So you’ve decided to pay for some sexy time. Congratulations! Since many important people in my life rely on income generated through “adult” labor, I endorse your choice. But as with all of life’s opportunities, there’s a right way to do it and a wrong way. Whether it’s a spontaneous trip to a naughty massage parlor or a meticulously planned epic evening out with someone professionally sexy, these tips should help you secure and enjoy the erotic provider of your dreams.

Use the internet. There are many, many outlets featuring hot folk for hiring, and there are good people on all of them, so I can’t recommend one over the others. (“Good” meaning honest, but also skilled at their labor.) Use your noodle—the head one—when it comes to selecting whom to contact. If someone has high-quality pictures and the body of a top underwear model but only asks for $150 an hour, you should probably be suspicious. Bait-and-switches are common even on sites that charge hundreds of dollars per ad, but if you use common sense, you should be able to avoid these. (Speaking of that, if you discover the person at the door isn’t the person in the ad, you should probably leave no matter how life-threateningly horny you are. Dramatic misrepresentation is a red flag for further dishonesty.)

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Don’t waste their time. It’s normal to feel uncertain or nervous about your decision, especially if you’ve never done this before. Meeting a stranger in intimate circumstances can be intimidating, and you might have concerns about the legality or the stigma around what you’re about to do. But don’t be the guy emailing without a sincere intention to book. He or she might humor you if you’re playing interested but hard to get, and obligingly try to convince you they’re the one you want. But there’s also a chance the worker you’re interested in will decline to see you or blacklist you—time-wasters are universally reviled among all stripes of sex workers—and you can be sure that if you do eventually follow through, they’re going to show up already annoyed and expecting you to be as obnoxious in person as you’ve been in their inbox.

Take time to do your research, and be confident about whom you’d like to meet in advance of contacting them. If you have a question that would make or break your choice to schedule, and that information isn’t already available to you, you can ask: Do you have any tattoos? If I cover the cost, would you be willing to arrange a hotel? But make it brief and thank them for their time in your first communication.

Know what you want. Are you looking for someone to act as your sub for spanking and bondage? Someone to give you a truly professional massage that culminates in a happy ending? Someone to take out to dinner before retiring for private time? Figure out what your ideal scenario is and then look for someone who specializes in it. Maybe you found an escort you think is super hot, but since you only want a massage, you’d like to pay her half her usual rate. Maybe you love the look of a certain hung dominant, but are only interested in him being your bottom. Fantasize all you like, but leave it at that.

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Civilians think that the world of sex commerce is a free-for-all with no limits, and that’s true inasmuch as it’s true of all our capitalist endeavors: You can surely find someone selling whatever you want to buy. But you don’t need to convince someone who isn’t selling it to be the one selling it to you. Surprise! Not every sex worker is willing to engage in every conceivable sex act. Don’t trust the word of a bunch of review-board dudes over what your provider his or herself actually tells you on their website, or directly in your communication.

You’re not going to like this part, which means it’s arguably the most important: Do not ignore a sex worker’s stated rules or boundaries. You’ll waste a lot of time (the cardinal sin) and piss off everyone involved if you keep trying to figure out ways to avoid giving a strict screener your legal name, or providing references, or whatever his or her requirements might be. If you know you are never going to show your driver’s license, don’t reach out to one who asks for that. If you know you want an array of options for genital stimulation, don’t book with someone who only does sensual massage. It’s always possible that, even with your most careful research, you’re going to hire someone who doesn’t offer something you want. While that’s a bummer, it’s not the end of the world. There is no excuse, ever, for pressuring or manipulating another person to accommodate you sexually, even if you’re paying.

Keep it classy. If you’re drawn to someone who advertises with lots of acronyms and euphemisms for sex acts (DFK, MSOG, DATY ... Google it if you must, but you might be happier not knowing), that person might not mind you referring to those terms in your correspondence or phone conversation. But the idea that using the word “Greek” instead of “anal” provides you or them with some sort of plausible deniability in terms of the law is, well, incredibly stupid. If someone lists a “menu” on their site of what they offer, cool; you already know the different makes and models of sex that will be available to you. If they don’t say anything explicit on their site, they probably won’t reply to an email that mentions your life-long love of taint-licking.

Putting graphic descriptions in an email or voicemail is not smart or necessary. Your provider already knows you want some degree of sexual contact during your appointment even if they don’t say so in their ad. There’s no reason to crash around like a horny bull in a china shop by stating the obvious as crudely as you can. (Or even as suavely as you can. Sorry, but dudes have a way of making things sound super gross when they try to use their “sensual” persona, like talking about “oral pleasure” or “extremely responsive nipples” or some other pretentious nonsense.) Does your desired one post pictures of themselves in suggestive poses or revealing clothing? Do they talk about loving to meet new people and being known for their open-mindedness? Do they charge by the hour? If yes, you’re both on the same page. If you’re frustrated by the state of affairs that keeps you and another adult from communicating clearly about what your time together will entail, I’d suggest donating energy and money towards decriminalization efforts. Nothing good can come from trying to force a conversation that makes the other party uncomfortable or unsafe.

Be reasonable. Your sex worker isn’t there because of their lust for you, or even their like for you. They’re there because it’s their job. Interrogating them about their own tastes, proclivities, and the authenticity of what they wanted you to believe was an orgasm is boorish and will cast a sour pall over the proceedings. “What do you want to do?” is one of the most groan-worthy things you can say to a sex worker, because odds are they want to be texting their friends, watching a Bravo marathon, or fucking the person they’re dating instead of you. If you’ve selected someone who seems to take their work seriously, they will probably put much effort into making you feel desired and appreciated, without you directly requesting or demanding it. To strain this illusion past the point of credulity by asking them to say they love you (yes, some men actually ask for that!) or tolerate nosy inquiries into their personal life may result in them declining a repeat and even blacklisting you for possible emotional instability. The best way to get a sex worker to like you—assuming you like them, and want to repeat or simply want a good reference—is not to “give” them a dozen orgasms but to tip them well and be easy-going.

Just ABC. Always Be Considerate. Shower there immediately, or show up freshly showered. Never insist on having your ass licked even if you showered, because you almost certainly didn’t wash thoroughly enough for that. If anything seems off—namely your provider’s behavior—you’re not obligated to stay. I’ve talked a lot about the other party so far, but your safety and comfort are also important. So do what you need to do to protect yourself without being so paranoid that you insult or freak out the person you’re with. (Obsessively asking them how often they get STI tested? Dick move. Constantly checking the windows to the hotel parking lot for cop cars? Terrifying.) If you bail on an appointment last-minute, it will minimize drama if you leave half or all of what they’re owed for the time you scheduled. If you adopt an attitude of respectful friendship (or at least friendly acquaintanceship) toward the person you’re hiring, you’re setting yourself up for a good time. A little empathy and practicality will go a long way towards ensuring both of you get what you deserve out of the encounter.


Charlotte Shane is a writer living in New York and tweeting from @charoshane. Her TinyLetter is famous among those who love emotions and long emails.

Illustration by Tara Jacoby.

Adequate Man is Deadspin’s new self-improvement blog, dedicated to making you just good enough at everything. Suggestions for future topics are welcome below.

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