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Flying Pretty Outing – Part 4

October 13, 2017


This is part 4 of a series of posts about a trip I went on.


College Campus
I decided that I should change back into my skirt.  I walked around the college campus.  I visited the department where I would have been a student.  I passed only a few people.  I asked a couple students for directions at one point.  They helped me without hesitation.

I drove the long distance back to the airport.  Near the airport, I stopped at a gas station.  I was unsure how to get to the airport rental lot.  I asked a man at another pump.  He told me what he could.

Rental Car Return
I found the rental car return location successfully.  I drove in and stopped.  I collected my belongings.  Two people were quickly processing my car.  I was tired.  I did not care how I was dressed anymore.  I got out and placed some charging cables, etc. into my suitcase.  I headed inside.  My skirt and I pressed on toward the airport desks.

I checked in at a kiosk.  I spoke to the lady at the desk.  The “danger and risk” of going out in public had almost entirely stopped impressing me.  It was kind of cool!  I went through security with no incident whatsoever.

I found the gate for my flight.  Then, I looked for somewhere to eat supper.  I found a place that took about ten minutes to make my meal.  I stood in front of this place and watched some history documentary.  I would look toward the passing people from recently arrived airplanes.  I saw something that I have not experienced in a while.  Some people were looking at me as though I was shocking or unusual.  Some took long looks as they went by,  Others have a slight look of shock.  I wonder where THAT airplane was from!  I just kept on waiting for food and watching the program.

When my food arrived, I went to my gate to eat it and wait for my flight.  At this gate, no one talked to me.  A woman to my right left after thirty minutes.  Shortly, later, a muscular man came and sat in her seat.

Time out.  Here is an observation I made while sitting there:

  1. Many years ago, when I would go on an outing, I would avoid tourist attractions because I did not want to be where people had cameras.  I did not want them snapping pictures of me and sharing them on the Internet and exposing me.  I do not worry about that any more because a crossdresser has lost its exotic mystery.
  2. A few years went by and I started to avoid teenagers because they carry phones with camera and might snap my picture.  That does not worry me any more.  Teens seem to do that less.  Also, I am not that interesting because crossdressers are not so unheard of.
  3. On this trip, I found something new to be afraid of.  I learned to be wary of adults with cameras taking “selfies” (pictures of themselves with friends).  These days, it happens a lot.  And it happens in unexpected locations.  It is a risk!

There were people up ahead who were snapping frequent group selfies.  I was in the background.  I would try to orient myself in a way so that my face was out of view.  There were other occasions on this trip where I realized that I had unwittingly photo bombed a selfie.

Eventually, I boarded my flight.  I sat between between two men.  One man binge watched a television show the entire flight.  The other man was on his phone.  I pulled up a class I was taking on my phone.  Eventually, the second man started watching a television show as well.  I started watching gun fights on my right and monsters on my left.  I often had to rewind my video so that I could see what my much less exciting educational video had to say.

I asked the man on my left about his show.  He talked to me about it and then returned to watching.  Later, he and I had a long conversation.  It was really good.  I learned a few things from him.  I left that flight a better man, I think.

I had a long layover after that flight.  I did not want to change back into menswear yet.  I did not go to my gate just in case someone from home who knew me would be waiting there.  I walked around the concourse.  I bought some doughnuts and found somewhere in another gate to sit and eat them.  No one there spoke to me.  One woman smiled at me.  I left there and visited the restroom.  From there, I found an ice cream machine.  I ate ice cream while walking the concourse.

I visited a store in the airport and bought some gum.  I asked the clerk if she would take my picture.  Then, I changed clothes, went to my gate, and eventually went home.


The last picture from my flying pretty trip.  The clerk in this store was very kind to take my picture.  She acted like it was an everyday experience.


The bad part
The worst part of this trip was I had a run in my pantyhose for the last two hours of my trip on the second day.

The best part
I do not know.  I know I was happy to do it in a dress/skirt.  I felt good.  I felt pretty, or maybe well dressed.  I felt normal.  There was no magic.  It was just nice.  I am OK with that!

To everyone who saw me and did not care, Thank You!


From → True Stories

  1. Pat Scales permalink

    Great post. It really does seem to be that the more you get out and about the easier and less scary they seem to become. It really seems like all went well with not adverse incidents.
    You did mention that while at the airport gate that there were some people who seemed to be taking a long or extra look at you. I would not put much weight on that. In your regular encounters you seem to get out and about without causing much stir at all. At airport gates all many people seem to be doing is sitting bored and waiting while doing nothing other than people watching. Bored people, with nothing to do except people watch will give a little more attention to those whose appearance is more interesting than others. In regular civilian life people are simply going about their business and are not in search of bemusement.

  2. I like your look. I have not managed to wear a skirt while flying yet, but ballet flats are the best for getting through security. Happy travels!

    • Thank you. Ladies’ flats were so much easier than my men’s shoes that first time I went through security! I though, “I should always do this!” When I got through the corral in security, the thing that surprised me that first flight was how MANY people I would have to walk past as I walked to my gate. Literally thousands of people were walking through one airport in the opposite direction. Of course, since this was a first time, I felt like every one of them were looking at me! In my recent flights, I felt like surprisingly few people were looking at me. I honestly wondered if most people did not notice. I guess my outfits were not that noticeable.

Trackbacks & Pingbacks

  1. Flying Pretty Outing – Part 2 | joeypress
  2. Flying Pretty Outing – Part 1 | joeypress
  3. Flying Pretty Outing – Part 3 | joeypress

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