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July Haircut at a Men’s Barbershop

July 21, 2017


Ever since November 2014, I always wear women’s wear to the barbershop.  Once again, it was time for me to get a haircut.  This time, I wore my knee-length, denim skirt.  On top, I wore a purple blouse with a white, collared shirt loose and unbuttoned.  I also wore nude pantyhose and black flats.  As always, I wore no make-up, jewelry, bra, or wig.  I was just a man in a skirt.

Something significant here: I have not been shaving my legs all summer.  I have used Sun-In to bleach my leg hair so that I can wear shorter skirts.  This was my first outing in nude pantyhose and bleached hair.  I can see the hair through the pantyhose when I look in person, but I cannot see them when I look in a mirror.

I have been trying to find a new barbershop lately.  This time I went to a new barbershop that only caters to men.  This is the first time I have gone to a “men’s barbershop” while crossdressed.

The Barbershop

I walked into the barbershop and entered the waiting area.  There was only one man waiting.  Because of a wall, he was the only person who could have seen me.  I never saw him look at me.  I crossed the room, signed in, and returned across the room to a seat.

A woman came to check the list.  She looked at me.  She seemed unsure or confused about what was going on.  She took the man to cut his hair.  Eventually, another woman came and took me to cut my hair.  I was seated in the chair beside the man.  Again, I never saw him pay me any attention.

The barber and I talked about gardening and children, etc..  Eventually, we realized that she has cut my hair before at another barbershop before I did such things in skirts.  Once we started talking, I felt like she became more relaxed.

My barber took me into another room and washed my hair.  Then, we went to the cash register so I could pay.  Since we were alone, I asked her if she could tell that I had not shaved my legs.  I was worried about looking tacky due to compressed hair under pantyhose.  These pantyhose are Leggs Sheer Energy in medium support.  They are rather light weight.  She told me that she could not tell.  I thanked her and left.

Thrift Store

On my way to get some lunch, I stopped at a thrift store.  Some of the other people in the store took notice of me if I passed near them.  Otherwise, I was ignored.  I was hoping to find a khaki skirt, a denim skirt that truly falls to my knees (this one is three inches too short), or a good top.

I found a khaki skirt.  It was knit and a little stretchy.  It what exactly what I have been looking for!  I tried it and a top on.  The skirt was too small, and the top was too big.


I went to an international restaurant for lunch.  It was early.  There were no other customers in the restaurant yet.  The owner, a man, greeted and seated me.  Another man took my food order.  I ate my food.  The owner was at the cash register.  I paid and I left.  I only interacted with men.  No big deal.

Consignment Shop

I once read a fashion blog post.  The woman said that when you shop for shoes, try on shoes and leave.  If you think about a pair of shoes twice after you have left, then you should go back and buy them.

My next stop on this outing was to a consignment shop to buy a skirt I have thought about several times since I tried it on.  I walked into the store and over to the skirts.  The employee, a young woman, asked me, “Is there anything in particular you are looking for?”  I saw the skirt and took it off of the rack.  I replied, “Yes, this skirt.”  Then I walked over and bought it.

After I bought it, I tried on a black dress that I saw on the rack.  It fit me unusually well (because it did not have a defined waist and it hung to my knees).  However, it was stretchy and skin-tight on me.  I asked the employee for ideas on what to add to the dress.  A customer, who was out of sight, eventually could not contain herself.  She walked over to put in her opinion.  She checked it out and complimented me on the fit.  Then she took over giving me advice.  She was totally cool with this man in a dress.

I did not buy the dress.  It had too deep of a neckline.  Also, it was probably too snug on my body.  I am not sure if I could go out in such a form-fitting outfit!  I probably ought to dress my age!!  I took my blue and white maxi skirt and went home.

Future Work

I still intend to go to a “real” men’s barbershop while crossdressed.  By “real” I  mean a barbershop where only men work and where a dog might be welcome to sit in the waiting area.  (This might be a regional phenomenon.)



From → True Stories

  1. I suspect that our dress wearing patterns may diverge a bit. I have not been able to get out much while dressed but I do dress around the house with some frequency. That is one of the benefits of aging and now being an empty nester. If I had that well fitting black dress I would have bought and dealt with the deep neckline.

Trackbacks & Pingbacks

  1. Using Sun-In to Bleach Leg Hair | joeypress
  2. Lunch and August Haircut | joeypress

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