The Radical History of How Strap-ons Pegged the Patriarchy

Five years ago, Broad City featured a now-legendary episode in which Abbi Jacobson hooks up with a dude who asks her, rather abruptly, if she wants to “switch it up.” She thinks he’s talking about switching positions until he pulls out a strap-on dildo and asks to be pegged.  

Instead of recoiling at the request, Jacobson gleefully embarks on the ride and spends the rest of the episode waxing philosophical about the unspeakable power of a woman fucking a man in the ass with a wearable silicone phallus. 

It led to a flurry of activity across culture sites and social media, causing what appeared to be a new sex trend to emerge. We’re still talking about it, too — just last week, Men’s Health published an article espousing the virtues of getting pegged and how to do it, explaining that many men enjoy it for its prostate-stimulating effects and patting readers’ heads with the gentle reassurance that liking it has “nothing to do with sexual orientation.”

That belief — that pegging isn’t necessarily “gay” — is kind of revolutionary. I’ve been in the sex industry for nearly a decade, and when I first came into porn — which, of course, is a microcosm of sexual norms and desires — there were a lot of unwritten rules around the way men could be depicted sexually and none allowed for anything even close to what Jacobson or Men’s Health proffer. Back when I signed on, there was a clear divide between “mainstream porn” and “the gay side,” and male talent that had worked on the latter before trying their hands at the straight stuff were heavily stigmatized. 

While “gay 4 pay” was a term that had meaning on the gay side, it didn’t hold any water on the straight side — what made a man “gay” wasn’t his sexual orientation, but which sex acts he engaged in. For this reason, even male talent on the “straight side” who were strapped by cis women were taboo, because any man being penetrated anally was innately “gay,” and therefore, “dangerous.” 

Looking at the industry and wider culture today, it seems silly that these distinctions and discriminations ever existed. But those beliefs didn’t just materialize overnight — they were shaped by centuries’ worth of culture and human expansion, both of which were accented by the invention and proliferation of the humble dildo. 

Dildos appear as archaeological artifacts in the Paleolithic period thousands of years before the invention of pottery, domestication of animals, invention of agriculture, settlement in cities, the Kinsey Report and, of course, Broad City. From ancient Japan and medieval China to the frescoes of Pompeii and pamphlets circulated during the French Revolution, no human culture has lived without them. 

The same goes for strap-ons, which are just dildos attached to a wearable harness. Though the current pegging craze makes strap-ons seem like some sort of newfangled fuck item, they’re really not — strap-ons and pegging have been around for thousands of years, too, and people of all genders and orientations have been fucking each other with them for just as long.

Strap-ons range in material from stone and deer antler to jade and alabaster, crossing economic caste and status, and many featured saddles and steals for the wearer to tie on. You can even see them being strapped on in contemporary art:

They’re all over classic theater as well. In his play Lysistrata, Aristophanes depicts the women of Greek city-states staging a sex strike to compel the men in power to end the Peloponnesian War. If it wasn’t clear Aristophanes was a dude, consider his predictable take on female hysteria. Suffering from convulsive dick withdrawals, the women discuss rounding up some strap-ons to satisfy their craving for cock. Granted, this was 411 B.C., but the year doesn’t matter — the penetration-focused view of female sexuality is timeless, a classic example of the ever-present assumption that women need penetration (from men) in order to experience pleasure. 

Later on in history, the hereditary politics of medieval Europe assessed queen consorts by their potential to produce male heirs. The value of a royal bride was a smooth dynastic transfer of male power. She was insurance against ruination. And when war or plague periodically devastated the population and its workforce, aristocratic and ecclesiastical powers-that-be often responded with rhetorical campaigns boosting the value of family and women as procreative vessels. Theologies of repopulation granted women a single pleasure from sex: knowing that she had done her duty to the state, her prince and God. 

For women of the time, sex was something to endure rather than anticipate or enjoy. In a rubric that limited sex to the means of reproduction, the act was categorically penetrative. And penetration was (in theory) exclusively a male prerogative. The recipient was, therefore, innately feminine. One’s literal position during sex became indistinguishable from one’s identity. Being penetrated — or penetrating someone else — classified you. By that logic, then, taking a strap-on made you inherently feminine. 

Modern times haven’t escaped that binary, but there are more contemporary corners of sexuality in which a “feminizing” act like getting pegged holds a different kind of value. Take BDSM, for example. Dominatrixes have long worn strap-ons to satisfy their male submissives, most often in houses of prostitution and dungeons where a perversion of the natural order isn’t only welcomed, but begged and paid for. 

