The Time I Tried Out To Be A Prostitute

I was in grad school, which — have you been to grad school? If you’ve been to grad school, then you know the moment that I’m talking about. The moment where you start getting automated student loan payment calls from Sallie Mae, Inc. Now, “Sallie Mae” sounds like a cute and charming and folksy name, the sort of girl who grew up on a farm, among fields and cows. In real life, this is not actually the case. Sallie Mae is actually a huge and heartless corporation.

What Sallie Mae does is, she starts making these robo-calls to you, reminding you of how much money it is that you owe her. You can press a button during the call to ask for a “deferment,” which means that you will still owe her money, but you will pay it later on at some absurdly compounded rate of interest. But — and this is the “but” part — even to get a deferment, you still have to listen to the part where the robo-voice reminds you of how much money you owe her. For example: “Ol-i-ver… Mill-er. You cur-rently owe… ninety-eight thousand… six hundred… dollars and… seven cents.”

It was at this point that I stopped thinking of Sallie Mae as a cute hillbilly girl. I more began to think of her as, say, Trinity from The Matrix: an unstoppable leather-clad dominatrix ice queen. A relentless bitch, basically. I imagined her chasing me through city streets, trapping me in some blind alleyway. “Look, I just need to ask for another defer–” I would say, but it would be too late, for she would have already jumped in the air and karate kicked me in the face in slow-motion. Five times she’d kick me, all before I even had time to hit the ground. And then she’d wrench out my gold fillings as payment, but not before giving me one final kick. And then she’d remind me that I still owed ninety-seven thousand more dollars.

I was starting to worry about money, is what I’m saying.

Which is how I decided to become a prostitute.

Why or how I came about this decision I have no idea. I take no responsibility for any of the “thoughts” that I had in my early twenties. I mean, I also thought that I should grow dreadlocks. I don’t take responsibility for that thought either.

I think I dimly remembered that prostitutes made money. I remembered this from watching movies on Cinemax, I guess. Anyway.

Signs that I had not thought this plan through very well included:

1) I already had a girlfriend, who surely was not going to react very well to the “Hooker” plan. (“Oh, you’re a hooker now? Let’s just throw you a big ol’ hooker party!”)

2) I am not gay, which is unfortunate, gay people being cooler and all. And I am not even slightly bi.

However, I did have the internet! Plus DSL, which I had just gotten. It’s important to remember that before the advent of DSL, the internet was totally f-cking useless, unless you really liked standing around making comments like “God, I hate this” while waiting for a page to load.

Anyway, using the power of the internet, I found the most reputable house of prostitution for men that I could locate in the New York City region. I sent in my “glamor shots,” i.e., my profile pictures. I figured that the house of prostitution would never contact me, or that it would take them three months to contact me. And then there was the me-not-being-gay-problem. And then there was the me-having-a-girlfriend-problem. Maybe I could take her out to dinner and explain it all. “How’s your chicken? Mine’s a little tough. I’m a whore now.” …Or maybe not.


I have to admit that I had ulterior motives. I was in grad school for creative writing, and I thought that being a male prostitute would give me plenty of stuff to write short stories about. Or maybe a memoir. I mean, it’d be pretty easy to write a best-selling book about living in New York City and being a hooker, am I right? Several people have done that.

I was also experiencing a common problem that I have experienced throughout my entire life: visualizing an event in completely unrealistic, impossibly romantic terms.

…And so, when I visualized this future career as a whore, I invariably saw myself in some all-night dive bar in New York, smoking black French cigarettes and looking impossibly aloof and sad. I would be sitting by myself and talking to the bartender and saying things like, “This city, you know, is a terrible bitch-goddess. …But sometimes, at night, if you treat her gently, she will open up, and reveal herself to you, like the luminescent black orchid that flowers but once a year.” And the bartender would say to me: “You’re not a MAN-WHORE, are you?” And I would shake my head sadly and say, “No, no. …Nothing so simple as that, my friend…”


But as I clicked the “send” button to forward my photos to the house of man-whorery, I realized that none of this mattered. They would never call me back.

