I thought I knew it all, but I quickly realized we learn little about our own pleasure

by Kaitlin Fontana, Chatelaine

“You go up and down, and stuff comes out,” Luna Matatas says to the camera while stroking a dildo that looks like a very realistic penis. Matatas is a Toronto-based sex and pleasure educator, and she’s talking about how most people think about hand jobs. She will spend the next hour disabusing me of that notion. Or rather, deepening it: Hand jobs are not just about going up and down, and stuff coming out. They’re not just about foreplay, or at least they don’t have to be. And they’re not just about making someone with a penis have an orgasm, though they can be. They’re also—maybe especially—about the person giving the hand job. Seriously.

I’m watching Matatas’ “10 Tips for Hotter Handjobs” tutorial, which lives on the pleasure-education website O.school, and it’s much more than the video version of a Cosmo headline. It’s part instruction, part commiseration, part therapy. I will laugh. I will be humbled. I will find my erotic centre in the act of a hand job.

O.school is an online, sex-positive sex-ed platform that includes more than 300 videos (and dozens of articles) and could best be described as a thorough post-secondary education in the arts and acts of pleasure, including biology, psychology and philosophy. O.school was founded in 2017 by Andrea Barrica, a queer woman who had spent seven years working in San Francisco’s start-up scene and who raised more than US$1 million from investors to launch the site. It has since amassed a significant video library on topics as varied as choosing a dildo, dating after divorce, healing from sexual trauma and putting stuff in your butt (among many other subjects). All tutorials are taught by experienced instructors (a.k.a. “pleasure professionals”) who have been vetted by Barrica and her team, including medical professionals, sex educators and counsellors. Did I mention the site’s offerings are free?

There is a sizable gap between the sparse sex ed of youth and the experiential sex-ed of adulthood, and gaps always threaten to turn into vacuums if unfilled. The sex ed most of us get is about the drawbacks of sex—scary all-caps phrases: UNWANTED PREGNANCY! DISEASE! DEATH! A BAD REPUTATION! But what if we had also been taught about sex’s vast landscape of pleasures?

How much time would we have saved ourselves? How much would we have gained? What would our sexual selves be like now if we had spent as much time learning that the clitoris has 8,000 nerve endings as we did learning about chlamydia?

Quite simply: O.school is online sex school, with a focus on the pleasure you derive from sex as opposed to its potential dangers. And it’s unlike anything else that currently exists in the realm of adult sexual education.

In the 1999 Alexander Payne film Election, high school senior Tracy Flick, played by Reese Witherspoon, is an overachieving, pushy candidate for student council president with a profusion of extracurriculars.

In 1999, I was 16. I was student council president. And president of the drama club. I had a key to the school, as Tracy does. But there was an important distinction. In Election, Tracy is f-cking her math teacher (and, she thinks, is in love with him). I wasn’t f-cking anyone…yet. Except myself, and barely. In the dark living room, under a blanket, to Scully and/or Mulder, on Sundays between 9 and 10 p.m. Mountain Standard Time, only.

Twenty years later and I’m still Tracy Flick-ish, but in another way: I am the Tracy Flick of Sex (Tracy F-ck? Sorry). I’m sexually smart, capable, capacious; I make plans and schedules. I get up early to do it. I stay up late. I pack a sensible bag. I do it with many, many people (see my series on non-monogamy). I am extracurricularly dedicated to the pursuit of carnal knowledge (by day, I am a writer and director of TV and lm). I am borderline arrogant about my level of dedication. I am proudly slutty, I know it, and so will you.

So when I stumbled across O.school while on an Internet deep dive about squirting (as one does), I thought it was a cool idea that I didn’t need. What could the Tracy Flick of Sex have to learn from an online sex school? As it turns out, more than I might have thought—and it made me realize that most adult women could benefit from some sexual re-education.

I grew up in the public school system of the 1990s. Sex ed amounted to a few hours, divided by binary gender, in a beige classroom. Mine was taught by a well-meaning but deeply desexualized public health nurse who coughed with Freudian realization when one of the projector slides said “Pubic Health Nurse” under her name.

Because of videos shown in my grade 7 classroom, I knew how my period worked with clinical accuracy; I didn’t know the joys of period sex until I started having it.

Enter O. school.

“If you go to Reddit [for sex ed], it can be abusive. On YouTube, there’s millions of videos but they’re not curated,” says Barrica, who grew up in a Filipino Catholic home and is a victim not just anemic sex ed but abstinence-based obliteration. “I got the fear-based, shame-based stuff,” she says. “You’re this perfect white flower. And when you have sex, you mash the flower, and you’re never going to be the same.” Barrica started O.school to close the gap that she herself faced.

