If You Want a More Thoughtful Boyfriend, Try Pegging Him

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Want to make straight men better in bed — and better feminist allies? The path may be simple: fuck them up the ass. According to one brand new book, the path to making men more compassionate, appreciative and playful may be straight through their butts.

In The Ultimate Guide to Prostate Pleasure: Erotic Exploration for Men and Their Partners, Charlie Glickman and Aislinn Emirzian make the case that straight "men who get into anal penetration are among the most secure in their masculinity: because they've examined themselves, faced their fears." Despite the title of the book, the authors make the case that the payoff for prostate play — specifically by a woman using a dildo or other toy — isn't just pleasure. It's liberation from the masculine straitjacket, with happy consequences that extend well outside the bedroom.

In a deeply misogynistic culture, there are few greater fears with which men are raised than the fear of being labeled as someone who acts like a woman, allowing himself to be penetrated. There's a reason why insults like "pussy" and "cunt," when thrown at men, are so much more inflammatory than "dick" or "prick." Reducing a man to what he already possesses is mildly insulting at best. Calling him a female body part that men penetrate with their penises: fighting words. (Never mind that many women never have heterosexual vaginal or anal intercourse; our cultural myths suggest that all do, or at least should.) In his Myth of the Modern Homosexual, historian and cultural theorist Rictor Norton explains that the term "asshole" developed as a homophobic (and thus woman-hating) slur; while women and men both have rectums, a man who is anally penetrated has lost his manhood, and thus become feminized. Norton implies that this is why we don't often call women assholes: the word has no particular power to wound someone who isn't anxious about preserving masculine status.

Glickman and Emirzian acknowledge that this myth is persistent: "The idea that penetration is an act of dominance is almost certainly tied in to sexism and the notion that the woman's role is inferior. Plenty of men have absorbed these ideas at a subconscious level. Even if a man doesn't think it is an act of dominance when he penetrates his (male or female) partner, he may still hesitate to switch roles because he is afraid that it will mean losing his masculinity if he takes a turn catching instead of pitching." Women absorb these ideas as well. "Quite a few women discover that they've absorbed judgments about how men, especially their partners, should behave," the authors point out. In other words, your guy may want you to do him in the ass — but you may have to contend with your own doubts. Does it mean he's secretly gay? Or worse: can I still be attracted to him — or respect his masculinity — after I've pegged him?

As real as these anxieties and stereotypes are, they're eroding fast – "more and more male–female pairs are discovering prostate play and having a grand time doing it," Glickman and Emirzian write. One obvious question is demographic – who's making this "discovery," younger or older couples? In an email interview, Glickman told me that "more younger men are curious about it than in previous years, perhaps because of less homophobia and perhaps because there's more discussion of male sexual pleasure, rather than performance. But other younger men often have more resistance because they haven't yet shed their ideas around masculinity." In general, men are probably "more willing to explore (prostate) pleasure at 50 than they might have been at 25. Older men generally have more experience with ‘don't believe everything you think' so although they're more likely to have hurdles to overcome, they have more practice with it."

The payoff for clearing those hurdles, Glickman says, is nothing less than the radical transformation of heterosexual sex. In 2011, Glickman wrote a column entitled "How Pegging Can Save the World," arguing that no other erotic experience a man can undergo can create greater empathy with women than being penetrated by his partner. "For men who have never been on the receiving side of penetration, sex is something that happens outside the body. And when sex is external to your body, it can be easier to do when you have a headache or you're not quite in the mood. A lot of men discover than when sex is about catching rather than pitching, their mood, their emotions, and their connection to a partner can often have a bigger influence on what they want to do and how it feels." Men, Glickman and Emirzian suggest optimistically, will be a lot less likely to rush foreplay once they've experienced how long it takes to relax sufficiently in order to comfortably take a dildo (or other sex toy) in the ass.

For women, Glickman and Emirzian write, the experience of pegging a man can be equally revelatory, suggesting that "many women who use strap-on dildos discover how much work, responsibility, and (sometimes) power can be part of fucking someone." It's intellectually reckless to impose political meanings onto private acts, but it seems telling that in an "End of Men" era where exhausted and stressed-out women already are shouldering so much more "work" and "responsibility" than ever before, those burdens are extended — in a novel way — to the bedroom as well.

"There's a common myth that anal sex only hurts the receiver," they say; it's too often assumed (especially when it's a man doing the penetrating) that he's taking pleasure in causing discomfort, while the "bottom" (usually a woman) gets pleasure only out of making her guy happy. "We suspect this is also why some straight guys may fear that their female partners want to penetrate them not for mutual pleasure, but as some kind of passive-aggressive payback." That's just not true, Glickman and Emirzian insist, and the sooner men get over their anxiety and guilt, the more fun they and their partners will have. And maybe, just maybe, we can peg our way right out of sexism itself.