Dude Looks Like a Lady :: Boys Who Like Boys Who Look Like Girls

by Gerry Visco

EDGE Media Network Contributor

Thursday June 2, 2011

Drag queens have been attracting straight men to the bedroom (and more risqu locales) since the good old days of ancient Rome. And although shows like "Ru Paul's Drag Race" have led to a greater awareness and acclaim for drag queens, many admit that looking like a woman is still a great way to attract men. Many drag queens prefer to date gay men, and not all like to have sex in drag. But for those who like hook-ups with no strings attached, then the relationship between straight-identifying men and drag queens can be exciting.

"My experiences with straight men as a drag queen have been hot and heavy," said Jordan Fox, a 27-year-old nightlife personality and model. "I get picked up when I'm in drag at the clubs by tranny chasers and straight guys. They love my long legs and my edgy style. I serve face, which is very passable. They love the fantasy. They know you're a horny 'boy' and will more than likely put out."

Fox is notorious for going out to clubs in outrageous outfits and sometimes even in clown drag. His outr couture serves him well. "Some guys are freak chasers; the more insane you look, the more turned on they are," said Fox. Although he said he doesn't like sex in drag, he will usually go along with the fantasy. It's the morning after (if it lasts that long) that is less felicitous.

"In the morning or afternoon when the drag is off, some of the men get uncomfortable when faced with the reality they're with a boy from Brooklyn and not a super model from the future," Fox admitted. Although disenchantment is standard morning-after fare, gender issues can compound it. But if hooking up with a macho straight guy fulfills your gay male fantasies, Fox has this advice: "Put on a wig, some gloss, and some heels and hit the clubs!"

Twenty-something drag queen Miles DeNiro is a waitress and karaoke hostess at Lucky Cheng's, a Lower East Side bar notorious for rumored sex acts in the bathrooms. Pulling no punches, on DeNiro's Facebook page she labels herself a "prostitute at Lucky Cheng's."

"Straight guys are there for one reason, and that's to get their rocks off," said DeNiro. "They're all so fucking needy. They want your constant attention to live some sort of fantasy: he's the man and you're the hot girl/boy. It's fucked up."

The fantasy is not reserved just for men. Women go to Lucky Cheng's also, for bachelorette parties, or even with their husbands. "Recently a couple came in and we took them to a tranny party after the bar closed. The wife sat there, danced and watched her husband get the skankiest lap dance from a chick with a scary fucking dick and she was into it. We get lots of couples," she said.

But DeNiro prefers to date gay men. "Give me a daddy. A man who is older, who doesn't care that I do drag because it's not a turn-on for him, who understands it but doesn't want to fuck me in a dress and a wig. I don't do that. I like to be a boy when I'm doing the nasty," said DeNiro. Despite these turnoffs, DeNiro finds doing drag empowering. "I turn into a totally different person when I'm in drag -- a bossy, mean, nasty little girl."

Dancer Alexis Mateo, a Florida-based former contestant on season three of "RuPaul's Drag Race," prefers to exclusively date gay men. "I've never been attracted to straight men. I like gay boys -- the relationship is better," she said. Many straight men adore her but she considers drag as a job and not a sexual pleasure. Nor will she permit a secret relationship, or play the role of a woman.

A Walk on the Wild Side

By all accounts, straight men prefer to keep things on the down low, whether they're closeted guys, married guys, tranny chasers, or just plain old "straight guys." For many men, tranny chasing is a time-honored pursuit.

In the '90s, drag queen performer, writer, and personality Linda Simpson staged her play "The Tranny Chase," at P.S. 122. This month, she will unveil a new work, "The Emperor's New Codpiece," at the Laurie Beechman Theatre. Simpson, who has been doing drag since the late '80s Pyramid Club days, said that the allure of a man who looks like a woman has not waned over the years.

"Straight guys attracted to transgender women don't want their desire to be known by others. It's equated with homosexuality because it's easier for a guy to say they like another man than to say they are attracted to a drag queen or transsexual," said Simpson.

But for some men who have sex with men, hooking up with a man can feel more comfortable when the man looks like a woman. Simpson continues: "The narrow categories are ridiculous anyway, whether it be gay, bi, straight. Tranny chasers are sexually adventuresome while being repressed -- they don't want to be considered gay or queer, they may not want to go a gay bar and overall have straight or hetero interests but they like it different in their sex lives," said Simpson. "Let's face it: femininity is attractive, whether it's a hetero woman, a transsexual woman, or a gay male dressed as a woman."

