The Tranny Chaser Chaser

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

Wakefield cooked up his own drag persona two years ago for a pansexual play party called Spam. He has no qualms about dressing for success. As Pickles, he says, “Oh, my God, I can hook up with hot guys! The men at Eden made me want to get more outfits, try to dress sexy, and actually have it be a fun sex party for me.”

Wakefield, a veteran promoter going back to the legendary, early-’90s He’s Gotta Have It gay sex parties, concedes that his Pickles persona might be a result of his reaching mid-life. “As I get older,” he explains, “I’m still attracting guys, but when I started to dress up in drag, I was getting major positive sexual attention from very hot guys. It was like, suddenly, I had that sexual awakening I had when I was younger. I can do this thing and I’m attracting attention from very sexy guys that are willing to do pretty much anything.”

Eden’s hostess Sweetie has been throwing sex parties for trans and their admirers almost as long as Wakefield, the height being his Third Sex party at the Vault, under the once-infamous, now gentrified, triangular corner of Ninth Avenue and 14th Street. He was also slow to connect cross-dressing with sex, especially with straight guys. “When I first started doing Sweetie,” he explains, “I had no idea that men could be attracted to someone dressed up as a woman. And I was astounded by the kind of men, the absolute epitome of manhood: Strapping, thick-necked Guidos from Brooklyn with these horse cocks were sniffing around for somebody in a dress. And it totally turned me out.”

Sweetie is a drag queen, which means that he self-identifies as male and dresses that way most of the time. “As a girl, all of a sudden you’re really appreciated. It’s like manipulating your body to create this more feminine form,” he says. “I got really immersed in that world, but at the end of the day, that world is not absolute reality. On the gay spectrum, I’m an overweight, femme, balding, over-40-year-old-man. I’m like cancer in the gay world.”

Hitting one or all of these walls sexually as a gay man is something that’s echoed by many tranny chaser chasers. Andrew, 44, is a gay man who started chasing tranny chasers when he was living in Milan. One night, he caught an image in the rearview mirror of his Fiat of his cheap, plastic, neon-green earrings bouncing up and down while being double-fucked by two Italian stallions. “Now that I’m back in New York,” he says, “I visit this party. It feels less scary than it did in Milan, where I just wasn’t connecting socially and it became my only real human contact.”

Daniel Harris summed up the malaise in his memoir Diary of a Drag Queen, where he describes being a middle-aged, lonely, and sexually frustrated New Yorker until he accidentally discovered chat rooms where he dressed as a woman to lure straight guys.

The ultimate irony is that the tranny chaser doesn’t want to admit or be reminded that the “woman” he’s with is a gay man. “I think if you would tell this guy, ‘You know what? I’m a gay man and I’m only putting this on because I know you’ll be attracted to it,’ the minute you said ‘gay man,’ he wouldn’t be able to get an erection,” Sweetie notes. She also considers it demeaning to a true transsexual or even a dedicated drag queen. “Michael’s brought his little gay friends,” she complains. “He’s told them. ‘Oh, girl, come get in drag, you can get great dick.’ But when they come down the stairs and I look at what shape they’re in, I’m furious. Furious! I don’t really express it, but I’m pissed. I don’t want the face of my party to be some limping, tit-underneath-one-arm, bad Halloween drag.”

There’s something anachronistic about trans admirers—not dissimilar to the get-ups of most drag queens. Eden Underground hangs on the polarities of ’50s-style hyper-masculine and hyper-feminine to keep all its plates in the air. Maybe it’s part of the historical detritus of gay shame—trans admirers fearing being considered gay and the gay men chasing them not wanting to be sissies. “There is such a fear in gay men about laying that down and saying, ‘I’m going to be every stereotype tonight that people have thought about gay people for the past 500 years,’ ” Sweetie says, “that we identify as women.” That, and the fact that that’s the only way they’re going to be nailed by straight guys.

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