The Woman Who Slept With 100 Men in One Day
10 min read
At first, it was the Airbnb owner I felt sorry for. I once had a friend who rented out her flat for a year while she was abroad, and came back to discover it had been used as a brothel in her absence. Deep cleaning doesn’t even begin to cover it. And so when the recent YouTube documentary “I Slept With 100 Men in One Day” went viral recently, I could only imagine how the landlord of the posh London apartment where Lily Phillips performed her stunt might react.
“After the day was finished, Lily, under her own name, left a review on the Airbnb listing, saying, 10 out of 10, would 100 percent recommend,” the documentary’s host, Josh Pieters, told me. Phillips was, however, less enthusiastic about her feat of endurance sex. The reason the film has become so talked-about is that one short clip—viewed 200 million times on X—shows her crying in the aftermath of the stunt. “I don’t know if I’d recommend it,” she says.
Phillips is 23, and Pieters is 31. Watching one young content creator present another in a way that invites such a straightforward moral judgment feels like a generational shift. Having grown up in an era when the worst thing a good liberal could be was “judgmental” about pornography and other ostensible vices—and feminists who criticized the sex industry were dismissed as prudes—I was surprised by Pieters’s undisguised skepticism about Phillips’s feat. (Pieters showed his subject the documentary before broadcast, he said, and she did not contest her portrayal.) Perhaps, I wondered, the relentless normalization of online porn has created more space to be open about its excesses. Immediately, I thought of Billie Eilish, then 19, telling Howard Stern a few years ago that watching porn as a child had “destroyed” her brain.
And sure enough, the overwhelming reaction to the documentary has been revulsion, not only among conservatives—the commentator Ben Shapiro said that Phillips had “made herself into a sex robot” whose soul was stained—but also among feminists. The British columnist Tanya Gold claimed that Phillips “is not very bright and will soon not be very well.” One of the best-rated comments on YouTube, with 36,000 upvotes, called the documentary “the best anti-porn film I’ve ever seen.” The former sex addict turned exuberant Christian influencer Russell Brand showed up in a leopard-print cardigan to offer a rare note of empathy, saying the stunt was an attempt to “defibrillate divinity down here on the lower levels.”
Phillips’s aesthetic is that of the girl next door, rather than cartoonishly inflated adult performer. She’s an OnlyFans star who sells $9.99-a-month subscriptions to her explicit content, and makes thousands of dollars more by recording bespoke videos for her fans, and taking their phone calls. Her recruitment method for the “100 Men” stunt—offering to sleep with any man who filled out an application and took an STI test—brings the claustrophobic, intimate nature of internet fame to its logical conclusion.
Pieters said he owed it to his audience to show them his genuine reaction to her work. “I grew up in the generation of porn being available to us as teenagers on the internet,” he told me. “It would take a lot to shock me or upset me, but I think the level of sort of extremity, and the extremes that we witnessed while making this documentary, certainly made me feel uncomfortable and was something that was completely new for me.” The documentary even has room for that most stigmatized of human emotions toward sex: disgust. When Pieters enters the bedroom in the rented Airbnb after Phillips has finished her feat, his cameraman gags at the smell.
As a pure artifact of internet culture and social mores in 2024, “I Slept With 100 Men in One Day” is hard to surpass, starting with the fact that all the bad words are censored in the YouTube version because the video platform demonetizes obscene content. (Yes, a documentary about a self-professed “slut” bleeps the word slut.) Then there’s the power dynamic between Pieters and Phillips. This isn’t an all-powerful journalist getting to define the reputation of a hapless subject. Both are content creators operating in the attention economy, and both are aware that Phillips’s stunt could help their careers. Pieters, who moved to Britain from South Africa to play cricket, first became famous through political pranks such as tricking the far-right provocateur Katie Hopkins into accepting a fake award in front of an offensive slogan in 2020. Eventually, though, he decided to change the focus of his channel to making documentaries, and “100 Men” is his first attempt.
In his film, Pieters is unsparing about the lack of glamour involved in Phillips’s stunt. Afterward, Phillips recounts that one man guilt-tripped her because she was running behind, and could not give him the full five minutes—five minutes!—he had been offered. “I guess when you’ve promised something to people who support you, it’s kinda hard to let them down,” she says.
“But it’s up to you, right?” Pieters says. She sniffs, holding back more tears.
That line is typical of Pieters’s demeanor in the documentary, and it’s one of the reasons his film succeeds so well. He isn’t kinky, and says so. He comes across as a nice boy. He makes no attempt in the documentary to exude a worldly, knowing, cool-with-all-this attitude, much less the sweaty-pawed enthusiasm of the laddish era of gonzo journalism. Instead, Pieters appears to be the only person on-screen who cares about Phillips’s happiness, rather than fulfilling their own fantasy or enabling her career. Without ever saying anything that demeans Phillips, he declines to conceal his belief that what she’s doing is a bad idea. (She seems casual about the STI testing and invites the men to bring their friends, unvetted, at the last minute.) Every fiber of my being wanted her to give up pandering to clammy masturbators and have a proper relationship with someone as decent and sweet as Pieters. Look! Isn’t it nice to have a conversation with a man instead of charging him money to see your vagina?
Yet however free Pieters and his viewers might feel to express their concern, the OnlyFans economy has a momentum of its own. Some attention-grabbing stunts, no matter how widely criticized, also reveal an appetite for more. Neither the backlash to the film nor her own stated misgivings have deterred Phillips from continuing in porn. She now maintains she wants to do something even more extreme, by having intercourse with 1,000 men in a single day.
