This is my mission: to find a hooker, contact her and then have sex with her. For extra bonus points, I’m hoping to dodge both jail time and gonorrhea.

I’ve never had sex with a hooker. Never seen the appeal. Where do you even find one? How much do they cost? Do you tip? Can you haggle?

I’m determined to complete this exercise not as a “writer” per se, but as a dude who wants to get a prostitute. No professional hook-ups. No cheats. So I begin with every New Yorker’s starting point when searching for goods or services: Craigslist.

Most of the ads are junk. The same girls (like “HOT ASIAN SENSATION!!”) post ten times a day and phrases like “SEXXXY!” clutter the subject lines. One post is titled, “I want to kick a man in the balls!” I’ll pass, thanks. One implores, “Miss Kandie is gonna SPANK YOU*******Miss Kandie is gonna SPANK YOU.” Tempting. (By the way, ALL CAPS IS NEVER SEXY. NEVER.) There’s a spectacular body for $200, but her head is cropped out of the picture. Nope. I’m not dropping two bills on a potential burn victim.

It’s a fun little world. In a bizarro reversal of a Girls Gone Wild ad, their nipples are clearly visible but their eyes are censored with those little blurry marks. I learn nifty new acronyms like “GFE”: “Girlfriend Experience.” The escorts are classified as either “Independent” or “Agency.” Hoping to cut out the middleman, I target Independent.

Are these sites legal? Kinda sorta maybe. To shield themselves from liability, their disclaimers specify that the ads are for conversation and companionship only. If sex ensues, chalk it up to spontaneous chemistry between two consenting adults. Right. Just like when you buy a latte from Starbucks, you pay $4.55 for snappy conversation with the barista and then he gives you a Venti on the house.

­Both Craigslist and VillageVoice.com are busts. My breakthrough is Eros.com, an aggregator of escort profiles. It’s the Orbitz.com of booty. In a handy sidebar, Eros displays each girl’s key stats: age, bust, weight, height, hair color and ethnicity – the important stuff, the things that define our essence. The copy is cleaner, the pics less raunchy and the girls better looking…with higher prices to match. Some go for $2,000 an hour. Only a few are cheaper than $500 an hour, and those look like early season dropouts from The Biggest Loser. Generally speaking, a hooker’s cost is inversely proportional to her weight.

On a Thursday afternoon at work, I spend three hours combing through Eros profiles, consolidating the top candidates on a spreadsheet, noting their price, stats, desirability and contact info. It’s a lot like prepping for my fantasy football draft: optimizing value and minimizing cost.

Over an IM session with my buddy Jamie, we copy and paste the girls’ URLs back and forth, debating their relative hotness, risks and probable freakiness in bed. “Nah, you don’t want that hot blonde,” Jamie types. “It’s like buying a German sports car instead of a Honda. It seems like fun but you’ll overpay and she’ll break down.”

And just think! For whatever cockamamie reasons, people believe that prostitution objectifies women.

I filter the candidates. I rank them. After Jamie helps me determine my fave five (possible sponsorship opp for T-Mobile), I settle on an escort named Julia. Her stats: 24 years old, European ethnicity, blonde hair, green eyes, 5’3”, 107 lbs., 34B, 22” waist and 33” hips. Her photos have class – they could pass for an erotic fashion spread in W.  $500 per hour. I make the call.

“Hello?” A girl’s voice, quiet and muffled. This catches me off guard. I was expecting voicemail and a phone tag game of cat-and-mouse.

“Hi, Julia. I saw your profile on Eros.com, and, ah, you’re very beautiful…” Oh sweet Jesus. I’m stammering. Am I a freakin’ 16 year-old asking a girl to the freshman dance? “I’m wondering if you have any openings soon?”

“For tonight? Yes. That is fine.” As advertised, she speaks with an accent, maybe Russian.

“Ah, not tonight. How about tomorrow, Friday? Are you free at eight?”

“Yes. Call me at seven. And I’ll tell you where to go.”

Is it really that easy? Huh. As Jamie says over IM, it usually takes three weeks just to see his dentist.

On the afternoon of our “conversation and companionship” rendezvous, I withdraw $600 from my checking account, leaving a new balance of $87. How much should I tip? A waitress needs a tip because the bulk of the bill covers the restaurant and overhead. But a hooker has no larger organization (besides maybe her pimp). So does she really need additional cash? Then again, when you tip a waitress, you’re not stuffing an unwelcome penis in her vagina. I’m torn.

Three hours until the companionship. I down two beers. I shower and change into first-date clothes. I count $500 into an unmarked white envelope and slip the envelope into my blazer. This is a delightful perk: I’ve always wanted a reason to walk around with an envelope full of cash, Sopranos-style, tucked in my jacket pocket.

