You know, I really thought that I had posted all of this at one time or another, but apparently I’m either wrong or I can’t find it!
If y’all are reading this, you presumably know that I travel a LOT for my job, and I do the majority of it cross dressed. Yepper, I definitely qualify as an expert when it comes to “flying pretty”. In fact, at the risk of bragging, I'm pretty sure that I am the one that coined that particular phrase a few years ago.
I get countless comments and emails asking for advice on this and that, and so this post is intended to address the majority of those questions and concerns. Anyway, here is my preliminary post on the “do’s”, the “Don’ts”, and the “how to” of flying cross dressed.
1. Surprisingly enough, the airlines and the TSA are experienced and well trained in the proper way to deal with the transgendered. You are not going to shock or surprise them, and they are not going to hassle you.
2. Never try and fool the airline or the TSA as to your real name or gender. If you are gonna fly pretty, you just need to accept it in advance that the airline and the TSA people you are going to deal with will know beyond any shadow of a doubt who and what you are. If you can not accept this, then you should just go ahead and skip the whole adventure and fly drab. The reality is, if you make any effort to hide your real name or gender from the airline or the TSA, I can 100% guarantee you that you will not be boarding an airplane and you may even end up spending some quality time speaking with law enforcement.
Don't get me wrong, this does not mean that you need to approach any of these people and wave your hand frantically above your head while shouting "I am a male!" What it does mean is that you need to give your real information when you book the flight, and you need to present a legal and unaltered state or federal ID that gives your true and legal information.
3. You do not need to specifically tell the people that you interact with "I am transgendered." Let's face it, when you are dressed as a woman, and present an ID showing that you are male, this is abundantly clear and so there is no need to state it.
4. Speaking if ID, don't worry, your male ID will be just fine. As I said, the TSA is used to seeing this and it won’t throw them for a loop. The inspector will probably look long and hard at you and your ID, but he will ultimately pass you through. In the hundreds of flights that I've taken, I only ran into an issue once with this and it was because of a brand new inspector who was still being trained. In that case, she just quietly called her supervisor over and he politely asked if I might have another form of ID to show them just to give them more confidence that I was the same person shown in the ID. Even with this small hiccup, they were quiet and respectful, and at no time did I feel like I was getting undue attention. Quite honestly I was honored - they really had trouble believing that I was a guy!
5. Shoes! I can't speak for anyone else, but I love my pretty shoes and it will be a cold day in hell before I travel in flat or boring shoes! Now having said that, you do need to use a little common sense. Two or three times I have headed off to a 12 hour day in airports wearing new shoes that I thought were awesome and reasonably comfortable, just to discover after a bit of walking that I had made a serious mistake because the shoes were too tight or too loose and wound up being very painful by the end of a day of walking. The moral of the story is that you need to keep in mind that a day of traveling by airline can involve a lot of walking and so you need to be sure that your shoes are going to be comfortable enough for the long haul and hike.
6. You also want to keep in mind that your shoes will have to come off when going through security. A lot of women's shoes have a number of small straps and buckles that can make for an amusing spectacle for those around you while you are balancing and hopping on one foot while trying to take them off. So my advice is to plan ahead - either wear shoes that are easy to get off and on while you are standing, or just stop and loosen the buckles before you enter the security line.
7. With the advent of the new back-scatter body scanners, traveling pretty just became a bit more annoying. It will quite likely flag you for further inspection if you wear a corset, if you wear breast forms, or if your garment has any kind of decoration on it like sequins. Not to worry though, because the worst case scenario has you pulled to the side and patted down by a female TSA inspector. In fact, in my opinion, you should just go ahead and be mentally prepared for this pat down inspection to happen in any case. It is quick and professional and no big deal, so just be mentally prepared for it and don't get anxious if you are called to the side for one.
8. When it comes to wearing breast forms, you enter a slightly gray area. They are considered a medical prosthesis and so are allowed through the check point despite exceeding the maximum size for liquids and gels. The gray area is that you technically should declare them and send them through the x-ray machine to be inspected. In practice though, I have gone through these check points twice a week at countless airports around the United States and not one single time has anyone commented on it. My advice is to say nothing and just go ahead and wear them through the check point. If they want to make a fuss about them (and again, I fly a lot and they never have said anything) then the worst case scenario is that you may be asked to step aside for further inspection.
