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To directly answer your question, it depends on where you live.
Here in the south, you know when you've been made.
On one outing to Chattanooga Tn, I wore a long flowing chiffon dress, pale pink with a flower print.
I felt very passable, NOT, one woman stared at me for a good 2 minutes when she should have been walking in the other direction. I feel the make-up was too long worn and showed 5 o'clock shadow. :(
One thing that helped me was to NOT let my g/f help with my makeup, what works well for her does not for Yolanda.
Also I let my bangs cover a lot of my face, sweeping then to the side instead of letting then go straight down worked for me and got me from a No-Pass look to a sometimes passable look.
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A lot more people really don't care or don't notice than we think. I know I'm read all the time but I've gotten to the point where as long as I am treated according to my presentation I don't really care!
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I'll add a bit. My wife and I stroll through malls quite a lot, as we end up in situations where we need to kill time and what better place to do that?
So, we've had a number of situation where one of us will nudge the other and say (subtly) "Do you think that that person is a CDer?" We've never had a situation where we could tell for certain that the person in question was male.
There are a lot of GGs out there who display various characteristics that are associated with masculinity, but they almost always trump that characteristic with a blatantly female-only characteristic like makeup, nails, or dress, just as a CD will do. Unless a person displays one of the very few blatantly male-only characteristic (like a beard or a prominent bulge) there is always some doubt and that doubt will carry the day.
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That was a question that I never could answer until this past week when I went to DLV. Now that I've had a whole week out and dressed in the main stream world I've come to realize that it does not really matter. Those that read us simply say nothing for the most part. Others want to talk to us, but in a positive way. Not once did I receive or hear a negative comment.