This posting is my attempt to put into words the rather muddled point I am in my thinking about it.
The thing that strikes me most at this point about "orthodox" crossdressers -- the people who post on crossdressers.com, or alt.support.crossdressing, etc. -- is that they seem to me to be acting out almost a parody of society's notion of femininity.
I've more or less grown up being exposed to feminist ideas, which I've taken to because their critiques of female gender roles mirror my own complaints about society's male roles.
I notice that many of the things about the feminine role that seem to fascinate these CD'ers are the things that feminist thinking ties in with dis-empowerment of women or oppression.
Some of the things I see:
- CD'ers expressing themselves in a sort of giggly, gushy "girly" way, including referring to one another as "girls". It seems to me to express "don't take me seriously, I'm just a silly girl." This reflects the idea that feminine women aren't really grown-ups.
- CD'ers fascination for bras, pantyhose, high heels, make-up, and shaving body hair. For women, these are connected with the expectation that a woman's body is not acceptable as it is, she has to hide it or modify it before she can be seen in public. (I know many women who feel ashamed if anyone sees them without their make-up on, even at the gym.) High heels in particular damage the body, but I've talked with many women who say they have to wear them for work.
Interestingly, while bras, wigs, pantyhose, etc., seem to be essential to orthodox CD'ing, dresses and skirts are not. As women have shifted over to wearing only pants and shorts, so have CD'ers. - One magazine article that was copied to one CD website described going on a CD'ing cruise, and the reporter noticed that most of the CD'ers were what we in the US would call conservative, Republican men. I've noticed a fair amount of hostility to feminism and feminist ideas in CD circles, and little sympathy.
I've also seen the complaint among wives and SOs of CD'ers that, although CD'ers talk about getting in touch with their feminine selves, this doesn't seem to make them any more empathic with the women in their lives. Sometimes their obsession with CD'ing makes them even less considerate that the average male. - The overwhelming majority of orthodox CD'ers refer to themselves (at least while CD'ing) with women's names.
My theory at this point is that orthodox CD'ing -- pretending to be a women part of the time, and dressing and acting like a man the rest of the time -- is a way for a man to deal with his own discomfort with traditional gender roles, without having to challenge those roles.
By temporarily being a woman, including changing their name, they get to act out all those things that they envy in the feminine role that they aren't allowed (and would not allow themselves) to do as men. The "feminine self" that they get in touch with is their fantasy of the priviledges they think women have. They can ignore the disadvantages of being a woman, including the discomforts inherent in the things they like about femininity, because they can return to being men whenever they want.
Note that the kilt websites also don't challenge gender roles. Indeed, a constant theme is finding ways to prove your manhood while/despite wearing a kilt. ("I'm a man, I say it's a kilt and not a bloody skirt, and I'll prove it by pounding anyone to a pulp who doesn't agree with me.") The testosterone levels at "X marks the Scot" and "kiltmen" can be a little suffocating.
In this respect, what we do here is more radical and more of a challenge to society than even the most extreme CD'er or drag queen.
It may also explain why there are hundreds of websites, businesses, bars, etc., that cater to CD'ers, but only a few small, struggling businesses (and a few websites) for men who want to wear "feminine" clothing without trying to pass for women. CD'ers can take their roles "off the rack", while we are more or less having to make it up for ourselves. CD'ers are dealing with known quantities, and can follow well-trodden paths. What we are doing is much harder: each of us blazing our own trail, and dealing with all the dead ends, back tracking, and brush clearing that that involves.
This still leaves me with the question: why am I doing this?
My analyst (everyone in the NYC area has an analyst, just ask Woody Allen

But then I remember a feminist writing something like this:
Maybe I just like skirts and petticoats (and other flouncy, frilly, silky, etc., things.)conventional wisdom has it that when a girl climbs a tree, she's trying to prove she's as good as a boy. But maybe she just likes to climb trees.
And don't want to have to pretend to be someone else in order to do it.
-- AMM