From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 5): Sleepover Sexting and (Virtual) Sleepover Sex

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From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 4): Camp Cabins

Lolita (Italian translation)

In Lolita (Vintage Books\Random House, 1991), Lolita confessed to Humbert that she had pre-teen “sapphic diversions” with Elizabeth Talbot - Lolita’s tent-mate at summer camp. Nabokov wrote:

Her astounding tale started with an introductory mention of her tent-mate of the previous summer, at another camp, a “very select” one as she put it. That tent-mate (“quite a derelict character,” “half-crazy,” but a “swell kid”) instructed her in various manipulations. At first, loyal Lo refused to tell me her name.

“Well,” she said. “[...] her name was Elizabeth Talbot, she goes now to a swanky private school, her father is an executive.”

I recalled with a funny pang the frequency with which poor Charlotte [Lolita’s mother] used to introduce into party chat such elegant tidbits as “when my daughter was out hiking last year with the Talbot girl.”

I wanted to know if either mother learned of those sapphic diversions.

“Gosh no,” exhaled limp Lo mimicking dread and relief, pressing a falsely fluttering hand to her chest.

Hence, in addition to bedrooms, hotel rooms, and prep school dorm rooms, schoolgirl sleepover sex happens in camp cabins as well. For example, on the “Postcards from Europe” episode of the Hot Girl Talks podcast (Aug 18, 22 [YouTube]), Carly Weinstein, an influencer with 175K Instagram (IG) followers, informed her co-hosts, Halley Kate (246K IG followers) and Jazmyn “Jaz” Smith (147K IG followers), that part of going to summer camp is seeing “plenty of vaginas” “inside of them” “all sides of them”. Carly,

“If you went to camp, you’d know that you saw plenty of vaginas in a lifetime and probably the inside of them. And probably all sides of them. Because at camp, you just are, like, crazy. It’s just a thing. I don’t know, like, people who went to camp know. Just camp things.”

In “Reality Check From Young Voices”, a chapter in Katie Cappiello and Meg McInerney’s Slut: A Play and Guidebook for Combating Sexism and Sexual Violence (The Feminist Press at CUNY, 2015), 17-year-old Danielle confessed that “lots of sexual firsts” happened at her “typical Jewish summer camp” like the filming (oral) sex tapes. Danielle shared:

“I go to this typical Jewish summer camp, where promiscuous behavior is practically encouraged and cultivated [...] with no parental supervision, there are lots of sexual firsts for everyone [...] There is one girl in particular, Georgia, who is really petite and very pretty [...] Josh and another boy coerced - basically forced - Georgia to give them blow jobs, while others filmed it on their phones.”

In Not That Kind of Girl, Lena Dunham shared that when she was a teen camper, she could not stop staring at her summer camp counselor’s “tits”. Lena wrote:

[...] [I] couldn't stop eyeing everyone else, staring at their round asses as they dressed, the dusky hairs emerging from the bathing suits. “You are so bicurious!” Lena's camp counselor said after she caught Lena: “[...] watching her tits swing as she changed.”

The following summer, then-14-year-old Lena found her “truest love”. “[Johnny] was blond, from South Carolina, and just shy of twenty-two.” In her bunk, Lena fantasized about discarding her: “[...] clothes, approaching Johnny, and letting him put his hands all over [...]” her body.

On the “They’re Just Not That Into You...” episode of the Hot Girls Talk podcast (August 4, 22 [YouTube]), Halley shared with Carly and Jaz: “You can also pop your cherry [i.e., have an orgasm] by riding a fucking horse. One of my friends […] she literally told all of us when we were like 9-years-old, ‘Yeah, I popped my cherry by riding this horse.’”

For The Cut’s 2014 Summer Sex Week feature, Maureen O'Connor posted, in the True Stories section, “10 Awkward, Nostalgic Stories of Summer-Camp Sexual Awakenings” (July 7, 2014). The piece related: “ten people’s most vivid memories of summer-camp sex — and sex gone awry, and confused preteen discoveries, and other strangely nostalgic humiliations.”

In the first memory, “Fake Orgasms Sweep Horse Camp”, readers learned about “horsegasms”, which was when a Camp Rim Rock horseback rider had an orgasm via a horse. The quest to have horsegasms arose after Lauren Petersen, the “alpha girl” of the cabin and a New Yorker, shared with her cabin mates that she was getting: “‘tickling feelings’ while grinding on a Western saddle.” Consequently, Lauren’s cabin mates, including the then-11-year-old storyteller, went on a “craze[d]” quest to have a horsegasm.

