"The first rule of Fight Club is You do not talk about Fight Club.
The second rule of Fight Club is You DO NOT talk about Fight Club."
If you've read the novel or seen the movie Fight Club you are familiar with the above two rules. I often think it's interesting that crossdressers have similar rules when it comes to crossdressing:
You DO NOT talk about crossdressing!
There is this fear that if the general public finds out that a man enjoys dressing up as a lady then he will become a castaway, a freak, or less of a man. I find this fear interesting because although there is a stigma that comes with crossdressing there is nothing inherently wrong with one gender dressing in the other gender's clothes. So what is at the root of this fear?
Grown men can sometimes behave like little boys. They will try to find any little "flaw" in another guy to make him feel small. Males try to dominate not only women but other males around them. Correction, "insecure Males" try to do this. The worst thing is sometimes they succeed. They don't succeed because they are bigger, or have more money, or are more forceful, but because other males would rather let someone mess with them than to make a scene and stand up for what is right.
Where do you rank? That's how intimidation usually starts. We've all had a conversation with a person, be it male or female, and they try to figure out where THEY rank in life by figuring out where YOU rank. How much money you make, how many women you've slept with, what kind of car you drive, where do you vacation, how much can you bench press, etc.
When you step back and you hear a dude try to lower your rank by him boasting how great he is and how you are nothing compared to him you have two choices: You can either feel small next to him, or you can look at him in the eyes and say "Good for you."
I believe more crossdressers would talk about crossdressing in casual conversation if they came from a place of sharing their crossdressing experience:
a) With the right people.
b) Focus on how FUN crossdressing is
c) How ridiculous yet exciting walking in heels is
d) The challenge that is doing hair and makeup
e) How silly it would be for Human kind to only allow one Gender to wear dresses.
Some guys play golf, others play "girl," and they should not feel ashamed to talk about it.