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Sex

A Female Sex Worker Compares Notes with a Gigolo

I hired a male counterpart to see what the other side of the transaction looks like.
February 18, 2015, 6:45pm
Photo via Flickr user Jenna Jaafri

My roommate recently sent me the link to Cowboys4Angels, a male escort site for women.

"We should get drunk some night and call these guys!"

My roommate and I are both escorts. We've talked about the importance of maintaining a proper ratio of sex that we enjoy to work—it's a mental health issue. My dance card stays full enough to make paying for it questionable, but I will do absurd things in the name of female solidarity, which is why I'm scheduled with Tom for seven tonight.

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I'm tired. I had an overnight the day before with a bright and extraordinarily talkative lawyer who overpaid and ordered me a computer at 2 AM, and it's out of that stack that I'm "donating" $650 for two hours with this kid who looks like he's in a boy band.

My friend looks at my loose plaid shirt and jeans. "Really? That's what you're wearing?"

"Shut up! I'm paying HIM."

The booking process answered both of my questions: How do sites like these weed out the women who are having a laugh, and how do they screen for law enforcement? A deposit, of course. They took my credit card, full name, address, the works. Escorts operate under the assumption that vice cops can't use credit cards for busts, don't use their own names, and are legally not allowed to impersonate people. Except for high-level federal cases, I've never heard of the credit card companies issuing false accounts.

His first six months were non-stop: weekends in San Francisco, overnights in New York, a rush of cash and molly and no sleep.

I wanted one hour (small talk and sex easily fit in an hour, surprisingly) but unless I sprang for two I would have to see my companion in public, for a "meet and greet." Getting "personable" at my place takes a minimum of two. ("Personable" is the most vanilla euphemism I have ever heard in this context, and I find it charming.)

I asked for someone tall and funny. Someone in the six-foot-four range? It feels good to flex my height fetish in an appropriate context. Except the booker didn't have anyone that tall. He recommended Trent, who apparently has a native-New-Yorker sense of humor. On the site Trent is shiny and convex and looks like the kind of guy who was mean to me in high school. No. I accepted the booker's next recommendation, though: Tom is chiseled and beautiful enough to be in a Taylor Swift video. His bio on the site has only one picture, in which he's wearing what looks like a jean blazer and a significant pout. He may not be my type, but I should trust the professionals.

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The website looks like it was designed in 2002. In fact, I designed an escort site in 2002, and next to it Cowboys4Angels looks like someone threw Tinker Toys and Ken dolls on a quilted bedspread. The featured men are all in Las Vegas, where they are the subject of a reality series on Showtime called Gigolos. They hew to the stereotype: lots of flexing, smoldering at the camera, abs you could grate cheese on. One has hair almost to the small of his back. Another is leathery and wears pastel shirts to match his frosted tips. It is assumed that jacked and complimentary equals automatic lady boner.

The escorts on Gigolos are shot full face, no blurring or backlighting, and bizarrely, so are most of the clients. The old chestnut that money exchanged is for time and companionship only and that anything else that occurs is between two consenting adults of legal age seems stretched particularly thin here. Perhaps legality is the concern of a back office compliance department. Or perhaps because of the gender switch-up, it's assumed that any sex is utterly voluntary.

There's a good bit of earnest talking to the camera about female desire and no one having time to date. It's excellent TV: the perfect ratio of erotic fascination and repulsion.

I have always felt contempt for men who want me to pretend to be turned on when I couldn't possibly be, but from this side I get it.

On the day of the appointment, as I scurry around getting ready, I develop serious nerves. I'm using the apartment I keep on the Upper East Side for work. It's a box with a bed, a nightstand, and a tiny Ikea couch. Other than those items of furniture, it contains nothing but condoms and sex paraphernalia and about 40 changes of sheets and towels. It will not pass muster as a place where someone actually lives, and I don't want to scare him, make him wonder if he's about to be busted. I'm also worried about the exact sort of nebulous emotional crap that my ad copy is designed to assuage, which gives me a new appreciation for my clients' fears. My work persona is "friendly, enthusiastic, intoxicating," precisely because I worry that when Tom shows, he will be sullen or dull—that he will look around the room with resignation and then ask me where I want him to stick it. I have always felt contempt for men who want me to pretend to be turned on when I couldn't possibly be, but from this side I get it. I want this kid to be a good liar.

I'm more critical of my appearance than I am when I am the product. My hair could be shinier. My lips are a mite dry. I hate it when men rock up flaking everywhere. It's hard enough to seem turned on by Uncle Fester without having to stare at literal disintegration. Are my eyebrows unkempt? Is he going to be grossed out by that? I do what I can. As I look at myself and the bare room and think about the fact that I changed the time twice because of work, I realize something: I am a bad client. This actually carries with it some shame. Paying for sex is hard, guys.

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At seven on the nose, I got a text from the handler: Hello hun!!! Tom will be ringing the bell in 5 min. . . I hope you are ready for some fun.