When I was 11, there was a fake-orgasm craze at Camp Rim Rock’s horseback riding camp for girls. It started when Lauren Petersen asked if anyone else had “tickling feelings” while grinding on a Western saddle. Lauren was the alpha girl of my cabin. She was cool and tough and came from New York and had a Beastie Boys cassette [...] If Lauren Petersen felt tickles on horses, then feeling tickles on horses was cool. Soon everyone was feeling tickles, or trying to feel them, or faking them. It was like the Salem Witch Trials. I will never say whether my horsegasms were fake.

Cruel Intentions 2: Manchester Prep (2000)

On a related note: On episode 06 of Amazon Prime’s Cruel Intentions (2024), streamers learned from Cece that years before she matriculated at Manchester College, she broke her hymen on a “Gorgeous palomino named Lucky.” Cece’s confession may have been inspired by Cruel Intentions 2: Manchester Prep (2000) where Cherie Claymon, a freshman at Manchester Prep, was forced to have a horsegasm while posting in Central Park, which was all part of a plot by Kathryn, an upperclassman, to turn Cherie into the "premier slut of Manchester Prep." Kathryn commanded Cherie, “Up and down. Back and forth. Faster! Faster!” And Kathryn asked Cherie, “How does that feel?”

In “Sexual Shaving Rituals”, a submitter submitted that, as a form of seduction, she and her then-12-year-old cabin mates used to shave their legs in the open on the campgrounds. But when she was 13, as a form of seduction, a 16-year-old female camp counselor asked the 13-year-old and another camper to shave her vagina. Outside. On the porch of their cabin!

We always shaved our 12-year-old legs outside, where the boys could see, sitting on towels spread over the pavement that connected the girls’ camp to the boys’ camp. When I was 13, my counselor got me and another camper to shave her vag before she met up with her boyfriend. We did it outside on the porch, her lying down and us on either side of her, giggling.

In addition, the teen exhibitionist counselor used to tell sex stories in the cabin. In a bit of S&M, the teen sadist “dared” the girls to put Gold Bond on their vaginas. (One can safely infer that the counselor (regularly) found pleasure in putting Gold Bond on her vagina; hence, the referral.) Although she was straight, the counselor got a “perverse kick out of it”. And after the counselor discovered that the submitter’s “prepubescent tits” were being pawed behind the bunk bed, the counselor gave the camper comforting advice.

She was 16 and told us all her sex stories. She once dared several girls in my bunk to put Gold Bond on our vaginas. It was so cold that it stung, and I experienced a kind of sensitivity generally reserved for varsity S&M games. I think the counselor got a perverse kick out of it, even though she is straight. She is now a wedding planner.

Still, she gave me some good advice: When my prepubescent tits were getting squeezed like tiny stress balls during make-outs behind the bunk, my counselor said I should tell the boys, “Be gentle.”

In “The Girl Who Discovered Orgasms”, in a bit of a sleepover cabin sex plot twist, a submitter admitted that she had sex with the cabin! And, consequently, she had her first orgasm. "

I had my first orgasm at Jewish summer camp, the result of dry-humping against a cabin.

But someone must have seen her “dry-humping against a cabin”. Right? Subsequently, she lost her virginity at camp a few years later, and to commemorate the occasion, she had five orgasms that night, including one in the cabin’s shower.

A few years later, I lost my virginity at a summer camp on a kibbutz. I had sex five times that night, including in the shower, and came every time! Talk about getting off to a good (blessed?) start.

Liara Roux shared in her memoir, Whore of New York: A Confession (Repeater Books, 2021), that while 5th graders, she and the "very beautiful" Melissa had girl-on-girl sex at camp in the woods of the Catskills where they kissed, Liara put her breast in Melissa’s mouth, and Melissa put her finger into Liara. Roux wrote:

One day, when we were walking to whatever activity was next, she asked me if I wanted to skip it [...] As we got further away from the camp, she stepped off the trail. I followed her. We wandered through the trees, and I tripped over a rock hidden under the snow.

We got to a clearing and she plopped on the ground, then started making a snow angel. “What about your pants?” I asked. “Won’t they get wet?” [...] “They already are.” I blushed at the implication. Seeing my flushed face, she stood up, walked to me, and kissed me [...] I couldn’t hold myself back. I kissed her, putting my hands around her neck, pulling her in.

[...] I pressed myself against her and we fell in the snow [...] I rolled on top of her, kissed her again [...] She wiggled, unzipping her coat, unzipping mine, and our hands were on each other’s chests, grasping at softness. I kissed her neck; she moaned and put my breast in her mouth [...] After much maneuvering, she pulled off her glove and stuck her hand down my pants. The chill of her fingertips pressing into me.

We walked back to camp, our faces flushed.

