Congratulations! The first one is the hardest.
I fly, on average, four times a month. Never had an issue with TSA. I suspect at the larger airports having someone fly pretty is a non-event for the TSA staff. They may even like the change in their routine. Just give them legal ID that matches the name on the ticket and you should be good. Giver yourself plenty of time.
Kelly nailed it about thee long lines. But with the summer travel over, the planes are still packed, but the lines seem to be shorter. Cannot wait for the holiday travelers.
I travel light and rarely check luggage. Before flying pretty, I would just throw my bosom buddies into the roller bag. I only recall one inspection. I actually had two sets in my bag. They may have been the only things in my bag. The agent asked me what I had. I just smiled and said some breasts................ forms. He opened my roller bag, opened one of the boxes and said “Ahhhhhhhhhhhhhhhhhhhh, yes you do.” Smiled, closed the box, zipped the bag back up and said, "you are good to go. Have a good trip." Smiled again and said, "you have a nice day." It was pretty humorous.