Hooking

Pic by Sally Mann

People often ask me, both in interviews and during casual conversation, if I sleep with people for money. Or sometimes they skip the asking part and just assume that I do, or at least that I have. The truth is, I have been paid for sex only once, and it was by accident, and the one time I actually tried to make it happen, I failed.

Back when I was squatting in London, during the much-blogged-about “Squallyoaks” period of my life, I lived for a while with a girl named Lydia whose life’s ambition was to become a whore. I found this very amusing. I was always trying to explain to her that prostitution is rarely a profession one aspires toward, but more often one that is fallen into, likely out of desperation. (I of course understand that this is not always the case–I’m aware of this random thing called feminism–and that many people enjoy making money in exchange for sex, but I’m generalizing.) Still, Lydia, in all of her glorious airheadedness, somehow managed to constantly fail in her attempts to whore herself out. At first, it was clear she was aiming too high on the high-class escort ladder (her daily attire was far more True Romance than Belle de Jour). Other times she’d ask for too much money, or make crazy demands of potential first time clients (“I’ll only fuck on red satin sheets”), or she’d make appointments and then accidentally go into a K-hole and not show up. The list goes on. I constantly made fun of her for this, to her annoyance. However, after my sole attempt to be a hooker turned out to be a disaster, I suddenly felt bad for having been such a snob, and, whatever… unsupportive. “I’m so sorry Lydia,” I wrote on her FB wall in the hours after my failure. “Turns out being a whore is a lot harder than I originally thought. xoxo”

But I’ll start with the story about the time that I was paid for sex, accidentally. I’ve actually already written a detailed post about this, but I’ll paraphrase it for you. It was just a few days after I moved to New York, about two and a half years ago now, and out of a combination of loneliness, horniness, drunkenness and desperation, I put up an ad up on the ‘casual encounters’ section of Craigslist. Out of all of the potential, bottom-of-the-barrel suitors who responded to my ad, the most appealing by far was a 32 year old Hasidic Jew named Isaac who described himself as “tall, slender and clean.” To make a long story short, Isaac came cover, came in my mouth, and then asked, “How much?” Me, being the innocent and sexually naive person that I am, asked, “How much what?” He responded to this with a puzzled glance, then said, “How much money?”

Clearly, he thought I was a prostitute, but I wholeheartedly had not considered this until the moment he said the word “money.” I guess I hadn’t thought about whether or not it would be unusual for 25 year old middle-class white girl to be causally trolling Craigslist at 4am, searching for some honest, no-strings attached sex with a creepy, married, Orthodox stranger. As I hadn’t planned on how much money I would ask for, since I hadn’t planned on asking at all, when the question was raised I panicked and said, “Uh… $50.” After I said it I instantly realized, upon seeing the delight in his eyes, that I should have asked for way more. But whatev, it’s 50 bucks more than I’d ever been paid for sex before.

The time I tried to be a hooker and failed happened about three months before this, while I was living in London. I was sleeping with this older guy, a 45 year old photographer named Elliott. He beat my up and stuff, like sexually. It was cool. I suppose, in hindsight, he was the person who first introduced me to S&M. The sex wasn’t that intense, but there was definitely the occasional ball-gag and nipple clamp involved. What he liked most was to mentally dominate me, and to “punish” me if I ever disobeyed him. Like this one time he invited me over his house, and I showed up 45 minutes late, so he refused to fuck me and instead just tied me to his dresser and jerked-off onto my face. Stuff like that. And he loved making me beg for sex, it was his favorite thing ever. I like it too, although I pretended I didn’t.

So anyway, I was dating Elliott. Or we weren’t really dating, technically, we were just sleeping together. I asked him to be my boyfriend like 500 times but he always said no. But whatever, that’s not the point. The point is, a few months into the relationship he told me that he was going to be my pimp, and pimp me out to all of his friends. He didn’t ask me, he told me. I obliged, because it sounded kind of hot, and because Elliot was really handsome and well dressed and rich–“old money” British family–so I assumed all his friends would be handsome and well dressed and rich too. Score!

I was really excited about my first hooker appointment. Elliott explained how the whole thing would go down to me over the phone: “He’s my old friend, a total gentlemen,” Elliott said. “He has rented you for one hour. Show up to his apartment at 8pm. He can do whatever he wants to you, but no anal.” I said alright, sounds glamorous.

So I showed up, and just as I had hoped, the guy was really good looking. Late thirties, tall, sandy blond hair, total prep school vibes. We talked for about two minutes, during which I made boring conversation, asking him how he knew Elliott, etc., but it was clear that he had no interest in talking, so I gave up and we started making out. Then some other stuff happened, normal foreplay, whatever. Eventually we start fucking, and obviously I wanted to be fucked in the ass, solely because Elliott had told me it was forbidden. So I said, “Elliott said said he doesn’t want me to do anal, but I’m up for it if you are,” and the guy responded, “Since when is this about what Elliot wants?” So that was that.

The sex good, no complaints. I was really into the guy physically. Like if I saw him in a bar, I probably would have flirted. My only complaint was that he was a bit too nice. Like, during sex, if you want to spank someone, you just do it. You don’t ask them first, because by asking you completely negate the effect of the spank. And if you spank someone and he/she doesn’t like it, it’s no big deal, because he/she will just ask you to stop. Ya know? (#LifeAdvice) So yeah, this guy was the sort of guy who would ask before spanking me. A bit too British, in the bad way, if you know what I mean. And then at one point he was fucking me, and I began to dish out some mild dirty talk–“I love the way your dick feels in my ass,” etc., no big deal. And in the midst of this I said, “You think I’m a whore, don’t you?” But like in a sexy-voice, porn way, ya know? But when I said it he immediately stopped, flipped me around, looked me in the eyes and said so sincerely, “No, not at all! I think you’re great!” lol

So the next day I called up Elliot and told him the story, minus the anal part, and he loved it, and told me I did a great job. Then I asked, “So how much do I get?” And he said, “How much what?” and I said, “How much money?” (You see a pattern appearing?) He then, seemingly confused, explained that he never once mentioned money, and that he was sorry if I had assumed otherwise. I then started screaming about how of course I thought there was going to be money involved, since it’s generally implied you will be paid when your pimp sets you up to fuck strangers. “Why on earth would I fuck your friends for free?” I shouted. “Because I told you to,” he responded, calmly, “and you will continue to fuck my friends, whenever I tell you to.” I told him no, I would never do it again, unless I was paid. But of course I did, two more times over the course of the next couple months, for free, because he told me to. God, I can be so weak :)