"Straight guys are attracted to a feminine form, whether it be transvestite, cross dresser, or transsexual. Men love hot stockings, sexy perfume, high heels, and the sensuality of men who get in drag," said Sweetie.

Some of Simpson's tranny-chasing encounters occurred during the '90s at bars like the Edelweiss on 43rd Street and Eleventh Avenue. "That was definitely a walk on the wild side, a meat-market disco and bar where men came in looking for working girl trannies." The club was shut down several times by NYPD for prostitution and drug trafficking.

Other Times Square hangouts in the '70s and '80s like The Grape Vine and The Gilded Grape were full of drag queens and their johns. Simpson said she preferred to find her own tranny chasers at clubs like the Limelight where she would meet bridge-and-tunnel club kids who styled themselves as straight. "The nightclub Mother was a big fave among guys on the prowl for trannies," she said.

While tucking it is still a valued art, these days there are fewer gender-bending surprises for straight guys when it comes to hookups, likely due to the anonymity of the Internet. Less than 10 years ago, the now chic Meatpacking District was roamed by an army of tranny hookers who plied their trade on straight, mostly married men, many of them driving in from New Jersey, to buy some hot forbidden sex. Sadly, tragic or fatal results sometimes befell drag queens that fooled tricks with their gender.

Rumi Missabu of the Cockettes, the San Francisco gender-bending group popular in the early '70s, fooled a few straight men in his time. "Unlike others in the troupe who had beards, I would try to pass as a woman and by the time the straight got me home and turned me over, it was too late." Missabu once became involved with three straight Latino brothers, two of who went to confession directly after having sex. "The image of one of the brothers pounding on the closed church door to confess haunts me to this day," he said.

Becoming a drag queen can also revitalize gay men, making them feel sexier and more attractive. Daniel Harris, author of "Diary of a Drag Queen," penned a humorous account of his experiences. When Harris hit a midlife crisis in his '40s, he found he was having trouble attracting the kind of men he used to in the past. He discovered drag, and later wrote that all he has to do is put on a lam thong and the median age of his sex partners plummets 20 or even 30 years. The men he nets as himself are not nearly as desirable as those he snags in drag.

Trans Women and Straight Men

Calpernia Sarah Addams, actress, musician, author and activist, considers herself a fully transitioned transsexual woman. Addams is known for her memoir used for the 2003 film "Soldier Girl," which dramatized her romance during the Gulf War with a soldier who was harassed and murdered for his relationship with her. She now identifies herself as a woman, and only dates heterosexual men.

"I don't have anything that gay men desire sexually, and my body is fully female now, so I have everything straight men desire sexually. My issues are about them dealing with my history," said Addams. "Straight men dating drag queens (gay boys who dress up like girls for shows) speaks toward issues of being closeted, and the overlap between gay and straight culture. In the bedroom, it is still male genitals and male genitals."

In most cultures, drag queens have had a historic appeal, and in New York City, it's no different. With the abundant ethnic minorities, there's been a rampant tranny-chasing scene, by the Latinos, Southeast Asians, and Hasidic Jews. The gay bars of Jackson Heights and Woodside could transport you to la vida loca, if that's what you want.

Simpson, drag queen philosopher extraordinaire, puts it aptly when she confides that when it comes to tranny chasing, there's something for everyone. "Whether you're a plain old drag queen, a drag clown, or an amateur with your wig askew, there's still someone out there for you," said Simpson. "It's very positive to realize there is universality. There's a fetish out there for everyone, whether they're big, small, black, Chinese, a twink, or whatever. Everybody in some way is appreciated."

Sweetie, the legendary drag queen performer who came to New York City from Detroit and took the Pyramid Club and Jackie 60 by storm, is also a wise sage when it comes to the sweet appeal of drag queens amongst heterosexual men. "Straight guys are attracted to a feminine form, whether it be transvestite, cross dresser, or transsexual. Men love hot stockings, sexy perfume, high heels, and the sensuality of men who get in drag," said Sweetie.

Apart from the physical appeal, the promise of getting lucky works like a charm. "There's less of a dance that you have to do with genetic women. A guy and a tranny have the same thing on their mind: a hot hookup," admitted Sweetie. "Guys who into that hot sexual experience will meet their match with a tranny."