The Second Most Beautiful Girl in New York

A while back, a friend of mine boasted that he was spending time with a hot transsexual. Now, my friend—let’s

A while back, a friend of mine boasted that he was spending time with a hot transsexual. Now, my friend—let’s call him Ryan—is quite the ladies’ man. Despite his perplexing androgynous style—tight jeans, guy-liner, the occasional wig—Ryan always shows up with a gorgeous young woman on his arm.

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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.”

The Second Most Beautiful Girl in New York