The Great Cross-Dressing Divide

This past summer, a blog friend asked to interview me for their cross-dressing blog. It began easily enough, but, well, you’ll see…

Q: Slip, eventually you figured out there were lingerie enthusiasts of a different type out there. When and how were you introduced to Cross Dressers? How did you react?

I first really met cross-dressers at my blog. I knew of them before; but not the real psychology or even that I was a “lingerie fetishist.” lol  I’ve since learned there are varying degrees of interest, technical terms, personal interests or reasons — and I don’t consider myself an expert. But I think that, as a lingerie lover myself, I have a greater empathy because we all share the enthusiasm. We are all charmed by lingerie and I’d say more observant and understanding of the intimate details of the garments and the power they hold. Powers that go past the “powernet” and other materials *wink*

My first reaction six years ago was rather how I feel today: I just love to share the love of lingerie, especially the classic or vintage styles, and to accept that intimate apparel shares more than a physical proximity to our intimate body parts, but the intimate parts of our lives. There were some bumps for me along the way, things I failed to understand because lingerie and the love of it is closely tied to gender, gender roles, etc. and as a woman, those can be uncomfortable buttons to be pushed… But facing those things has only lead to greater understanding of myself. So I am truly grateful for the conversations I’ve had with those who identify themselves as cross dressers and/or lingerie fetishists. And that’s how I’ve mainly come to see cross-dressing (or CD) now, as  one part of a multifaceted continuum of lingerie fetish.

Q: This is fascinating to me. You see, I imagined that lingerie was a very natural mode of expression and celebration for women. Easy, routine stuff, just part of the scenery if you will. I have always been charmed, as you say, by the power that intimate garments have to change my surface appearances. Can you easily describe the power that lingerie holds for you?

Oh, see this is where you hit those uncomfortable buttons! lol

For many men, putting on underpants or a jock strap is just routine, pragmatic stuff; so on one hand, you can understand the sentiments… But when you say that right after saying that lingerie is a “very natural mode of expression and celebration for women” — a completely contradictory statement — you expose a rather romantic or wistful notion. It too would be more understandable on it’s own. But the two paired together communicate a lack of understanding of what it means to be female…

Women’s bodies have never really been our own. They’ve been controlled, judged, modified, commodified, for so long — including right up to present day politics — that our female bodies are The Body Politic.  At the root of this, the basic points of attraction or “beauty,” are connected to deep biological imperatives; but the legislation and control of it, public and private, by men and women, are cultural points exacerbated by what we call “culture” — a pervasively male dominated culture.

Men’s ignorance to what we suffer, endure, is borne of their positions of power; intellectually we women understand that male privileges deprive men of “knowing,” just as white people cannot know what a Native American or African American has and does endure.  But this can be intolerable at the personal relationship level. We often block all this because we don’t like to think about how the men we love just don’t get it, or even care to… But it takes most of us women years to find comfort in and with our own bodies, on nearly every level imaginable — and even when we find personal comfort, the cultural judgements and political control remains.

So when confronted by the confessions of a cross dresser, a sissy, etc., we hear their dreams, their presumptions, their stereotypes… The things many cross dressers seek in feminine finery strike at the heart of these painful issues, which is why so many women are so uncomfortable, consciously or not, with their partner’s desires.  His fantasies of “what it’s like to be a woman” can seem almost misogynistic. Especially when they “joke” about how when they wear panties they “have the best of both worlds: the luxury of lingerie without the nasty menstruation.”  Until women can honestly face what’s going on in their heads and hearts and understand it well enough to communicate it all — in as safe and accepting environment as cross dressing men want when they share their own secrets — there rather remains this dissonance, this distance, between them.

…I’ve spent a lot of time talking with hurt and confused women about this. In nearly equal numbers to cross dressing men.  It’s not that women don’t want to understand and accept their partners, but they want to be heard and understood themselves. Both men and women have a lot of learning and accepting to do.

I know you wanted a more poetic answer about lingerie and feminine power — and it does exist!  But it’s less beautiful if you don’t understand the real struggle it took to get to that point.

[I know you’d like a short answer to this — and honestly, I am trying! But this answer can’t really be shorter without sounding mean, offensive or so incomplete as to be nonsensical.  If you’d prefer, I can post this at the blog (perhaps even more in depth because I really don’t want to sound like I’m bashing anyone and trying to be concise about this seems like I’m being too blunt about a subject which can be painful for everyone) and you can link to it along with the more “poetic” answer?]

Seconds later, I panicked and sent this:

I’m really REALLY nervous about sending this to you… I don’t know that I’ve articulated it well and worry that I’m offending you–offending anyone. I don’t mean to! Like I said, the bumps of all this have led me to beautiful things, understanding, acceptance of others and myself — have led to better grinds too lol But it’s a complicated subject! …I’m actually starting to sweat!  

After minutes which seemed like years, I heard back.

O, please, don’t sweat! My ruminations are very happy things… honestly.

Yes, we are on tender ground here, but believe me when I say that I have a empathetic ear here, and very sincere agreement with everything you said below. Especially with the truths that power structures have tended to favor men and shackle women, and that the cross dresser sometimes operates from horribly misogynistic places ….

I feel very privileged to be having this discussion with you Slip. I am very grateful for your openness, and can’t wait to pick up the discussion again.

But we didn’t.

Weeks later, I asked if I could share this here. I received a gracious “Yes.”

But weeks, months more, would pass before I could bring myself to do it.


Eventually, based on a number of conversations (phone, chat, and email), I decided I had to; too few people are.

What I’m struggling to say clearly and fairly is that the fantasies of cross-dressers, sissies and sissy maids are terribly difficult to discuss — and the reason is fear.

Fear on behalf of the male who risks being met with ill-regard, ridicule, rejection…

Fear on behalf of the woman who is listening, trying to understand, who also feels ill-regard, ridicule, and rejection, attacks on herself and her gender.

Her fears may be unfounded in terms of the culturally programmed but wrong “He’s gay!” response (but we nevertheless know we cannot compete in that area) and the equally wrong “He’s at least bi!” (which means we worry that a commitment to us will never be fully satisfying for him), but we do have valid concerns:  All those buttons about what it means to be female are pushed.  And, as I said, we may forgive our men for their privileged ignorance to what our daily existence is like, but how can we deliver their seemingly sexist fantasies without being hurt? Deeply hurt?

Both sides need to be heard here.  Felt heard on a very emotional level.  Once they both are, what seems to be a vast divide can rather easily be crossed. (No pun intended!)

If you can both wrap your minds around the concepts of cross-dressing and even sissy maid sluts as mere role play or cosplay, then it’s really not so different than any other sexual role play: Each of you is playing a character. A character steeped in stereotypes, sure; but temporary outlets for healthy fantasies. It’s really no different than playing pirate and wench, Little Red Riding Hood and the wolf, cops and robbers or whatever other erotic fantasy you have.

But in order to get there, you both have to share and you both have to listen until each of you feels heard, understood. Each of you must have your dreams and your pain acknowledged.  Once you do that, you can find such play more than possible — you’ll find it thrilling!  And not just CD play either; all your sex will be better because you’ve increased your intimacy.  And that’s a cross you both can bare bear.

(Those last puns were intended! *wink*)

Should you need my help, feel free to contact me here.

PS  Should the blogger — with whom I am still great friends — wish to identify themselves, they are welcome to. But not required to. *smile* Hopefully we have done great good here!

Image credits: George Maciunas cross-dressing.

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