Reader, they called me back the next morning. In fact, I was woken up at eight-thirty in the morning by a call from the shrill Eastern European woman who owned the escort agency. “Hi this is–“ I can’t remember her name so let’s just call her “Elena” “–this is Elena from the Something Or Other Escort Agency! Am I speaking to Oliver?” I was still rubbing the sleep from my eyes and trying to snap into instant job-interview mode.

“This is Oliver,” I said.

“I got your photos last night and I liked them! Now, I just have to ask you a few questions!”


“First of all, tell me! What are you? It didn’t say on your application! Are you gay or are you bi or straight or what?”

It is to my everlasting shame that I had not figured out an answer to this question in advance. I had agonized over it the night before, while filling out the application at my girlfriend’s house. I knew that if I said “straight,” they wouldn’t hire me. But I wasn’t gay. Could I check off “bi”? But wasn’t that the same, in essence, as checking off “gay”? But I needed this job; I needed the money. …I had tried to think of what I was capable of doing. Could I have anal sex with a guy? No. Could I go down on a guy? No. Could I kiss a guy? Maybe, if I was very drunk and he wasn’t incredibly old or anything like that. Could I let a guy go down on me? Again, maybe, if I was very drunk and if I wasn’t watching while he did it or anything like that. What I was secretly hoping was that the gay men that I met would be so distracted by my charm and conversational witticisms that they would completely forget that we were supposed to be having sex with one another. “Gosh, Oliver, you feel that the new Star Wars movies completely tarnish the memory of the original trilogy? How fascinating! Please, tell me more…”

Elena was already not pleased that I had paused before answering her. “Oliver!” she said. “So which is it? Gay or straight!”

“Ummm…” I said. “I’m… umm.”

I realized, somewhere within the deep recesses of my brain, that I was handling this job interview in the wrong way. The point of job interviews is to tell the person asking the questions exactly what they want to hear. But in this case, telling the interviewer what she wanted to hear could lead to my having sex with a strange man in his darkened New York apartment. I experienced a strange mental breakdown. I couldn’t say yes or no. I couldn’t answer either way.

“Uhhhh…” I said. “Er. Ah. Um.”

“Um?!!!” she shouted at me. “‘Um?'” she said. “What is this ‘um’?! There can be no ‘um’ here! These are important, high-class people that we are talking about! I’m sorry, but I just don’t think that this will work out!” And then she hung up me.


Thus ended my brief foray into man-whorishness. Total elapsed time of the interview: forty-five seconds.

It is perhaps for the best that I didn’t become a whore, although I doubt it. It’s not like I really make money these days at my writing job. One of my fans who sends me fan mail works as an escort in Texas: I had originally planned on having sex with her. Escort sex! For free! But this was cancelled due to my poverty and general aura of incompetence.

Anyway, she’s a prostitute for real. And one time, she was talking about a client who had to cancel an appointment. He paid her, even though he canceled: eight hundred dollars. Eight hundred dollars for forty-five minutes! And he paid her because he didn’t cancel in time! Like it was a doctor’s appointment or something.

At the time, I was earning twenty-five dollars for each essay that I wrote, so I tried to do the math — 800 divided by 25 is what, with a ratio of 45 minutes to the four hours that it takes me to do an essay… I stopped quickly, not because I’m so bad at math that I couldn’t do it, but because it was making me depressed. I would have had to write forty articles a day, or some such horrible number, to make the same amount that she makes in an hour, just for being hot. Yes, she’s hot. But it’s not like she’s responsible for being hot. It’s not a like a choice that she made. It just happened, is all.

And then I got depressed. I’m mostly depressed these days. But maybe if I was a whore, my depression would be more romantic? That’s what TV and movies tell us, anyway. That being a hooker is deep.  And I believe this, more or less. Because I still imagine things wrong: I still imagine things as being more beautiful and awesome than reality lets them be. And so, if I could actually be a hooker, then maybe prostitution would give my depression meaning and texture. Maybe I’d feel better. Instead, I’m just a regular guy. What a bum deal. Thought Catalog Logo Mark

Thumbnail image – Prostata

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