize that she was stopping traffic and making me wait even longer to enter the store.

Eventually, traffic cleared and I entered the store.  As I entered, there were several people waiting in line at the cash registers.  I felt like everyone was looking at me.  I believe no more than half were looking at me, but I did not spend much time checking.  I just tried to hurriedly get into the racks of clothes.

I walked to menswear and bought two dress shirts with the help of a female sales clerk.  The clerk showed no reaction to my outfit.  There were perhaps five other men shopping around me as I shopped.  They were roughly 50 to 60 years old.  Some were shopping with their wives.  Although I noticed a few glances from their wives, this experience was not unlike my shopping experiences when wearing menswear.

Getting in line was tough.  I knew I would probably have to stand with people all around me.  Fortunately, there was no wait.  The cashier looked me in the eye and was warm and friendly.  The manager who has seen me on previous shopping trips was there.  Perhaps she was training my cashier.

After that, I walked out of the store to my car.  The return trip was not nearly as frightening.


From → True Stories

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