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Christmas Shopping 2015

February 20, 2016


“Have a nice time”
Once again, I went to another town to do my Christmas shopping while crossdressed.  This year, I had bought a lot of clothes that I felt were nicer than any I had ever owned before.  I do not get out much.  So, I decided to take several outfits to wear.  Before I left the house, my wife was awake and getting ready for her day.  She does not like it when I go out in public (or when I crossdress at all.)  She knew I was going to have this outing.  When I was about to leave she said, “Have a nice time.”  I could tell in her voice that she was not just offering me a rote statement.  She was not fully comfortable with herself for saying it.  She was stretching herself.  I think that might have been the kindest moment between us concerning my crossdressing.

McDonalds For Breakfast
I drove to the other town.  I put on my first outfit in my car.  I went to a McDonalds for breakfast.  I put on my black and white skirt, black flats, black hose, a red top, and a black cardigan.  As always, I was not wearing makeup, wig, breasts, etc.  I was a dude in a skirt.  I bought my food at the counter and sat at a table in the restaurant to eat.  I marveled at how I was not significantly frightened.  I noticed a few people trying to get another look at me as they left.  Otherwise, no one else treated me differently than normal.

Shopping at a Toy Store
Next, I went to a toy store.  As I pulled into a parking space, a woman was getting out of a car in the next parking space.  She motioned for me to stop and she got a glass bottle out of my parking spot.  Then she went on into the store while I parked.  Later, when I walked into the store, she saw me and said she hoped she did not scare me.  I saw in her no reaction to my outfit.  I was impressed.  While shopping, I was stood in an aisle trying to decide between items.  Another woman came into the aisle I was in and stood near me looking at the shelves too.  She was not afraid to stand by me.  We eventually started talking about gifts.  It was just normal.  Normal!  I shopped in the store for over an hour.  I spoke to a few customers.  No one treated me oddly.  Some people took a look, but it was not significant.  I eventually got in line, paid, and left.

Hosiery Store
I went to a hosiery, etc. store.  I bought some hosiery.  I have found that whatever style of hose I start to like, they are discontinued in common stores.  Fortunately, I can stock up at this store.  One clerk talked to me for a while and asked me questions about crossdressing.  She complimented me on my personality.  They were completely welcoming and friendly to me.  The manager remembered me from before and asked how I was doing.  There were other customers in the store, but I never paid them any attention.  I went to a few other clothing stores near there.  The only interesting thing that happened was I got two distinct reactions while holding the door open for a couple ladies.  One woman said thank you, but her face showed that she was not comfortable even speaking to me.  The next woman coming behind her smiled at me and thanked me warmly.

Below is a picture of me in one of the clothing stores:


Shoe Store
I went to a shoe store.  They had very few customers.  I asked an employee for help.  She went into the back and found me a lot of large sized flats and boots.  She brought them out for me to try on.  She sat on the little foot stool and I tried on every pair and tried them out.  We talked and laughed at how some shoes seemed way too grandmotherly and did not match my style.  A man sat three seats down from me and messed with his phone while he waited on his wife.  I never saw him pay me any attention.  Next, I went to the discount rack and looked for shoes that would fit.  A female customer was there.  She gave me warm smiles and talked to me while we shopped and tried on shoes.

Lunch at an Italian Restaurant
I changed into a black dress with a white, unbuttoned shirt over it.  I put on my heels.  I went to an Italian restaurant.  I had to sit in the lobby with a couple other customers for 5 minutes.  I was seated.  I ate my food.  I paid for it.  Some people looked, but that was about it.  I have found that once I am seated, eating in a restaurant is not very different from eating in menswear.


Christian Book Store
I put on some flats and went to a Christian book store.  A male customer held the door open for me as I approached.  A couple staff members approached me at different times and offered help.  I was treated well by everyone.

Shopping Mall
Then I went to the mall and did some shopping.  The picture above is of me in a store at the mall.

Target and a Compliment
I changed into an orange top, a denim skirt, a black cardigan, and black flat shoes.  I shopped in a sporting good store.  Next, I went to a Target.  I am normally nervous about going to Target.  I was not nervous this time.  While walking past the women’s clothing section, I saw a black and white sweater dress.  I had to try it on.  The ladies at the dressing rooms were very kind and helpful.  They liked the dress, but I did not get it because it was too short on me.  When I bent over, it rode up a LOT in the back.  I asked and one of them
happily took a picture of me.


I did the rest of my shopping I needed to do at Target.  I went to the busy checkout area.  I got in one line and waited.  I looked around and saw another line empty.  The cashier looked Hispanic.  I went to her line in hopes to learn some Spanish.  As soon as she spoke to me I realized she was from southern Asia.  She was friendly and polite.  We spoke a little.  At one point, she said, “I hope this is not inappropriate, but I saw you walking earlier and I thought, ‘what an interesting outfit’.  I like it.”  Those are not her exact words, but she was communicating what I understood to mean, “You have a creative fashion style.  It is different and bold and I like it.”  I got the feeling that she did not think it was crossdressing but very avant garde fashion.  I thanked her and asked her if my outfit looked OK, does it match, does it look my age, etc.  She said it was very good.  It was color coordinated, it matched, she commented on each part, and then said it was beautiful.  She have given me a kind, thorough, sincere compliment.  I welled up a little.  I almost cried.  That was clearly the best part of the trip.  Eventually, she told me she was from Sri Lanka.  I looked up how men dress in Sri Lanka.  I think I now understand that my outfit might not have looked very feminine to her based on her culture.  Men wear a lot of skirt-like outfits there.

Supper in a Restaurant
Next, I changed clothes again and went out to eat for supper.  I went to a sit-down restaurant.  I was wearing my heels, a black and white stretchy pencil skirt, a black blouse, and a white, unbuttoned outer shirt.  When I walked in the door, I realized that the restaurant was empty.  The hostess seated me.  She was friendly and talked to me a lot.  Then the waitress came.  I ate and asked her to take my picture before I left.  The manager walked over while she took my picture.  The manager started giving pointers on where to stand and how to stand.  She talked to me for a while afterward and she was complimentary of my shoes, etc.  Eventually, she dropped in that she had a girlfriend.  I thought, “Ah, that is why she is engaging me so much.”  They were all friendly and greeted me farewell.


Next, I headed home.  That evening, I told my wife about all of my outing.  She still does not love it, but she is becoming more understanding.  And, she still loves me.

Through it all, this outing was the most normal feeling outing I have ever had.  Almost everyone seemed to pay my outfit no attention.  People would glance down when I approached.  They did not seem to be forcing a fake warmth when they spoke to me.  I did not pay attention to others very much, so I did not notice many stares.  I detected almost no negative reactions to me.  I occasionally forgot that I was doing something unusual.  The worst thing that happened was I got a small run in my pantyhose near the end of the day.  I had a very nice time, just like my wife had wished for me.


From → True Stories

  1. I applaude your confidence to got out in public – you’re taking steps to help show the world that it’s okay to be a guy in dress, or a guy in heels, or a guy in flats. I struggle with understanding why the world makes it so uncomfortable for us to choose and wear fashions we feel like. So, thank you for all that you’ve done, if only I had your confidence.

    Keep the stories going!

    • In my experience, the world is not reacting. It is all in my head. People take a look, but they do not attack.

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