This is a tough subject to broach as it goes to the heart of the individual crossdresser! I do not wish to hurt anyone feelings, but if you search your most inner self it all seems to come to the center of the conflict that you may have with yourself! A crossdresser has several "outs." It is my considered opinion that you have to first determine where you are on the crossdresser's continuum. I have my own definitions of this and I won't go into it here, but if you enjoy wearing the clothes - ONLY then you are on the continuum. For some of us it goes beyond that and as I have said many times in the past, there is no right or wrong place to be! Just accepting the fact that you are a crossdresser is means enough to be on the continuum. We know for a fact that there are those of us who are quite content to remain "in the closet!" and that is OK!
Beyond that, the sharing of "our gift" does become a challenge, especially if you are "new" to this realm of "self." It would appear that the most important people that one would have "problems" sharing with are family.
Strangers, sales people, waiters, waitresses, hair stylist, -like, who cares what they think.

Most of us have been thrown out of better places than these people know!

(Bathroom usage Excluded) no one is going to "call the cops" or the PC police, you will not be drug off by your hair, beaten, taken before the minister of societal approval and sentenced to beheading or dunking! OH you may get some stares or even pointing and laughing, but its the old old adage, "stick and stones may break my bones but words (or actions) will never harm me!"
What is it worth to you - those of you who are considering going out in public - to be who you think you are!!!?? Does not suppressing this part of you do more damage to your psyche than what, if any "slings and arrows of outrageous fortune" do to you by the "great unwashed!"
Please remember, those that do not wish to go out - THERE IS ABSOLUTELY NOTHING WRONG WITH THAT.
I can only speak for myself and I approach this "telling others" (again family excluded) as a "need to know basis." I usually have my "portfolio" with me just in case someone wants to see pictures, but beyond that, it is usually just none of their business - when I am buying skirts or dresses or under-garments or make-up! If I need or want help I will ask for it and if they ask "Is this for you?" depending on their tone of voice or body language or most of us can sense a hostile attitude, I simply say "yes it is!" If I sense any hostility I will look them straight in the eye and ask, "Do you have a problem with that?" Depending on their response, you can either walk away, shop somewhere else or ask for the manager and simply tell them that their employee does not seem to want to provide you the service that you were lead to expect from their establishment! I have heard of these employees being fired on the spot! Just how gutsy are you?!
When it comes to family, I will pass on advice. All I will say is if you plan to talk about it, be prepared. We all know the first question - "Are you gay?" and the second one "do you plan to transition?" After that it can depend on who you are outing yourself to. Spouse, children, aunts, uncles, brothers, sisters. Many of our sisters here are much more well versed in these responses than I so I would defer to their expertise!
As for employers, be familiar with their personnel guidelines. Most employer human resources have written guidelines for transgendered employees now! If your employer does NOT - be very careful, that is, if you like your job!
This is primarily what we are here for, to support each other and share our own expertise and experiences so as to help each other, so ASK!
Go Forth Woman - and BE!
Love you all,
Virginia