I completed a round trip flying pretty. On Wednesday the 16th I flew from Phoenix to Chicago, and then on Sunday the 20th I flew back to Phoenix.
On the trip there I went thru the id check with no problems then came the body scanner and within a minute of exiting the scanner an agent told me I could go. I got to the boarding gate and boarded the plane with no problems. Ended up sitting on the aisle next to 2 guys who never paid me any attention. After landing in Chicago got off the plane with no problems. When dealing with TSA or the airlines I showed them my male ID if asked for it. I took the subway and a bus to my hotel. Checking into the hotel I show the clerk my male ID and had no problems. I filled out the necessary paperwork and was given the key to my room. I wore a dress that went a few inches below the knee with wedge shoes.
While on the trip I was always dressed en femme in either a skirt or a dress. I brought absolutely no male clothing, and did not even pack any female slacks.
Coming back there were no major problems. After exiting the body scanner a female agent did a pat down on a side of my wig and on my shoulder. no problem and took maybe half a minute. On the plane back I had a row of 3 seats to myself, so my conversation on the plane was basically with the flight attendants. I wore a long skirt and top with a sweater over it coming back. Wore shoes with about a 3/4inch heel.
Also I would like to thank TxKimberly for responding to my pm and offering encouragement.