Christine, your story reminds me of the first time I went flying as female, but mine had an odd twist.
I was an airline captain (hard to believe, I know). The only airline that served my destination non-stop was (ta-da) the airline that employed me. At that point only a few of my co-workers were aware of my trans-status. On the fateful day I packed my bag, drove to the airport, then got on the bus that would take me from the parking lot to the departure terminal. When fellow crew members boarded the bus as anticipated, I had reading material to bury my face in hoping I wouldn't be recognized. No problems.
In the days before TSA there was still security, but no ID check. After my bag was scanned I went straight to the gate, filled out my 'non-rev' form, and presented it to the agent, who didn't bat an eye. I received my boarding pass then got on the airplane when the flight was called. I knew in advance a flight attendant who was a friend was working the flight. She recognized me immediately, smiled, and put me in the front row. At the conclusion of cabin service she grabbed the open seat next to me and we chatted during her non-busy time. When we got to the arrival gate I deplaned, then made my way outside where the friend I was going to visit picked me up.
This happened almost twenty-five years ago and it all sounds so, so easy. The reality is my heart was in my throat from the parking lot until I was in my seat in the cabin. So much could have gone wrong that didn't, and I don't know why. I had a lovely visit. I remember absolutely nothing about the return flight; it must have been uneventful.
I can't even imagine the terror you must have felt as you approached your first TSA agent. By now they must have seen most variations in the human condition, and might have even been trained to deal with us appropriately; but you didn't know that. I'm impressed you had the courage to do what you wanted, then decided to do it again and again. There's a lesson in all of this—do stupid stuff, it will probably work out better than you thought it would.