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Road Trip Dressed Pretty

May 31, 2018


Today, I went on a road trip to a town a couple hours from my home to see some family.  I wore a red skirt, a white shirt with black horizontal stripes, a black cardigan, nude sheer pantyhose, and black flats.  My skirt fell to just below my knees.  I could wear such a short skirt because my legs look shaved because I bleached my leg hair.  (If you are reading all of my posts, I suppose you are growing sick of hearing about the bleach thing… Please accept my apology.)

I just realized that I never got a picture of me in the original outfit!  How did I forget to do that?!?  Oops!  🙂  Well, here is a picture of the outfit on hangers:

red_skirt_and_black_and_white_striped_shirt_black_cardiganRed skirt, black and white striped shirt, black cardigan

When I was sufficiently far from home, I stopped in a small town for breakfast.  I went to a fast food restaurant.  There were only three couples in their 70’s and one employee in the dining area.  The couples were in three separate tables along one wall.

One of the older men watched me from the time I left my car.  When I ordered, he could not see much of me.  I do not think the woman who took my order ever saw what I was wearing.  She did glance down once, but I think she just saw that my lower garment was red.  I am not sure if she could see that it was a skirt.

A man came into the restaurant and got into line behind me.  I sat at a table.  A female employee was seated at the table next to mine.  I was on the opposite side of the room from the older couples.  While I ate my breakfast, Fox News was on the television.  The man who was behind me in line received his food.  When he walked past me, he glanced down to see my lower half.

Later, the employee who was seated near me let out a big sigh and started to get up.  I asked, “Have you been here all night?”.  She smiled politely.  She responded that she simply was not a morning person.  I reassured her that it will not stay morning all day.

When I finished eating, I discarded my trash.  I looked toward the other diners.  All six adults were looking at me.  I walked on out of the restaurant without much concern.  What else could I do?  When I sat in my car, I was facing the restaurant.  There was some animation inside.  The customers were talking to each other.  I think they may have been laughing at me and making remarks to one another.  That man who had watched me enter stared me down as I left the parking lot.  I just looked away and drove.

I did not like this experience, but I was not changed by it.  I was still ambitious to continue my trip while dressed pretty.  I chose to go to that restaurant in that small town.  Therefore, I chose to have that experience.

Consignment Shop
Near my destination, I saw a consignment shop.  I decided to stop and go in.  There was one employee.  There were also two ladies shopping together.  The employee greeted me.  I started browsing the store.

Everyone basically ignored me the whole time I shopped until I asked the employee for some help.  She was very casual.  She seemed very comfortable helping a man in a skirt.  I asked the employee if she gets other guys like me in her store.  She said I was her first.  I was surprised because she seemed experienced.

I tried on some items and she gave me opinions on them.  The two customers never paid me any attention that I could observe.  I bought a gray skirt.  I thanked her and left.

Department Store
My destination was a small country town.  There was a department store downtown that I wanted to shop in.  I found a parking space right up front and walked in.  There were numerous customers.  I was uneasy about being seen here.  I assumed someone like me would not be very welcome here.  As far as I could tell, only one customer paid me any attention.  When I passed this one woman, she leaned around so that she could see between the racks to figure out what I was wearing.  She basically disregarded me after that.

I did not buy anything in the department store.  It was time to go visit with some family after this.  I changed into some menswear and continued my day.

Return to Consignment Shop
When it was time to drive home, I stopped back by the consignment shop to say thank you.  I also wanted to ask for advice about what to wear with the gray skirt.  I was the only customer.  The employee started pulling out shirts for me to try on.  While this was happening, A woman came into the store.  Then, a little later, a man came in.  I thought, is he like me?

Another Male Shopper
I told the employee, you might be about to have your number two guy.  I went to my car and got my gray skirt.  I tried on the tops with it.  I walked around the shop freely.  I found more skirts to try on.

Later, I asked the employee about the man.  She said, “No, he is shopping for his wife.”  I heard her talking to him.  He spoke in a manner that was very country.  He did not sound like or look like a man who was into fashion.  She asked him, “Is she about your size?”  He said his wife was.  Later, I heard him ask the employee to tape up the bag because he did not see the point in wrapping the gift in wrapping paper.

This man was willing to buy a dress and a necklace for his wife.  He was able to buy the dress in ten minutes.  He was not sensitive enough to wrap it.  Personally, I think the dress was for him.  I think the salesperson never doubted his story.

The light weight, somewhat flowy, cute black skirt that I bought with the
black and white top.

I ended up buying a black, light weight skirt, a tan, business skirt, and a black and white top that is made out of a very silky/stretchy material.  I thought the top looked so good with my gray skirt that I wore that outfit home.  The skirt is a little large.  I intend to alter it.  The clerk thanked me for coming.  Then she came around the counter and hugged me.  Her parting words to me were, “You look very nice.”

gray_skirt_black_and_white_topThis is the outfit that I wore home.
The skirt is slightly too big in the hips.  I intend to alter it.

Mexican Restaurant
I drove to the next big city.  I ate lunch at a Mexican restaurant.  There were people standing outside of the restaurant as I approached.  There was no reaction to me.  Inside, the hostess asked how many and seated me like normal.  A couple of employees did look down at my lower half on two occasions.  No customers seemed to pay any attention to me.

I walked to the salsa bar and got some salsa.  While I was there, two different men spoke to me.  I think the gray skirt was not very attention-getting.  I think most people did not see that I was crossdressing.  That was excellent!  I assume that anyone who did see that I was in a skirt simply did not care.  I attribute that to the bigger town having more diversity.  In any case, it was kind of thrilling to be dressed such that I felt beautiful, and to be in a crowded restaurant, and to be uninteresting.  I felt like throwing my arms up and cheering (or spinning and singing like Maria in The Sound of Music)…  Something like that.

I ate my meal and then paid.  I stopped by the men’s room on my way out.  A man came in while I was washing my hands.  I looked in the mirror and saw him walk by.  He never even glanced at me as he walked past.

Outside, I walked past a few people standing around.  They did not pay me any attention.  I returned to my car and drove the rest of the way home.


From → True Stories

  1. Pat Scales permalink

    I like the outfits you have selected for your travels. As noted each outing seems to get easier and less stressful. When I have had to go on long car trips by myself I have dressed pretty. I typically have worn either a blue or brown denim skirt with a top. Unlike you I do wear makeup and a wig and love wearing a bra with my forms. It was always a bit scary stopping to use a bathroom on the interstate or stopping for something to eat but it is well worth the experience.

    • When you go out like that to a restaurant, do you use your natural voice, or do you try to make it more feminine?

  2. Like the black skirt and top a bit better than grey one The red one looks good too even though you did not wear it.
    Legs look great too in the hose.
    Thanks for sharing and have a fantastic day.

    • I think the gray skirt looks better, now that I have altered it. However, I too love the black one. I feel pretty in it. I also bought a tan skirt. I have been wanting a khaki skirt, and the tan one is close. It is a straight skirt, like the gray one. The straight skirts make me feel confident. I think it is the fact that they are not flowy. They seem more manly, like how a man in an an apron or a bath towel does not seem feminine.

    • The hose have some shine designed into them. The camera’s flash really brings out the shine. It is interesting to look at the gray skirt picture. There is a mirror behind me and you can see the backs of my legs. They are a noticeably different color in the reflection. These pantyhose are rather hard to see when they are not in direct light.

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