And Lindsay shared with Vera Papisova in the Teen Vogue piece "23 Masturbation Stories: Girls Get Real About Self-Love" (AUGUST 4, 2020), which is a compilation of preteen and teen masturbation stories, that she had a "freaky camp friend" who indulged in self-love. Lindsey enjoyed masturbating at camp too, but she only wished that she had known that, besides her "freaky camp friend", other girls masturbated too. Lindsay shared:

"I wish I knew that other girls masturbate, too! And that no matter what way you do it, it's not weird! Most girls don't open up to their friends about that stuff until college, unless you have the occasional freaky camp friend." - Lindsay

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 1): Becca Moore, Miley Cyrus, Jessica Simpson and Julia Fox

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 2): Lola Kirke, Chelsea Handler, and Lena Dunham

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 3): Restless Virgins | Zoe, Isabel, Annie, and Whitney

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 3): Restless Virgins | Zoe, Isabel, Annie, and Whitney

Abigail Jones and Marissa Miley exemplified in their New York Times Bestseller Restless Virgins: Love, Sex, and Survival in Prep School (William Morrow\HarperCollins, 2008) that, in addition to hotel rooms, sleepovers can happen in boarding school dorm rooms and in the family guest room too. 

Per Jones and Miley, both Milton Academy alumnae, the shocking sexual behavior and unrelenting promiscuity of the privileged Milton prep school students that they wrote about in their book actually happened during the 2004-2005 school year. In a sort of synopsis of their book, Jones and Marissa wrote:

Milton Academy educates the best and the brightest [...] It’s an American story about teenagers surviving high school, confusing lust with love and sex with power, and searching for self-worth. Their experiences are the stories of privileged adolescence.

Jones and Miley described the typical Milton student as preppy trust-fund babies whom drove BMW convertibles and whom were known to “complain about their cleaning people”. Specifically, the Milton schoolgirls were described as “thin” and ”designer-clothing-clad”, and the schoolboys were described as “dressed like budding yachtsmen in navy blazers, khaki pants, ties and loafers” (i.e., “quintessential WASP[s]”).

As for Milton Academy, it was established in the late 18th century in Milton, MA, and was described as: 

“[...] the breeding ground of privilege [...] the elite school that has educated luminaries like the Kennedys and Roosevelts; and T.S. Eliot [...]” with a Forbes dining hall that: “[...] was more like a private dining room of an exclusive club [than a cafeteria].”

What follows are recaps of four Restless Virgins: Zoe, Isabel, Annie, and Whitney:

Zoe

Jones and Miley wrote that Zoe, a then-15-year-old sophomore at the prestigious Milton Academy, like a number of other schoolgirls whom attended the prep school, was fond of performing oral sex on schoolboys. For example, after dining one Monday, Reed, Brady, and three other schoolboys proceeded to the Athletic and Convocation Center (ACC) where they: “[...] punched in the security code, and slipped inside.” Subsequently, Zoe, “slipped inside” the ACC as well and joined the boys in the hockey team’s locker room, where she performed oral sex on the five schoolboys - consecutively. Jones and Miley wrote: 

She knew exactly what to do. She kneeled and began: one boy, then the next, oral sex performed on all five in turn.

And that was Zoe’s third teen oral sex orgy - consecutively, because Zoe had performed oral sex on schoolboys that Saturday and Sunday too. Jones and Miley wrote: 

Zoe had spent part of Saturday night giving head to three guys in a dorm room, and part of Sunday night doing the same to three guys in the same locker room. Monday night was not novel [...] 

In addition, two weeks later, Zoe performed oral sex again – in a hotel room. Per Jones and Miley, Brady, a Milton schoolboy, attended a birthday party [i.e, Zoe’s Sweet Sixteen] at a hotel [i.e., Marriott Hotel in Copley Square] where Zoe welcomed Brady to the hotel room in her bra while two other teens were having sex in the bathtub. Jones and Miley wrote: 

When Brady arrived, Zoe and a friend opened the door to the kids’ room in their bras. Alcohol was everywhere [...] someone pulled back the shower curtain to reveal a girl and a guy having sex in the bathtub.

A report in The Phillipian, “Milton Academy Reports Additional Oral Sex Incidents” (2005), elaborated on the hotel room teen debauchery.  Per The Phillipian, Zoe and another schoolgirl were topless when they welcomed Brady and other guests to the hotel room. And, in addition to teen bathtub sex, “other guests were engaging in sexual acts”. For example, Zoe performed oral sex too, but, reportedly, only on one schoolboy. The Phillipian: 

The 15-year-old female student at Milton Academy who allegedly performed oral sex on five members of the Boys Varsity Hockey team is reported to have performed the same act on two members of the team and on another 15-year-old boy the day before in the same locker room [...] In addition, the same girl reportedly attended a birthday party in a Boston hotel room during which alcohol and sexual favors were freely exchanged. The party at the Marriott Hotel in Copley Square in Boston took place two weeks after the alleged locker room incidents, but before the scandal was exposed to the public [...] The same source told the Boston Herald that two topless girls […] welcomed male guests to the party. The source also observed the same girl perform oral sex on another boy, as well as other guests engaging in sexual acts.

