THAT'S SO NAUGHTY!
THE ROLE-PLAYING GUIDE THAT WILL CHANGE YOUR SEX LIFE
Most people who know what I do for a living would expect my closet to be stocked with sexy getups—a naughty nurse costume, a frilly maid’s uniform, a too-tight secretary outfit, you name it. I seem on the surface to be the sort of woman who would be an expert at role-playing, that sexy game where a couple take on new identities to fulfill a naughty fantasy. After all, I write about sex for a living, and I’ve covered everything from hookup culture to pornography. Surely, a sexpert like myself would have tried her hand at some erotic theater, right?
In fact, I’ve never come even remotely close to playing makebelieve in the bedroom. The truth is, I’ve been too scared! It’s challenging enough to feel comfortable being yourself during sex, let alone someone else. Plus, what if my partner found my fantasy freaky? What if I bungled the dialogue? What if I started giggling... or worse, what if he started laughing at me? All these anxieties have kept me from giving it a try, until now. There’s never been a safer time to confront my fears. I’ve been in a loving relationship with my fiancé, Christopher, for more than a year now. He wouldn’t laugh at my desires, even if they included something kinky like dressing up as stuffed animals (this really is a thing, and it does it for some people—just do a Google
search for furry). And then there’s the fact that I’m tired of feeling like a prude whenever I hear friends dish about their role-playing adventures.
So, thinking now or never, I decided to jump right in... but not without some help. I asked sex experts, along with everyday women, for their tips on how a newbie like myself should get started. Here’s their advice and how I put it to the test.
NO. 1 First, Figure Out Your Fantasy
If you already have a sexy scenario in mind, you can skip ahead... show-offs! But for beginners, Laurie Watson, a sex therapist in North Carolina, says a trick that always works for her clients is heading to a hotel bar and pretending to be strangers picking each other up for the first time—just make sure one of you reserves a room ahead of time. Then, there are always classic power dynamics to fall back on, like cop and criminal or doctor and patient—take your pick.
Rose M, a 28-year-old from Vancouver, British Columbia, who works at a luxury-car dealership, tells me her favourite scenario is that of the naughty housekeeper (she suggests going with the obvious by bending over a little too far in your frilly black-and-white skirt to dust something). “I actually used to be a housekeeper when I was younger, and it was something I fantasised about but never brought to fruition,” she says. “Maybe that’s why I like it now, because it hits close to home!” And yes, many of these scenarios— housekeeper, hot professor—sound cliché, like something found in the cheesiest of cheesy porn, but that’s because they work! And like Rose, you can (and should) turn to past experiences for inspiration. Maybe you were a swimmer as a teenager and always wanted to give that other cute swimmer mouth-to-mouth... it’s definitely hotter when you’re living a fantasy you always wished would happen.
NO. 2 Now Share It
Ian Kerner, Ph.D., a sex therapist in Manhattan, says that “all good roleplaying starts with sharing your fantasy.” Easier said than done, Kerner! What if your partner thinks that you need him to take on a different persona in order to get turned on or that your wandering mind means you have a wandering eye too? Well, Kerner has a trick for that— bring up your fantasy as a compliment. Say, “I had this really hot dream about you last night. You were a professor and I was your student...” By including your partner from the get-go, you make it clear that your fantasy is just that—and no, you don’t really want to sleep with your yoga trainer. Once you’ve brought up the what, it’s time to explain the why—and yes, sorry, this part is non-negotiable! Telling your partner that you have a doctor fantasy isn’t enough—through no fault of your partner’s, you could find yourself in the company of Dr. McCreepy when you were hoping for Dr. Hot and Stoic. If you want to have a truly sexy experience, you have to describe what it is about that particular scenario that gets you going (the better you explain your fantasy, the more likely it is to come to life in a way that gets you off rather than makes you feel weird). “Maybe a doctor is sexy to you because he’s in control but generally clinical and sort of cold, so the idea of roiling his passion through your desirability is sexy,” says Kerner.
Okay, sure, but how to describe this without feeling foolish? Erin T., a 30-year-old attorney from Washington, D.C., says, “I actually think it’s really hot to lie in bed and talk about fantasies and turn-ons,” she says. “But another thing my boyfriend
and I have done is e-mail fantasies back and forth—I send him one, he sends me one. We don’t see each other every day, and doing that builds excitement and is basically e-mail foreplay for our next visit.” Believe it or not, they have a shared Google Docs spreadsheet that details all the scenarios they want to try. These two go straight to the head of the roleplaying class—naughty valedictorians!
NO. 3 Establish Some Limits
Before losing yourself in a character, be sure to let your partner know what you’re comfortable doing and what’s going too far, especially if you’re experimenting with a punishment scenario. If you get caught engaged in espionage (you dirty spy, you!), do you want a verbal reaming or a light spanking on the butt? Same goes for when you’re playing a role that triggers an emotional response. Let your partner know your limits, and establish a safe word that’ll bring the action to a halt the second you’re uncomfortable.
NO. 4 Set the Scene
A wardrobe change isn’t mandatory for role-playing, but it can definitely add to the fun. For some women, a wig— going from brunette to red or from straight to curly—can really help you get into the idea of a new identity, says Kerner. The same goes for dressing up your environment. You probably won’t be able to transform your bedroom completely into a classroom for a hot-for-teacher scenario, but wheeling in a chalkboard or desk will go a long way.
