It wouldn’t surprise me that there’s latent sexism in some of the older literature about crossdressing, however I think “escape from the male” argument still has validity.
(Standard disclaimer, I’m not saying any of the following necessary applies to all crossdressers, let alone those who feel to one degree or another that their personalities don’t match their bodies.)
As boys we’re less sure about what “being a man” is, than what it’s not—not gay and not female. So it’s not surprising that if we want to express our “not manly” sides, we don the dress to do so.
If you look at a lot of crossdressing behavior it’s not about emulating the everyday lives of women, rather it’s emulating the parts of their lives we find most attractive—and frankly some of it has more to do with our imagination and “grass is greener” feelings than actuality. So I think it often has to do with being “not male” rather being “female.” For example, we love dresses and skirts, even though the vast majority of women wear pants most of the time. But a skirt is definitely “not male.” Or to take another example, the well-known passivity of many crossdressers en femme in the bedroom probably isn’t reflective of how they view women’s role there. In fact if you’ve ever dated a Sweet Gwen the Innocent, you know how frustrating it is to have to be responsible for not only your satisfaction but her’s as well. Instead, the passivity is probably more a chance to step aside from the pressure to perform and be the one who gets to just lay back and enjoy for a change.
The other part is crossdressing probably a particular form of escapism that someone might engage in anyway—in sense how different is it from the hard-core Trekkie who learn Klingon, the Rennaisance Faire folks, or the folks for whom Burning Man is the highlight of their year. I’m sure I started crossdress in part to escape the misery during my teens of
being one of those kids on the outside looking in. Why did I put on a dress rather than a Starfleet uniform? Beats me. That’s where other propensities toward crossdressing came into play.
The third factor in “escaping” is similar to the point the Myers-Briggs (temperment theory) people make about being able to do something that’s not “naturally” your style. You can do, but much like writing with your opposite hand, it takes a lot of effort. So if you don’t feel fit well into the masculine gender role, it is undoubtedly relaxing to slip into another role that feels more “natural.” Since it’s pretty common for some crossdressers to try to butch themselves up by being alpha males, so it’s possible some of them ended up in the high-stress positions that were observed.
As far the “forced femme” fantasies and behavior of some crossdressers, I see it mostly as a guilt avoidance mechanism. I agree that undoubtedly sexist views of women as “lesser status” come into play, but part of it is simply related to doing something that society views as strange.
And that’s where crossdressing really does expose still lingering attitudes of women being inferior to men—and sadly it’s an attitude that lingers deep inside many woman as well. A female friend of mine put it well: “By rejecting femininity in males, we inadvertently promote gender discrimination. We admit to the world that women are inferior. We are our own worst enemies…. Shouldn’t women recognize that men wanting to emulate us is a step in the right direction for true equality? A man striving to be like a woman discredits the premise that men are naturally superior… it shakes the foundation of culturally engrained gender roles.”