Why was Zoe involved in so many oral orgies? Jones and Miley opined: “The acts were part of an implied social change: oral sex for social clout.” 

And there were receipts too. For example, Reed, another Milton student, learned, via cell phone photos, that during Sunday's oral orgy, Zoe wore a rugby shirt. #preppy In addition to photos, unsurprisingly, there were Milton schoolgirl sex tapes as well.

Isabel

Not to be outdone, Reed had teen sex in a W Hotel suite during a school trip to Times Square. “Reed arrived at the W Hotel with his bag of preppy clothes and a strip of ribbed Trojan condoms, ready to take on New York City.” Conveniently, Isabel decided that she wanted to lose her virginity during the school trip. Why? “She couldn’t imagine being a virgin when she graduated from high school.” 

In the suite, Isabel performed oral sex on Reed as he was “glancing at the basketball game”. After it took him 15 minutes to penetrate her, he “threw her up against the couch and then the windowsill, pumping into her from various directions”

The next night at the W, after “Josh and Erica rolled around on the king-size bed”, Erica performed oral sex on Josh, which fascinated Josh because he couldn’t believe that: “Erica had just swallowed his cum. He was impressed [...]”

Back in MA, to Isabel’s delight, her parents let her have a sleepover with Reed. Consequently: “Isabel sneaked into the guest room, where Reed was supposed to sleep alone, and brought condoms. They had sex for the second time, passed out for a while, woke up, had sex, passed out, and did it all over again. Isabel was happy [...]”

(Interestingly, Jones and Miley related that not only did Reed and Isabel go to Ivy League schools, forty-four Milton graduates from Reed and Ivy’s class went to Ivy League schools as well, including four to Yale, nine to Brown, and a whopping twelve to Harvard.)

Annie

Annie was described as having wavy blond hair “past her soldiers” and “[s]he was fleshy, a Rubens girl with a curvaceous body, breasts the size of baby melons since they’d first cropped up in fifth grade” Annie, who started wearing eyeliner in the fifth grade, “accentuated” her “oversize breasts”, because she “loved” that she looked 18 instead of 13. 

Annie: “[...] learned at an early age that sexual performance, especially a good one, often brought rewards, especially attention from the boys she wanted to like her back.” Consequently, Annie’s “sexual education” began at a party the summer before 8th grade.

By high school, Annie had earned so much sexual experience that: “It would've been easy [for Annie] to teach her friends how to give hand jobs.” 

On vacations and weekends, Annie, in a matching Victoria’s Secret bra and thong set, would sneak out of the house to see Scott for a sleepover, but always after midnight. “Throughout the years, she gave him orgasms and he made her feel desirable [...]”

Hervé Chapelier 

And one night, after her senior year orchestra performance, Annie, who carried her flute in a pink-and-black Hervé Chapelier bag, had a sleepover at Teresa's, whom turned off the alarm system, which allowed Scott to enter through the garbage, which allowed Annie to give Scott a sleepover hand job in Teresa’s basement.

Whitney

Whitney had long brown hair and “[...] an unusual combination of beauty and grace, slim and delicate after a decade devoted to figure skating.” And “[...] as one of the popular senior girls herself, she knew it was her duty to look hot.” “Her hair razor straight, and she flipped it occasionally with her hand [...] Whitney wore flawless makeup and knew she looked good.”

Whitney, who “pulled her first thong around her narrow hips in the seventh grade”, “wanted: attention from the hottest boy in her class.” Consequently, during her freshman year, Whitney lost her virginity to Nick on his dorm room couch. They stopped using condoms after their third time.

During the summer before 11th grade, Whitney: “[...] tiptoed barefoot down the stairs and sneaked out of her house.” Despite not having a driver’s license, Whitney drove her mother’s new car to the beach with Nick. Subsequently, the teens returned to Whitney’s for a sleepover: “[...] where they had sex against the wall she shared with her parents.”

On the night of her senior year First Dance, Whitney “was out for pleasure”. Thus, she danced with Tripp until she escorted him off the dance floor. Next: “Whitney and Tripp found themselves wandering across the main quad and toward a football field.” On the bleachers, “confident in her hand-job skills, Whitney gave Tripp a hand-job,” because she was not sure if she could give him “head” due to Tripps “huge!” and “enormous!” penis. Despite Tripp's size: “She wanted him inside her, thick and encompassing, painful in that really, really good way” - on the prep school’s bleachers. 