9. Something that most women would think of but that might not occur to all of us, is that the makeup you are carrying in your purse or carry-on is probably a liquid or a gel, and so it must be treated as such. This means that it has to be placed in a medium sized zip-lock bag and sent through the x-ray machine. If you leave it in your carry-on or your purse, it will be caught, and you will be pulled aside. If you do not want the hassle or the attention, then just place it in the zip-lock bag and place it in the bin as you are supposed to.
10. Oh, and don't forget that your sparklies (jewelry) will have to come off before you go through security. Your wedding ring can stay on, and if your ear rings are small and modest, you can probably get away with leaving them on too, but nothing more. So take the bracelets, bangles, and large ear rings off before you go through security.
11. Bathrooms can be a bit more dicey, but probably not the major show stopper that a lot of us would fear it to be. Most modern airports of any size will have "special needs / Family" bathrooms available that are gender neutral. Again, this is with the larger airports - all bets are off for the really small regional airports. All of the international airports I have been to have these private bathrooms, but some only have one or two, and some have a lot of them. I have not made any effort to specifically note which ones have them or where they are, but off of the top of my head I can tell you that Austin, Detroit, and Atlanta have them all over the place - pretty much everywhere there is a male and female bathroom, you will also find these "special needs" bathrooms. Salt Lake City, DFW, and Charlotte have a few scattered here and there through the terminals, but they are not at every restroom location. Oh, and don't forget that the bathrooms on the plane are gender neutral, so if you can hold it until the plane is up in the air, then you will be good-to-go!
12. What do you do if there is no gender neutral bathroom available? I would have to be honest - I don't have a full-proof answer for you on that one and so you will need to make your own decision. Considering the possible consequences, I am going to be brutally honest here. In my case, I am not entirely passable, but I think that I am close enough that people are not sure if I am male or not, and so they are unlikely to make a fuss if they see me entering or leaving the women's bathroom. Now you are gonna have to be brutally honest with yourself. Are you at least passable enough that people won’t be sure that you are male? Do you think it will make a difference if they know for certain that you are a male? I can't answer those questions for you . . .
I think that takes care of most of the fussy details, so I'll also offer a few general suggestions:
1. The very first trip that I made, I was scared to death, and so I had a “back up and punt” plan in place. I had a Tupperware container filled with water in my car, along with a washrag, soap, and a change of clothes. I figured that if things got ugly, my worst case scenario would have me washing up and changing my clothes in the car, and then returning to the airline counter. Mind you, I know for certain that you will not need this plan, but it may give you confidence knowing that you will have that option available to you.
2. When I travel in the summer time, I carry a small bar of soap (think Hotel soap) and a small thing of deodorant in my liquids and gels bag. Wearing a wig, breast forms, hip pads, nylons, and a face covered in makeup, all while carrying my tool box, luggage, and a backpack around in the heat, can make for a bit of an unpleasant situation. While I have only rarely had to actually use them, I want the option of cleaning up and smelling presentable if I need it.
3. I always stop before entering the TSA checkpoint and get prepared for it. I take my sparklies off and put them in my purse, I undo the buckles on my shoes, and I take out my laptop and liquids and gels bag. That way, when I get to the x-ray belt, all I have to do is put my stuff on the belt, and reach down and slip my shoes off. This sounds silly, but I guarantee you that the first time you fly pretty, you are going to be very nervous and extremely self-conscious, and you would be surprised at just how ungraceful this is going to make you. You will be likely to fumble with and drop things, and otherwise make a spectacle of yourself, so it will be much better for you if you just get prepared before entering the checkpoint so that you just have to set your stuff on the x-ray belt.
4. At the other end of the x-ray belt, don't stand there to put your stuff back together. When you sent it through the x-ray machine, you probably had to place your things into a plastic tub or bin. Just pick up your bags and that bin and take them off to the side where you can always find seats set aside just for this purpose. There, you can put yourself and your things back together in comfort and without everyone standing around you and waiting for you to get out of their way. If you want to demonstrate the value of this principle to yourself, next time you get dressed, try putting your strappy heels on while standing, and just imagine that there are a dozen people standing behind you and waiting on you, and the conveyor belt in front of you is shoving all of your things and theirs down to the end in an avalanche of bags and belongings . . .
5. As hard as it may be to do while you are scared and nervous, try to relax and enjoy yourself, and try to be friendly to people. We are a bit unusual, and not everyone has actually met people like us. You have the chance to make their first impression of the transgendered, so do us all a favor and try to show them someone that smiles and is friendly!
Originally Posted by ShannonDragon
