Sex can be a drag. On the other hand, drag -- men dressing in women's clothes -- can be very sexy indeed.
Guys who cross-dress come in many varieties. There are male-to-female transsexuals who, though woman-identified, still have pre-transition bodies beneath their frocks. Tranny cross-dressing is primarily about gender identification, not sexuality -- some male-to-females are gay, some bi, some kinky and others as thoroughly vanilla as your grandma.
Things get a lot more sexy, though, where transvestites are concerned. Classically defined, transvestites are folks who get off wearing the clothing of the opposite sex; we're not talking about guys who go out on Halloween wearing bad wigs and big fake boobs. It's generally agreed that the vast majority of male transvestites aren't gay-identified at all. More likely we're talking about somebody like nice Mr. Macy down the street, who gets a boner putting on wifey's frillies while she's at the bridge club. And many of the men who get off on *other* guys in full drag think of themselves as straight, too; just ask any transvestite hooker about her johns.
Still, it's no surprise that plenty of the guys turned on by women's clothes are in fact gay or bi. Queer men are in a great position to cross those "boys wear blue" boundaries. Many more-or-less effeminate men find that drag lets them play with self-image in rewarding ways, exploring the blurrable frontiers of gender while feeling sexy as hell.
But drag isn't just for the less-than-butch. One beefy guy, the kind of gay man who could pass for a motorcycle mechanic even if that wasn't just what he is, confesses, "I like wearing women's panties, the silky kind. Sure, men's underwear is available in all sorts of sexy varieties, but there's just something about slipping on panties made for a woman that gets me off. That's it, though; other than that, no women's clothes." And even men in the leather community, with its supermasculine image, have been known to trade their boots for high heels. In "leather and lace" events, leathermen compete in cowhide, then transform themselves into fashion models that could give Miss America a run for her rhinestones.
Drag can also spice up a sex scene. Messing around with gender can be big, hard fun in which women's fashions are near-indispensable props. It need not be anything elaborate, though. One guy showed up at an unsuspecting fuckbuddy's house carrying a paper bag, popping into the bathroom and emerging shortly thereafter in nothing but a velvet miniskirt and elbow-length gloves. "It was a total shock," says the host, "but I just hiked up his skirt and got busy."
Cross-dressing scenes can be playful or seductive. They can also be just plain nasty. "One guy I know, a butch little hairy fireplug of a man," says a kinky queer, "had me dress him up in Frederick's-of-Hollywood-style bra, panties, and stockings, and then treat him like a slut. He loved it. Actually, we both did."
These "forced feminization" scenes can be like playing with fire; after all, homophobes think that gay men are sick for "wanting to be like women." And misogyny rears its ugly head sometimes, too. But, like any other kink, if approached consciously and consensually, cross-dressing can be fancy, fuckworthy fun. "I'm pretty clear," says the motorcycle mechanic, "that I'm not a woman, and don't want to be a woman. I just like wearing panties. I'm cool with that, and so are the guys I have sex with."
Ken in public, but Barbie in the bedroom? Sure. Why not?