You might imagine that being someone like Ashlee Dupree would be fairly glamorous – or at least exciting. Sure, you’d have to prostitute yourself in order to experience it but once you decided to step over into that world, you’d be surrounded by powerful men and piles of cash. La Perla and limos would probably be a part of your everyday life.
Now, maybe her life is exciting (I’ll admit it: I’d be pretty damn excited if I got a Post sex column). But the time I spent around a group of high-class — which really only means highly-paid — hookers tells me otherwise.
I wasn’t, as my bank account can surely attest, having them school me on how to break into their field; I was doing an investigative feature for a magazine on the thrilling lives of the women who catered to the sexual needs of the rich and famous. But the sad – and yet perhaps not terribly surprising – fact of the matter is that their lives weren’t thrilling; they were downright depressing.
This doesn’t mean I wasn’t on the receiving end of riveting gossip about their various famous and infamous men. I heard all about the predilections and desires of actors, musicians and famous-simply-for-being-famous clients (the most disturbing bit of information I gleaned, next to hearing about a guy who, um, ate, a woman’s excrement: some of these guys couldn’t perform when it came down to it so they were literally parting with up to $10,000 simply for a night of cuddling).
I found out about the billionaire heir turned Hollywood producer who gave the hookers he hired bit parts in his movie, about other producers who set up fake casting calls — complete with offices rented in Beverly Hills and attorneys brought along to make the scenarios appear legit — to try to manipulate these girls into having sex gratis via the casting couch. And about the legendary producer who required the girls he used to eat certain foods the day before they were coming over so that their “water sports” went down exactly as he wanted them to. The lead actor who only agreed to sign onto that big movie because he’d been sent two of the industry’s best girls to coax him. The world-famous TV host who tried to hire one of these girls and get a tabloid to write about it in order to squash rumors that he was gay (there was a scheduling conflict so the deal ended up not happening). The tenured Harvard professor who liked to have girls force him to eat out of a dog bowl and put burning cigarettes out on his back.
Then there were the shocking discoveries I made with my own eyes. A guy who called himself a photographer but had served time for pandering (and was well-known in the community for supplying Hollywood’s highest rollers with women) invited me over to see the many portraits he had taken of one of the world’s most beautiful women, a multi-Academy Award nominated actress, when she was just starting out.
“Okay,” I said. “But what does this prove? And how do I even know you took them?”
He shrugged. Then I noticed, among his photos, an old issue of a now-defunct women’s magazine, this beauty on its cover. I turned the page and saw that he had the photo credit.
“How did this come about?” I asked, knowing that I knew there was no way he’d ever been established enough to have been handed such a high-profile assignment. “Did she request you for the shoot in exchange for you keeping quiet about her previous career? Was it a pre-condition for her appearing in the magazine?” He only shrugged again and I finally understood that the shrug wasn’t a proclamation that he was telling the truth but an indication that he would let the photos do the talking.
Another bit of data that sent me reeling came about because I ended up getting a hold of a disc that contained the contents of a laptop which belonged to a pimp who’s now serving time in a Cuban jail. This disc contained many juicy elements, including IM conversations between the incarcerated guy and a well-established madam who’s since been busted and lists of clients and girl. While I expected to see Charlie Sheen and his ilk on there, instead I was privy to names I was unfamiliar with but which were all highly Google-able: the biggest car dealer in a Midwestern city, for example, and successful attorneys and bankers from across the country. Still, the most interesting piece of information was a list of his girls — for smack in the middle of the porn stars, Penthouse Pets and Playmates was the name of an actress who still works regularly and whose romantic travails are considered relevant enough to be covered in the tabloids. If she was willing to delve into such side work, I could only imagine how much the Cuban jail dwelling guy had been able to get her.
But these girls looked a lot different up close than they did in documents. Once I was sitting across the table from them, looking into their eyes, I didn’t see seductresses who, with their bodies, wielded power over the world’s elite. I saw fear, confusion, a ridiculous amount of plastic surgery, and a strong desire to do something — anything — else. I saw people who spent outrageously, at least in part to dispose of income they were ashamed to have earned, and who would thus have nothing to show once their years of hard living caught up to them and their looks were gone. I saw women blotting themselves out with chemicals and constantly chasing the next thing so they wouldn’t have to examine too closely what they were doing.
It wasn’t only the men they needed to forget about, either. I heard tales of madams that treated the girls far worse than any client ever could. One in particular would send girls on jobs to places like Turkey and then shut off her phone so that if they ran into trouble, they’d have no one to call. Girls would have to literally beg her for the money they were owed (one told me about having to “send someone” — a guy you didn’t want to mess with — to collect) and deal with a series of lies, shady excuses and threats. “If you were unavailable when she wanted you, she’d threaten to tell your boyfriend that you were a hooker,” a girl told me over the phone.
The more I found out about these girls, the more poignant their struggles became. One of them told me that when she was little, she wanted to be the ice cream man so that she could “give ice cream to everybody.” (The sought-after delicacy she doles out now is a tad more NC-17 and she wouldn’t dream of doing it gratis.) She’d had so much plastic surgery — three nose jobs and six breast surgeries as well as chin, nose and under-the-nose implants — that many surgeons refused to work with her. And yet she still wasn’t satisfied. “I’ll look in the mirror still and go, ‘Argh,'” she confessed. “I wonder why people like me — and then I realize it must be my personality.” She thought continuing to improve her looks was the way to heal what ailed her but going to the gym three times a day and getting in the best physical shape of her life didn’t prevent her from spending months sitting in front of the mirror and crying.
Perhaps none of this is surprising, considering the fact that this woman had oral sex at 12, lost her virginity at 14, and had been married four times by the time she was 34. Still, how she got to that place isn’t clear. Her family sounded remarkably normal — her sister was a schoolteacher and her step-dad a pastry chef! For the most part, however, she didn’t seem terribly interested in finding out; instead, she just tuned reality out with Xanax.
Another girl — one who’d long since moved on to another profession — told me that you can never really escape the career even after you quit. She recalled running into a girl she used to do jobs with at brunch one day. “She was with her husband and you could tell they were quite affluent,” the woman I interviewed told me. “It was clear from the way she said hi to me that she hadn’t told him about her past.” She sighed. “So many of these girls stop but then have marriages that are analogous to prostitution. Most of them never really leave it, no matter what they tell themselves.”
Anna David is the author of Bought a novel which details the lives of kept women. You can learn more about her work and upcoming projects here.