Eventually, Tripp would have Whitney over for sleepovers where she would repeatedly perform oral sex on Tripp. Jones and Miley wrote: “She’d just spent the weekend hanging out at his house, meeting his mom, joining his family for dinner, and giving him head.” 

However, sleepovers at Tripp’s didn’t stop Whitney from having sleepover sex at Nick’s as well, where the teens would: “have sex, smoke, eat, and have sex again.”  Jones and Miley wrote: 

Whitney disappeared for weekends at a time, telling her mom she’d come home on Saturday and then not showing up until last Sunday night. Entire weekends were consumed by the void of Nick’s bedroom. The two of them would have sex, smoke, eat, and have sex again.

Whitney had her first orgasm during a sleepover with Nick, which was described as “delicious”. It happened “[...] in Nick’s bed, his aunt's bedroom nearby, at some odd hour of the night [...]” And Jones and Miley wrote of Whitney and Nick: “She’d given him head a million times.” Hyperbole?

Jones and Miley didn’t write full profiles on all the Milton students. Some of the students were briefly mentioned, like Josh, whom, while at his Cape house: “[…] a girl asked Josh if he wanted to have sex [...] He got a condom, played it cool, and fumbled his way out of virginity.” At Jillian’s summer house, she dragged Oliver into a bedroom where: “[...] she found herself down to a bra and hooking up with Oliver, who was in a T-shirt and socks. The condom was on. He entered. Four seconds later, he withdrew.” And Caroline, “with her pretty face and [naturally] blond hair”, while her parents were upstairs, lost her virginity in her living room as Almost Famous played in the background. Caroline “[...] spontaneously cried halfway through,” but she thought, “Wow. This is happening. This is nice.” Jones and Miley wrote: “She couldn’t wait to do it again.” 

Interestingly, of Restless Virgins, Natalie Morales of the The Today Show blurbed: “A shocking look at the sexual behaviors of privileged teens [...]” On XM’s Oprah & Friends Gayle King blurbed, “As I was reading, I had to keep flipping back to the beginning where it says Restless Virgins is a work of nonfiction [...] all the things in the book really happened.” And in 2013, the Lifetime Movie Network released Restless Virgins: A sex scandal that shook [a] Massachusetts prep school, Milton Academy in [the] 2004-05 school year (IMDb).

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 1): Becca Moore, Miley Cyrus, Jessica Simpson and Julia Fox

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 2): Lola Kirke, Chelsea Handler, and Lena Dunham 

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 2): Lola Kirke, Chelsea Handler, and Lena Dunham

Lola Kirke is an actress (Sinners, 2025 [Warner Bros. Pictures]) and country singer. Lola wrote in the memoir, Wild West Village (Simon & Schuster, 2025), that when she was 10-years-old, her 15-year-old sister Emi (Jemima Kirke [Girls, 2012 (HBO)]) asked Lola to pose in her “underwear, holding a [Marlboro Medium] cigarette”. Lola pleaded, “But I’m only ten, don’t you think-” Nonetheless, the risqué portrait was completed and hung, framed in gold, in the foyer of their West Village brownstone. Of the portrait, Lola wrote:

The naked ten-year-old smoking version of me hung framed in gold in our foyer forabout a decade, until we moved. [...] Our home was part house, part museum, curated expertly by my mother.

Lola related that throughout middle school, she had a friend “from down the street” named Tilly. Lola shared that during that time, she would dry hump Tilly, which Lola described as a game, where Lola fantasized that she was “an unspecified businesswoman in love with her boss [i.e., Tilly] and his son [i.e., Tilly]”. Lola:

All through elementary school, I was either an unspecified businesswoman in love with her boss and his son (my friend Tilly down the street played both), or a sort of simple country wife. While the former game involved a lot of dry humping [...]

After Lola related that she used to play “an assortment of sex games with Barbies”, she wrote that she and Tilly exhausted “most” of their “playdates unknowingly enacting the plots of bad pornos”. Interestingly, Lola wrote that she didn’t really consider Tilly to be a friend. Why? Because Lola and Tilly were “essentially fucking”.

In addition to Tilly, Lola shared that she and a girlfriend “made out once behind the port-a-potties at a wedding”, and, like Julia and Ella, Lola and Erin played: “an eighth-grade game of spin the bottle”.

A year after discovering her father’s infidelity, which was when Lola was in the 7th grade, during the summers in East Hampton, Lola started spending more time with Bettina Richards Goldblatt. Bettina’s home cost “Twelve million dollars,” which caused Lola to write: “While we were wealthy, we weren’t Bettina wealthy.”

