The Tranny Chaser Chaser

Gay guys who like straight guys who like guys dressed as girls

I’m no stranger to the walk of shame, but this is the first morning I’ve ridden the R train into Manhattan with metallic blue eye shadow smeared across the upper third of my face like a sloppy Warhol silkscreen. I’ve spent the prior evening at a bacchanal called Eden Underground: a sex party for transsexuals and their admirers in Park Slope that just rang in its one-year anniversary. What brought me to the polymorphously perverse bi-monthly Friday night was a search for gender identity’s Yeti: gay men attracted to the straight men who are attracted to transsexuals—the tranny chaser chaser.

At the party, plenty of hot, blue-collar trade search for transsexuals. Those gay men who cross-dress solely to chase these guys are called everything from “deceitful” to “blackface,” but “midlife crisis” probably comes closest. They are going after what they can’t have—dressed as men, anyway. Sweetie, Eden’s large-and-in-charge mistress of ceremonies, sums it up as cruising for men they “could never get wearing a pair of jeans on a Saturday night.”

José Muñoz, an NYU-based academic who writes extensively on gender, asks, “So they’re gay men who turn to drag to get straight-acting or butch guys?” adding, “It fits into so many fantasies of the predatory homosexual out to prey on nominally straight men.” Muñoz mentions those turn-of-the-century, New York sexual superstars along the Bowery called “fairies” that George Chauncey details in Gay New York. Many heterosexual men “alternated between male and female sexual partners,” Chauncey writes, but the fairies, those willing to oblige these working-class men, “simply offered to perform certain sexual acts, especially fellation, which many straight men enjoyed but many women (even many prostitutes) were loath to perform.”

The first thing to get one’s head around is that most of the tranny chasers themselves are straight. Bruce, a 42-year-old truck driver and Eden attendee, demonstrates his macho bona fides by opening a beer bottle with his teeth. “I’m from Long Island,” he jokingly explains of his countrified ways. “We didn’t have can openers in the woods.”

Folks like Bruce make headlines when they have famous names like Eddie Murphy or (according to transgender prostitute Toni Newman) L.L. Cool J. Soccer star Cristiano Ronaldo was reportedly caught with three transgender prostitutes. Even Matt Lauer and Gavin Rossdale, Gwen Stefani’s husband, have allegedly taken walks on the wild side. Married New York GOP ex-Congressman Christopher Lee resigned after Gawker published a Craigslist ad featuring a shirtless photo of him with the headline “Sexy Classy guy for passable TS/CD – m4t – 39 (Cap Hill)”: That’s “TS,” as in transsexual; “CD,” meaning cross-dressing; and “m4t,” male-for-transsexual.

At first blush, the codified nature of the party evokes a parochial high school prom more than a sex party. In the AstroTurfed changing area just off the entrance, a sign prohibits touching without asking permission first. Not that the reminder is necessary for Eden Underground’s attendees, who prefer to engage in “mini-dates” before walking off arm-in-arm to a quiet corner to get it on.

In the front room, where most of the socializing takes place, a leggy transsexual in tight satin pleated shorts crosses the room while Lil’ Kim’s “How Many Licks?” is playing, catches a stripper’s pole with her arm, spins to the ground, and suggestively raises and lowers her high heel. A young stud bounds up from his seat and opens his shirt to display an overly tattooed torso. She nods approvingly, runs a gloved hand over his toned abs, and they wander off together.

There’s nothing overtly gay about this party: Even oral sex is sheathed in condoms, and the industrial stench of poppers is absent. Michael Wakefield, who lives upstairs and runs the space, often attends as his alter ego, Pickles. “Some of these guys are bisexual,” Wakefield says of the trans admirers, “but most are straight-identified and the straight-identified ones are definitely not part of the queer community.” Even so, “These are all chicks with dicks,” he hastens to add. “That’s what the guys are there for. If they want a girl with a vagina, they’ll get a girl.”

Elden, a straight attendee, agrees. “Pre-op transsexuals—what are there?” he rhetorically asks. “Three of them?” We’re talking outside, where I’m back in male attire (except for that eye make-up). If I were still in drag, he assures me, he’d most definitely fuck me. So why is he willing to fuck a gay man in drag, but not any of the men he identified as gay back in the party? And why do the gay guys lusting after guys like Elden get cold feet about doing what would attract this straight trade in the first place—dressing as a woman?

“Most gay guys are really drag-phobic,” Wakefield points out. “So a lot of them don’t even see it as an option. They just won’t come back. I had a friend who came to the party as a gay guy and got no action because the focus is on the trannies.”

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