When Kate White became editor in chief of Cosmopolitan in 1998, she worried that she’d quickly run out of ideas to fill the magazine’s monthly quota of blissfully sinful secrets that will blow your man’s mind. In White’s 14 years at the helm, the magazine valiantly reached for an electric toothbrush, a string of pearls, a hair scrunchie, a handful of refrigerated marbles, edible body paint, tomato sauce, and “a small bit of mango” to introduce Cosmo readers—and their unsuspecting boyfriends—to unprecedented levels of sexual innovation. But in the summer of 2003, White landed on a sexual accessory so unforgivably weird that it would come to exemplify the ludicrousness of Cosmo sex tips forever. “99 Ways to Touch Him: These Fresh, Frisky Tips Will Thrill Every Inch of Your Guy,” White wrote on the magazine’s June cover, then teased: “(Our Favorite Requires a Glazed Doughnut).”

The pastry made its appearance in tip No. 30, spoken from the mouth of an apocryphal anonymous boyfriend: “My girlfriend gets a glazed donut and sticks my penis through the hole. She nibbles around it, stopping to suck me every once in a while. The sugar beads from her mouth tingle on my tip.” Soon, tip No. 30 ascended in the public consciousness to become known as the most infamous Cosmo sex advice of all time—even stupider than the one where you take a sip of hot water into your mouth, introduce a penis, and gargle. Tom Wolfe skewered the doughnut line in his 2004 novel I Am Charlotte Simmons, and Maureen Dowd used it as evidence that feminism is stalling in her book Are Men Necessary?. If a real person actually admitted to executing the move, it was performance art in the service of mocking the magazine. In “I Tried Cosmo’s Weirdest Sex Tips So You Don’t Have To,” Anna Pulley advises against choosing a chocolate glaze: “It looks like shit. Actual, literal shit.”

The public shaming did not compel Cosmo to skip dessert. This month, the magazine republished the doughnut move, asking writer Krista McHarden to give the decade-old advice another test drive. McHarden leaned into the critique. “Let’s cut the shit,” she wrote. “This has got to be Cosmo’s wackiest, craziest, most batshit battiest sex tip, right? It takes home the gold medal in the insane sex tips Olympics and it doesn’t even try.” And yet, she concluded: “putting a doughnut on your boyfriend’s dick is suuuuper fun.”

That’s what White thought, too. In the face of criticism, she remained unfazed and repeated the tip in future issues, in her 2007 advice book You On Top: Smart, Sexy Skills Every Woman Needs, in the 2008 Cosmo’s Guide to Red-Hot Sex (which adds that “the sugary texture of your tongue will add an interesting new dimension”), and in the 2010 collection Cosmo’s 365 Naughty Nights: A Year of Hot Sex, all without a hint of self-recrimination. (The magazine also published an item on a study suggesting that the smell of doughnuts “increases penile blood flow” in men—so it’s not just the visual.) In her book, White shot back at Wolfe: “Perhaps he was just jealous no one had ever tried it on him.”

And of whom, exactly, would Wolfe be jealous? (When I asked Wolfe for comment through his publisher, I was told he was too busy “working on his next book” to answer the tough questions.) It’s not clear that anyone actually put a doughnut on a penis before Cosmo promoted the tip. White says that the tips that made the magazine in her era were culled from staffers’ own sexual histories or else crowdsourced from reader-submitted entries, which were presumed to be road-tested but were not fact-checked. The specific origins of the doughnut tip have been lost to time, but what is known is that in 2003, if you had an idea for a new thing to put on a penis, Cosmo was listening.

Before it made the cover of Cosmo, the doughnut trick surfaced only at the extreme fringes of the publishing world: obscure erotica; the 1995 sexual recipe book The Foreplay Gourmet (which also included instructions for the erotic application of a tortilla); and in 2000’s Swell-Wimp: Sexual Exercise as a Means of Reducing and Controlling Weight, a satirical send-up of medical self-help books that touted the doughnut as a handy tool for strengthening penile muscles. “There are several serious dieting and fitness websites that have linked to Swell-Wimp,” author George Tylutki told me in an email. “Clearly they have done so without reading the book. I guess it’s possible that what started as an absurd idea about using doughnuts to strengthen the penis got taken up as a serious foreplay technique.” Then again: “I doubt that I originated the idea,” Tylutki says. “The connection of sex and food is ancient. Like slathering the body with chocolate, honey, etc., eating a bagel or doughnut (or something similar) off a penis probably goes way back. The only thing modern about the ‘tip’ is that sticky doughnuts of about the right size are readily available.” Thanks, Krispy Kreme.