According to Mistress Matisse, a dominatrix in Seattle, the types of clients that come in for this kind of session can be cleanly divided between those seeking physical pleasure and those looking for a transformative emotional experience. “The pleasure of pegging for men can be purely physical, because some men enjoy prostate stimulation,” she explains. “I call these ‘cooperative kink scenes,’ meaning that they don’t want or need a whole lot of role-play or Dominant/submissive energy to go with the physical sensation.” The overall goal with these scenes, she says, is to “bring someone physical pleasure in an unchallenging environment.” (The challenging environment, I assume, is the matrimonial one — many men still feel uncomfortable asking their partners to provide this experience, which is the reason why people like Mistress Matisse have fruitful careers.)

But, the dominatrix is getting something out of it too. “Having him helpless UNDER me, the control, watching his face as I penetrate him, his combination of lust and fear — it’s such a rush,” she says. “It may sound like a cliché, but when you’re just body-slamming your entire weight down onto a dildo up a man’s ass as he howls and writhes, it feels powerful. It’s a safe, consensual way for me to process and vent blunt emotions like anger physically. Afterwards, I feel a little lighter.”

The relationships between Dommes and subs can be complicated and generalizations can be dangerous, but the inversion of power that occurs in scenes like these can be a very transformative escape for the man who feels pigeonholed by his own power. Being penetrated is one of the most acquiescent, vulnerable positions anyone can assume, so male submissives upbraided by their mistresses may experience something close to transubstantiation in their demotion to the rank of “woman.” After all, it’s difficult to be anywhere else when someone’s silicone cock is up your ass. “In every really good pegging scene I’ve ever done, there’s a moment where I look into the eyes of the man I’m penetrating, and I see something in him shift and change,” she continues. “It’s a little bit of sexual disruption.”

Which brings us back to Broad City. Did it mark a narrative shift away from the conservative case that butt stuff for men was exclusively homosexual? 

I wouldn’t be surprised if it did. That episode, coupled with greater trans representation in the media and the way that things like bathroom bans brought awareness to the idea that phalluses can belong to any body, seems to have opened up a hole — sorry, whole — new world of pleasure for men; one they can access with far less shame than ever before. 

Take my friend Michael Vegas, a much-loved and attractive adult performer with acting chops that made him incredibly popular when I entered the porn industry during its “feminist” and “romance” boom a decade ago. But the whole time he was penetrating nice ladies for the camera, he was harboring a major secret — he loved to be strapped. He had worked on the gay side, and when he entered the straight side, this was a tenuous situation he had to deal with. He didn’t want to be stigmatized or blacklisted for liking things up his ass. But his good nature and powerful performances made him likable enough that when he was outed as crossover talent, it didn’t impact him much.  

Emboldened, he started a now-defunct Tumblr blog called the Gape Gatsby (you guys have got to stop giving us humanities degrees) where he posted pics and videos of him being fucked in the ass and gaping, but without showing his face. Over the years, he saw his Tumblr become wildly popular, getting feedback from men and women who enjoyed his “kink.” That inspired him to elevate it to the level of other mainstream work — it was time to show his face and his asshole in the same shot. 

Bolstered by the positive response, he started PegHim.com, a site that brought high production values to scenes of him getting pegged by mainstream talent like Ana Foxx, Siri and myself. It took a decade of building relationships and reputation to get there, but now, the site is wildly popular, something he credits to the dynamics of his shoots.  

“There are a lot of people who ask me, ‘How do you get women to do this?’” he says. “It’s just helping them understand that they don’t have to become someone different to participate in it. They can if they want, but it’s just a tool. It’s just a strap-on. You don’t have to become your boyfriend or husband’s Domme in order to fuck him in the butt.” He invites you to think about a dominatrix. “If she wants to get her pussy licked, she has to tell the person to lick her pussy,” he continues. “She doesn’t become submissive because she’s getting her pussy licked; she’s laying on her back because it’s comfortable and she needs it, but it doesn’t change the power dynamic. Just because you need to get fucked and you’re face-down, ass-up, doesn’t mean you’ve become somebody’s bitch, it means you know how you like it and how to make it fucking happen.”

When I ask him what he thinks this shift in acceptance has come from, he agrees that it has to do with increasing awareness around the nuances of gender, sex and sexuality, but he also has a more abrupt answer. “Women have made it more acceptable,” he says. “You can have a bunch of your buddies going, ‘That’s gay,’ but if a woman says, ‘That’s hot,’ the power of shame is gone.” 

Women, it seems, have always had men pegged. 

---

Sovereign Syre

Sovereign Syre is a writer, comedian, adult performer, internationally published poet (not a joke) and prolific podcaster (totally a joke). She is currently the co-host of the historical podcast ILL REPUTE! documenting the lives of controversial women along side Siouxsie Q. James, and the co-writer of digital shorts on Unholy Bible Study.