Extreme sex stunts are not new, although the practice has until recently fallen into abeyance. Fellow survivors of the 1990s might remember the documentary Sex: The Annabel Chong Story, where a gender-studies student had sex 251 times in a day. At this distance, my brain has helpfully scrubbed most details, except for the visual of a long line of men waiting for their turn, and Chong’s complaint that she kept being scratched by their fingernails.
The next year, the adult actor Jasmin St. Claire claimed to have managed 300, although the journalist Evan Wright, who attended the filming, put the number at barely 100. Wright compared the event to combat, in having “the sense of being in a group of people deliberately and methodically engaged in acts of insanity.” St. Claire ended up needing to ice her genitals halfway through, and she was summoned onto Jerry Springer’s show afterward so the audience could express its disgust. “That’s where America really is a beautiful country—it allows nasty pigs to be on national TV in the middle of the day,” she said.
In 1999, the porn star Houston breezed past the competition, having sex 620 times in an event confusingly named the Houston 500. (Afterward, she had her labia trimmed, and promised to auction off the remnants.) “It’s not about sex,” Houston said at the time. “It’s just a freak show, basically.” Across the internet, you can find the rumor that the record is currently held by Lisa Sparks—more than 900 times, in 2004—but Sparks herself has written that it was about 150, and that “I was so bored during the event that I order[ed] McDonald’s (hey a fat girl has to eat!!).”
From this, you might gather that these sex stunts are rarely sexy. For the women, the events are, at minimum, a grueling double shift down the hump-mines. But the demands of high-volume sex also tax the men, many of whom are plagued by performance anxiety when the big moment arrives. Phillips’s event had a high dropout rate in the days beforehand, which surprised her but not me. The porn industry, in the days before Viagra, was full of wannabe male stars who talked a big game and then found the bright lights and onlookers to be a real turnoff. Fantasy is one thing; reality is another.
One observer of the Houston 500 divided the male participants into three groups: “the professional, the hopeless, and the hopeful.” After Phillips’s event, one of the few men who agreed to be interviewed by Pieters said that he had no regrets: He had been a fan of Phillips from her earliest days on the site, and flew in from Switzerland to have sex with her. But another man was shaking. If his identity was revealed, he said, his father would “kick me out straight away.” Yet another man gave Phillips a rose before their assignation; it was still there on the bed, in its wrapper, amid the dozens of condoms strewn around afterward.
For women in the online sex industry, success requires self-promotion and a certain amount of self-abasement. Performers get attention at the cost of becoming objects of pity and hatred. Much of Phillips’s previous self-promotion came from podcasts optimized for insecure, combative men—ones that, as Pieters put it, are “hosted by the type of people who probably have a poster of Andrew Tate on their wall.” The Whatever podcast, which has 4 million subscribers on YouTube, is the most obvious example, with episode titles such as “Do Modern Women DESERVE Chivalry?” and “Picky Travel Nurse DEMANDS 6ft3 Man Who Makes $100,000+ Per Year?!” If your kink is watching two guys in hoodies berate eight attractive younger women in low-cut tops, while simultaneously charging their audience $20 to have a single message read out on air, Whatever has you covered.
These forums offer sexualized rage bait—the classic format sees a blithe, happy sex worker talk about how much money she is making, and how much she loves her job, while being peppered with aggressive questions about her “body count” and whether feminism is a lie. If she storms out of the studio, cleavage bouncing, so much the better.
No one is forcing women to go on Whatever and be humiliated, of course. It’s a living. Like Phillips’s sex stunt, these podcast appearances by OnlyFans stars are the product of a hustle culture where it’s considered better to monetize your objectification than endure it without compensation. If a man has to pay $20 to send you a message calling you a rancid slut who will never find love, who’s the real loser?
The difference between “100 Men” and the pre-internet sex stunts is that many performers in the 1990s hoped they could use their fame to break into the mainstream entertainment world. Houston, for example, wanted to star in a sitcom. Now there is no mainstream: Phillips is using the publicity to drive more direct subscriptions to her OnlyFans. “Gone are the days of movie studios and music labels controlling what artists and actors can and can’t do,” Pieters told me. Content creators are “their own production company, and they choose what they get to put out.” The same impulse toward virality—and controversy—that saw Logan Paul record a video in a Japanese “suicide forest” is now driving creators such as Phillips to promote their businesses outside the OnlyFans paywall. (One major difference is that unlike Paul, Phillips probably won’t end up interviewing Donald Trump.) Extremity sells, and as TV producers and newspaper editors have yielded to social-media platforms, there are no gatekeepers to curb its full indulgence.
If anyone is exploiting Lily Phillips, it’s Lily Phillips, which raises thornier questions than some feminists might like. “I Slept With 100 Men in One Day” might superficially be concerned with sex, but it’s also an insight into the end point of liberalism, as manifested through the internet. Online porn is not going away, and America makes only the barest attempt to keep it hidden from minors. Online gambling is booming. Significant players in Silicon Valley are all in on cryptocurrencies—many of which are transparently scammy. Robert F. Kennedy Jr. is preparing to go to war with the regulator that tries to protect Americans from catching preventable diseases, supported by regular people who have been told by influencers that milk pasteurization is “woke.” We have become deeply uneasy with the concept of authorities saving us from ourselves.
There’s a reason we’ve started appending the word porn to glamorized versions of real phenomena: food porn, property porn. We know that porn is a fictionalized version of sex, and understanding the sometimes grim mechanics of its production would spoil the fantasy. Stunts like “100 Men” make people angry partly because the lie becomes too obvious to deny—and partly because neither a performer’s discontent nor the public’s seems likely to change anything. “Everything Lily Phillips did in this stunt was perfectly legal, yet it’s causing such a huge amount of outrage,” Pieters told me. So how, in a more liberal, less religious world, “do we know where the lines are, and where to go and where to stop?”
