When you're new to crossdressing the world can be a scary place. You feel a great deal of fear and insecurity being in femme around others. You're afraid that they might think of you as being "weird," a "pervert," or that you're "crazy."
You know what? You're probably right, they probably do think that about you.
But how you maneuver through the awkwardness of a situation and the uncomfortable feelings makes all the difference.
You have to ask yourself, "what is at stake?" and "Does this person's opinion of me actually matter?"
For example lets say you are buying something in the lingerie department and the sale's clerk looks at you funny. This makes you feel uncomfortable. Now put yourself in her shoes. She sees this guy in the lingerie department looking uncomfortable which makes her feel weird. So now she's thinking you are a little creepy, and you are now both looking at each other like "what's wrong with her/him."
You know what, let her look at you funny. Smile and say "hi." Remind yourself that you are not there to be her friend, you are there to MAYBE buy something. She doesn't really care who you are or what you do. She's more interested in your money. Does her opinion of you matter? Not really. So you can bring your guard down and enjoy yourself in the moment. The more comfortable you are in the moment the more comfortable the clerk will be. It's the equivalent of putting a bullet between the eyes of the pink elephant in the room. Done, the elephant is dead, can we carry on with having a good time now?
Now, if the stakes are a little higher, say we're talking about discussing crossdressing with you're employer, family, and/or friend etc. then it helps to focus your energy on making sure they are at ease with the idea of your femme self. Focus on how they are feeling and reassure them that there are stranger things in life. NORMAL IS NOT creating a gender dichotomy and then expecting the ENTIRE HUMAN RACE to stick to the gender that matches their birth sex. THAT'S JUST A CRAZY EXPECTATION!
Most crossdressers will tell you that they feel a physical change when they are in femme. It's like endorphins running through their bodies. They are aware that the world in which they are in is no different than it was before they got into femme yet they experience (they FEEL) the world in a different way, because their bodies feel different. The body not only feels different because their center of gravity has changed do to wearing heels and putting on breast forms, corsets, etc, but because they feel emotions they usually don't feel while they are in guy form: emotions that make them feel sensual, delicate, sexy, soft, gentle, flirty, giggly, OPEN TO THE ENTIRE EMOTIONAL SCALE WITHOUT HOLDING BACK. You see, women generally speaking, are considered "emotional creatures" thus WOMEN HAVE FREE ACCESS TO ALL EMOTIONS, while men on the other hand hear things growing up such as "boys don't cry," "be a man," "stop being such a girl." Crossdressing is a great tool for men to allow themselves to FREELY experience ALL EMOTIONS!
Have you ever met that one black guy that plays the "racist card' every chance he gets? Someone cuts in front of him in line and all of the sudden he thinks "it's because I'm black isn't it?" Or have you met the woman that constantly plays the "sexist card" and thinks to herself when she is not chosen for a job "it's because I'm a woman isn't it?
This brings me to the "reality" some crossdressers create for themselves in their minds. Some crossdressers, to a certain extent, play the "crossdresser card." Thinking to themselves, "if I go to dinner at a restaurant I'm going to be treated poorly because I'm in femme." This could be true depending on which restaurant you attend but chances are if you carry yourself with style, confidence, and elegance you will be treated just like "everyone else." Sometimes the trouble arises because some crossdressers don't want to be treated like everyone else, they want to be admired, given complements on how fabulous they look, and treated like VIP. After all they spend a great deal of time getting ready. But lets be honest, who likes anyone that walks around telling people "Don't you know who I am?"
Of course as you read this you may think to yourself, this all makes sense, I get it now. But this is consciousness that is best understood when experienced in the real world, through action and not on an Internet page. And it's not reserved to crossdressers, you can see this "reality creating consciousness" everywhere. Just put it in action yourself. Go out and greet the world the way you'd like the world to greet you and see what happens. BUT also keep in mind that some people are going through a rough time and they simply want to be left alone. So try not to think of them as assholes for not returning your smile. In those cases pull out the "compassion card."
Here is Eckhart Tolle artfully describing the arising of presence on both the personal and societal levels: what our lives are like before the awakening of consciousness, and how we can practically navigate the process ourselves.
Speaking of lingerie store watch a couple of guys in a lingerie story with Pamela Anderson as their sale's clerk