Dating a Prostitute


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Although Pretty Woman, a movie I didn't enjoy starring an actress I don't like that I haven't seen in a solid decade, was seriously my only reference point for how to behave and what to do, I didn't think a formal, tuxedo affair was the way to go with this, and not just because I don't own a tuxedo. I would have to wing things from here.

Jasmine was going to meet me at a restaurant downtown at 7:00 p.m. I felt that was a good time for a late dinner that made me seem like an adult, plus, for the next few hours we spent together, it would stretch into what I figure is a sexy time of night. As you may have noticed, I'm a complete idiot. I don't date a lot.

The restaurant was fancy in that way that there are no crayons on the table and no one wears pieces of flair. I showered twice before leaving my house, proving to myself that I have a weird kind of OCD about strangers and sex, and headed out. Arriving 35 minutes early, I proceeded to drink at the bar until Jasmine finally arrived.

As a man with some ability to make people laugh, in my day-to-day machinations I've dabbled in flirting with attractive women before; I've even had success. I don't want to brag, but I have touched a boob before, and it was just swell. So I'm no rookie at this sort of thing. That said, Jasmine was like sex that something had arranged in the shape of a person and held together with a shimmery black dress and lipstick. If sensuality smelled like bacon, this girl would have been Jewish kryptonite. I was a little stunned. Also a little drunk.


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I'd hit that. Why do you think they call it "porking"?

She said hello and gave me a kiss on the cheek as she took a seat next to me at the bar. Because I'm sly and shit, I literally leaned back a few inches to look at her ass. It really was sweet. We made chitchat briefly as I tried to think of a cool way to bring up giving her a wad of cash I had in an envelope because she was a prostitute and I was a john. Luckily she was on top of that like stink on a monkey and had her tiny purse on the bar before I figured out what I wanted to say and suggested I just slide my donation inside. I guess we work on the honor system. That's nice.

Jasmine had a very shrewd way of deflecting pretty much any question I asked her and turning it into a question about me instead. Over the course of dinner I learned that she loves what she does, she has been doing it a couple of years, and she would not show me her booty clapping skills in a restaurant, but something else could be arranged. Other than that, I didn't get very deep into her, so to speak. Although she did admit to liking the movie Dude, Where's My Car? which I found highly suspect.


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I once called Steve Jobs the da Vinci of our generation. Please don't support anything I do.

I finished my steak and garlic mashed potatoes while she ate a vegetarian stir fry and we discussed our plans for the rest of the evening. I wasn't sure how butt clapping fit into a non-sexual scenario, but I was also pretty unsure what the fuck I spent $1,200 on. The only idea I had readily available that might kill two birds with one stone was dancing. We had discussed that on the phone, and she was DTF -- Definitely inTerested in the Foxtrot.

Because I dance like a palsied child in the final throes of succumbing to a new disease on the frontier, I hadn't really wanted to do this, but of course I had few other ideas that didn't involve mini golf or going to a clinic the next morning, so dancing it was. Besides, I was about six drinks into the evening at this point and at the cusp of dancing by myself anyway. So I went clubbing with a prostitute.

If you've never spent an inebriated evening cutting a rug with a lady of the night, all I can say is that it does amazing things for your self-confidence. Jasmine had me convinced I was like the bastard child of Michael Jackson and Justin Timberlake, only possibly with a mightier dong and highly appealing earlobes, which she had a habit of biting while we danced. I knew this was all for show, but it was a show I had paid for, and a show I was putting on for a crowded room of sweaty strangers as well. And you know what? I liked it. I felt good about myself. It was all fake, and I didn't care.


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I'm like a fuckin' gazelle or some shit with this dancin'.

I had no sex with Jasmine that evening. When we parted ways, she kissed me on the lips and may have left her tongue somewhere in my chest cavity, after which I coolly said "awesome." I didn't learn about where she came from, if her real name was in fact Gerty, if she fell into prostitution to pay for a drug habit or after being abused as a child, or anything like that. That's not really my business anyway.

I learned that she was paying for a Ph.D., however, and the next day when I called to tell her I was going to write an article about our night if she was cool with it, she said yes and also told me that she only sees men she either pre-screens or scouts out ahead of time. She'd actually been spying on me at the restaurant for a while before we met. She told me she sees no more than two guys a day, four days a week, and I was more fun than most of them. Also she took me into the women's washroom at the club and made her ass clap for me. It was fucking amazing.

I will probably never pay an escort to go dancing with me again, but only because it's kind of a costly way to spend an evening. It was fun, and Jasmine was a lot more fun to hang out with than I had assumed ahead of time. And why did I assume it would be different? Hard to say -- it probably had something to do with whatever assumptions most people make about women who charge money for sex. What did I learn? The only difference between an escort and, say, your sister is probably that an escort charges money. They're both regular people, though. And also that ass clapping is awesome.

For more sexy sex sex sex, check out If Sex Was Used to Advertise Everything and 21 Things We Secretly Suspect about the Opposite Sex.

Like any good artist, I have a preferred medium. Some artists work best in oil, some in watercolor, some with sculpture, and others with photography. My medium seems to be debauchery, and I can mold it like an old sticky-fingered pro. Having already experienced an orgyand delved into the realms of fetishism and stuff people store in their holes, I thought "What's left?" and then I Googled some things, got sleepy, woke up the next day, and had an idea -- prostitution.

Before you get all giddy, I didn't sell myself for this article, but I am aware of a handful of truisms -- there are escorts everywhere, and they all advertise themselves as offering companionship. What kind of companionship does a lady you know nothing about offer for the discerning gentleman with an excess of cash? I mean, besides the obvious. This would be no more about sex than the orgy was. It was an experience.

