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I Hired a Coach to Watch Me Have Sex

Because roses for Valentine's Day are cliché.

Alex, my girlfriend of 14 months, is unmoved by all holidays, but the lion's share of her indifference is reserved for Valentine's Day. While I shudder at the thought of sitting down to a prix fixe menu at a white tablecloth restaurant or any of the other set-piece activities we're urged to take part in to commemorate a dissident Roman priest from the third century, I've somehow also managed to feel some vestigial guilt when, in the past, I've ignored the day completely.

I've since decided that if I'm going to do Valentine's Day, it needs to be commemorated in a way that is bespoke, authentic, practical, irreverent, and ironic. That's why Kenneth Play has braved the cold to come to my apartment. At my request, he's here to teach Alex and me how to fuck each other better. What better way to celebrate the day—and thumb our noses at an increasingly prudish and uneducated America—than with a round of advanced sex ed?

As luck would have it, Alex and I both feel and agree that we do a top-notch job already, but it seemed foolhardy not to explore what a highly esteemed professional sex coach could do for us. Not least because I've personally witnessed Kenneth transform a room full of non-squirting women into squirters and their partners into female-ejaculation facilitators at one of his "PlayLabs," a group sex ed event he hosts every month or so. That particular scene became a fleshy, moaning, groaning, dancing fountain with people literally, then figuratively, gushing over the "sex hacks" the former fitness competitor imparted. What's on tap for Alex and me tonight is a Private PlayLab, which is ordinarily priced at a princely $1,000 for a three-hour session. Kenneth has offered us his counsel on the house. Some people have friends who'll fix their car or do their taxes gratis (especially if they then write an article about it). It's like that.

"I offer a no-questions-asked full refund if they don't think that their sex life isn't completely transformed by the session," he tells me. "But I haven't had to do that yet."

The logic that underpins the hands-on way Kenneth delivers his sex ed is clearly presented on his website:

"When you want to improve your yoga practice, you go to yoga class. When you want to learn how to cook, you spend some time exploring in the kitchen. I believe that what you want to change in the bedroom has to be changed in the bedroom." 

That made perfect sense to me. Alex was, as per usual, fully on board with a new adventure and Valentine's gift that promised to keep on giving. When Kenneth arrives at my apartment, he is holding a suitcase. He asks for a glass of water. Alex and I are drinking tequila on the rocks. She drank tequila the first time she had a threesome with two guys and since then it's become a sort of ritualized, perhaps Pavlovian prelude to varsity-level envelope pushing.

Kenneth begins by asking us to think about our sex life holistically.

"There are three main things that we have to consider here," he says. "Alex's sexuality, Grant's sexuality and the sexuality that you share as a couple. By understanding you more individually, we can begin to see how you can better complement each other in bed."

Alex talks about her previous experiences of being tied up and suspended, reiterating that that power exchange is more her thing than mine. Kenneth then asks her out why she finds it easier to orgasm via oral with me than with her previous partners.  

"From the very beginning he was just super enthusiastic about going down on me," she says. "That helped me let go of thoughts about him being bored or feeling obligated. I could relax and I could cum."   

To his horror Kenneth then learns that Alex loves nothing more than when our sweaty chests squeeze together and produce a fart sound, sending her into hysterical laughter and necessitating a five to ten minute break.

"Well I'm not sure what I can do with that," he says, taken aback. "But what I can see is that Grant, you love to service Alex, and Alex, you like to be submissive, so let's start with thinking about Grant being dominant as an act of service."

With that, Kenneth urges us to move into the bedroom and follows us, suitcase in hand. He tells us to get undressed. Getting naked in front of Kenneth doesn't feel particularly odd, but having a third party direct the action is novel. Kenneth opens his case, which is full of rope and a few floggers. With the skill and speed of a yachtsman, he begins trussing up my naked, blindfolded girlfriend like a roast, directing her to address me as "sir" as I give her instructions.

It takes a little while, but I eventually stop reminding myself that this sort of thing feels a bit silly, and take notice of how different Alex seems in this new context. It seems that the awareness she's devoting to sensation and instruction has shifted her into another gear.

"See how relaxed she is?" he asks once she's securely hogtied. "Alex isn't a submissive person in real life, but now that she's helpless, there's nothing she can do but focus on sensation."

While we're having sex, Kenneth is instructing us both in giving and receiving what he calls "tactile data." The goofiness and cackles that ordinarily punctuate the sex we have are absent, but with Kenneth's guidance, it feels like we've managed to unlock and access another level.

After around 90 minutes in this altered state, Alex asks Kenneth to give us a refresher in the sex hack he's become renowned for: making it rain. Kenneth pulls out a disposable pee pad from his case and places it beneath Alex's bottom, then hands me a black latex glove to put on. With skills honed during his years as a personal trainer, Kenneth then invites Alex to make the mind-muscle connection, use her Kegels to clench around then push against my inserted fingers.

Once Kenneth is satisfied that Alex knows how to manipulate these muscles, he then begins to school me on the way I apply pressure to the anterior wall of her vagina. Like a yoga teacher, he makes small ergonomic adjustments to our positioning. Within a minute, a squishy sound heralds the opening of her floodgates.

"She's about to squirt," he says confidently, and within seconds she does, each dramatic expulsion of liquid accompanied by a disconcertingly loud scream.

While Alex has squirted before, we hadn't quite figured out how to make it happen reliably and on cue. After a break, we attempt to make it happen again without any additional tutelage from Kenneth, and have enough success that another pee pad must be employed. Alex is barely done gushing when Kenneth gathers up his gear and moves to leave.

"I like to leave couples alone so that they can reconnect after a session," he says, and exits my apartment as quietly as he can.