start small get some panties wear them when ever you can when you sleep, if you can pull it off or can remain comfortable go tucked during the waking hours. the salvation army is a good idea (course im low on money so i might be hitting there soon) if you dont know who works there or dont care what they think get what ever you like the look of.
not too sure how to go about the makeup. at first id recommend cding in neighboring towns where no one would know you.
contrary to how good the advice is i have no experience in this. all answers are just logical given the goal you've stated and the info you've given.
try some of this and give us your feedback also as stated some more info about you would be good
help us to help you, help us to help you, help us to help you
