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  1. First off many are not comfortable even stepping out the door dressed in the gender they want to be so this is going to be a huge step.
    Okay, most of us try dabbling with makeup for various reasons, blending in is A number one while other reasons might be for attracting someone while out on a date, at a bar etc. Focusing on cisgender females, many who master the art will spend countless hours in front of a mirror, view countless hours of video "how to do..." and so on while a transgender person may not and most likely will not do this including me.
    So at just under 60 years old I was prompted by my best friend to do a makeup session at Macy's. It's not important where but by a seasoned professional When you do this they will explain everything to you and there is no cost if not pleased with the results or the products cost too much.
    The focus is, they have been were we are at and most have done hundreds if not thousands of make overs in regards to makeup so unless you get a newbie you will learn without what cisgender teenage girls go through.
    If you are passable, don't tell them you were once male, if you are not passable, be honest and tell them, trust me in most cities they have seen it all I am sure.
    If you want to learn how to do this for day time then go in the day time, the same is true for night time but I suggest beginning with day time so you can get use to this unless you are the type that does not go out in the day time.