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Dear Playboy Advisor: I Want to Be a Male Sugar Baby

The Playboy Advisor on sex work, spit, choking and hooking up with professors

I’m a recent college grad who has decided to make a life change: I want a sugar mama. I have an entry-level job and almost no disposable income, and I’d love to get a fixed allowance with minimal effort. I know these relationships are common and can be set up on various websites, but for a straight guy, is it as simple as creating a profile?—J.S., Cincinnati, Ohio

There’s no shame in using what your mama gave you to get yourself another mama, and there’s definitely no shame in being a kept man. So why aren’t more young men enlisting generous older dames to sponsor their checking accounts? Because nothing is free. While there are more avenues than ever before to explore a mutually beneficial arrangement with a stranger, expect to earn every Venmo transfer you hope to receive. These relationships involve a lot more than “minimal effort,” starting with the search for the right partner. Sugar, SugarD, Sudy and are the most popular apps and websites for facilitating transactional relationships. As with any online dating, more apps mean more potential partners who will request photos and ask screener questions (“What are you into? Are you dominant or submissive? How big is your penis?”) but ultimately waste your time by ghosting you.

Before creating an account, you’ll need to start thinking about sex differently. Transactional sex is not just about pleasure; it’s about focusing on her pleasure. Sugar mamas and daddies tend to be older, so you should hook up with an older woman beforehand if you haven’t already. Their pleasure points are different, as are their bodies. When you build your profile, clearly state your expectations. Spell out that you’re looking for a fixed allowance. There’s power in being direct.

And once you’ve set up a date, get cultured and groomed before seducing a sugar mama. It’s silly, but you need to spend money to make money. Invest in a tailored suit from a mid-market retailer like Bonobos or Suitsupply. Learn the basics of wine selection and dining at prestigious restaurants. Familiarize yourself with the best upscale bars in the city—somewhere you won’t be gawked at by other recent college grads. Ask your date questions, and be polite.

Finally, don’t undress in front of her before money has been discussed. As with any transaction, you need to negotiate. Don’t lowball yourself. Your tight body and sexual stamina are worth more to this woman than you may think. While you’re at it, consider devoting the same amount of time and energy to finding a better-paying job and securing your future. The only thing more satisfying than spending someone else’s money is spending your own.
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I like sex that involves a lot of spit, from kissing to oral. It’s hard to keep going with this fetish, though, once lube is introduced. Essentially, once a woman lubes me up, she won’t go down on me for the rest of the night. And some women prefer to use lube during intercourse versus me using my spit. Are there any pitfalls to telling female partners that mine is a spit-only bedroom?—T.L., Manchester, England 

Spit is sexy, but only in the right context and when there’s enough to go around. Swapping spit during a hardcore make-out session? Seductively spitting on your girl’s vagina before you push deep inside her? Sloppy, spit-soaked blow jobs? Yes, yes, yes! But even if a partner shares your fetish, what happens when your mouth runs dry and friction settles in? For example, the more alcohol, cannabis or recreational drugs you consume, the drier your mouth gets.

Unless you produce more saliva than the average person—enough to sustain multiple reapplications during a marathon fuck—it’s smart to keep a bottle of lube bedside. If the silky but synthetic quality of lube is what turns you off, try coconut oil as an organic alternative; just make sure to ask your partner first, as coconut oil upsets the pH levels in some women’s vaginas. Lube isn’t usually necessary for traditional intercourse, so I doubt your woman friend will complain if you go natural. If she does, tell her the sight of her slobbering all over you is a major turn-on. If that doesn’t do it for her, or if she automatically whips out her own travel-size K-Y Jelly before sex, she’s obviously not the right match for a saliva enthusiast like yourself. Whatever you do, do not proclaim your bedroom to be a spit-only zone. Making sex non-negotiable will turn off many women completely. Oh, and don’t even think about doing anal without lube. You want your bedroom looking like that spit-soaked sex scene between Rachel McAdams and Rachel Weisz in 2017’s Disobedience—not Deliverance.
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I started sleeping with my hot professor but didn’t know he was married—he doesn’t wear a wedding band because he’s in what he calls an “unconventional” relationship. I’ve since learned his wife also works at the university. I realize I’m just an escape from his boring, middle-aged life and I want to end it, but the semester is only midway through. What’s a respectable exit plan for a girl who did something unrespectable?—M.P., San Diego, California

or a man who claims to be unconventional, he isn’t very original. As for affairs with college professors, many of us have been there. Such relations are richly appealing to students: They’re taboo, they make us doe-eyed dimwits feel special and they ensure lectures are more fun. But as you’ve learned, almost every illicit affair comes with an expiration date. Props to you for recognizing how pathetic your professor is, not only for cheating on his wife (unless his “unconventional” marriage expressly permits multiple sex partners) but for using his position as a superior to get laid. If anyone is undeserving of respect here, it’s him.

Now let’s talk exit strategy. When I was an undergrad, my plan included wearing oversize flannel pajamas to class to send the message that sexy time had ceased. But you’re better than that, so here’s some advice from a woman who graduated college when you were still learning about the birds and the bees: Take the mature route and tell him, via text or in person, that you know he’s married and you can’t continue this affair. Block him on social media to make it clear. Tell him you hope this won’t affect your class work. (I really hope you’re not taking an ethics class from him.) If it does, remember that you have the upper hand. He’s one vindictive grade away from sinking his pension—and probably his marriage.
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I’ve found a lot of women like, and even request, to be choked during sex—but not slapped. I got in trouble recently for slapping my girlfriend while fucking her. We usually fuck aggressively, so now I’m confused. What’s the difference in eroticism between choking and slapping?—A.W., Castle Rock, Colorado

Here’s some general advice: Nothing makes much sense in life, especially the nuances of carnal desire. Having said that, choking and slapping are in the same category of Abusive Fetishes That Require Consent, but that’s where the similarities end. You’re right that many women like to be choked during sex, and most aren’t masochists. It’s often a turn-on to relinquish control to another human, especially one who is hovering over your pulsing body. A lot of women enjoy coital slapping so vigorous that their cheeks sting, their ears ring and they see stars. I know this to be true because I’m one of those women, but I also know I’m in the minority.

Choking, or the more extreme erotic asphyxiation, is commonplace these days. The dynamics equate to a titillating dominant-submissive power play. There’s also the physical effect: When blood flow to your brain is restricted, the release of adrenaline and endorphins causes a dizzying rush. Getting slapped may feel more like punishment, and that sudden stimulus activates dopamine receptors in some women. For others, it just feels like pure physical abuse. When it comes to pleasure, we’re all wired differently. As for your partner’s preferences, it’s not your job to ask her why; your job is to ask yourself if you can deliver without compromising your own pleasure or crossing her lines. Doing either could eliminate the eroticism of your sexual dynamic completely.

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So You’re Into Choking...

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