Playing Prostitute

My new best friend Madeline is a prostitute. I have a love/hate relationship with Madeline: I love spending time with her and hearing all of her crazy sex stories, but I also hate her because I’m like, “It’s so annoying that you are you, because I want to be you instead.” Since meeting Madeline, on a daily basis I ask myself, “Should I become a whore?” It’s clearly a very difficult decision. I have no moral qualms with prostitution — in fact, I think it sounds like a pretty classy job — and I’m also totally jealous of all the money Madeline makes simply in exchange for fucking strangers, which I constantly do for free. However, I would prefer not to be chopped up into little pieces and thrown into a swamp in New Jersey. That’s what happens to whores, right?

Madeline has been an escort for over two years now (the high class, cool kind, not the tragic streetwalking kind), and has lived and worked in various places around the world: New York, LA, Paris, Belgium, and anywhere else she decides to travel. In fact, sometimes she travels just to fuck people: She has a client in Paris who flies her over every couple of months for a debauched sex weekend; for a while she was a mistress to a Saudi prince who took her on exotic vacations; she’s always going to Vegas for one client or another; etc. What I’m trying to say is, she’s good at her job.

One of Madeline’s New York clients is a 61-year-old retired businessman named Edward. Edward is a billionaire. He’s been married three times and is a self-proclaimed hopeless romantic. Following his last divorce, Edward decided that from then on he would only sleep with more than one woman at a time. The reason for this, he told Madeline, is because he falls in love far too easily–if he’s alone with a woman, he falls head over heals; he can’t control himself. So now, to prevent this from happening (because love, as we know, always ends in tragedy), Edward only has sex in threesomes or more. Oh, to be rich…

Madeline meets with Edward about once every six weeks. Their meetings generally follow a similar pattern: He invites her for lunch at a nice restaurant in Manhattan. When Madeline arrives Edward is seated at a table waiting for her, sipping a vodka on the rocks. There is always another girl at these lunches, invited by Edward, and Madeline doesn’t know anything about the second girl until she arrives. Together the three eat a light meal and have a couple drinks, and afterward Edward walks them to a nearby hotel, one whore on each arm, and they go up to his room and fuck. Each girl leaves with $1,000.

This article comes from the Thought Catalog ebook, Girls?

“You should come next time,” Madeline said to me one afternoon a couple weeks back. She was chugging a Diet Coke and plucking her eyebrows, her pupils dilated to the appropriate size of someone on 20mg of Adderall. “It’s just such easy money, and Edward is actually really sweet. Like I’d probably fuck him even if he didn’t pay me. Well… probably not actually, he’s pretty old, but like it’s not terrible. And he gives really good head.” I sat staring at her thoughtfully, stroking my chin for dramatic effect. Could I actually go through with this?, I wondered silently. I thought about what my radical Christian mother would think if she knew I was selling my body for cash. Then I got distracted and started thinking about how cool Catherine Deneuve’s hair looks in Belle Du Jour and considered whether I could pull off a similar style. Then I drifted off and daydreamed abstractly about that scene in True Romance where Patricia Arquette and Christian Slater are wrapped in blankets, sitting in front of that billboard — she’s crying, confessing to him that she’s a call girl, and he’s being his sweet, placid self and telling her he doesn’t care, and then they say “I love you” for the first time. Fuck… I love that movie.

“Give me twenty-four hours to think about it,” I told Madeline, to which she responded, “Just do it you loser,” to which I said, “Alright, fine, whatever.”

The following week Madeline called Edward to ask if she could switch up their formula and be the one to bring along a friend. She referred to me flirtatiously as her “twin.” See, Madeline and I sort of look alike: we’re both 5’9’’ with shoulder-length blonde hair and big tits. If you’re into skinny bitches we’re not your type, but (conveniently) most pervy old men seem to be into our aesthetic. “Fucking the two of us together will be like seeing double,” she told Edward into the phone. He said he liked the idea.

Edward arranged for us to meet at a fancy brunch place on the Upper West Side at 12:30 p.m. A bit early for a threesome, in my opinion, but I wasn’t the one making the rules. That morning I was sort of nervous. Just because I fuck someone for money once doesn’t mean I’m a prostitute, does it?, I wondered while trimming my pubes. Really all I’m doing is helping out a friend. I help friends with work stuff all the time–I edit their articles, I give them feedback on their artwork, etc. It would be rude, maybe even PREJUDICE of me not to help Madeline with her job, just because she’s prostitute… right? I flushed my pubes down the toilet, decided that I’d spent enough time “thinking thoughts,” and walked to the kitchen to take two shots of tequila.

“Threesomes are the best jobs,” Madeline told me on our taxi ride uptown. “You only have to do half the work, and they never last very long because guys can’t hold back with two pairs of tits in their face.” She flashed me one of her practiced, perfect smiles. “Seriously, you don’t have to be nervous.”

“I’m not nervous.”

“Yes you are, I can tell. You have that weird rash thing on your neck that you always get when you’re nervous.”

“Fuck. Can I borrow your scarf?”