While in East Hampton, Bettina would pay Lola compliments. For example, Bettina complimented Lola on her lips, because, per Bettina, Lola had “DSL” (i.e., “dick-sucking lips”). However, per Bettina, she had “nicer eyes and hair” than Lola. Interestingly, Shayla, Bettina’s nanny, purchased Bettina a bra that “generously gathered her chest fat into breast-like mounds.” (In “Oblivion”, a post on Medium (Feb 7, 2022), Lola wrote that Bettina “slept in a sports bra to prevent sagging”.) Of Bettina’s breast-like mounds”, Lola wrote: “She was becoming so grown up, just like I wanted to be and secretly felt I already was.”

One summer in East Hampton, after Lola “wandered upstairs to discover a trail of girls from Bettina’s day camp lined up outside her bathroom door”, Bettina introduced Lola to the pleasures of (pre-teen) masturbation (via a waterfall).

“You guys,” I announced myself, “what are you doing?”

“Shhhh!” they all hissed through retainers I envied.

Suddenly, Bettina flung the door open. “Ugh! I’m so refreshed!”

“ `Cause you showered?” I asked, confused.

“No, idiot.” She grabbed my wrist and yanked me into the bathroom, then lay down in the tub. Spreading her legs wide on either side of the faucet, she turned it on, letting the water spill into her crotch. “But you don’t want it too hot!” she admonished.

Within seconds, her hips were pulsing in a strange rhythm, and she was laughing maniacally [...] [Lola wrote in “Oblivion” that Bettina “began to moan.”]

Bettina told Lola that she had learned the masturbation technique from “Samantha from Sex and the City”. And in “Oblivion”, Lola wrote that she learned from one of the girls that Bettina’s masturbation technique was called a waterfall. “Bettina’s doing a waterfall.” And Lola elaborated in “Oblivion” that the trail of girls were waiting for their turn to masturbate, because after Bettina grabbed Lola’s wrist and yanked her into the bathroom, the girls protested, “No fair! She’s cutting!”

After dinner that evening, Lola told Harry, a boy one year her senior, about Bettina masturbating, to which Harry exclaimed, “Dude. Masturbation is THE BEST. You gotta try it.” Consequently, Lola took Harry’s advice and lowered herself into her “antique bathtub”. The water “pressure had only two crude modes: off and full on.” With her “legs spread and lying back” and a few seconds after she turned the water on, her body “cramped and seized until it entered a fugue state.” Within minutes, Lola was “at it again.” Lola wrote in “Oblivion”, that “[...] after a few moments [of masturbating], I began to feel as if I had been murdered. A sweet, beautiful murder.”

And just like Bettina, Lola was addicted to having orgasms. So much so that Lola started masturbating via the jets in Bettina’s pool. And Lola wrote that when she was alone, she would use her hand, and she even masturbated while watching films. Lola

I spent the rest of the summer either doing exactly this or figuring out ways I could. My interest in Bettina’s snacks was quickly replaced by an intense romance with the jets in her pool. Pretty much any time I was alone or shrouded in darkness, my hand was in my pants. Even during films like What a Girl Wants and The Life of David Gale. I was sick. An addict.

In “Oblivion”, of her addiction, Lola elaborated: “I spent hours doing what I later learned was fucking myself into oblivion. I imagined what it would be like to [sic] it with somebody else.” And Lola wrote that, even though she was only 12, her “sex drive was an 11 out of 10.”

Liza Esquibias posted on People “Chelsea Handler Is Ready to Spill 'Lots of Tea' in New Netflix Comedy Special The Feeling” where Esquibias wrote: “[…] while some topics she mentions are more controversial than pickleball, Handler tells PEOPLE she doesn’t regret a thing.” In the piece, the comedian confessed to Esquibias, “I shared lots of tea in this special, just when I thought there was no more tea to spill.” Since Chelsea is featured in this essay, it would only make sense that the tea that she spilled on Netflix included schoolgirl sleepover sex and (group) masturbation.

The Feeling, 2025 (Netflix), the title of the comedy special, is in reference to a pre-teen group masturbation session that Chelsea participated in during a back-to-school sleepover at Jodi Repati’s house in New Jersey. Chelsea related that when she was 8-years-old, she broke her arm at her family’s Martha’s Vineyard summer house. Chelsea described breaking her arm as a pivotal moment in her young life, because after she returned home from the hospital, she mistakenly “slammed” her cast down on top of her “Pikachu” (i.e., her vagina). Consequently, that night, Chelsea discovered how to masturbate. Chelsea said,

“I was like, ‘Ow,’ you know. And then it slid down, like, two more centimeters, and I was like, ‘Brrr’. What is that zone?” And I went out that night and found out exactly what that zone was.”

When Chelsea returned home to New Jersey that fall, Jodi Repati, Chelsea’s best friend, invited Chelsea to a back-to-school sleepover where “nine 8-year-old girls” were “gonna get The Feeling.” In other words, masturbate “face down in their sleeping bags”.