Perhaps it was inevitable that some day, somewhere, someone would put a doughnut on a penis. When White took the reins at Cosmo in 1998, young women had few outlets for reading about sex outside of the Starr Report. Crowding around a Cosmopolitan beat sneaking to the family desktop that moved at dial-up speed. Helen Gurley Brown, who ran Cosmo from 1965 to 1997, had made a “bold, gusty, irreverent magazine,” White says. But only when White took over did the magazine actually get “very candid” about just what a fun, fearless female does when she hops into bed. “This was a time when young people were clamoring for information, and they couldn’t get it from their friends,” White says. “We gave them permission to enjoy having sex.” For all its ludicrousness, Cosmopolitan presented a vision of limitless sexual experimentation, no shame. Cosmo wasn’t just a magazine that would tell you to put a doughnut on a penis—it would also put it on the cover, then reprint it in three books. And women bought the magazine, even if they didn’t really buy the tip: When White left Cosmo in 2012, she’d grown its audience by 700,000 to rival Helen Gurley Brown’s peak circulation of 3 million.

Of course, Cosmo was always an imperfect vehicle for sexual education. Young women were hungry for knowledge, but Cosmo was hungry for copy. Though she worried about running out of sex tips early on, “surprisingly, there just always seemed to be fresh things to say,” White says. “Fresh” may be an overstatement. White may have had to reach deep into the pantry to find new sexual fodder, but once a tip entered Cosmo’s rotation, it could be repurposed indefinitely, no matter how absurd. “Readers would age out of the magazine, so if there was a little bit of recycling, it was reaching a fresh, new group of women,” White says—hence the doughnut tip’s impressive lifespan.

Then the Internet came and exploded opportunities for women to talk candidly about sex. Many of these women challenged the wisdom of Cosmo’s anonymous boyfriends. The accessories were ridiculous, and the please-your-man framework was offensive. The Cosmo sex tip became a parody. And now, the magazine itself is in on the joke. When Marina Khidekel, Cosmo’s current deputy editor, pages through a binder of early 2000 issues of the magazine, she suppresses a laugh as she reads off some lines: “Turn him on like crazy.” “Put on a show for him.” “What men really want in bed.” “We do our sex tips with a wink now,” Khidekel says.

Since Joanna Coles took over in 2012, the magazine has jettisoned its most problematic tips—the ones “where pleasing the guy is the main priority”—while acknowledging the absurdity of the simply silly ones. “We’ve been making a concerted effort to write the sex tips with more voice and humor,” Khidekel says. “We want it to be good for her. We want her to laugh and to have fun. And we want her to have as good a time reading the sex tips as she’ll have enacting them.” That allows the magazine to continue to churn out sex tips on the newsstand every month while anticipating the criticism that hits when sites like Jezebel and this one get ahold of the issue. Krista McHarden’s doughnut-on-a-penis review managed to be both a searing critique of the ridiculousness of the tip and an enthusiastic endorsement of the laughter it produced between her and her partner. As Jezebel’s Erin Gloria Ryan put it: “It seems that, like Skynet, Cosmo has gradually become self-aware.”

Whether the strategy can keep Cosmo relevant remains to be seen. At the end of last year, Cosmo’s newsstand sales dipped, and it dropped from the top-selling women’s magazine to No. 3. Maybe women just don’t need a magazine to tell them how to have sex anymore, no matter how winkingly the subject is presented. Or maybe, as White suggests, what women really want is the doughnut, served straight up.

Correction, March 1, 2014: This post originally misstated that Cosmo’s current deputy editor was reading coverlines from old issues of the magazine.