How To Hire A Hooker (Or Prostitute, Or Masseuse, Whatever)

Buying a hooker is tougher than you might think.
I know. I tried three times before I finally succeeded, and even that was kind of a fiasco. And one of those attempts wasn’t even for me.
You see, one night in a drunken state, my friends Ryan and Bryan suddenly revealed to me that they had this fantasy about double-dogging some bimbo together. This was a surprise, but the bigger surprise was that they wanted me to subsidize their fantasy – they wanted me to participate and triple-dog a prostitute with them. Considering that the two of them were built like scrawny chihuahuas with chronic bronchitis, the thought of the two of them attempting to mount a hooker brought to mind images of gang-rape by a bunch of wire hangers.
But it turned that they didn’t want me because I was a brawny he-man with a cock the size of a vodka bottle… it’s because they thought I had enough money to buy the call girl. I didn’t. However, they kept bugging me over and over again that I must have the money, they were so horny, they needed someone… so I offered to procure the prostitute for them as a compromise, saving them the trouble of actually finding one. I began to leaf through the local paper’s “hot massage” section.
It ended in disaster, of course. The first call ended abruptly when Ryan slapped the phone out of his hand. “Don’t use my name!” he said hoarsely. The second time I used Bryan’s name…. and then Bryan panicked. I hung up. I might have had some success the third time using pseudonyms for the both of them, but then Ryan refused to give out his address, apparently not realizing that the prostitute wasn’t simply going to wander around the east side of town until he showed up.
The fourth time I called a transsexual and actually spoke to a real person, and could have actually hired him to satiate Ryan and Bryan’s feverish desires… but my tender conscience wouldn’t let me pull a Crying Game on these two bozos. Besides, Bryan was my ride home. We spen the rest of the evening ignoring the increasingly eager messages left by the transsexual, who was apparently having a bad night and looking to pick up some business.
But in that moment I realized that there was a gray area that’s not written about: How does one pick up a hooker? I mean, I’m all for women’s rights… but I know there’s a lot of guys that just aren’t getting any nookie without money or a hit album on their resume. Some guys have to pay for it. And so, in the spirit of commerce, I offer The Ferrett’s Tips For Picking Up Hookers.
Don’t Go With Streetwalkers.
You might think that the streetwalkers are the easiest to find – after all, they’re easy to find, they’re relatively anonymous, and they take cash.
Think again, my friend.
For one thing, spotting hookers is a lot tougher than it seems – well, in small towns, anyway. In New York and Las Vegas, it’s a bit different. In large cities, hookers flock together like those little birds that clean hippos’ teeth on the Serengeti. They’re happy to yell out en masse, calling out like squawking ravens – Blowjob! Blowjob! Blowjob! they cry, and it echoes throughout the streets, loud enough to wake apartment dwellers up out of a sound sleep, which is just one of those nice little touches that adds so much atmosphere to living in a big town.
They know they can scatter when the cops come, and as such they transform into fuckmuggers. Walk through a crowd of desperate Las Vegas hookers and you can get such a thrill you barely have to pay anything – they’ll grab your crotch, touch your nipples, whisper phone sex tantalizations in your ears… and then abruptly turn into Don Rickles the moment you walk away, having noticed the large running pus-filled sores on their lips and the fresh crackpipe burns on their hands. Yes, large cities offer quantity… but you have to go elsewhere for quality.
Or so I am told.
But in small town, maybe you have one or two hookers. They don’t hang around together for fear of being caught – which is kind of a shame, because I’d love to hear the shop talk that would take place between hookers in a small town. I’m sure they have a lot in common, service the same weedy-looking desperate men on alternate nights, could compare which streets are safest. Maybe offer hints on getting smegma out from between your teeth. If I could be a fly on the wall anywhere, it’d be at a diner with two small-town soiled doves yakking it up, except that I’d probably get stuck to the wall.
But anyway, it’s easy to drive by some scantily-dressed tramp at one in the morning and say, “Hey! A hooker!” But you have no investment at this point. The difference between noting a potential hooker from a car at twenty-five per and actually stopping your car to accuse her of being a hooker is tremendous. What if this is just someone who’s lost her way home from the latest heavy metal concert? You could wind up with your eyes clawed out, your sclera pooled on the ground like soggy scrambled eggs as you blindly mutter apology after apology. And then there’s the undercover cop thing. It’s times like that you wish that you could look through the local high school yearbooks and try to find her picture, maybe see if she was voted “Most Likely To Become A Prostitute”.
And even when you’re not looking, there’s problems. My friend Bryan has twice picked up what he thought were hitchhikers, but turned out to be garden-variety strumpets. This has always led to horrifically-awkward moments, mostly involving conversations like:
“So where do you want to go?”
“Anywhere you want, honey.”
So far he’s managed to extricate himself from these predicaments, but I remain convinced that one day Bryan will find himself receiving what he thinks is a grateful hummer from a happy hitchhiker, only to find himself out of spare change at the wrong time.
Be Prepared.
It takes a certain kind of mindset to continually walk around with a wallet full of cash and a sleeping hardon – but this is what it takes if you want to undress with success. Because hookers beat out waitresses when it comes to bad timing – waitresses always ask you questions when your mouth is full, but hookers always ask the question when your wallet is empty, and you want their mouth to be full.
For some reason, they always seem bolder when you’re in groups, not realizing that it takes only one prude to ruin a potential gangbang for everyone. But until Heloise gets off her skanky butt and writes, “Heloise’s Hints For Prostitutes”, I guess we can forgive this.
But it’s up to you. The two times streetwalkers have approached me were both bad opportunities:

