Crossdressing

May 31st,

I like crossdressers, I do. This is actually not the pro-domme trope you’d expect. In certain alt-sex circles, it’s quite trendy of me.

I dislike bad crossdressers.

What do I mean by a bad crossdresser? I mean those who do it negatively (”forced” crossdressing, punishment, humiliation) or in a careless and inattentive fashion. Women in menswear? All over it. Men in makeup and heels? I swoon for the guy behind the MAC counter. Fuuck! Pretty men in makeup — love it, love it. But I cannot get my juices flowing for a hairy man in badly fitting pink nylon.

My friend Antonia, aka The Artist Usually Known As Thrash, taught last night’s TES meeting about crossdressing. As a costuming nerd I was hoping for a full transformation, which, for understandable personal reasons, we didn’t get. While she was clear that her views on female supremacy and crossdressing-as-flattery were not the only way, it was great to hear any cogent explanation.

The first time I saw Antonia dressed, it took me a full five minutes to realize that “she” was not actually, as she would say, a “perma-girl”. As a woman, Antonia is beautiful and she passes. She takes such obvious joy in her preparation that it is hard not to coo over her: nails, hair, makeup, grooming, corsetry and lingerie. I’m not a sissy, she quips; I’m a Barbie. Dress me up. Adore me.

I never had a client like her, and I am almost a little glad. Antonia is the first to tell you how long going high-femme takes. I’m not that. Unless I am doing a photoshoot (and even then), I will shave as little as I can get away with. (Above the knees? Ha! It’s either a second date or your birthday.) I do not blow-dry my hair every day. I’ll do basic makeup, but false eyelashes are strictly a photographic thing. I will not tan, I refuse to consider acrylic nails, and I will shuck my high heels in an instant if there’s kicking involved.

The trappings are fun for me as costume. I do not sexualize it. My appearance as an object, as this girlified thing, does little for me. If it works for you, great — for most of my partners, my appearance is near obligatory — but I will feel sexual attraction and fuck and suck and come totally independent of whether my legs are shaved or not.

When you are not a girly-girl, how do you work with a partner who wants to emulate that in you? What if they sexualize “your” rituals of feminine beauty, expecting in all their efforts to fall short of yours — when you don’t have or enjoy those rituals? Would you feel that your partner had unrealistic expectations, was trying blindly to squeeze you into his fantasy mold? I think I really might. It’s tricky.

I wish I’d stayed to ask these questions, but I was still recovering from a dose of The Sick that currently has me on Cipro. I wanted the rest. I’d been woken up at 7:30 by an insomniac Lawyer with a sudden need to give me a massage, with oil and all. 7:30! Although if I must be awakened at that hour, that’s possibly the best (and I wish the only) way to do it. Oh, there was a brand-new vibrator during the sex that I decided had to follow, and I think I destroyed a year’s worth of brain cells during one of my orgasms. But then I was tired. And still sick. And on antibiotics that could kill anthrax.

Speaking of sex toys: my first toy from Edenfantasys has STILL not shipped! But I picked it out and justified it and had it approved by the administrator and accepted the assignment and hopefully, hopefully will have it within the week.

Things are busy on the business end. I may be away or unavailable for much of June, as I will be shooting like mad. I’ll emerge again at TESFest (I’m volunteering) and I hope to pick up session work full-speed again in July.

4 Responses to “Crossdressing”

  1. 1 Maria
    June 12th, at 9:59 pm

    I dated a cross-dresser once. He wanted me to teach him how to be a girl, but he was so embarrassed about wanting it that I nearly had to force him into it.

    I taught him the rituals my mother taught me: how to shave one’s own legs, french braid, never let your panty lines show, how to lower your eyes and touch your hair when you like a boy. And I taught him the rituals the cheerleading team forced upon me: eye-liner, bikini waxes, winking.

    I wanted to share an image of beautiful, strong, stand-alone femininity I was only just discovering myself. I wanted to share the joy and solidarity of womanhood.

    Eventually, I realized his vision of girly and mine were completely different. Mine involves a-line skirts, high heels, collared shirts, perfectly understated make-up, pearls, french manicures, and legs only crossed at the ankles, never the knees. His involved glitter, fluorescent nail polish, blue eye shadow, hot pink blush, more glitter, short skirts, tube tops, thongs, and polyester.

    In short, his idea of beauty, the image of womanhood he adored, worshipped, and wanted to emulate was that of slutty 14 yr old girl. He didn’t care about womanhood, he just wanted men to whistle when he walked down the street. I’ve never been so offended. And late at night, when I’m honest with myself, it still hurts.

    I wish he had been like Antonia.

  2. 2 Paul
    July 12th, at 11:31 am

    That’s such a shame about Maria’s boyfriend/crossdresser. I am a bit of a novice at it; but am a male that would be very interested in her vision of ‘girly’. I would like to delve into crossdressing more—but definitely in the realm of which Maria is talking about. I’ve always been attracted to emulating the classy sophistication that feminism inherently has. As an artist, I really enjoy the fashion sense to being a good looking woman and would love to wear some cute, but classy outfits to experience my feminine side and celebrate what Maria called the ’solidarity of womanhood.’ She’s sounds very intelligent; and I hope she didn’t let that old boyfriend hurt her. She sounds really cool.

  3. 3 SheenV
    July 14th, at 11:36 am

    Interesting post! I’m a crossdresser and I appreciate your views on men who do. I also like Maria’s ideas about it. I’m by no means a beautiful CD as you describe - I go for more the androgynous look in women’s clothes - I would love to try going all of the way.

  4. 4 Aarkey
    September 23rd, at 12:05 pm

    A much belated, but long reply… I had to respond in greater length than I thought would be reasonable here.

    Either way, I just wanted to say thanks for the inspiration (Maria who commented to your blog was a big inspiration too) - either way it’s always nice to hear when a woman can say something positive about crossdressers, especially within a FemDom context. That seems to be painfully rare :(

    My full reply his here… I hope HTML works…
    men-in-drag-pt-i-understanding.html

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