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3 Things I Learned From Hiring a Prostitute

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.

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Felix Clay

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