I call Julia at 7 p.m. She’s not there. I call her several times but she doesn’t pick up. I leave three messages, straining to keep the panic from my voice, and soon I feel like Jon Favreau from Swingers. Just as I’m about to phone one of my backups, she calls and we push the appointment back to 8:30 p.m. “Come to the corner of 61st and 1st,” she says. “Then call me when you’re there.”

On the subway, I long to tell someone – anyone – that I’m on my way to see a hooker. When I’m at the intersection, she gives me her exact address and I wonder if she (or some undercover vice officer) is peering at me from a window. The uncertainty is hot.

Her building is an Upper East Side walk-up, the kind that probably fetches $2,000 for a studio. Or four hours work. I get to her door, wishing I drank a third beer. Deep breath. I knock.

Relief! No pimp, cop or bait-and-switch troll. Julia answers the door and looks exactly like she does in her ad. Better. She’s wearing a black skirt and fitted black blouse. We shake hands awkwardly; I forget to kiss her on the cheek (my original plan).

Leading me into the room, she throws me a comforting smile. “So what do you do?”

“I’m a writer. How about you? I mean, what do you do when you’re not…doing this?” Smooth, Jack. Smooth.

“I’m a student at FIT.” With her accent, it’s pronounced “stuuuudent.” “I study Home Product Development.”

“Ah, HPD,” I say.  “You know of it?”  “No, but that’s gotta be the acronym, right?”

She doesn’t really laugh, and that’s okay because it’s not really funny. If this were a date, it would end before we ordered appetizers. I take in the room as we bumble through the chit-chat. White bed, white curtains, white sofa. A TV is set to the smooth jazz music channel. Nothing on the walls. No knick-knacks from Europe, no evidence that anyone lives here.

I remove the envelope from my jacket and place it atop her dresser nonchalantly, like I’ve done this a thousand times. I doubt she’s fooled.

“Have a seat.” She says, flirting maybe a little. She counts the money and looks satisfied. I ask her about HPD. We joke about Paris Hilton.

“So.” She pronounces the word with two syllables. She adjusts herself on the couch, scoots closer to me and puts her hands on my chest.

“So.” I kiss her. Thanks to clichés spawned by Julia Roberts and Richard Gere, I’m worried she won’t kiss on the lips. But she does. And deeply.

She backs away. Looks me in the eyes. “You…you make me shy,” she says. “You make me nervous.”

“I make you shy?”  She fires a magic bullet. She says the one thing – the only thing – that could possibly put me at ease. “You’re different. Cute.”

Days later, after sober, cold analysis, I realize that this is what she would say – what she has to say – to every client. Her job is to make customers feel special. But in the moment, I bought it. Textbook GFE.

She unbuttons my shirt. I slip off her blouse. Her body is flawless: lean, toned, tan. We kiss and grope and writhe. She takes my hand and guides me to the bed. We lie down.  “Do you have a condom?” I ask. Another great line, Jack. Does a fisherman have a rod?

“I do, as a matter of fact.” She laughs a little. In one fluid motion, she reaches behind her, plunges her hand beneath a pillow and ferrets out a condom that she flicks open. It’s almost like she’s done this before.  She slips on the condom, teasing me with her fingers. She starts to take me in her mouth. Despite her lingerie-model body, despite her obvious technical prowess…I still can’t stop overanalyzing. This girl can’t be into it, can she? The blowjob is a hooker’s TPS report.

So I try to throw her off her game, surprise her. I turn her on her back and tease her body with kisses. She’s breathing heavy, but I’m not falling for the act. More foreplay. I still doubt this is doing anything for her.  But the clock is ticking. So I enter her. We begin with missionary. Soon my hyper-analysis melts away and the sex is just sex. I check the time on her TV: 8:42 p.m. She returns my kisses but avoids eye contact. She lets out a few “Oh babies” and a stream of quiet “ooohs.” I’m skeptical.

At 8:53 p.m., she gets on top. She crouches over me, ninja-like, supporting all her weight with her legs, pumping up and down. It’s impressive. I keep an eye on the clock, terrified of running into Hour 2 and the $1,000 zone. 9:02 p.m. We switch to doggie style – her small body easily rocking back and forth – and she breathily repeats, “Come baby. Come baby.”

But it’s only 9:06 p.m. Why would I do that? At $500 an hour, each minute of sex costs over eight bucks. That’s a quarter for every two seconds. So we’re back to missionary. 9:15 p.m. She pulls me off her and gives me a surprised look. She hops off the bed and goes to her dresser, pulling out some lube. She squirts out a dollop then squeezes me. On top of me again, she repeats “Come baby! Come baby! Come baby!” with growing urgency.

