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Christmas Shopping Outing 2016

December 1, 2016


Every year, I go Christmas shopping while dressed pretty.  That means I go out as a man while wearing women’s clothing.   I love doing this because it is an outing where I actually have a purpose.  When I used to have crossdressed outings, I just browsed stores, or walked around aimlessly.  My Christmas shopping outings, however, have had purpose.  Also, I could not run and hide if people were around.  These outings have really developed a lot of my confidence.

I just completed this year’s Christmas shopping outing.

I drove to a city that was not near my home.  I wore an orange maxi skirt, a black top, a cardigan/sweater that hangs down to mid thigh, off-black pantyhose, and flats.  I went to a store that opened early and started shopping.  I asked for some help at one point and one young employee looked me down and back up and then answered my question.  An older employee (possibly 50 years old) walked around the store with me trying to help me.  When she finished with one thing, she would ask if I needed more help and then she would help me with the next.  She did not care how I was dressed.  She did not mind being seen with me.  It was nice.

Next, I drove to an outlet mall.  It was not open yet.  I went to a diner-style restaurant that is part of a restaurant chain.  I have considered going to one of these restaurants before, but I did not because I was too uncomfortable.  These restaurants sometimes have more “blue collar” customers.  I felt brave enough this time.  I walked right in while wearing my pretty skirt and sat at the counter and ate.  I do not think anyone saw what I was wearing until I left.  I had a nice conversation with the older gentleman two seats over at the counter.

Next, I shopped in the outlet mall.  Nothing interesting happened, other than I took this picture


I drove to an old building that is sort of like a shopping mall.  I think this is when I changed into my knee-length, leopard print skirt (I wore one additional outfit that I cannot remember where I wore it).  I kept on the black top and long, black cardigan.  Nothing interesting happened there.  People saw me, but there were no interesting reactions.  I intentionally did not look to see how people reacted.  I am trying to let go of that nervous habit.

I drove past a strip mall.  One of the stores had a beautiful and fancy outfit in the window.  It was a dressy store.  I had to go in.  I put on my black, bootie, heels and walked in.  This store deserved heels!  The mannequin in the window was wearing a black top with little black bows all over it and a bright red skirt.  The skirt had a see-through outer layer and it poofed out.  It was very pretty.  I could never wear a poofy skirt like that, however.  I could wear the colors, though.  I browsed the store and a few other stores in the outlet mall.

I put back on my flats.

I went to a book store.  It is two stories tall and has a very open format.  I had gone here previously.  This store was very frightening for me the previous time I visited it.  Previously, I was scared about being seen and photographed.  This time, I was not worried.  I shopped as though I belonged there, and I was treated like I belonged there.  Guess what.  I did belong there.  I bought what I came for and proceeded on.

I went to a shopping mall.  There is a large open area at one point in this shopping mall.  I walked through it and I was not afraid as I was the last time I was there.  I visited several stores.  I walked through the makeup section.  Previously, I was uncomfortable being near the many fancy-dressed, pretty, female workers in the makeup/fragrance section.  This time I felt confident.  I felt strong!  I walked a full circle through the mall and went to the food court and ate my lunch.  I sat at a table in the food court.  At the table next to mine sat three men who might have been Middle Eastern.  They did not pay me any attention.  There were a few families at the various tables around me.  I have considered eating in a food court on many occasions over the years.  I believe that this is the second time I have done it.  Also, I believe it is the first time I have ever done it in a skirt.  It was no big deal!

Let me back up to tell about something kind of significant that happened when I first entered the mall.  There were three men doing some sort of manual labor at one of the entrances to the mall.  I walked into a different entrance.  However, those men saw me walking through the parking lot.  While I was crossing the driving lane that separates the parking lot from the front door, one of the men whistled at me.  I am completely persuaded that he was mocking me.  I was not affected.  It produced a feeling of annoyance or disappointment.  It did not produce a feeling of fear.  I believe it is true to say that it did not make me feel shame.  It definitely did not stop me!

I went to a “big=box” hardware store.  This is an achievement for me.  Once I went to a hardware store in a previous Christmas shopping outing.  I was very, very nervous then.  I felt like I was in a “man=zone”.  I felt less safe.  I believed that if anyone would say something derogatory, or look at me disapprovingly, it would happen in a hardware store.  Of course, nothing happened.  I walked through that store in my leopard print skirt and pantyhose and I was not afraid.  I and everyone else minded our own businesses.  I know I was way overdressed for a hardware store.  Ironically, though.  This was the only store I shopped in where I saw a woman dressed in a skirt and pantyhose.  (I did see women in tights at Target, but I am sticking with my distinction here!)

I put on a multi-colored, flowing skirt.  I went to a Christian book store.  I shopped briefly.  I was treated with respect or not even noticed, just like everywhere else.  One employee asked me if I needed help and she took me to find what I was looking for.

I put on a stretchy red skirt that comes to slightly above my knee.  I went to a sporting goods store.  Nothing interesting happened.

I went to a Target store.  I have felt uncomfortable shopping in a Target before.  In a previous outing, I went to a target and felt rather confident.  This time, I was completely at ease.  I still try to avoid being seen by children.  However, I was not scared to walk the main aisles this time.  I shopped in this store over an hour.  I bought plenty.  A few times I interacted with customers.  I was always treated with respect.  It felt really good shopping at Target.  I was surrounded by women shoppers who were dressed pretty.  They were wearing sweater dresses, stretchy pants, boots, cardigans, tights, dresses, etc.  It was lovely!

I shopped in a hobby/craft store.  I did not care how I was dressed anymore.  One customer drummed up a conversation with me about the products and the store.  I did not feel like she was patronizing me.  I am pretty sure she was not trying to make friends either.  I think she simply was being polite and my gender/outfit mismatch was irrelevant.  One employee happily helped me several times.

I shopped in another hobby/craft store.  Here I found what I wanted to find.  While at the checkout, I almost broke in line in front of four customers.  I apologized for my mistake and we all chatted while we waited.

Finally, I visited one more toy store.  I walked in at the same time as another couple.  They were in their early fifties.  The man held the door open for me as I entered.  I thanked him.  I talked to the employee and told him what I was looking for.  He tried to help me.  The couple started helping me as well.  The man and I joked about the two versions of the toy.  He commented on how one was just like what they made when he and I were kids.  I did not buy the toy (a slide puzzle) because I had already bought a similar one.  I was looking for a slide puzzle with a different image.   I thanked the employee and the customers for their help.  I went home.

Once again, the worst thing that happened on this trip was I got a run in the toe of my pantyhose.  I should have cut my toenails.

It was a great outing.  The only interesting things that happened was I overcame fears that had controlled my behavior in previous shopping outings like this.  Otherwise, this was a rather boring outing.  I feel like that description insults the amazing experience.  It was an excellent experience.  I was dressed pretty and happily in public.  The public did not care how I was dressed, and neither did I.


From → True Stories

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