I travel quite frequently, so I had opportunity to be with 2 t-girl escorts. Not at the same time of course. I choose escorts because otherwise it would be quite difficult to find a place where they go out (if any) in a new city and usually I was quite time limited.
First time I was quite nervous because it was my first time that I am paying someone for sex and the first time with trans in general. Her face was quite masculine but the body of a porn star - nice boobs, curves and fantastic ass. It was the first time I touch someone else dick, actually. Except hand job I was not so much interested in bottoming (never did it, but would like to try) or blowing her.
Second time I felt much relaxed. The girl was perfect in every possible way incl. beautiful face. Honestly, she looked like someone who I would like to marry. This time the chemistry was much better between us, like she really enjoyed her time with me (compared to the first time where you could feel that she is just doing her job). Maybe I was more relaxed, do not know.
I am lousy story teller, so in case you have any questions, feel free to ask me.