Unfortunately, I learned quickly in my cross dressing experience-my car wasn't the safe extension of my bedroom mirror at home. First I had to get to it, potentially drive it past people I knew and hoped it didn't break down.
Again, I wasn't alone and not even on the same continent as we will read from Paula: (Paula's Place)
A good while back (while Dinosaurs still roamed the Earth) I learned that a car is not a private safe place, I was dressed extremely inappropriately, high heel boots, leopard print tights and leather miniskirt (I know but have got better) not only was I deep in the closet at the time, I was so deep that I also sported a beard! I thought hat I was in a safe private place where I could indulge my little "hobby", and all was fine until I was stopped by the Police and asked to get out of the car so that I could see my tail light was out. The Constable who talked to me was good as gold, but his "mate" in the car behind was wetting himself laughing. Lesson learned!
Damn Paula! with all the love I can muster, rarely do I read of a person who has outdone me in the cross dressing crazy department! I am sure I have been the "butt" of many post "pull overs" police department stories. Never did catch them laughing to my face!
However, you do bring up a great point. Before you go into the world trying out all your "girl toys" you need to plan ahead ..at least with a story. When I was doing drag at gay venues, it was pretty easy for me to tell any questioning cops what I was-doing -drag! If I stopped at a so called straight venue on the way home and got picked out of the crowd as a CD...same story. Most just figured I was a gay guy anyhow in a dress and makeup and left it at that. Those were the days I did though, get approached by quite a few curious genetic women.
I don't think it ever gets easier but now I mostly confuse a lot of people as I transition (next post) and my drivers license picture even looks very androgynous (says male) but is clearly me. So first and foremost the police know I'm not doing anything terribly bad. Usually just being stupid.