My best friend's on-again, off-again boyfriend had just sent her one of those corny "Hey babe, what are you wearing?" messages. After getting her blessing to mess with him, I decided to beat this guy at his own game. So as a joke, with her by my side, I started sending her BF some sexy messages.
"I'm wearing pigtails and nothing else," I replied on her behalf. "What are you going to do about it?"
We spent an hour playing what amounted to an X-rated Choose Your Own Adventure. "OK, so he's pulling your hair while doing you doggie-style," I'd read from her phone. "Do you think we should go with 'Oh god, don't stop' or 'I'm flipping you over for a spanking, cowboy'"? We might have been laughing, but actually, it was pretty hot. OK, it was really hot. Obviously, the guy thought so too. Later that night, he called my friend long-distance for the first time in months and engaged in some pretty intense verbal stimulation.
That experience launched what has now become a full-blown side job as a sexting Cyrano de Bergerac. I've made it my mission to help jaded friends and strangers come out of their shell and embrace their sextuality. As luck would have it, I'm in a long-term relationship with an amazing man who "doesn't believe in texting" as a way to convey any sentiment (he's more analog, so our dirty deeds are usually conveyed either by smoke signals or letters sent by carrier pigeons). But that doesn't mean my gift should go to waste. ... It's my duty to pay my sextpertise forward. I've coached dozens of prominent, self-assured Don Juans (and Juanitas)—from New York Times journalists to Emmy-nominated actors, prominent magazine editors to Wall Street wunderkinds — and I've learned that there seems to be a direct correlation between having game in person and totally lacking it in the digital sphere.
When I tell people I'm a sextpert, most assume I'm talking about naked selfies and Snapchat. But while sexting can involve a quick pic, it's not a requirement (and it's safer without one). Sure, men are visually stimulated creatures, but a recent study revealed that women are twice as likely to sext as men are. So if you want to sext and you want the sexting to be sexy, you'll have to take charge. The trick is to send a clear signal that you want in on some virtual foreplay but to still make your message ambiguous enough that you can claim innocence of any dirty intentions. Here's how.
1. Paint a Snapchat With Your Words
So you get the sense that he's definitely down. Now what? I counsel against sending nudie pics. If it happened to Rihanna and Scarlett Johansson, it can happen to you! Plus, revenge porn is a big problem in this country, and you don't want some disgruntled ex exposing your boudoir shots all over the World Wide Web. Once you've been dating for a while, a naked pic or two may be fine as a memento. But for new sexters, just the thought of sex with you should be enough to get a guy hot and bothered. If your crush is bugging you to send pics, try painting a picture with words instead.
Guy: You're naked? PIXXX, please.
You: I would, but it might ruin my bid for the next mayoral campaign! Also, I just dropped my cell into this bubble bath I'm slipping into. Looks like I wasn't supposed to get the screen wet ...
(Note: Using the word wet in this context should be enough to get his mind racing. If it doesn't, his imagination might be malfunctioning.)
2. Cut the Cutesy Emoji
There are enough crossed signals when you're trying to convey emotions via text — why complicate it with a bunch of random icons? It's hard for anyone to get hot for a winking panda and a couple of pink hearts. Best-case scenario: He thinks you're doing an impression of Shoshanna from Girls. Worst? You remind him of his 6-year-old cousin. So cut the cutesy stuff, and keep this conversation adults-only. And if you find yourself overusing emoticons, follow my lead.
Guy: I give great back massages ;-)
You: :-) ;-) :-p
You: Sorry, just got a little overexcited by your semicolon.
3. Let Your Freak Fantasy Flag Fly
I find that the old trick to combat stage fright works doubly well for sexting. I just imagine the recipient in his underwear. And instead of the cute guy who asked for your number at the bar, you're texting with Ryan Gosling in Drive. Or Mr. Darcy. Eric from True Blood. (Whatever gets you going.) The fun part of sexting is to be aggressive, not passive, so don't worry about what a "nice guy" would think. Believe me, even the nicest guys appreciate some naughty. Need a reference point? Turn to an inside joke between the two of you, like how obsessed you are with Game of Thrones. Just play it confident and direct the convo. He'll take the hint.
Guy: You look so hot naked.
You: I look even hotter when I'm wearing nothing but my white robes, surrounded by my pet dragons.
Guy: Is that from GOT? Will you marry me?
You: Dracarys!!
4. Figure Out Your Sext Goals
I once spent two hours at a late-night after-party coaching a TV actor as he tried to phone-seduce a woman he'd recently slept with. Their messages were getting pretty hot and heavy, but we were also hitting the 3 a.m. mark and their banter showed no signs of slowing down. Sure enough, come 4 a.m., this lady was under the mistaken impression that the guy wanted to meet up for a repeat performance at his apartment. By then, he was too tired to continue the hanky-panky IRL. Extracting himself from the situation wasn't pleasant.
Her: I can be at your house in 20 minutes.
Him: Um, actually, I have to get up early tomorrow. Want to take a rain check for next weekend?
Her: I have to go out of town, it's my Nana's birthday.
Him: :-(
The girl felt rejected and misled, and he never heard from her again. The lesson? Don't dive into the digital dance of depravity without first deciding what you want the end result to be. Do you want to meet up that night for some nooky? Just looking for a sext buddy? It's all good, but having a clear idea of what you want to get out of the experience makes it easier to set boundaries and avoid that awkward 4 a.m. rejection. Let's try again.
Guy: Wow, you can really put your legs behind your head? When can I see this? U busy right now?
You: Actually, it's going to take me a while to untangle. Tomorrow? I can show you all the tricks I learned that summer interning at Cirque du Soleil ...
OK, you're in control; you've set the scene. And if I've done my job right, your texting fingers have a busy night ahead.
Drew Grant is a staff writer for the New York Observer.
This article was originally published as "I Am the Sext Whisperer" in the May 2014 issue of Cosmopolitan. Click here to get the issue in the iTunes store!
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Photo credit: Studio D
