This illustration best describes "The trauma of TSA for transgender travelers". It is from a CNN article of the same name from October 17th by Allison Hope. It is difficult to read. It details several horror stories perpetrated by unprofessional or mean-spirited TSA workers. As the article states; "... there may be a fine line between what the agency might classify as procedure and what a passenger would call a humiliating experience."
There is a smattering of unprofessional or mean-spirited workers in all service related jobs. Disrespect can occur at a Starbucks, a department store or during a routine police stop. The opportunity is there and depending on the motive/training of the person in charge, anything can happen from disrespect to outright danger. You cannot control other people. However, your reaction is totally under you control.
Before I give the link to the article, let me state that my experiences have always been positive, non-intimidating and professional. You mileage may vary. I do not self-limit my presentation when I travel. My Passport and ID both state "M" and the photos could certainly present me with a more feminine presentation, not unlike the illustration above. I always handle the TSA ID phase by brandishing my very best smile and stating "that photo was a while ago" or a simple "yes, the photo is me." (Sorry about the grammar faux pas.) The issue date on my Florida Driver's license and Passport both reflect that is true. (Note to self - get new photos).
TSA's mission is to protect the nation's transportation systems to ensure freedom of movement for people and commerce. I believe that they do not want to intentionally to publicly embarrass anyone. There are cameras everywhere. The TSA's goal is to expedite a mandatory screening process. It is our responsibility to make that as easy as possible. Keep in mind that when someone is performing a function and making a split-second decision about someone's gender, mistakes can happen, (sis or trans).
In real-estate there are three critical elements. I am sure you know then. Similarly, in situation where screening must occur, this call for our three best defensive options. Good Attitude! Good Attitude! Good Attitude!
TSA screens over 2 million passengers every day. If difficulty or a challenge occurs (they happen) seek the path of least resistance to accomplish your goal of boarding/traveling for your trip. If you feel wronged file a written complaint after.
I have air traveled by air both domestic/international and cruise internationally with no difficulty. I believe that if I looked nervous or uncomfortable that would trigger enhanced scrutiny. Agents are trained to look for that.
Travel is as routine as shopping/dinner out, so take a deep breath and present as you have the right/privilege. Be who you are. Escape and do not be intimidated.
Feel free to comment and ask questions. I will do my best to answer about my experiences.