I'm halfway through "Whipping Girl: a Transsexual Woman on Sexism and the Scapegoating of Femininity" by Julia Serano. It's very good and a good first book on the topic - there should be many more from many different perspectives! Serano includes her own experiences as supportive evidence and provides a good history of transsexuality in Western society. The only downfalls are that she has a strong us-vs.-them mentality regarding cissexual "experts" and often writes as though her opinion is the only correct opinion. If one approaches this book as one view on the topic rather than as the ultimate authority, though, the flaws are mere obstacles. As stated above, it's a great first book on the topic of transwomen experiencing the scapegoating of femininity.
The book, though, has forced me to come face-to-face with my own issues with femininity. I'm not among the dykes who think of femmes as "Uncle Toms;" I admit that I have tended to assume that many femmes fall/walk into the same pitfalls as feminine straight girls: not knowing and/or willing to take care of herself and, instead, using her looks to get someone to take care of her. I've known butches who do the same thing,though... And as for feminine men: I have respect for their crossing of strict gender expression boundaries, but I will avoid those who I know use it to get things out of people (same with masculine people who use their masculinity to swing their dicks all over people).
I'm certain that this disdain of femininity came from my past. There is a Biblical story of Jacob wrestling with some guy in the night, but it turns out to have been God. Disdain of this group of people (which I work to not actually take out on real people) is my wrestle with the compulsory femininity that had been prominent in my life until very recently. I'm under the impression that, once I've erased all my compulsory femininity, I can take on the femininity that actually suits me. This compulsory femininity is tied in with strict Catholicism, classism, heterosexism, etc. A clean slate allows me to release my past and to pick what I actually want.
Because I'm in a better place altogether now and there is a clear distinction between my "past" and "now" (I'm no longer in school, Wisconsin, dependent living, old relationship goals), it's easier to release its hold, at least in this aspect. It's easier to see that the stereotypes of the Earth Mother, Paris Hilton, and Jessica Rabbit are all parts of femininity and that it's ok to pick and choose different parts without the fear of falling into weak dependence. Refusing to wear a skirt because one doesn't want to be taken as femme is no different from choosing to wear a skirt because one doesn't want to be taken as butch/andro. I wore heels the other week for a job interview at Ann Taylor; I wore them because I felt like it. The world didn't end and the pain of walking in them made me sympathize with rather than bemoan people who feel like they must wear them.
Being able to articulate all this has made it less intimidating/controlling/big, which is now easier to leave behind me. I'm more comfortable in androgynous garb and I'm more attracted to androgynous people (which is another blog entry altogether), but that's just who I am and not a rebellion or escape. Don't be surprised if you see me in a skirt sometime! I still feel like dressing masculinely or femininely is drag, but I'm free to do it for me.