Jodi, “We’re having a back-to-school sleepover at my house on Friday night at 7:30. She goes, ‘Everyone’s gonna come over, and we’re all gonna get The Feeling.’”

Chelsea, “I walk in, and there are nine 8-year-old girls face down in their sleeping bags, just going like this. I was like, ‘Let’s fucking go!’” [Chelsea simulated masturbating vigorously.]

Chelsea joked that she masturbated insatiably and vigorously for 12 hours straight that night. Hyperbole? So much so that when she left Jodi’s house, Chelsea had rug burns on her 8-year-old forehead, and she was dehydrated. Chelsea,

“I couldn’t get enough of myself! I showed up at that sleepover at 7:30, and I didn’t get up from that position until 7:30 a.m […] I left that sleepover, I had rug burns on my forehead. I was so thirsty and dehydrated from sweating so much into my pajamas. I was like, ‘Does anyone have a Capri-Sun, please?’”

Chelsea clarified that she didn’t know that what she was doing was referred to as masturbation. She only knew that it felt “amazing”. Chelsea,

“And when you’re that young, you’re 8 or 9-years-old, you’re masturbating, you’re not really – You don’t even know what you’re doing is masturbating. You’re just like, ‘This feels amazing. Like, why didn’t anyone tell me about it.’”

In addition to using her hand to masturbate, Chelsea used a wall, her banana-seat bicycle, and a ruler during 8th grade math class. And she masturbated with a ladle during Thanksgiving dinner, which caused Chelsea to faint - at the dinner table.

The Wall

For further clarification, Chelsea said that while masturbating, she didn’t make direct contact with her Pikachu and that “thicker material” was best for optimal pleasure – even as thick as a wall. Chelsea,

“You’re not making direct contact with your Pikachu, you know? Like, you want a thicker material. Like, the thicker, the better […] You want, like, a wall. You see a corner, and you’re like, ‘I’m gonna fucking get you.’”

Banana-Seat Bicycle

Chelsea, an insatiable masturbator, would ride a pothole after school for almost an hour upon her banana-seat bicycle. Chelsea,

“And when no one says anything to you, like, ‘Hey, stop jerking off, you fucking pig.’ You don’t think that anyone even knows what you’re doing; so, I just did it all the time. I’d come home from school. I had a banana-seat bicycle. Now we know what those were for […] I’d go on little errands with my fake family that I created […] I would take my banana-seat bicycle, I would hit a pothole, and just fuckin’ ride it for, like, 30 minutes.” [Chelsea simulated masturbating upon the banana-seat bicycle.]

“My neighbor called my mom, ‘Your daughter’s been in our pothole in front of your living room window for 45 minutes.”

Math Class

During her elementary school math class, via a ruler, Chelsea climaxed - more than once. Chelsea,

“I’d go into school. I’d go into math class, and they had those desks with the apertures, you know, the openings on the desk and I’d have a Trapper Keeper in the desk and a ruler in the Trapper Keeper. And I would take the ruler, and I could always do one spin. [Chelsea simulated masturbating with a ruler.] I’d call it ‘a spin’. I’m like, ‘Do I have time for a spin?’ [Chelsea simulated masturbating with a ruler.] And I would – I would take the ruler, and I’d be like, “Brrr. You know?” [Chelsea simulated masturbating with a ruler.]

“And masturbating as a young person is just like masturbating as an adult. You do one round. You climax.”

“And then 30 minutes later, you’re like, ‘One more time! One more time!’ So, I would do it. I would think I’d be done, but I couldn’t resist myself. I couldn’t get enough. So, I would take the ruler back out, and then completely lose my shit, you know, during the class.”

Thanksgiving Dinner

To Chelsea’s dismay, after she fainted while masturbating with a ladle during Thanksgiving dinner, her mother advised her to masturbate in the privacy of her room, but her grandfather referred to Chelsea as a “little whore”, and her brother shared with the family that Chelsea masturbated “all the time.”

Grandfather to father, “So sorry about your little whore daughter.”

Chelsea’s mother to Chelsea, “Sweetie, that’s something that you wanna do in the privacy of your own room.”

Chelsea’s brother to the family, “She does it all the time!”

Interestingly, Chelsea opined that “masturbating as a young person is just like masturbating as an adult”.

During her Netflix comedy special, in addition to spilling the tea about her (group) pre-teen masturbation, Chelsea related to the audience and streamers that when she was 11-years-old, she had a girl-on-girl sexual affair with Martha McIntosh, whom Chelsea would visit during her summer break at a deli on Main Street in Edgartown, where Martha worked. Of Martha, Chelsea said, “And I want you to picture Amy Winehouse as an 11-year-old […] I was attracted to her right away.”

