The Second Most Beautiful Girl in New York

April 16, 2003, is another day she’ll never forget. Dr. Toby Meltzer of Scottsdale, Ariz., is known across the globe as the man with the steady hand. A mere six hours on the operating table and Jamie was finally the woman she’d always wanted to be. For a cool $16,000, the good doctor had worked his magic, so that what’s left looks pretty good and works. She says she can even have vaginal orgasms. “Dr. Meltzer is known for that, and that’s one of the reasons I wanted to go to him. That’s why he’s so expensive,” she said.

Now she exercises four times a week, drinks an insane amount of water, washes her hair only twice a week, avoids the sun like the plague, always wears heels and plucks her full, caterpillarlike eyebrows twice weekly, but warns “don’t overpluck!” But she says men seem most attracted to her inner self-confidence. She says that her surgery, which with tweaking and touch-ups has cost her roughly $50,000, has gone a long way toward getting her to the place she’s in now.

“I love who I am,” she said, adding that she gets hit on or asked out about five times a week.

Professionally, she’s branching out into special-effects makeup: She recently worked on a team that created the blood and guts for indie flick Cottonmouth. In part, she says she has this fair city to thank.

“Transitioning in New York is like paradise,” she said. “Yes, you deal with bullshit. You deal with people making comments”—that’s called getting “spooked”—“but I can’t imagine living anywhere else going through what I went through. Because I’d say for every person that would make a nasty comment, there are 10 people that will tell you that you’re gorgeous and that they love you and that you’re fierce.”

Dating can be risky. She’s heard the horror stories, like the story about the transsexual who went back to a hotel room with a guy she met at a club and she didn’t tell him and was like, “Oh, I thought he knew,” and he pulled a gun on her.

Jamie always tells guys on the first date. “I was not born a woman,” is the line she’s settled on.

She’s noticed a funny thing since making her transformation. Because of her looks—she calls herself a “top-shelf” transsexual—she gets hit on by all sorts, not just tranny-chasers.

She has a type—she likes confident, sexy, creative guys. But she’s found that these men, more so even than the men she dated pre-op, are frequently unable to live up to the swaggering open-mindedness they claim to possess.

“If I have a connection with someone, I’d like to think that they’d be able to respect that connection enough and respect themselves enough to not care about my past—that they would want to see what happens between us,” she said. “But I have had plenty of instances where guys don’t even give it a chance, or maybe they do give it a bit of a chance, and then they sort of drop off the face of the earth because it freaks them out.”

She counts her nine-month fling with my friend Ryan as her most meaningful post-op relationship.

“We had chemistry right away. She was mysterious,” Ryan said. “Then a friend of a friend hipped me to what her situation was. And I thought, well, she was so hot that it didn’t deter me in the least. It excited me, it intrigued me. Mostly I thought, ‘Wow, I respect this person.’ Usually when you’re attracted to a girl, you don’t necessarily respect her. But when I found out that she had done that and gone through it, and looks amazing, I immediately thought, ‘Wow, this sounds like someone who’s really fucking cool and worth knowing, in addition to being really hot.’”

He noted that he falls into a certain category of New York guy. “I think it goes back to the 1970s, to David Bowie. It’s kind of like a glam kind of idea,” he said. “You have these artists that are these kind of sexy guys, but they’re really identified as straight. They tend to be artists or nightlife people who kind of flourish in the sexually ambiguous New York underground. Guys who wear guy-liner and tight clothing and are aesthetically minded. They hang out at parties like Trash and NC-17, which is the basement of Lit on Thursdays.”

Sexually speaking, he said, Jamie “rocked my world. She was just like any other hot chick, man.”

For her part, Jamie said the relationship didn’t last because Ryan was emotionally unavailable. Ryan texted me the other night that these days he is “fucking a married cougar.”

smorgan@observer.com

The Second Most Beautiful Girl in New York