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Christmas Shopping While Pretty

May 20, 2012


One year, I went Christmas shopping in shorts and nude hose.  The next year, I determined that I would go in all femme clothes but, as usual, with my man head.  As the year progressed, I decided that I would wear darker hose.  At some point, I decided I would wear a skirt and heels.  And that is what I did.  I wore basically the outfit I wore when I volunteered at a clothing store: Teal blouse, black skirt, taupe pantyhose, black heels, no makeup, no wig, no forms.  I was a just dude en femme (because I do not want to be a girl) and it was awesome!

I was on a road trip.  I went to a city rather far from my home to do my shopping.  I had been told that the town was a very accepting place.  First, I went to a place that was a historic building that was a sort of shopping mall.  It was not busy and I parked very near the building at a parking meter.  I was nervous, but I was bold.  I had my emergency bag of menswear in hand.  I clopped into the building in my heels.  The floors were granite/tile, so my every step was noisy.  I decided not to be so nervous and I walked past the few men and women inside with the same air of confidence.  I remembered what other crossdressers have said about acting like you own the place.  That is easier said than done.

First, I went into a women’s clothing store.  I walked around a little.  One of the clerks watched me a long time but never spoke to me.  I left there and walked in the public section.  People would make eye contact, then notice my outfit and look down at my legs.  Then they would look away or maybe make eye contact again.  I said “good morning” or “hello”.  Normally, they would smile and/or return the greeting.

I went into another clothing store because my nerves could not take any more publicity.  This clerk was friendly and social.  I asked her for fashion advice.  She did not give me much useful information.  I eventually convinced her to tell me the truth and she said I was frumpy.  She said I needed fancier shoes and a sexier top.  She said I should lose the undershirt and get something with lace.  As we talked, she realized that I am not out like this very much.  She told me that she was gay.  She had just realized that this was, to her, my “coming out experience” and she started trying to encourage me and justify my right to be however I want to be, etc.  (That was all an uncommon experience.)

I relaxed and just started to forget my clothing.  I went into stores where it was just me and the male shop attendant.  They were equally friendly to me as if I was dressed my normal way.  My nerves were relaxing.  In clothing stores, I asked for fashion opinions/advice.

I went into a bath/fragrance store.  That clerk was a beautiful and beautifully dressed woman.  She seemed entirely warm and friendly.  She ex-foliated my hands and I asked her if she even noticed my outfit.  She said yes.  I told her what I was doing and I asked her for advice.  She said I looked nice, but it looked sort of librarian (I had to pull that out of her).  She was so kind.  She even recommended some stores down the street where some of her guy friends buy their skirts (I know, right?!?).

I walked down the street and visited shops.  I was starting to forget that I was dressed oddly!  In fact, after I moved my car, I forgot to bring my emergency bag.  This is when I swapped my heels for my flats.  This really made me more comfortable, both physically and also in my nerves.  Several clerks in the shops I visited mentioned their crossdressing friends.  I am sad that I cannot tell this story well enough to communicate how the day went and to relate how pleasant it all was.  The story seems unremarkable, but the experience was incredible.

The meter was running out and it was time for lunch.  I went to the Olive Garden.  It was a non-event.  I was the only person in the waiting area and I was seated immediately.  The host acted like it was no big deal.  I was seated near a group of men and they acted disinterested even though they noticed.  Another customer, a woman, looked at my legs several times and then never looked back.  My server never noticed anything.

Then I went to a real shopping mall.  By this point, I was starting to forget that I was dressed.  Except for the obligatory glance down when I met people in the aisles, everything was just like being dressed like a man.  I finally started buying Christmas gifts.   Sales people never retreated.  They never seemed unsure of themselves.  One sales girl in her 20’s walked around in the store talking with me.  It was very nice to have a woman walk with me while I was crossdressed.  She was one of those people who felt the need to say that she supported my right to …. whatever.  It seemed patronizing.  I am not a cause.  I am just a guy who knows he is dressing weirdly.

While I was waiting in a line to be checked out by the cashier, an older woman was in front of me in line.  Her friend, who was about the same age was standing to my right.  She was looking down at something, but she was taking a long sideways glance over at me.  In retrospect, I should have spoken to her and started a conversation and let her look right at me if she wanted to see.  Later, I did speak to her, but only to say, “Hi,”.  She smiled and said, “Hi,” back politely.

I walked through open the mall area.  I was more nervous, but no big deal.  I walked past big, burly, blue collar men with the same disinterest as when I walked past anybody.  I was walking while looking at my list.  I stopped looking at people’s faces to see if they noticed.  I was becoming comfortable in my own skin (and clothes).

The shopping mall was the only place where something negative occurred.  In one anchor store, as I walked by (not close by) the girls in the fragrance/make up area in one store all became quiet, and looked at me.  They walked around their booths to get a look at me after I passed.  These were those pretty cheerleader types whom, I predict, were catty and hard on other girls.  No one else the entire day looked at me like there was anything wrong with me.  Second, there were two teenagers in the main mall area who walked by as I was exiting a store.  They suddenly locked arms started talking close and had a silly manner about them.  I walked down the mall behind them.  When our paths forked apart, they immediately went for their cell phones (cameras).  I made sure to keep obstacles between us.  I do not think they got a picture or video of me.

After that, I went to Kohls and Target.  I wore shorts in Target, and I think that was wise.  There were a lot of kids about by this point.  In shorts, I seldom got the look down from people.  Then, I went on to where I was staying the night.

Summary of what I learned:

  • I can do anything.
  • I dress like an 80’s librarian.
  • I need to get a black undershirt.
  • I need prettier shoes.
  • Women think I have pretty legs.
  • I need to get clothes with more accents.
  • People in this town are accustomed to oddly dressed people.
  • I should shop Zappos for shoes.
  • I need a blouse with no pockets.
  • I need a skirt with pockets.
  • The day after I walk for a couple hours in heels, my feet will hurt.

From → True Stories

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