Portrait of a Lady, Pt. II

This time it's personal.

by Ashlea Halpern

Some are passable, pretty even, but most look exactly like what they are: men in dresses.

I'm flipping through a copy of LadyLike, a locally run magazine dedicated to the cross-dressing lifestyle, admiring the dozens of CD photos strewn throughout its pages [Paper Doll, "Portrait of a Lady," Ashlea Halpern, Dec. 14, 2006]. Sometimes the giveaways are subtle (jaws too square, hips too narrow, hair too big, etc.). And sometimes it couldn't be more obvious: Their shoulders slope forward like a Neolithic hunter who just clubbed a saber-tooth tiger and is now modeling its fur.

The coy smiles, the painted lips, those saucy over-the-shoulder winks — these women are exaggerated pictures of femininity, Vargas girls with five o'clock shadows. Compared to their coiffed hairdos and perfectly pressed-on nails, I feel downright mannish. Yet something about them excites me.

My man Andy begs to differ. "They're so fucking campy," he says, head shaking, only somewhat aware that the next logical step in my exploration of CDs is to dress him like one.

To date, the closest Andy's gotten to cross-dressing was masquerading as Ziggy Stardust for Halloween '05. But one bottle of Rioja and plenty of positive reinforcement later, and Andy was a ZIP code deep in CD land. He wore foundation, blush, eye shadow, eyeliner, mascara and lipstick. His first outfit was a black bra, frilly white panties and the leftover Ziggy wig. He looked a bit too campy for my liking — a red-headed Hedwig or a sneery Sandra Bernhard. He told me he felt ugly — "I look like I'm wearing a fucking diaper," he grumbled — so we traded the white panties for see-through boy shorts. His ass crack hung out the low-rider back and his penis squished into the lacy front like a slug folded in half.

"What do you want me to do?" he asked, hands thrown in the air. "Give me some direction."

Inside, I was laughing maniacally. But for his sake, I maintained a cool exterior, suggesting he pose in a Titian recline, make kissy faces like the starlet he knew he was, and do the Chuck Berry twist.

"You owe me, you know that?" he groused.

Andy was not a happy little cross-dresser. And so far, I wasn't feeling that loin-trembling lusty burn. I yanked off the Bowie wig, and gave him another outfit.

And there, sitting in his desk chair, wearing my vintage cardigan, black bra, girly green panties and cowboy boots, strumming an acoustic guitar with three busted strings, he actually looked ... pretty.

His makeup was starting to bleed, and his bangs were matted against his forehead. His legs, chest and pits were unshaven. He looked like a lesbian folk singer or maybe Liza Minelli, the sort of strung-out, slightly deranged queen you'd see in a Katsumi Watanabe or Nan Goldin print.

We snapped no fewer than 600 photos. For our private collection, of course.

When I grilled him afterward, he said he only felt pretty "from the neck up." He never sensed the emergence of a female personality, nor did his ladylike moves come naturally. More than ever, he said, it made him question cross-dressing's allure.

I tried to assure him of his female hotness, of his supple lips and surprisingly smooth complexion, but he only focused on the negative: the rolls, the love handles, the insistence that no matter what I said, I wasn't really attracted to him.

Typical woman.

Questions? Comments? Do you come from the land down under? E-mail ashlea.halpern@citypaper.net. No phone calls.