When we arrived Edward was waiting for us, just as Madeline said he’d be. He wasn’t bad looking: about 5’11, receding black hair, very tan, maybe Italian?, and stylish in a suit jacket, jeans and Buddy Holly glasses. I have no problem with older guys–40s, early 50s, yes please. When I was 19 I slept with a guy who was 52, and I remember specifically getting off on the fact that he was older than my dad. But I’d never fucked a guy in his 60s before. What would it be like? Would he get tired easily? Would he need Viagra to get hard? Would his balls be all saggy and weird? So many questions.

I’ve worked out, through years of interviewing people for journalistic purposes, that the quickest way to make someone like you is to ask them questions about themselves. People love talking about themselves–sometimes it’s best to just accept this and allow them to indulge while you smile and nod. And so I used my technique on Edward, and probed him about his life. What he responded, however, was not at all what I expected. A quick overview of Edward’s life: He was born in Mexico to a Mexican mother and American father. He grew up poor. At fifteen, his family moved to Arizona. He was extremely smart and what some called a math genius. By the age of eighteen he’d made half a million dollars gambling. He went to Yale. After college he applied to the CIA and was hired. He lived for five years in China working for the CIA, came back and continued work in America for a year, then decided he wasn’t cut out for the job and left. He started a business, then sold it for a bunch of money. After that he started another business and sold it for even more money. By the age of 48 he’d made enough money that he could devote the rest of his life to traveling the world, hopping from one orgy to the next.

“Did they teach you how to lie?” I asked Edward after he’d completed his life story.


“The CIA. Don’t they teach you how to lie? I need to get better at it.”

“Why do you need to get better at lying?”

“Because I lie all the time–I’m sort of addicted to it–but I don’t think I’m a very good liar because I keep getting caught-out.”

“What do you lie about?”

“You know… who I’m sleeping with, where I am, what I’m doing, how I make money. I’m a chronic cheater. My parent’s have no clue what I’m actually doing with my life. All of these things require lies. And one lie leads to another. You know how it is…”

He smiled and slowly sipped his vodka. “They do teach you how to lie. You want the quickie version?” he asked. I nodded my head too eagerly. “Well, firstly,” he began, “when you tell a lie, you should keep it as close to the truth as possible. Don’t fabricate false stories or excuses, because made-up stories are difficult to remember, and they’re even harder to back up if you do get caught-out. Secondly, don’t give away any excess information. If someone asks you how your night went, tell him, “It was good,” and leave it at that. Don’t throw in unnecessary details. You should never give people information they don’t need, because information is what gives you away.”

It was only when Edward stopped talking that I realized my mouth was hanging open. Whoa… he’s SO cool, I thought as I watched him pick at his teeth with a toothpick. Madeline, who had drifted off into her own texting universe, was jolted back to reality by our silence. “Sorry,” she smiled, “I’ve heard that story like 20 times,” then giggled and proceeded to stick her tongue down Edward’s throat.

Twenty minutes later we were at the hotel. “I’m going to freshen up,” said Madeline, and disappeared into the bathroom. By the time she came out, about thirty seconds later, Edward already had me bent over his lap with my tights around my ankles and his fingers inside me. It was immediately clear that he would be in total control of how this all went down. In real life I hate being told what to do. During sex, it’s all I want. Boss me around, pull my hair, slap me, spit it my mouth, call me a slut, put me in whatever position you like–I’m game. Basically, unless you’re drawing blood or calling me fat, I probably won’t complain. Sex is my time to surrender, to escape, to lose control (as cheesy as I know that sounds). Luckily for me, Edward was a great Dom–calm and confidant and with no reservations about telling us what and how to do things. “Get on your knees,” “Turn around,” “Sit on her face,” “No not that way, this way”–he was the conductor, and directed us with finesse. The only slightly awkward part was when Edward kept telling Madeline to put her fingers in my ass, and she kept saying, “I can’t, my nails are way too long,” and he kept being like, “Oh come on, just do it,” and then I was like, “Uhhh I’d rather avoid any intra-anal lacerations if at all possible, thanks.” But that conversation came to a quick end as soon as Madeline and I started giving Edward a double blow-job. The double DJ: a valuable distraction technique.

Less than an hour after we got to the hotel it was all over. And it wasn’t bad. It was actually (too?) fun. I mean, Edwards’s balls were kind of saggy, but I didn’t mind. Having balls in your mouth isn’t exactly the most pleasant experience on earth, whether they’re saggy or not. And I’d rather be paid a grand to lick a pair of saggy balls then be paid nothing to suck on some nice ones. Obviously.

“That was almost too good to be true,” I said to Madeline while depositing my cash into a nearby Bank of America ATM.

“Yeah, but Edward’s great,” she said. “Not all guys are so cool, and not all jobs are so easy. But like, you should still definitely be a whore.”

“I don’t know. What if…”

“But you need new shoes–something with a thin heal. And you need a new bag. And like, new clothes. If you’re going to be a high-class escort you need to look the part. No offense but you look way too indie now.”

“I’m not indie.”

“Yes you are. In their eyes you are. Believe me, you’ll make way more sucking a guy off in vintage Herve Leger than you will in some crap from H&M. You have to spend money to make money. That’s just how the world works.” She spit her chewing gum into her hand and threw it toward a nearby garbage bin, missing completely. “Then the next step is learning how to make the inside of your vagina spasm, to make your fake orgasms seem even more real.”

“Oh Madeline, you’re so wise,” I swooned. “Teach me how to be like you.” Thought Catalog Logo Mark

More From Thought Catalog