Erin T. is a French girl based in Delhi, and likes to wear classic lingerie and high heels to get into a 1950s housewife role. “I take off his shoes, rub his shoulders, fix him a martini, go down on him while he’s drinking it, and the next thing I know, my high heels are up around his ears,” she says. Think Mad Men, only sexier (yes, it’s possible). She recommends considering what type of man or woman in uniform turns you on. “If you’ve always thought cops were hot, you can get handcuffs and a fake police badge for less than ` 1,000,” she says. Just don’t lose the key!
NO. 5 Don’t Forget to Have Fun
After all this planning, it might feel like you’re about to audition for a role on Broadway, but don’t get caught up in the theatrics of it all—the aim is to feel turned on, not win an Oscar. If you break character and burst into laughter, don’t sweat it and move on, says pretty much everyone I talked to. “We were all good at playing pretend at one point in our lives—think back to your childhood and playing house,” says Monika D., a 25-year-old web developer from Mumbai. “Kids know they’re making up stuff, but they don’t care.” At a certain age, we’re supposed to put away the imaginary worlds and stop playing make-believe. The beauty of role-playing is that you don’t have to give that up (how deliciously disobedient of you).
NO. 6 Do It Already
Okay, back to my first time taking this role- playing stuff for a whirl. Despite my lack of experience, I’m pervy enough to have already had a scenario in mind: a visit to a masseur with wandering hands. I figured that this was a pretty low-stakes proposition— worst case, I’d feel silly but get a great massage from my fiancé; best case, I’d get some knots worked out and fulfill a longtime fantasy. Win-win, right?
Following the rules above, I tried to explain to Christopher what it was about the massage scenario that got me so hot—mostly the idea that I could inspire enough lust in a massage therapist that he would want to cop a feel. (Look, fantasies are rarely modest, okay?) I described specific images that came to mind: “Maybe you could slowly work your way up my inner thigh and, you know, ‘accidentally’ brush between my legs,” I told him. Christopher let out an intrigued “Mmm” and immediately grabbed at my leg. Turns out, the planning itself can serve as foreplay— way to kill two birds with one hot-massage stone.
When we settled on the scenario, the wardrobe was easy. Christopher wore a simple white tee shirt and
lounge pants, the uniform of seemingly every masseur. I wore a tank top and jeans, knowing that I wouldn’t be clothed for long. The dialogue practically came pre-written. We’d both had our share of professional rubdowns and knew the script well. The greatest challenge was how to turn our home into a spa, especially without a massage table. Christopher had never tried role-playing before either, but he had taken it as a challenge and told me he had it under control. I stepped onto our balcony, the ‘waiting room’, while Christopher readied things downstairs. He came out to greet me, straight-faced: “Tracy? Hi, I’ll be your massage therapist today.” I couldn’t help but laugh as I shook his hand, but I remembered what my experts had told me about rolling with the inevitable giggles and quickly recovered.
He walked me downstairs, where he had turned our kitchen island into a massage table by laying down a yoga mat and layer upon layer of blankets. Believe it or not, it looked legit. As newage music swelled softly in the background and candles flickered on our granite countertop, he calmly instructed me to take off my clothes and lie facedown under a sheet while he went into the other room to wait for me.
My ‘masseur’ soon returned and broke out some intoxicating mint-scented oil. My giggles had passed and getting into character proved easy—all I had to do was lie still, breathe deep, and let him rub me down. Such hard work! Every touch was filled with the electric possibility that his hand would stray under the sheet. Thankfully, it did... but only after much anticipation and teasing. There were plenty of opportunities for my pun-obsessed fiancé to have fun. As he ran his knuckles over a tight section of muscle, he purred in his best corny-porn voice: “You’re so knotty”. It was hilarious and hot, all at once. At one point, he reminded me
As He Ran His Knuckles Over a Tight Section Of Muscle, He Purred: ‘You’re So Knotty’. It Was Hilarious and Hot, All At once.
that I had ordered the full-body massage and took the sheet off entirely. I shyly asked, “Do you do this with your other clients?” He replied, “Never. You’re the first. I don’t know what’s come over me.” Soon, we were both naked, and he was helping me to ‘fully relax’.
I’ll spare you the explicit details, but I will say that if I could give his services a review, it’d be an enthusiastic five stars. Actually, that’s a total lie. I’d keep the secret of Mr Magic Fingers all to myself.
After all was said and done, and every muscle in my body had turned to Play-Doh, I realised that my roleplaying nervousness had been terribly misplaced. It wasn’t embarrassing, it was freeing, and it gave both of us permission to do things we wouldn’t have felt comfortable doing otherwise— fooling around on the kitchen table was the least of it. Christopher— usually the type to ask politely rather than order decisively—became delightfully assertive. For my part, I let go of my usual need to please and was able simply to relax and receive. I was a ‘paying’ customer, after all, and I was going to get my money’s worth! Don’t feel too bad for him though—he got a generous tip.
Afterwards, in a post-massage glow, we reviewed our first foray into role-playing. “That was awesome,” he said. “We’re definitely doing that again.” But next time, we’ve agreed to try out a new scenario: strangers picking up each other at a bar. Now we just have to find a local watering hole where the bartenders don’t already know our names.
You could play the smooth criminal…