Now he was dating a tranny, and talking about it as casually as if he’d recently begun incorporating onions in his scrambled eggs. He went on and on about how she was “totally fucking hot, man. Probably one of the hottest transsexuals in the world; it’s probably between her and some Thai boy.”

On a recent evening, I met the woman in question, the beautiful Jamie Clayton, at a bar in the Lower East Side. She is 5-foot-10, has long, wavy red hair, porcelain skin and big blue eyes. She sat upright in her stool, long bare legs draped on top of each other exposing upper reaches of thigh under a gray cloth miniskirt.

Now 30 and a makeup artist, she grew up as a boy in San Diego. Her father, Howard, who recently passed away, was a criminal defense attorney. Her mother, Shelley, is an event planner. Jamie always knew she was different. She used to stare at the hideous beast between her legs and wish it gone. She hardly ever touched it; never once out of pleasure.

I asked her if she was gay in high school.

“I guess,” she said. “I was gay by default. I was always just so feminine. I don’t think anyone who ever met me would describe me as a man.”

In junior high, she won the top awards for math and science, but the prospect of high school terrified her. She wound up at a magnet school for kids who’d been thrown out of other schools. She said that while her father might not have understood her, they got on well because she never got in trouble and brought home excellent grades. She wanted to be a makeup artist. Shortly after high school, it dawned on her that she should move to New York.

“I just woke up and something just clicked in my brain,” she said. “And I was like, ‘I need to be in New York; New York is fabulous.’”

It wasn’t until she got to New York that she realized a sex change was an option. She would go to Limelight and other kids would ask her if she had started taking hormones.

“I was like, ‘What’s that?!’ And that was that.”

The day she got health insurance, she began cold-calling doctors and asking them if they had experience working with transgender patients. No, no, no, no. Finally a doctor on the Upper West Side said yes. But it took another five years before she could save the money. All along she was taking the hormones.

“There was an almost instant calming effect that sort of like washed over me,” she said. “After being on them for a couple of months, they made me incredibly emotional at times. I’d find myself acting a little cuckoo, and then I’d realize, ‘Oh, my body’s sort of going through a change right now.’”

After a subtle boob job, Jamie was soon attracting the men she was looking for: What she would call straight men who have a taste for transsexuals and choose to ignore the extra baggage.

She met a photographer at a club; they dated for two and a half years. He said he loved her; they gave it a real go. He finally said he couldn’t deal. Now he’s married, has kids.

Then came a magazine writer. They had been dating a couple months, just having fun, so Jamie thought. Then one day out of nowhere:

“I’ll never forget it; I was 23 or 24,” she said. “I remember a very specific moment when we were literally in the middle of having sex and he asked me if I was in love with him. I had just broken up with [the photographer] shortly before, and I was like, ‘Why are you asking me that right now?’ And he said he knew that I liked him a lot, and that we got along really well, and he thought I was falling in love with him. So I said to him, ‘Are you in love with me?’ And his response was, ‘I can’t be in love with you.’ And I literally got up and put my clothes on and left and never spoke to him again.

“It was in that moment that I learned that I would never put myself in a situation, or that I would try incredibly hard to avoid situations where—because I thought that was really incredibly shitty for someone to say something like that: ‘Oh, I can’t be in love with you.’ Why? Because I’m different, because I’m a freak? Because your parents wouldn’t like it, because your friends wouldn’t like it? It hurt a lot. It sucked.”

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