What Barrica and her team have done is not revelatory on its face: Other sex- and pleasure-ed sites exist, though most favour articles over video content. OMGyes, another California-based start-up, which launched with a lot of fanfare in 2015, is the only close analogue to O.school in terms of extensive video content. It uses anecdotal, direct-to-camera interviews with women about their own first-hand experiences of pleasure as a form of education-by-conversation. This can be informative, certainly, but it also means you’re only hearing from one woman—who is not a pleasure educator—about why she specifically likes what she likes.

OMGyes also features some explicit content in the form of demonstrations, which show real women’s anatomy in close-up; it also offers a touch-screen stimulator so you can test out the methods of pleasure you hear women describing on an onscreen vulva. However, OMGyes costs $59 per season of content, and it’s surprisingly heteronormative and relationship-centric for 2019—we’re largely talking about straight, cis, committed sex here.

O.school is different. To start, it’s “exclusively inclusive,” says Robin Milhausen, a Canadian sexologist who has no affiliation with the site. “It’s totally inclusive related to sexual and gender identities. And it’s trauma-informed, taking into account people’s experiences.” This means that O.school has taken pains to exclude nudity and to present information in a way that doesn’t assume everyone is approaching pleasure ed from a place of complete acceptance (for example, if someone has been raped and is trying to rediscover their body, certain depictions of frank sex, or nudity, can be triggering).

O.school is also made for everyone to learn about their own pleasure on their own terms, from a basis of science, no matter their relationship type, body or gender. Or, importantly, age. “A lot of the YouTube sex educators are younger,” says Milhausen. At O.school, on the other hand, many instructors appear to be in at least their 30s, which may be more appealing to women in that demographic and beyond.

Milhausen, who considers sex a matter of academic importance even more than I do, is truly impressed by the site. “There’s never been a better time to be a sexual being, because there’s never been more information available, for free, and it’s so accessible. There’s a community for everyone,” she says, “so sometimes the amount of information can be overwhelming, which is why a website like O.school—which has really strong, vetted information—is helpful.”

As a brand, O.school wants to be the first place you think to look when you wonder about pleasure, because you trust its teachers to steer you right, just as you know to search, say, IMDb for factual information about films (such as what year Election came out). Barrica’s eventual goal is to provide pleasure education to a billion people; it’s a lofty aim, and she won’t divulge the number of current O.school users to put that in perspective. Right now, however, she just wants to make space for quality, zero-judgment pleasure-not-just-sex ed.

Indeed, while watching O.school videos like “Buttstravaganza,” I felt gratitude that the fledgling Flicks of today could take ownership and power over their own bodies. For me, it was a lot of teenage, pre-Internet fumbling toward ecstasy (the first time I came on my own fingers, my horror was Carrie-bleeding-in-the-shower level intense). I didn’t really learn about my own body and sexuality until I started meeting cool, queer, sex-positive pals in university for whom sexuality was more than just f-cking—it was political, radical, about bodily autonomy. It’s no coincidence that that’s what O.school’s instructors come across as: Trusted friends, who know not just their own bodies but many other people’s bodies as well. They embrace the empowerment that comes from sharing knowledge within and outside of their communities.

Most importantly, it’s funny and fun, like a great conversation with a very smart friend. I often fancy myself that smart friend. But I needed to be sure. Hence, “10 Tips for Hotter Handjobs,” my gateway video.

I watched as Matatas lifted the dildo up and coated it in silicone-based lube (best for prolonged contact, as it isn’t absorbed as quickly as water-based). She gripped the shaft with her left hand and, with a smile, held the fingers of her right hand on the tip of the dildo and drew them downward. Her fingers looked like the legs of a jellyfish stretching down to push off—if a jellyfish was hanging out on a giant sea penis. In other words, this technique looked ridiculous. But, she said, the jellyfish was an amazing sensation for the ultra-sensitive penis head.

My Flickian brain couldn’t deal. “That move?” I balked. I was dubious. So, like any good student, I eld-tested it.

“I am doing this for research,” I told my lab partner, who I will call V. “Of course,” he said. I gripped his lubed-up shaft with my left hand and drew my right fingers downward, looking V in the eyes (another top-10 tip, by the way). His eyes rolled back slightly, and he made a sound that told me I was on to something.