  1. Once, when I was walking with my twelve-year old stepbrother, I was propositioned. Tempting though it was, I was only fourteen at the time and I doubt she would have blown me for the bag of Spiderman comics I was carrying.
  2. When walking back to my car in Stamford, a large-boned black lady with an attractive smile came up to me and told me she’d give me a blowjob for twenty dollars because she needed bus fare. I was cash-poor, but offered a ride nonetheless since she seemed nice. She declined, but kept asking me about the money until I eventually brandished my empty wallet at her. This confused me for a long time, but eventually I figured out what was going on – this woman was motivated. I admired her for her can-do spirit, the way she refused to take a free ride because she didn’t feel she had earned it. No, for her that twenty dollars was simply a way of keeping score of a cocksucking well-done. If only there were more like her.

But learn the lesson: Make sure you’re prepared at all times. In fact, before I got married, I myself began carrying a small puptent around with me so I’d be ready when opportunity knocked. Light backpacks are quite inexpensive, rainproof – and happily, the fine for unauthorized camping within city limits is a lot less expensive than being caught screwing a whore.
Pay Her, Especially If You’re Still In School.
You’d think this would be simple. However, a football jock in our school fucked a streetwalker in a parking lot near our school, refused to pay, and then got the shit beaten out of him by the pimp who was waiting nearby. The cops interrupted the scuffle, and it wound up in the newspaper. Mark became famous, though understandably publicity-shy. Keep in mind that getting your name in the newspaper is nearly as humiliating as, say, having your dream of double-dogging a prostitute and subsquent failure to do so posted on a public web page.
Keep A Straight Face.
Now that we’ve eliminated streetwalkers as sources of sex, you might want a call girl. Avoid giggling. Preparation is a fine thing, and if you’re going to give a fake name make sure you a) have cash and b) have your name made out in advance, since there’s nothing more embarassing than telling her you’re “Mr., um, Doubtfire,” and then paying with a battered Diner’s Club card that reads “Fred Polesak”.
You will also have to leave a message and have her call you back. Sounding suave on such a message is far harder than you might think, since the mere act of leaving a message is admitting that you’re horny, desperate, and kind of pathetic – hey, that’s their demographic. Don’t worry.
Mentioning sex openly is verboten, incidentally. Remember, that’s illegal, and much like dealing with a bad drug dealer, you have to have them show up and then just pretend that hey! These drugs and sex just came out of nowhere!
Also, generally these sorts of things happen in hotels. Good hotels are notorious for screening out hookers, but generally you can call down to the front desk and ask them to usher someone up for you. When they ask what her name is and what she looks like, tell them, “I don’t know, but they all look good with their lips around my dick.” Generally that disarms ’em.