The attraction was mutual, because Martha invited Chelsea to her house, where Martha gave Chelsea Coronas, Camel Lights, and Martha asked Chelsea, “Hey, do you wanna go into my closet and take your pants down?” Chelsea replied, “Definitely. Like, ‘What’s next?”

Subsequently, Chelsea pulled her pants down before Martha performed oral sex on a flabbergasted Chelsea for about 15 minutes. Chelsea,

“And we go into Martha McIntosh’s closet. I pull my pants down, and she goes down on me for, like, 15 minutes. And I could not believe my good fortune.”

Just like for masturbation, Chelsea had an insatiable appetite for teen oral sex; however, Chelsea said that’s why she never had a daughter. Chelsea,

“You know. I went there every day. She’d go down on me. It was amazing [...] And that’s why I don’t have a daughter. So, I don’t have some horny 11-year-old that [sic] needs to be eaten out every 15 minutes.”

Eventually, Martha concluded that it wasn’t always better to give than to receive - oral sex. Chelsea,

“And then it was the end of the summer. I went to Martha’s every day – obviously. And it was the end of the summer, and we were in her closet, and she’s going down on me. And then I’m finishing my drink and my cigarette, and she pops her head up and she said, ‘Okay, you know, it’s your turn.’”

Ivanka Trump, who is most famous for being the daughter of Donald Trump, reminded us that schoolgirl sleepovers can happen in hotel rooms, too.

Vanessa Grigoriadis wrote in her New York Magazine cover story “Ivanka Aeternum” (The Cut\New York Magazine, 2019) that Ivanka threw a wild birthday party in middle school that included topless prep schoolgirls in limos and nude nymphets watching porn in Atlantic City's Taj Mahal hotel. Grigoriadis wrote:

Ivanka was always a good student, but she was no kind of good girl. For her birthday party in junior high, she invited about 20 girls from Chapin, her Upper East Side all-girls school, to the Taj Mahal in Atlantic City, all of them crammed into stretch limos without chaperones[...] The girls acted crazy: flashing people out the windows, whipping off bras and putting them on the limos’ antennae. In the hotel suite, they rented porn and ran around naked. Classmates who remained at home heard about the trip in excruciating detail and felt horribly left out.

Grigoriadis did not say if Ivanka participated in the prep schoolgirl debauchery at the Taj Mahal; however, Emily Jane Fox related in her New York Times Bestseller Born Trump: Inside America's First Family (HarperCollins, 2019) that, while middle-students at Chapin, Ivanka and a classmate flashed a hot dog vendor from their prestigious school’s classroom window. Of Ivanka, Fox wrote:

"She was in class. And Chapin is right up against a park on the Upper East Side - on the far east side [...] So, she was in a third floor [8th grade] classroom and looked down into the park and there was a hot dog vendor. And she and her girlfriend[s] flashed the hot dog vendor from the school window."

Lysandra Ohrstrom who took part in “flashing the hot dog man” elaborated on the incident in her Vanity Fair piece "Ivanka Trump Was My Best Friend Now She's MAGA Royalty" (November 17, 2020) In the piece, Ohrstrom elaborated that, due to Ivanka’s encouragement, not two but about five schoolgirls simultaneously flashed the hotdog vendor. Ohrstrom:

"One of the earliest memories I have of Ivanka from before we were friends is when [...] she goaded me and a few other girls into flashing our breasts out the window of our classroom in what has since been labelled the “flashing the hot dog man” incident in Chapin lore. Ivanka had basically been the ringleader, but she pleaded her innocence to the headmistress and got off scot-free. The rest of us were suspended."

[Disclaimer: To this day, Ivanka (openly) denies any involvement in the Chapin middle-school “flashing the hot dog man” incident.]

Lena Dunham related in her memoir, Not That Kind of Girl (Random House, 2014), that on a Saint Ann's eighth-grade class trip to Washington D.C., some of Lena's 14-year-old classmates: “[...] decided to go totally gay. It started with some light kissing on the [hotel] bed, then Jessica was topless and shaking her tits, clutching her own nipples and wagging them mercilessly in our faces.”

And Hallie Batchelder, a New York City-based influencer, shared on the “The Hamptons Confessional” episode of the Call Her Daddy podcast (Aug 28, 2024) that when she was 15, her mother caught her having anal sex in the hotel room during a family vacation in Aruba. Hallie (over) shared:

“Wait, when I was 15, my mom walked in. I mean, [I was] getting fucked in the ass on a [hotel] pull-out bed in Aruba.”

From the NY Times to Netflix: Schoolgirl Sleepover Sex Stories (Part 1): Becca Moore, Miley Cyrus, Jessica Simpson and Julia Fox