Finding: The jellyfish move is legit. I stopped to record said finding in my notebook. (JK, I saw the experiment through to its conclusion. I’m dedicated.)

“I think silliness is sexy,” says Matatas, who has more than a decade of pleasure-ed experience, in Canada and elsewhere. She started as a public health educator, branching out into pleasure ed when she saw that none of the sexual health education she was giving addressed it, even though everyone she met and talked to was seeking it. She came up with the jellyfish on the fly while being playful with a partner. “We should practise curiosity, communication and creativity” when it comes to sex, Matatas asserts. Aside from being a pathway to discovery, employing these qualities is also how we get over performance anxiety.

In contrast with the seriousness of traditional sex ed, pleasure ed acknowledges that sex can exist beyond reproduction for the pursuit of fun and connection with yourself and others. Its teachers reflect that: They’re happy, self-actualized people who have chosen their profession because they love feeling good. They know, and teach, that playfulness, being present and allowing for mistakes makes sex better. “It adds to the vulnerability,” Matatas says.

And while learning from seasoned pros like Matatas—who also leads in-person workshops on topics like “Group Sex 101” and “Banishing Bedroom Boredom” in Toronto—can feel intimidating, that’s where the one-on-one factor of the Internet comes in. “It provides safety and the ability to suss something out in private, away from our sex-negative culture,” she says. Milhausen echoes that sentiment, although she also recommends books. (“Middle-aged people grew up getting information from books,” she says, “so it’s often more comfortable than trying to wade through the Internet.”) And learning tricks from sexually fluent, diverse humans—according to Barrica, half of O.school’s instructors are people of colour, more than 70 percent are queer and more than 15 percent are trans or non-gender-conforming—doesn’t mean you have to be one yourself, or even a non-monogamous Tracy F-ck.

If you’re intimidated by the cool/queer aspect, consider this: Would you trust a carpenter who only owns Ikea furniture, or an agoraphobic travel agent? Likely not. So why would you want pleasure education from someone with a less dynamic prism of sexual understanding and ability? “Women may feel more comfortable learning from somebody who looks like themselves,” says Milhausen, “but I want all of us to step outside that and learn about our sexuality from people who have amazing knowledge and experience.”

And while the demographic that flocks to O.school tends to be younger (20s to early 30s), some of the most engaged and vocal users are, anecdotally, women in their 30s to 50s. That’s no surprise to Milhausen. “Mid-life is a time when we start to reflect on all different parts of our life,” she says. “How do we feel about the job we’re in, how do we feel about the relationship we’re in, how do we feel about our bodies and our health? It’s a common time to look inward and think about your sexuality.” Matatas also sees a lot of thirty- to fifty-something women in her in-person classes, in part because they’re in a “few f-cks left to give” phase of their lives, as she puts it. Along this line, Barrica tells me that one of O.school’s users, a woman in her 70s, had her best orgasm ever after watching one of their videos.

After watching several O.school videos myself, I realize the site’s most important lessons are more philosophical than technical. What choice most empowers you sexually? What makes you happiest? How do you have that conversation with yourself? For this Tracy Flick, these were the true aha moments (aside from the jellyfish thing). Good sex is not about skill, but about discovery; not what you know, but how much you can play, experiment and enjoy yourself while seeking knowledge. Watching O.school’s videos will teach you new techniques, but like any good class, they will do something better than that: They’ll teach you how to think differently. To see yourself not just as a body but also as a brain and heart, in pleasure-seeking terms.

And furthermore, they’ll remind you that the best students are the ones who never stop learning. I am no longer a 16-year-old control freak furtively masturbating to David Duchovny’s smirk in the dark, and the sexual self I am now will continue to evolve.

Cut to: The slut formerly known as the Tracy Flick of Sex. She watches “F-ck Lube Shame: Why You Need It.” She takes notes on water- vs. silicone-based, liquid vs. gel vs. cream. She nods vigorously when instructor Jess Melendez—a frank and friendly sex-toy expert with a winning smile and an admirable eyebrow game—asserts that lube shame stems from patriarchal notions of what our bodies are supposed to do when sexually excited. “I’m here to tell you that there is nothing wrong with your body. If you wanna use lubricant, that is super rad, okay?”

Then our Former Flick learns, for the first time, that “buttholes are super thirsty,” and so a liquid lube is not best for anal. She nods studiously. She goes to her local sex shop and buys new gel lube, for she has more experimenting to do, more learning.

And when learning involves dildos, then school ain’t bad at all.

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