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Doll Dishes on Oswalds: "I used to be the token gay on the sidelines, now I'm in the game and coming full circle."

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Introducing Doll, Racked's first transgender guest blogger. Always secretly wishing he'd been born a Barbie, Doll was a young army brat who grew up and became a citizen of the world. After landing in Manhattan, he became a New York fashion insider, working in a high-powered industry position, living a life worthy of a feature film.

After mysteriously vanishing from the scene, Doll recently resurfaced and has embarked on a new roller-coaster ride of a journey. Follow his transformation, week by week, right here on Racked.

"Not all Oswalds look like Penguins."

"Always have him wanting more. You got it?"Cher in Clueless

Doll: An "Oswald" is what the Barbies call our ever-changing night-on-the-town benefactors. The name comes from one night at The Plaza with a stout older gentleman who was a dead ringer for Oswald Cobblepot—a.k.a. The Penguin from the Batman movies.

Not all Oswalds look like Penguins, but, at the end of the day, all Oswalds want the same thing: The company of beautiful women.

Manhattan is an ocean filled with Oswalds of all shapes and sizes—all willing and able to foot the evening's bill. As a Doll (in training), I've learned exactly how to rope in an Oswald—by watching my Barbies, especially Cher.

Always make them come to you.

According to Cher—the expert—it takes more than just looking pretty. A girl must use her feminine wiles and subdued flirtation to secure an evening's sponsorship. Strategic positioning—or, as I call it, prime real-estate—and good lighting are essentials. I've seen the Barbie’s do it a million times and I've taken mental notes.

The Barbies will position themselves within an Oswald's earshot and use calculated eye contact and body language to obtain the first glance. Cher also advocates speaking loudly about a specific topic that will peak his interest—this topic changes with age and appearance of said, targeted Oswald. If that is still not working, another extremely effective strategy is the use of bathroom breaks. The female figure always looks better standing and this can be the essential deal-sealer in beguiling your evening's benefactor.

My first experience securing an Oswald as a Doll-in-transition happened accidentally. The other day, Cher and I were at The Plaza, as usual, having a drink when we roped in a pack of young Northern European financiers. They immediately addressed me as a "she," and treated me like the girl I am inside.

Outsiders are finally seeing me as I see myself and it's exhilarating.

The Oswalds paid for our cocktails and invited us to join them at Bagatelle. The next night at Eurotrash-tastic Bistro Bagatelle—yes I'm talking about that d-bag Meatpacking eatery that has a doorman, guest list, and DJ to complete its club-like atmosphere—I pranced in channeling Agyness Deyn's androgynous-chic. Perched on my chair, I sipped my bubbly and decorated our table.

I used to be the token gay on the sidelines watching the Barbies and the Oswalds, now I'm in the game and coming full circle.

Next week: The importance of religious discipline in reaching the feminine ideal.

Until then, Au Revoir.
· Read all Rated XX [Racked]