Finding the Right Woman


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Where do you find an escort these days? I'll spare you the deception of pretending I had no idea. What am I, a guy who doesn't know where to find escorts? I work on the Internet. You find them on the Internet.

I suppose there are still women working street corners out in the world, but that seems far more tragic to me than escorts operating online, and I didn't want to be a part of that. I suppose we should establish now my ethics on this matter, because surely some will disagree -- I am not against prostitution. Exploitation? Absolutely -- fuck that shit right in its ear. However, I feel that if an adult woman who is in control of her own life wants to charge money for sexual services, it's not a lot different from anyone else charging for massage services, or to be a clown at your birthday party, except the balloon animals are way more fun. They have an ability others are interested in that they have monetized. If that upsets you, it's probably because you have an issue, not them.

Naturally, I'm opposed to human trafficking, sex slavery, underage prostitution, violence, and substance abuse, but I really believe a person can sell sex and not be involved in any of that, just as you can be a pot smoker and maybe not be involved in Mexican drug cartels, the beheading of civilians, organized crime, robbery, and meth-related buggery. So there's my caveat at the beginning; don't piss on me about exploitation later.


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"I smoked weed and now I'm going to break into your house and fill your sugar jar with feces!"

Anyway, there are any number of websites you can go to that will give detailed lists and ads for escorts working in your area, depending on the size of the city you live in. As it happens, my city has hundreds of them. How do you pick the right one?

A lot of the women I noticed offer things like half-hour rates, which was kind of not what I had in mind. Basically I wanted to rent a friend for the day who would hang out with me and outwardly pretend to be interested in and attracted to me. Like Pretty Woman, I guess, only afterward I wouldn't want to drop kick my television. This would require a few hours. And if $60 was typical for a half hour, I was going to probably go broke making this happen.

Right away I noticed a handful of fun facts about working ladies in my area. There are a number of busty Asian women who have almost the exact same ad and, if I had to guess, are either law enforcement or guys waiting to stab me and take my wallet. So that was a no. The other thing was that anyone over 30 is called mature, and they often show pictures of their asses only.


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"Hi, I'm Sapphire. Thirty-five years' worth of poop has passed through this turd cutter. Like it?"

I have nothing against ass; I'm even quite fond of ass. Ass is wonderful. But, to be crass, I'm shopping for a person here -- shouldn't I get to see more than an ass? Everyone has an ass. If you just show me your ass, I can't even tell if you're a woman. These could have been shapely fellows who like to jog and don't do much high-impact muscle building for all I know. Maybe I'm old-fashioned, but I like people to have faces. In a sad twist, faces were the least prevalent anatomical feature shared by most escorts. Some even blurred them out. Feel free to discuss what this means about the culture of paying for sex as a whole. Faces? Don't need those!

Since I was actually looking to spend time with this person rather than just swan dive onto them boner first in a hotel room, I made a judgment call and decided to eliminate any prospects under 25. I'm sure they're all super nice girls, but the idea of trying to chat with a 19-year-old prostitute while we eat nachos seemed like the setup for a terrible film that ends with me dying of alcohol poisoning. In the end, I opted for a woman who claimed to be 30, intelligent, and articulate and has the sweetest booty I would ever see. Also, I should mention, it could clap. I've never seen clapping booty. I was sold.


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Hand applause is being polite. Ass applause shows real enthusiasm.

My new BFF's name wasn't mentioned in her ad. She called herself a college-educated super freak, though, so I assumed she had one that wasn't going to be Starla or Boobaroni. The only way to find out was to call.

The Setup


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Her name was Jasmine. Secretly I suspected that her name wasn't Jasmine at all and was instead something like Mildred or Gerty, but that's OK. I called at 9:30 a.m., which in retrospect probably made me seem like quite the eager beaver. I'm not 100 percent sure of peak times in the working day of an escort, but I think maybe mornings are downtime. She answered on the second ring and sounded breathy and a little throaty. If a boner could answer the phone, that's the voice it would use. Not bad at all.

I said hello and for no good reason immediately followed this by saying I did not want to have sex. Literally, she said hello and I said,"Hi. I don't want to have sex."

I've probably made thousands of phone calls in my life, and I once told a pizza guy I loved him before I hung up, but this was pretty much the dumbest call in the fastest time in my lengthy phone career. I heard something like a grunt on the other end and she said "OK." This shit was going swimmingly.


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Smooth as silk.

I explained to her that I wanted to spend time with her, but just like a date. I wanted to pay her to go out with me, have dinner, and chat. I should have started with that.

She was very open to the idea and asked me where and when. Not once on the phone did she herself mention anything about sex or money, which I figured was a pretty professional way to handle things. You never know if I'm a completely moronic police officer, after all.

I tried my best to clarify what it would cost me, but she insisted that everything I needed to know was online, and if I was serious, I'd know what to do. Basically this meant me doing math. Math that meant, if we spent four hours together, I was going to be shelling out $1,200 plus the cost of dinner, since I imagine she wasn't big on going Dutch. This was the first moment that doubt and trepidation set in. She put a value on sex, but now I had to put a value on funny. Would this article be $1,200+ funny? Maybe I'll break even if everyone who reads it donates a dollar to the "Help Felix Clay Get His Head Out of His Ass" Kickstarter this will inspire.


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Makin' that phat cash.

We settled on a time and a place and ended our conversation. I had just solicited a prostitute. My family would be proud, if they weren't worse people than me already.

Hahaha Thanx Cayla! Had a good laugh!

Shot babe xx I enjoyed the read as well!