At 9:24 p.m., she sighs. “I’m too tired. I can’t do this anymore.” She peels off the condom, dispenses more lube and takes me in her hand. My suspicion about the “ooohs” seems validated, as she makes the same little noises when giving me a hand job that she made during sex.

Well. Since she’s doing her job as a prostitute, I might as well do my job as a journalist. We’re both professionals. As she massages my cock, I start to ask her some questions.  “If it’s not too personal to ask, how many guys do you see in a month?”  “It depends,” she says, sitting up in the bed while jerking me off. “Sometimes five guys in a day, sometimes I go two days with no guys at all. A good average would be three a day.”  I do the mental math as she strokes me. Even if it’s only two guys a day, that’s over three hundred grand a year. “Do you have to share it with anyone?”  “Nope. Independent is the way to go.”  “You don’t have a…” I’m embarrassed to say the word. “Pimp?”  “A pimp?” She laughs. “A pimp. You don’t need pimps anymore. We have the Internet.”  As she’s working me, I take her free hand in mine. “So what do you do for security? What if you have – you know, scary clients?”  “I guess I would scream really loud.”  “And how do you stay clear of the police?” That awful smooth jazz is still playing in the background.  “You trust your instincts. You’re careful. I never see guys outside of this apartment. If the guy looks shady, I turn him away.”

I’m getting closer to release. “Do you like what you do?”  “Sure. I’m sexually satisfied, I’m independent and I have peace of mind.”  Peace of mind. I know it’s an illusion, but I get the sense that we’re sharing a connection. I like her. She’s confident, gutsy and smart. Now I’m fascinated. I want to know more.

“What kinds of guys come to see you?”

“I break it down into five categories. One: guys who are just curious. Two: guys who can’t get sex. Three: guys who are sickos. Four: guys who are married and want something discreet on the side. Five: guys who are into the kinky stuff. Oh, and maybe there’s a sixth category – really young guys who want to improve.”

“Do your friends know what you do?”

“No. I don’t tell anyone. My friends think I have a wealthy family who likes to spoil me, and that I have a boyfriend that I spend a lot of time with.” She giggles. “The lies can get complicated.”

After a few minutes of this hand job/interview, she can tell by my squinty-face that I’m about to come. In what seems like a remarkable coincidence but is probably just habit, her heavy breathing and faux “ooohs” return. Just as I’m on the edge, she takes her free hand and holds it between my cock and my face – a shielding motion – just like in football games when the net goes up behind the goal posts for the extra point.  She hands me a box of tissues, helps me clean up.                       

The clock says 9:37. I know I should go. But there seems to be real warmth as she lies next to me, smiling. “How’d you get started?” I ask.

“I grew up in Prague. When I was 16, my best friend – a girl – took me to see this older guy who was a Japanese translator. This is how I lost my virginity – in a threesome with my girlfriend and the translator. He paid us both.”  Ironically, I’m enjoying the “conversation” part of the transaction. “Have you read Crime and Punishment?” she asks.  I nod. You’re kidding me. A Dostoyevsky reference?  “It’s like the character Sonya, the prostitute,” she says. “Sonya is innocent. She thinks that she’s morally pure. And that’s how I view it, too.”

“But dating must be tough,” I say.

“It is. When I date guys…I feel like I’m being used. I don’t like giving the sex for free.”

This phrase would haunt me. Maybe she’s breezy and self-assured, maybe she earns more in a month than writers do in a year. But this inversion of erotic values – preferring the hooking to authentic human relationships – suggests, well, I don’t know what exactly. But it suggests something complicated, something I want to learn more about. I’m captivated.

“Julia, I have a confession. I’m writing about this.”  “Okay.” She looks bemused. She’s seen it all and then some.  “I’ll change your name, hide your identity. Are you okay with that?”  “Sure.” She shrugs her naked shoulders. Then she looks at me, maybe with a hint of accusation. “You think you will understand prostitution from this one night?”

We don’t speak for a few beats. She’s right and I know it. And then the painful truth sinks in: I’m the bigger whore.

It’s time. I grab my boxers and jeans. She stays naked, probably to shower. I gesture at the TV and ask, “Do you like smooth jazz?”  “No! I hate it.” We both laugh. The moment feels real.  “What do you like?”  “Trip-hop.”  Pronounced Treeeeeep-hop.  “Yeah, I guess that wouldn’t work for the i-bankers.” I take out four twenties from my pocket. Then I add a fifth, my last. A tidy 20 percent. “Well. Thanks again.”

She smiles. We walk to the door. I kiss her on the lips. Now I’m enthralled. I want to learn about her double life. I want to crack her code. I want to see her again. But I know I never will.