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Flying Pretty Again

July 25, 2018


It was time for me to fly down to be with my family.  I had enjoyed having the house to myself for several days.  I decided to take this trip in a skirt.  I wore pants to the local airport.  It would have been nice to have left the house pretty.  I chose not to risk it.

I wore an orange top, and a royal blue maxi skirt that has white, tie-dyed horizontal lines on it.  I wore nude pantyhose and white Keds.  I felt confident about my outfit, but I have since wondered if I looked bad.  You know what?  I do not care very much.  I felt good about my look.

My flight had one layover in a large airport.  I wore menswear to the large airport.  Then I found a restroom and changed into my nice clothes.  I walked out of the bathroom stall and washed my hands.  I was not uncomfortable washing my hands in a mens room in a skirt.  I was really rather relaxed.

I walked out of the restroom.  There was a restaurant that I wanted to get lunch at nearby.  I was not relaxed enough to wait in that line, though.  I needed a few minutes to get used to being dressed in such a crowded and public place.  I traveled toward the gate for my flight.

I found that I did not look at other people to see if they noticed.  I occasionally saw people glancing at me.  Often, I was too distracted.  I do not know for sure, but I presume that I was so relaxed because of my Ballroom Dancing outing earlier in the week.

I found where my gate was.  Then I found a restaurant nearby to buy lunch.  I got in line and bought my food.  They were out of ice, so I did not buy a drink.  I went to a vending machine.  A woman was there taking a very long time.  The machine was not accepting her money.  People started collecting behind us.  She eventually turned to me to apologize and to ask for help.  There was a moment of pause when she realized that I was dressed unusually.  She followed through asking for help.  I tried to use my card on the machine and that failed as well.  She and I walked away from the machine together talking.

I said good-bye and went to another restaurant to get a soft drink.  This restaurant was also a bar.  When it was my turn, the man took my order.  The female bartender smiled at me and looked down.  She said, “That’s an interesting outfit.  What’s the occasion?”  I told her that this is just something I like to do.  The man gave me my drink and told me it was $3.25.  I think I said, “Wow!”  He told me that I could come back for a refill if I wanted one.

I went to my gate and sat down.  I was surrounded by people.  I ate in peace.  Then, I went for my refill.  The smiling woman filled my drink.  I returned to my gate.  My seat was taken.  I sat in another gap.  I started watching a movie.  A woman walked up and I offered her the seat to my right and started to scoot over to the left.  She said no and sat on the end of the row.  Later, after she had walked away and returned, her seat was taken.  She told me, “I will take you up on that seat now.”

She sat down beside me and talked to me for the next thirty minutes.  Clothing never was our topic.  She was very friendly and interesting.  She was a retired mother.  She was educated and confident.  Her flight was leaving from the other gate beside mine.  Eventually, I had to get up to board my plane.

I boarded without incident.  I sat by an older man.  I started watching my movie again.  The man and I did not speak to me until just before landing.

At my destination airport, I stopped in a shop and asked an employee to take my picture.  She was more concerned with her ignorance of how to use a camera than she was with my outfit.  She took my picture and I thanked her.


I found a mens room and changed back into my pants, etc.  Then, I went to join my family.


From → True Stories

  1. Pat Scales permalink

    I can appreciate your concerns with how you would be perceived in such a public, yet secured, place. I think it was wise of you to go thorugh TSA in your male clothes and then change once you had passed security. I remember one time, many years ago, changing into a girdle with shorts in one of the mens rooms at the airport. I was underdressed above the waist and wore beige pantyhose with shorts and boat shoes for the flight. I do not recall any adverse reactions.
    Congratulations on another milestone.

    • When I have gone on trips with layovers, I have often changed into something pretty at the layover, and flew to my destination happily dressed. Then on the return flight, I would go to the airport dressed pretty fly to my layover and change into my men’s clothes for the last leg. Airport security was always very professional and respectful when I was dressed pretty. Perhaps they were quite disinterested. Standing in the corral with all of those people free to stare was awkward. But even that was not a big deal. People had plenty of time to look at me and take note of anything that was visible. Then, they lost interest too. The corral was tougher than facing security.

  2. Sure seems like you had a good time and did look great while traveling. For me it has been a while since I did any traveling pretty. I do hope to at least go out this year for some type of Halloween fun. Not sure if I will be able to do much else as my life partner just does not understand nor wish to allow me to be me. Oh well. I have kind of hidden the other side of me for at least 60 years, what is a few more months.Have a fantastic day and thanks for all your postings and pictures. Hugs,  Lisa 🙂

  3. I am fascinated with the variety of how crossdressers present themselves! Thank you for the picture. As far as the TSA, when I travel I am “full on girl mode.” After passing through a TSA check point a few years ago, I asked if they had to handle crossdressers in a special way. The agent said no. I also asked if they prefer people not cross-dress. He also said no. Once, I was pulled over to be closer inspected because I had an underwire type bra. It was no problem.

  4. Pat Scales permalink

    It is always interesting as each of us, in our own way, work to stretch the envelope.
    Last night I came home and changed out of my slacks into shorts over my beige pantyhose. We decided to go out to eat to a nice restaurant that had a good price fix Thursday nights. My wife decided to get out of her day outfit into a nicer matching top with teal capris. I said that perhaps I should consider taking off my pantyhose and at first my wife agreed but then she said I could leave them on since most of the patrons at this restaurant are our age or older and may not notice me wearing pantyhose under my shorts and even if they did they may consider it to be support hose.
    It was very nice to be out at a nice restaurant wearing my stockings. I do not know if anyone observed them or not.
    After dinner I went for a walk along the water. Again, I do not think that anyone notice my stockings but if they did I did not notice that they noticed.

    • Wow. That sounds very nice. It makes it very special when it was she who suggested that you did not need to change. I have gone out in shorts and skin-toned pantyhose and I am convinced that almost no one notices them. I have seen the difference when I have worn more obvious pantyhose. However, even when I have worn a skirt in public, people do nothing in reaction other than look at me a couple times. Beyond that, they treat me like normal.
      Be sure to thank your wife for being so kind to you. Consider buying her flowers.

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