Originally Posted by SCEagle
No, no...
Try to clarify here:
Male name on government ID. Male face to match ID. Female clothing. No changing, just travelling "as is".
Perhaps Air Tran?
Just kidding, I've always had some fun marketing ideas for this airline. Seriously, I don't see why you would have any problems with the TSA, airline, etc. given your scenario. You may get some perplexed looks, but kudos to you for having the courage to be yourself.