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Retrying the Shorts Outings in a Skirt

November 17, 2016


Yesterday, I went to three restaurants in women’s clothes (with shorts) and pantyhose.  No one seemed to notice.  Today, I decided to go back in a skirt.  The significance of this is that these businesses are too close to my work for me to be crossdressing if I want to keep this part of my life a secret.

I packed a denim skirt, and a black top that has a black cardigan built into it and black flats for my outing.  I was wearing Hanes Smooth Illusions off black pantyhose (I find this brand to be rather pretty in off black).  I put on my shapewear at home before going to work.  That made changing clothes quicker and simpler.  It made going to the bathroom while I was at work a whole lot more complicated!

I went back to the restaurant where I had eaten breakfast the day before.  There were four female customers standing and talking where customers place their order.  I awkwardly waited.  I stood behind a short drink refrigerator so they could not see my lower half.  They moved on.  I placed my order.  The lady who took my order was not the same lady from the previous day.  She stood behind the counter and she could not see much of my outfit.

I went to the cash register to pay.  I stood in line behind two of the previously mentioned female customers.  I paid without incident and sat down to wait for my food.  Customers came and went.  There were not a lot of people in the restaurant.  Most were there for to-go orders.  The table in a restaurant hides your lower body enough that people seldom notice that you are a man in a skirt.

I left there.  I noticed no reaction to me.  I stopped in a shop next door and shopped briefly.  I was treated with respect.

Later, for lunch, I put back on my outfit and went back to the grocery store.  People looked at me and then glanced down at my shoes or skirt.  This was unlike the day before.  Today, people noticed my outfit, but there was no greater reaction.  I saw the brightly colored employee I met yesterday.  I spoke to her.  She saw me and said, “I LOVE it!”  She gave me a hug and walked across the store with me while talking.  She again encouraged me to live my life.  She asked me, “How do you feel?”  I thought that was interesting.

Afterward, I went to a clothing boutique.  I shopped briefly.  An employee spent some time talking with me and trying to help me find a top.

I did not go to any of the other places from yesterday’s outing.  Being so close to home and work was stressful enough.  I did not want to add any additional risk to my outing.


From → True Stories

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