Sex and The Single Drag Queen

(Betty Betty Nice)

Standing up on stage, the New York drag queen has the world at her high-heeled feet. Cheered on in crowded clubs and showered with adoration and applause (not to mention free drinks), these talented performers are often found at the white-hot center of the city’s storied nightlife. But what happens when they step offstage into the rough-and-tumble realities of sex and dating in New York? A lot more than you might think.

We chatted with a few of New York’s notable names in the drag world and found out some surprising things about sex and the single “lady.” Les Simpson, who’s been working on the scene as Linda Simpson since 1990, said that when he started performing, his sex life took a dramatic turn for the better. “There is a sexual component in that there are a lot of guys who are attracted to drag queens. So all of a sudden you realize you’re a fetish item or a sex object.” He found that not only was he having more sex but he was doing it with a wider range of partners, too. “It allowed me to meet a lot of people that I normally wouldn’t have, like Hasidic Jews or Puerto Rican construction workers.”

The only drawback was that most of these guys, while always hot and raring to go, were more of the “tranny chaser” types, which meant they were not exactly into long-term relationships. But that was fine with him. “I’m one of those people who enjoys being single,” he confides. “But after a while, to tell you the truth, the tranny-chasing thing becomes a bit of a drag—no pun intended.”

However, for newer drag queens like Pickles, a.k.a. Michael Wakefield, it can be a bit of a godsend. Wakefield, who co-hosts a drag sex party with Sweetie called Eden Underground, got into dressing up as his female alter ego when he found that, even as he was approaching 50, it became surprisingly easy for him to have some serious sex with some sexy, younger dudes. “When I’m in drag as Pickles, I’m prettier as a girl than as a guy,” he says. “When I’m dressed up with my makeup and tits and everything, I look good!”

Through the Eden parties, Wakefield even discovered he had a taste for a kai-kai, too. “Kai-kai” is a term for drag-on-drag sex that’s been around for 15 years but has become recently popularized by resurgence of another gay slang term: kiki. “I was never interested in playing with drag queens until I started doing these parties,” he tells us. “Now it’s something I’m known for.”

But for Wakefield, who has a boyfriend whom he met while out of drag, all this drag sex is just for fun. In fact, that seems to be a common theme with the drag queens we spoke to, where flirting and fun in the workplace rarely translates into any sort of serious relationship.

Logan Hardcore, a.k.a. Logan Slaughter, is one queen who’s intent on keeping dating and work life separate. Slaughter also has a boyfriend (whom he met on Fire Island sans wig) and knows where to draw the line between his show world and the real world. “It’s my job,” he says matter-of-factly. “It goes in a drawer at the end of the night.” Last month, when he and his boyfriend decided to move in together, they made sure to get a two-bedroom apartment so that he would have a room to for the drag. “It’s my drag cave,” he says, laughing. “We call it the Special Room. I can go in there when I’m mad and throw glitter around.”

Previously, Slaughter says, he’d often been approached by guys who wanted to mess around with him in a dress. But he told us that, unequivocally, he would never have sex in drag. “There’s nothing comfortable about having a huge wig attached to your head, makeup all over yourself, your dick up in five pairs of pantyhose and heels on your feet.” As for kai-kai’s, he actually took that concept a step further and had a year-long relationship with another New York drag queen, Epiphany, a.k.a. Calen Tomaszewski. “I didn’t feel a competitiveness,” Slaughter says, adding that the real challenge was sharing space. Literally. “Where do you keep all the wigs, wardrobe, makeup…and who’s getting ready in the mirror at this time and who’s not.”

Tomaszewski has similar rules of engagement for sex and dating. That is, he prefers to keep it out of the workplace. “It has to happen somewhere else, which is anywhere where it’s not my job and I’m not in drag.” If he meets someone at a show who is interested, they have to be interested in him first. “The next time we see each other, I have to be out of drag,” he adds. “I don’t want to even entertain the idea of dating someone who is sexually attracted to Epiphany.”

Though Tomaszewski doesn’t get as many propositions as he used to. “I’ve been told I’m actually kinda scary when I’m in drag) he says that he’s open to the chaser option, with some caveats. “If a hot, straight guy comes up to me and wants to go home with me, I’m not gonna say no,” he says. “But I make sure that he knows the wig is coming off the second I open my front door.”

Overall though, Tomaszewski says that most of his sex life happens out of drag, adding that the ratio of attention he gets as a guy versus a girl is 80/20. “I get a lot more attention out of drag,” he shares. “I think some drag queens don’t put any sexual energy into themselves as boys, whereas I put a lot of energy into how I look and present myself as a boy.”

So, whether they’re dressed up or down, it seems that the New York drag queen keeps her datebook pretty full, whether it’s with relationships, sexy tricks or straight chasers. That seems to be a shift from not long ago when drag queens were often sexual pariahs in the über-masculine world of gay bars. But now it seems there is a new acceptance and interest in them not just as performers, but as potential partners. “I think younger people are a little more open minded in terms of gender exploration, “ says Simpson. And Slaughter agrees. “Being a drag queen hasn’t adversely affected my dating life,” she says without hesitation. “I get to meet more people through my performing in drag. So that makes it a positive.”