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My Twenty-Eight Years in the Oldest Profession

Twenty-Seven Years in the Oldest Profession by Sita Kaylin

* I write using the female pronoun but not all prostitutes are female.

What I do for a living. I entertain. I stroke ego’s. I’m a friend, lover, party girl, fuck toy. I don’t pick fights (for the most part) or nag. I’m paid to be the ideal woman. However, it’s more than having no hair in spots and smelling sweet. It’s being down for whatever—within reason—and sometimes a sounding board. Or a sweetheart to cuddle with. The job is complex. Especially with ongoing clients. Regulars, we call them. It’s almost never just lying on my back and being sexy. It’s a marriage of sorts. Based on an arrangement. Money for time/energy. Once the negotiations are over, it’s best to never bring money up again. Unless special circumstances require it. Tricks don’t want to be reminded why you’re there. They know they pay me, obviously. The fantasy is that I’d be there even if they didn’t. Hookers walk a fine line between shrewd businesswoman and faux girlfriend. If we’re good, they forget altogether that they paid for the pleasure.

The job requires empathy and tongue-biting. My clients drive me bonkers, but they almost never know that. I provide a safe space for them to be themselves. Freak flags and all that. I’ve never been a judgmental person—it’s served me well in this business. You want me to gather my saliva and spit into your mouth? Gross, but let’s do it! As long as Benjamin’s are in play, I can do most things. Most. I do draw the line. Truth be told, I’m pretty basic in what I like in my own sex life. I don’t need whips and all that (I did in the 90’s). I prefer connection, chemistry and deep kisses that light my bathing suit area on fire. That said, when I’m working, it doesn’t matter what I like. Sure, it helps that I enjoy sex and making men feel good, but otherwise, I’m not there for myself. They wish I were. They can bite me.

Here’s a weird insider tidbit: Back in the day, they only cared about their orgasms. I liked it that way. Then, about eight years ago, clients began giving a shit about mine. Groan. I don’t want to come with them, but it does zero good to tell them that. It would crush their ego. Not to mention get me locked into a whole conversation as to why and then they’re reminded why I’m there. So I fake it. I’m the Meryl Streep of faking it. It’s not that I’m loud or make a huge to-do. I act like I shouldn’t. That it feels so good and I don’t want to come that soon. That’s also the key for me; I want that part of the program over with so I go into the act almost right away these days. I rouse them later, “You! You’re not supposed to make me come that hard and that quick!” Giggle, hug, see you next week. That may sound cold or detached but trust me when I say I’m an over-giving pro. I’m a people-pleasure by nature. Sometimes I wish I gave less, however, it would take more energy not to be myself so fuckit. Whatever it is I do, I assume is working since I’ve had a ton of repeat clients, some well over ten years. I’m good at what I do. I’m not every prostitute, I’m one type. We’re as varied as shells on a beach. We’re not all wallet-stealing ho’s with little conscience or sipping champagne on private jets. Most of us exist in a middle economy. The Radisson and Red Lobster. Hyatt and Houston’s.

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