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Chrismas Shopping In Womenswear

May 13, 2012

Every year, I set aside one day to go Christmas shopping.  I take the day off from work about a month before Christmas and try to get all of my shopping done.  Normally, the stores are deserted and I get a lot done.  It is great!

One year, I put on men’s shorts and nude pantyhose and did my shopping.  The following year I took it a bit farther.  I put on a blouse, ladies shorts, nude hose, and fake Keds.  I was wearing all women’s clothes.  This is the story about that outing.

First, I needed to stop by the Apartment Complex office.  I was quite nervous about this.  It had been a long time since I had been there dressed this way.  The girl I used to go see and and sit and talk with had left that job.  I did not feel comfortable going to the office dressed this way and visit with the new people who had filled her role.  I was determined that this time, I was going to do it.

I walked across the parking lots to the apartment complex office.  I felt pretty confident on my journey.  At the door, I was hesitant.  I walked in.  Instead of the new girl, there was a guy.  He immediately looked at my feet or lower legs.  I handed him my rent and said I was there for a package.  He took me to where they put FedEx deliveries, etc..  I started looking through the boxes for anything addressed to me.  The guy walked away.  He walked to a place where he could potentially see me.  I do not know if he really needed to go there, or if he wanted another look.

While I was looking, I heard something behind me.  The apartment manager was in their kitchenette.  I continued going about my business.  I found the package I was looking for.  I stood up and walked to the guy and introduced myself.  The manager reintroduced herself to me.  She was rather new as well.

The guy sat back down at his desk.  I stood about ten feet in front of the guy while I spoke with the manager.  He was free to take any looks that he wanted to take.  That would have been too stressful for me previously.  Where did such daring confidence come from?!?  I stood in front of someone who knew my name dressed in all women’s clothes and I was looking away so that he could stare me down.  Through it all, no one seemed to treat me oddly.  I suppose I became more “out” that I used to be!

Next, I went shopping.  I went to a shoe store (for me), and a clothing store.  Afterward, I walked down the strip mall to a restaurant.  On my way to the restaurant, two women were working outside of a jewelry store.  The younger took a look at me and then looked straight to my feet/ankles.  I thought, I am not subtle at all!  Maybe I chose the wrong outfit!  I walked by them.  I looked toward their store as I passed so I could see their reflections in the glass.  The girl was looking at me.  She said, “Why don’t you come inside?”  I did.  She never paid any further attention to my lower half.  I left there and went to the restaurant.  The waitress took an immediate look at my feet/ankles and then treated me normal afterward.  No further looks.  I walked to the rest room and passed two hispanic customers.  They both looked straight to my legs.  I was sure I was wearing too obvious of hose.  (Leggs Active Support, color: nude.)

After I left the restaurant, I went shopping elsewhere.  I shopped for over an hour.  I did not notice anyone pay any specific attention to me.  It was great to be free and out dressed how I wanted to be dressed!  Again, it was a non-event.

I went back to the jewelry store.  I looked around some more with the girl helping me.  Eventually, I asked her, “I noticed you looking at my outfit when you first saw me.  Do I look tacky?”  She said that she was just surprised to see me in shorts (65 degree weather today (18 C)).  I asked, “Did my shoes look funny?”   She said she looked and saw my legs and just thought I did not have much of a tan.  I thought, “does she mean she thought I didn’t have a tan, so I wore hose?”  I spoke with her a little more and discovered that she never noticed the hose.  She never said that she noticed I had shaved legs.  I think she saw something that did not look exactly right, but never studied it to figure it out…  We partial crossdressers are more invisible than we think!!

All in all, I had a WONDERFUL shopping experience. Oh, and I bought my wife some earrings at the jewelry store.

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From → True Stories

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