Angelina Jolie by David lachapelle

Cathryn Berarovich is something of a renaissance sex worker; she was until recently employed as a stripper but has held numerous interesting jobs in the industry (and she’s currently an excellent columnist on this very website). Each week, she shares her stories in Harlotry.

The relationships all sex workers, but especially prostitutes, have with their clients and the relationships clients have with their favorite sex workers are strange and many-layered. On the surface, there is the business arrangement: the client pays the whore to fuck him (or her, I guess, though women don’t seem to buy sex). At the moment the money is exchanged, everyone knows what’s going on and from there on out the prostitute has to help the client forget there was ever a transaction involved.

Nobody wants to pay for sex. Sure, there is the odd guy who gets off on the very act of paying, who prefers to pay, either because he enjoys the humiliation, or because he enjoys the power of getting something he wants by an action so simple as throwing a few pieces of paper at his desires, but even those men don’t usually want to see the payment as an intrinsic part of the exchange. They still want to believe they’d achieve the same result if money were subtracted entirely from the equation.

Back when I was a whore, I browsed the m4w erotic services section of Craigslist as frequently as I posted my own advertisements. Naturally there were a few gigolo hopefuls on there, but mostly it was men advertising for prostitutes. None of them actually said they wanted prostitutes, though. There were no “Wanted: Jovial Trollop” headlines. They all wanted a “non-pro,” a “needy student,” or a girl next door with bills to pay. I’d imagine that most of the women responding to their advertisements were, like me, baby hookers who hadn’t yet figured out how to appear polished and expensive and were therefore somehow more enticing to the group of men who pretend that buying sex is different or somehow better if the girl doesn’t sell it regularly.

(Headline photo of Angelina Jolie by David LaChapelle)

Even when my time as a whore was stretching into its sixth month and I had the ropes about as well figured out as any bratty eighteen year old could hope, the phrase “I haven’t been doing this very long” or “I only just started” was my best friend. Most of the men who hired prostitutes on Craigslist believed that anyone who’d been working for more than a few months must be jaded and greedy. Never mind that I’d been jaded since I was fourteen and greedy for even longer, pretending to be a clueless newbie made me nonthreatening and made it easier to believe I was genuinely attracted to my clients.

I’ve written before about how most patrons of sex workers just want to be wanted for a little while. An overwhelming number of the men who responded to my advertisements on Craigslist included pictures or at least physical descriptions of themselves, sometimes both. The photographs never matched the physical descriptions and the photographs were often far too old to be accurate but the message was clear, “please find me attractive,” they said, “please want me,” “You’d fuck me for free, right?” I had no interest in doing any such thing, but I was certainly willing to pretend.

Perhaps the most obvious instance of clients wanting to elicit some genuine sexual response in me, their prostitute, was their insistence on getting me off. I’ve mentioned this before, but never really gone into it in depth. Almost every client I ever saw, though, wanted me to have at least one orgasm during the course of our appointment, they all seemed to want to make me come as much as I didn’t want to come, and they tried everything. They brought warming lubricants, sometimes they asked me to bring a vibrator for them to use on me, they tried going down on me, and when all else failed they simply requested or demanded that I come for them.

“Don’t fake it,” they almost always said, “I can tell when a woman’s faking.”

They could never tell.

I suppose I was lucky, both that I never encountered a truly sexually skilled client, and also that they always brought the wrong paraphernalia. Warming lubricant just reminds me of that amazing warming face wash Bioré used to make; vibrators, even Hitachi Magic Wands tickle me, and not in a sexual way; receiving oral sex bores me at best and disgusts me at worst.

One of my co-workers at the fetish house I’m currently employed at always says “[the clients] are here for you.” I’m not sure there is a channel of the sex industry where this is truer than in prostitution. In fetish work, so many clients are ashamed of their predilections and just want to know that the weird stuff which turns them on turns someone else on too, while in prostitution most guys just want to have a reasonable facsimile of a normal, unpaid sexual encounter. They want to get a girl off and feel good about it as much as they want to fuck a girl who normally would laugh them out of town, were they to approach her in real life.

The problem, though, is that no matter how good a whore is at her job, the client always knows, somewhere in his head, that he’s paying for this woman’s time and renting access to her body. The client also knows, deep down, that even if she claims she’s never done anything “like this” before, she probably has and she’s probably done it with a bunch of other guys. It’s hard to truly believe in a whore’s orgasm, which is, I think, part of why all my clients always tried so hard to get me off.

It was sweet, really, how clueless yet determined they were. Every time I started to build my moans into a masterpiece of artificial bliss, they would stop what they were doing, scrutinizing my face to see if it really looked like I was coming. I hoped they’d never pull such a trick with a civilian woman, and would gasp “no, don’t stop!” or something similar, but–considering the techniques some of these men employed to make this whore come–I wonder if I was doing more harm than good.

I imagined how a civilian woman would feel if, for example, a man told her he was going to give her the orgasm of her life and them proceeded to limply tongue her vaginal opening. I wondered if that civilian woman would be the kind of lady to sit up, speak up, tell the guy he was doing it wrong, show him what to do, and even draw a diagram if necessary. I doubted that any of the ladies in my clients’ dating pools were likely to do any such thing and I worried I was doing the female population of Chicago a disservice with my dedicated, Oscar-worthy performances.

I always comforted myself with the reminder that while a part of my job did involve teaching and guiding, it was more important to ensure that my client enjoyed himself. It wouldn’t have been fair of me to turn their sessions into an interactive class on oral sex, and I was probably the wrong woman to teach such a class anyway. And so I faked it. I faked it hard and heavily, and to such an extent that anyone who hadn’t actually seen me come could never tell the difference.

My performances always paid off. Their faces would light up. “Did you just come?” they’d ask. I’d make my affirmative reply as sultry as possible, and suddenly they’d break the silence about my other clients. “None of those other guys have ever gotten you off, I bet,” they’d ask, halfway daring me to say, “oh totally, I get of at work all the time. You’re but the latest of many, buster.” I never said that–nor did I tell them that they wouldn’t know a clitoris if it danced naked in front of them, putting on a light show and waving semaphore flags at the same time. No, I always told my clients that they were the only one to ever get me off, and if they became regulars I continued the fiction, “You’re my favorite client, I mean, I almost feel like I should be paying you, you always make me come so hard.”

They were always so pleased with themselves. I always assumed it was because they believed they had stirred the cold and over-welcoming bosom of a whore, but thinking about it now there might be more to it than that. It’s very possible these guys had literally never actually gotten a girl off before, and who knows how good their previous partners had been at faking it. They could even, like I did in my personal life, hold a strict, no-faking-ever policy. If that was the case, it’s understandable these guys would feel good about themselves and I really can’t blame them.

I remain conflicted about whether I handled the orgasm situation well. My clients could probably have used a little gentle suggestion here or there, but overall there was very little I could do to improve their techniques. I’m pretty adamantly against orgasm faking, as it does no one any favors, but in the context of work sex I think it’s not only okay, but actually not remotely a bad idea. After all, the clients are ultimately there for you, possibly even more than they’re there for themselves.