Nightlife » Sex

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

by Gerry Visco
Thursday Jun 2, 2011

Drag queens have been attracting straight men to the bedroom (and more risqué 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 outré 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."

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 lamé 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.

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  • , 2011-06-02 09:20:51

    Clearly defines the difference between a drag queen and a Transsexual woman. Drag queens are about fantasy. They are effeminate gay men in costume. They put on a costume for the night and take it off at the end of the night. Since gay men are attracted to masculinity, drag queens are forced to look for trannie chasers or straight guys with a fantasy(typically drunk) to have sex with. Sadly, a relationship rarely occurs because the fantasy disappears as soon as sex is over and the lights come on. Transsexual women live 24/7 as a woman and they identify as a woman, not as a gay man. They are not into tricking men for sex. Their motive is for transitioning is to live authentically and it is not about living to satisfy a man’s sexual fantasy. While a drag queen can remove her costume at any time and go back to living as a guy, a transsexual woman must deal with living in a world that is often unkind to people who are gender variant. They deal with discrmination in employment, housing, and piublic accomodation. Dating, family life, and marriage can be very difficult issues. Can you understand why transsexual women do not want to be identified or confused with drag queens? They are as different as apples and oranges, or more accurately as different as women and gay men.

  • , 2011-06-02 10:12:53

    Calpernia Addams hit the nail on the head when describing the difference between men who are trannie chaser or "straight" men with a sexual fetish for drag queens and cross dressers. It’s about closeted gay or bisexual men fulfilling a sexual need. They are turned on by a penis, the bigger the better, but the fact that it’s on someone appearing female somehow psychologically makes them feel it’s OK and doesn’t make them think they are homosexual; however,believe me that it’s ALL about the penis. I really think the terminology of gay. bi, straight is outdated. Sexuality is often fluid and is much less likely to be confined to those rigid categories. As a post-operative transsexual woman, I have nothing that these trannie chasers want. I only date straight men because my anatomy is female. My presentation and identity is female 24/7. A guy needs to be open minded to understand my history but basically no gay man is going to be attracxted to me so that fear should be removed from the equation. Unfortunately most straight guys still can’t escape the stigma associated with transsexuality that the cultural messages have taught which makes finding a relationship hard. Will a guy be secure enough in their own sexuality to bring me home to meet the parents and family and his buddies? Usually not.

  • , 2011-06-02 11:19:39

    I do not regret having Gender Reassignment surgery regardless of whether I end up in a relationship with a man or not. Being Trans is not a choice. The only choice is to live honestly and try to correct the biological error or to continue living as others want you to. The relationships that I see working out for post-op Transwomen are often lesbian relationships with women or other transwomen. I believe this is because women have far less rigid cultural sexual and gender roles than men. There seems to be much less social stigma for two women to be together than there is for two guys. Also, I’ve noticed that Transwomen who are professional with high salary careers tend to get paired up. Obviously, the partner’s attraction to the rich lifestyle overrides the stigma that one might incur from being with a Trans person. Until the culture becomes more tolerant, I doubt this is going to change. The obvious message here is that someone doesn’t transition to find a man because odds are you won’t. Still the satisfaction of living honestly is worth that price if you ask me.

  • , 2011-06-02 11:49:21

    To make things even more complicate we should discuss Crossdressers, another part of the Transgender umbrella term. Not all crossdressers are the same. From my personal experience some CDs say they identify men but have a feminine side that needs to be expressed periodically. That can range in need for expression from daily to on rare occassions. I suppose you could say they are "bi-gender" if you had to put a label on it. Next there are CDs who are probably transsexuals and primarily identify as female but they are often married with kids and do not choose to transition because they do not want to lose they life they have. They privately live a double life to keep their crossdressing a secret. J. Edgar Hoover is a famous cross dresser in his secret private life. They correctly fear losing their job and family if they were ever "outed". Their wife may know but usually chooses not to participate. Some wives will go out with their crossdressing husband but it is often to control the situation for fear their husband may hook up with another guy or CD. Then their are a few wives that go out with their husband looking for a third person or couple for sex. Next are guys who totally identify as male but have a sexual fetish for womens’ clothes, usually lingerie. These are often the so called "trannie chasers". In short, there are a lot of different types of crossdressers and CD relationships. Drag quuens, crossdressers, and transsexuals are each very different subsets of the diverse Transgender community.

  • , 2011-10-23 14:59:23

    Calpernia is wrong. Just because someone has a penis does not make them a man or male. A pre- or non-op transwoman is a woman. Drag queens who are not transgender (as opposed to someone like Calpernia herself back in the day or Sara Andrews today) may still attract straight or bisexual guys because straight/bisexual like the appearance of a woman. Now, if they actually have any contact is another story but I think this quote sums it up best "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." I celebrate women (gg or tg), crossdressers and drag queens.

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