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Bend Over, Bro: The Men Who Love Pegging

With one sex toy company proclaiming 2016 as the year that pegging takes off, it's time to re-evaluate the benefits of telling your boyfriend to bend over.
Illustration by Katherine Killeffer

This is the most vulnerable I have been in a long time. Flat on my back, pillow under my ass, legs akimbo; my ankles are so close to my eyes I can inspect the architecture of my bones. And then she's on me, all hot breath and readiness, a portrait of cockiness and control.

"Do you want my dick?" she asks, leaning over me, prodding at my most intimate space with something slippery and cold.

"Yes," I whimper. "I do…" and I close my eyes and think of Charlie Glickman.

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The year is 2011. Japan has suffered its biggest earthquake in over a century, the Arab Spring is tearing up the Middle East and the English riots are lighting up cities like Guy Fawkes. It's pretty safe to say the world is going to hell – and at this juncture, to suggest that the answer to stopping this big ball of dirt we call home death-sliding right down the pan can be found at the tip of a dildo is, well, borderline delusional. Unless you're sex & relationship coach Charlie Glickman PhD, that is.

Of course, when Glickman penned the blog post 'How Pegging Can Save The World' his thoughts were far from the above. Sadly, he wasn't saying the best way to patch up world peace was to have soldiers and cops pull on a pair of Triple Penetrator Dildo Pants. In fact, Glickman was advocating role reversal in the bedroom, as a way of offering straight men an insight—"when sex is about catching rather than pitching"—into their female partner's pleasure, potential discomfort and vulnerability. It's something that I can certainly attest to.

"[Pegging] won't make communication miraculously easy and it won't fix everything about sexism or gender-based inequities [but] what it can do (besides being lots of fun) is help people develop empathy, compassion, and understanding for their partners," he wrote. "And the more of that we have in the world, the better."

Five years on and Glickman's prophecy is inching (six, if you care to know) ever closer, especially if we take into account mainstream references in hit comedy Broad City as well as new year blockbuster Deadpool. Of course, pegging is nothing new. The 1976 Golden Age of Porn classic The Opening of Misty Beethoven featured a pegging scene; and the act emerged again, in bisexual and queer circles at least, in Carol Queen's 1998 sex ed video Bend Over Boyfriend, culminating with Dan Savage coining the term "peg" for the first time in 2001 after a vote on his blog, Savage Love ("bob," named after Queen's vid, was also in the running).

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Abbi considers pegging her date. Still via Broad City

Mainstream depictions on Peep Show (2005), Weeds (2006) and Dirt (2007) followed, but whereas these portrayals involved an element of shame or "putting something up a man's ass WTF" weirdness, Broad City and Deadpool celebrate pegging in a completely non-judgemental way. In the former, Abbi rises to the challenge (with a bit of wall twerking enthusiasm from Ilana) to peg her super-keen date and in the latter, pegging is thrown into the middle of sex montage like it's no big deal; it just happens.

Erotic content is also seeing a pegging boom that defies demographics. Extreme hardcore producers Evil Angel, which boasts a 99 percent male viewership, tell me that their Strap Some Boyz series (link NSFW) has grown in popularity in recent years. Couple-friendly luxury sex toy brand LELO tagged 2016 as the year pegging really takes off, after the sales of male "anal pleasure objects" increased by 200 percent in 2015. As LELO point out in their yearly trends press release, "the deepening knowledge of gender expressions and sexual identities" as well as "the language of non-binary genders" are freeing people, particularly men, from the conventional confines of sexual identity, gender, and pleasure.

**Read More: Inside a Factory Making Male *Sex* Dolls for Women**

Dr Chauntelle Tibbals, sociologist and author of Exposure: A Sociologist Explores Sex, Society, and Adult Entertainment concurs, telling me that such increasing acceptance of 'taboo' sexual play that destabilizes gender norms may point to wider social ideals about sex. "In the past 10 years we have seen such an explosion in public gender awareness, understanding, and a willingness to explore boundaries and the social norms that contributed to the construction of said boundaries," she says. "It's only logical that pegging is now something we see in a comic book Hollywood film (Deadpool)."

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r/pegging is a subreddit for pegging enthusiasts. Any of the 34,000 plus redditors post on everything from harness advice to "we did it!" confirmation images (link NSFW). I spoke to two of its members to find out why they got into pegging and the impact it's had on their sex lives. Drew Harris* is an American construction worker. We exchanged messages a few days after he'd first been pegged. "My wife thought the macho man/tough guy attitude was something she wanted in her life [but the expectation] was not making me happy as that isn't how I normally am and she wasn't very happy either," he told me.

A sample post from r/pegging. Screencap via Reddit

"When we switched roles [with his wife as the dominant sexual partner and he as the submissive] everything pretty much felt right for both of us." I also messaged 'getsome187' who has introduced pegging into his last four relationships. "Some of the girls would wonder if I was bisexual or felt inadequate by wearing a fake cock but they got over it," he said. "It's like I'm sharing something intimate with them and it brings us closer because there is a kind of vulnerability to it."

'M', who I messaged on the kink social network Fetlife, and who has pegged two of her male partners, agrees. "Sometimes it can be a really intimate moment, at other times it can be dominating and filthy," she says. "I definitely think it can bring you closer though. It's nice when someone trusts you with their vulnerability."

It seems that this shared knowledge of vulnerability stems from experiencing two sides of the same coin: that of penetration. "For a man who has never received anal penetration, sex happens outside the body," Glickman told me in an email. "So while men might intellectually understand the need for warm-up before penetration, it's not the same thing as experiencing it. There's a different perspective that comes from knowing on a somatic level and I've talked with lots of women who say that exploring pegging has given their male partners a more attuned, patient approach to intercourse."

Can pegging save the world? It certainly turned mine on its head. In the wake of pegging, instead of feeling emasculated, I felt empowered. All the social norms of being a straight man in the bedroom (I must be the penetrator, I must be in charge) had literally been fucked into insignificance.

"I think that any time someone is penetrating their partner, whether with a cock or a strap on, it's about pleasure," adult star and director of Guide to Wicked Sex: Anal Play for Men Jessica Drake told me in an email. "Everyone should try it once."