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
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