Well kids, I am here to inform you that the TSA just does't care about cross dressers.
I have just come home from yet another business trip where I packed for "Jennifer" and I and as always, no issues. The ONLY thing the TSA may review from an x-ray of your bag is your silicon breast forms. The silicon appears as a solid mass and depending on how it is packed, an agent may need to open your bag. When I pack my forms, I 1) put them on top so that any agent doesn't have to dig and 2) separate them and position them so they "look like" breast forms to the x-ray agent. This prevents the need to open the bag. High heels, makeup, wigs, none of that matters nor is even a blip on their radar. Women do travel too, after all.
You are not the first cross dresser going through an airport and you will not be the last. Pack your carry on with confidence and sally forth