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Flying Pretty

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A common item on many Crossdresser’s bucket lists (mine included) is to “Fly Pretty”. For many of you, the term probably doesn’t require any background. For the other three of you, here is the thumbnail sketch.

Blogger Kimberly Huddle coined the term in her blog Traveling Transgender. Kimberly would post her journeys, usually rising at the (pre) crack of dawn, dressing, then describing interactions with airline check-in agents, TSA personnel, and car rental staff, generally schlepping around large diagnostic equipment to fix finicky and maladjusted client machinery. Her blog launched dreams amongst her followers–like me–that one day we could do it too. 

The first post was 2006, the last was 2020, almost 15 years of sharing her travels while pretty, offering advice and humorous stories. Thanks Kimberly!

I had a two day round trip to Atlanta to be at my son’s graduation, where he was getting his PhD. A big day for our family, but I was traveling solo, as my wife was still down under. After a bit of mental back and forth, and encouragement from a couple of my GG friends, I decided it was my turn to fly pretty. 

With an early flight, and an hour train trip to the airport to boot, I was up around five to get ready. I had chosen a black and white dress that I thought looked business professional. If I was going to do this, I decided it had to be in a dress and heels (comfy heels, though). However, given the forecast for a hot day (in the 90’s) I decided against pantyhose, and to go with bare legs. That required extra time the night before with Nair and my razor.

The light rail train, given it was pre-rush hour, was relatively uncrowded and a non-issue (I’ve ridden public transport before, busses and trains, and I’ve never had an issue). Arriving at the airport, I was getting ready to check my bag. I always check bags, even when it is a carryon size. 

Immediately before I get ready to check my bag, I realize “what happens if my suitcase DOESN’T make it?” I’d be scrambling to buy boy clothes to meet my son later in the day. I quickly decide to carry it on. 

Next up was security. I presented my ID–guy me, of course–and the sweet TSA agent gives me the name “Dainja”, which she said suited me better, and which I thought I was cute. 

Now it’s time to scan my carryon bag. I scramble to remember the rules for carry-on’s (like liquids in a plastic bag). I take them out to be scanned separately–and then my bag gets pulled for inspection, because of an unrecognizable image–my can of shaving cream. The TSA agent opens my bag, finds the can, shakes it, puts it back in, lets me go. All in all, it was about a five minute delay. I wasn’t worried, but my preference is to maintain a low profile when I’m dressed.

Waited to board, boarded, and flew, with no issues. I didn’t interact with my seatmates much, but I did manage a row with two other women. It was a reasonably short flight, a little over an hour.

Arrive in Atlanta, and hear over the PA system the Atlanta Airport is the busiest in the world?/US? (can’t remember). 

I walk with pride. Five years ago, I was afraid to go out in public. Now, I’m walking (strutting) through a busy airport–in a dress and heels.  I navigate the train in the airport and the train to the rental car center without a problem.

The Avis line is about 30 people long. A few years ago, I might have freaked out. These days? Ho-hum. Like everyone else, I play on my phone, waiting my turn. Finally get to the front, agent refers to me as Mister Surname (I don’t care–he was polite) and he informs me my reservation was for the FOLLOWING day. After a delay of probably five minutes, my lower reservation rate goes poof, and the new rate is about double. So it goes. 

Pick up car, drive for a while, eat lunch at an IHOP (I’m not sure the waitress knew exactly how to deal with me). I needed a pit stop, but before I did I drove to the back of the service station, changed into boy me, did my business, and drove the rest of the way to my destination. 

I spent the afternoon and evening with my son, then attended his graduation the following morning. After graduation (thankfully only a little over an hour), we went to lunch with his fellow PhD graduate and their faculty advisor. My son’s seven year journey to get his degree (one year added for a change of school, and another year added because of Covid) was now complete (and even better, he had found a job).

I thought about dressing for the return flight, but decided against as being too difficult to pull off. In retrospect, a good decision, because the flight was delayed for about 90 minutes after we boarded, and the air conditioning wasn’t working well. I would have been miserable with the extra heat from the wig.

In short, as others like Kimberly and Kandi have written, it’s no big deal to fly pretty–but it is a nice thing to check off the bucket list. I’m glad I did it. As I have promised a future visit to my GG friend Renee, this was my “test drive”, and all turned out well.

Plus one other thing.

Atlanta traffic is just as bad as everyone says it is.

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4 Responses

  1. STL light rail goes out to you?
    Or did you have to drive into STL to catch a tram?

    Yes, ATL is the busiest airport. I lost a shoe running to catch a plane during my corporate clone days. When asked where my shoe was, I replied “on a people mover”. The pantyhose on my shoeless foot remained intact.

    Thanks for the shout out and I expect you to make good on you flying pretty here.

  2. Yes, the MetroLink has two stations each about a couple of miles away, less than a 10 minute drive. Park for free, take the train. It’s about an hour by train, versus 40 minutes or so for driving (but you have to park away from the terminal, so that takes longer). Dee has taken the train a few times, once for my train trip to Chicago, and another time to attend a U2 concert downtown.

    Was that the last time you WORE pantyhose?

    As to flying pretty to visit you, if I put it out in the universe it has to happen, right? I need to find a suitable race I can do next spring in your area the boy me can do and the rest of the time we can do Dee stuff.

  3. Wow!!! That’s so cool. Flying pretty is on my bucket list and planning on taking the plunge in September. Crossing my fingers it goes as a charm

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