As y’all probably know by now, I do a LOT of flying for my job. The good news is that if you manage to do a lot of this flying with the same airline, you collect “frequent flyer miles”. So - what good is that? Glad you asked! These miles can be used for a few things:
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Free flights where ever you wanna go when you collect enough points.
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Free upgrades to first class. The more points you have, the better your odds of getting that free upgrade.
Well, the moon and stars aligned and I got upgrades to first class on all of my flights to Indianapolis today. I figured what the heck, let’s fly dressed again.
(Note – if you think it was quite
that casual a decision you are vastly over rating my confidence. There was a good deal of indecision making the choice).
I still have the large ugly bruises on my legs that I’ve told y’all about before, but I decided I was gonna go with a short skirt anyway. What the hell, I’m already a male in a skirt, why worry too much about having ugly legs?
I wore a combination I think I look good in so that my confidence would be high as possible.
Since I have only flown dressed once before, I didn’t want to assume that I would get away with it again. Just in case, I brought a change of clothes, soap, and water in the car so I could wash and change if I had to. No worries though, nothing was said and no one messed with me.
Once again, I was a nervous wreck. I was so anxious that my hands were shaking.
I did get sort of a giggle going through the Austin Airports security though. As you approach the x-ray machine, they check your ticket against your ID. Well, as I approached the TSA official, I saw the same guy that was nice to me on my last trip just about break his neck to get to where
he could check my ID again. This is the guy I sort of thought might be flirting with me on my last flight. I’m still kind of confused as to why he would go through the effort this time. He smiled and was very nice, but went out of his way to call me “Matthew” again as he had the last time. So he seemed to be very kind, but emphasized the fact that he knew I was male. I don’t get it . . .
The lady that sat next to me on the flight from Austin fell asleep most of the way. At the end, she woke up and apologized for being so unsociable. I assured her it wasn’t a problem and that I had slept a good part of the way myself. She was covered in a blanket and said something along the lines of “I thought to myself wow I’m cold - she must be freezing!” - referring to me in the shorter skirt. Little did she know I had the opposite problem and was far too hot in the wig and makeup. Loved the “She” part though!
I had about a three hour layover in Atlanta and spent it watching videos on my IPOD, looking around every once in a while to see if anyone was paying a great deal of attention to me. Nope – far as I could tell no one knew I existed . . . until . . .
An older couple and a 5 to 6 year old girl came and sat next to me. Being a typical young one, she was all over the place. After a while, the woman told the girl to sit down and received the typical 6 year old argument.
“Why?” says the little one.
“Because,” says the older woman (Mother/Grandmother?) “ There are freaks and perverts around.”
I was shocked. I know I shouldn’t be surprised, but I was. I’ve been married over 20 years and have two beautiful children that are the light of my life, and here I sat wondering if the woman was referring to me. I looked up at her and she never once looked my way. I was torn. Maybe she was talking about me, maybe she wasn’t. Maybe she had no idea I was male and was making a general comment about a crowd of people. Maybe I could take the chance to have a word with her to let her know that most cross dressers are not freaks and certainly not pedophiles. Maybe this would be accepted in the spirit it was offered or maybe I’d end up with her husband in my face. In the end I decided it wasn’t worth the risk ad kept quiet.
It was almost time to board and so I went and stood by the boarding gate. A young lady I’d guess in her mid 30’s went out of her way to strike up a conversation with me saying she thought my shoes were cute. After the “freaks and perverts” comment, I was very grateful for the gesture and the conversation and so chatted with her a moment.

Landed in Indy, got my bags, and boarded the rental car shuttle. The driver asks that you give your name if you are “preferred” so I gave it to him. Everyone else he reads off like ‘Mr Jones, your car is space A2. Mrs Smith your car is b13.” When he came to my name, he just said the last name without adding “Mr” or “Mrs” – a small kindness showing that he was making an effort.
I got to Indy around 230PM and so went shopping straight from the airport.
Hit up two Goodwill’s, a Burlington Coat factory, DSW Shoes Warehouse, and Subway where I bought breakfast/lunch/dinner. Food in hand, I checked into the hotel and was treated with the same warm and friendly welcome I have always received at the Holiday Inn Express there.
It’s funny – I have days where I head out thinking I look my best and yet I don’t appear to pass so well. Today, on the other hand, I headed out feeling mediocre and was called “miss” and “ma’am” by every one I talked to, and believe it or not, I had gentlemen open and hold the door for me three times today!
Flying dressed is such a mass of conflicting feelings. On the one hand, it takes a boring travel day and makes it somewhat exciting. On the other hand, it makes me very nervous. When my stress meter gets pegged there is no “out” – you're stuck in the airline system until you reach your destination. Add to that the fact that it takes me two hours to get ready, and this means that to travel dressed I had to get up at 230AM for a 7AM flight.
I think I will not make a habit out of flying dressed – just to much hassle and to nerve wracking.