I hadn't realized it was possible for me to be more eeked out. It was possible. I feel vulnerable, about to be judged. I arrange his hundreds on the nightstand and answer the door.

Not Tom. Photo via Flickr user torbakhopper

Tom is indeed the guy in the photo. He doesn't have a hint of poutiness in person. Big brown doe eyes and perfect teeth, the sort of ethereal beauty that probably gets a lot of attention from men and 15-year-old girls. He's wearing a silk crew neck sweater and slim pants, and looks impossibly young for 25. With my heels, we are the same height. I offer him bourbon and he takes it. I don't know if I want to get him drunk enough to fuck or vice versa.

It takes me 30 seconds to confess I'm writing a story, which understandably puts him off. New people are already an unknown, and now he has to be the sex worker under a microscope. I hurry to tell him I am an escort myself. He looks me over more carefully, and then sits back into the couch, and we talk shop.

Tom grew up in a small town and moved to New York when he was 21 to model. He's done some runway but more e-commerce. He started working for Cowboys4Angels a year ago. His first six months were non-stop: weekends in San Francisco, overnights in New York, a rush of cash and molly and no sleep. The last few months have been slower. He's not sure why, but it's worrisome, as he moved from Inwood to a more expensive apartment downtown.

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"I made a lot of money, but it goes quick," he says. His modeling agent called him this morning and said that she'd seen him on the site. That has him spooked. He's asked to have his photos taken down and his profile changed to private, which will translate to no new clients.

He is quietly clear on one point: Women absolutely do pay for sex. There aren't as many of them as men, possibly, but there are enough for him to make a comfortable living. Almost all his clients have been in shape. I certainly can't say the same. I ask whether he thinks that women who aren't fit are too ashamed to see him. It's impossible to say.

He has a client with an iron pre-nup who wants to leave her husband for him, which he has explicitly said is a terrible idea. We agree: People are weird.

I wonder about the legal troubles and he says that his interview process was extensive. He's been instructed never to state anything too definitively, and trails off. I nod. When the crime is not an action but an intent, watching what you say becomes second nature. I ask him if he thinks there's a stigma against male escorts and he's careful to say that there's more of a stigma for women but it's still there. It's a perceptive statement, but I realize he's thinking about my reaction to everything before he says it, that this whole conversation is tailored to me. I do the same thing on the job. Being on the receiving end is amazing. It feels like I'm connecting with someone, and knowing that it's financially motivated doesn't change that.

I ask him for stories, and they are far crazier than my crazy stories. A Middle Eastern consul hired one of his friends in Florida and gave him access to her bank account, said she was in love. The friend pulled 50K in two weeks, "before she got mad at him." Another story involves a mountain of blow and four Saudi princesses. He goes regularly to San Francisco to see a Silicon Valley hot shot, eats at great restaurants, weekends in posh resorts. I'm no Mentat, but I think he's telling the truth. How many of his appointments involve sex? "Oh, all of them," he says. I'm surprised. Not even all of MY appointments involve sex.

We relax a little and I pour him more alcohol. Generally when I'm on this couch, I'm trying to calibrate my distaste or lack thereof for what is about to happen, and gauging the conversation. Clients want me to make the first move, but they want me to do so precisely when they think the moment is right, so I watch for the signs that they're ready to get on with it. Tom isn't making any of them, and I don't think I am either.

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The bourbon hits us both decently hard. I get the feeling Tom watches his figure, and I haven't eaten yet either. Our stories get less Pollyannaish. He tells me about a woman who hired him for months, developed feelings, and then accused him of moral depravity when they weren't returned. He has a client with an iron pre-nup who wants to leave her husband for him, which he has explicitly said is a terrible idea. We agree: People are weird.

"That's what escorting gets you, more than anything else. It's disorienting. It's great, I've never made so much money and traveled and everything, but…" He stares at the bed.

I chime in, "You're in the middle of so many people's emotional storms."

"Yeah," he says.

I look at his delicate profile and try to imagine scooting closer and putting my mouth on his. None of it computes. He's said that I'm hot, better looking than the normal clients—really attractive—but that almost all the women he's seen have been attractive. He's also said I seem smart, and that sometimes he has to do some mental gymnastics to help with vascular flow, but he certainly wouldn't have to in my case, cause of the hotness.

I imagine the shovelfuls of compliments generated by this sweet kid. The thought of him gutting it out with me is terrible. Do I feel so strongly about his volition because that's the normal way to feel or because I know what it's like on the other end? I can't tell. I don't want to have sex with him; what I really want is for neither of us to be uncomfortable. At any rate, when he sweetly raises his chin towards the bed, I say maybe later. I fancy he seems relieved.

The two hours come and go. At 8:45, I say I have to take a call, we hug, and he leaves. I am not usually such a wuss about sex, and it's not because I remembered my respectability at the final hour. It just seemed wrong.

I have a ten o'clock booking and I carry it off with no trouble at all.

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