Lola Kirke's WILD WEST VILLAGE: Schoolgirl Sleepover Hookups and the Allure of Older Men!

 

Lola Kirke is an actress (Sinners, 2025), country singer, and, most recently, the author of her memoir, Wild West Village (2025/Simon & Schuster). Lola shared in the memoir that when she was 10-years-old, her 15-year-old sister Emi (Jemima Kirke) 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 for about a decade, until we moved. [...] Our home was part house, part museum, curated expertly by my mother. 

Lola wrote that throughout middle school, she had a friend “from down the street” named Tilly. Lola shared that throughout middle school, 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]”.

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 [...] 

In addition, after Lola shared 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, in terms of (pre) teen girl-on-girl affairs, Lola shared that she and a girlfriend “made out once behind the port-a-potties at a wedding”, and she and Erin played: “an eighth-grade game of spin the bottle”.

Lola related that when she was a child, her family spent their summers, specifically “[...] Augusts topless on private beaches, doused in tanning oil (no SPF), [we] were heathens.” Thus, unsurprisingly, while at sleepaway camp, a fellow camper put the following note in the “Warm and Fuzzy” jar: “Lola walks around naked.”

At her sister’s Sweet Sixteen, Lola “danced all night in Mary Janes and a ripped slip dress a few sizes too big.” Consequently, the straps of the slip dress “kept falling, baring” Lola’s “flat chest to the rest of the party.” Of her pre-teen public nudity, Lola wrote: “But what did I care?”

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

“Oblivion” MEDIUM (Feb 7, 2022)

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 (teen) masturbation (via a waterfall). 

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

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

[Per “Oblivion”, Lola learned from one of the girls, “Bettina’s doing a waterfall.”]

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 had learned the masturbation technique from “Samantha from Sex and the City”. And, by the way, per “Oblivion”, 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.” 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. Lola even started masturbating via the jets in Bettina’s pool. When Lola was alone, she would use her hand. Lola even masturbated while watching films. Lola wrote:

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 despite the fact that she was only 12, her “sex drive was an 11 out of 10.” 

In the 6th grade, Lola enrolled in the SoHo Child Actor’s Studio and soon after, Dina, the studio’s teacher, became Lola’s manager. In an effort to get an agent, Dina had Lola memorize a contemporary monologue. Lola wrote: “The monologue she selected was from a Tennessee Williams one-act play.” To Lola’s dismay, the monologue was of a child prostitute. 

Initially, Lola’s career “went nowhere”. Consequently, she had to “hone” her “skills in plays at school and camp”. However, to Lola’s dismay, despite being a preteen, she was “cast as even more ladies of the night”:

A Thai streetwalker in the ensemble of Chess.

Clytemnestra, Agamemnon’s sex slave in the middle school’s Greek festival

“Mozart’s loose wife in Amadeus.”

“The silent, philandering one in Strindberg’s The Stronger.”

“[A] pregnant teenager in a play about Troubles in Ireland.”

By the end of middle school, Lola had secured her “very first screen test.” But she had nothing to wear “that would pass for a “regular kid”, because Emi had been dressing Lola “for years” in miniskirts and fishnet stockings. (Lola lost the part to Kristen Stewart.)

In addition to (pre) teen nudity, (pre) teen girl-on-girl hookups, and (pre) teen masturbation, a recurring motif in Lola’s memoir is age-gap relationships. 

Lola shared that when she and her sisters were in their youth, at one of her family’s legendary Christmas parties, one of her sisters offered David Bowie her hand as an ashtray; however, surprisingly, Bowie declined.

I wrote surprisingly, because I previously related that Nikki McWatters wrote in the Huffington Post piece “Predatory Teenage Girls” (December 13, 2012) that “Lori Maddox, a famous teenage groupie from LA, is alleged to have lost her virginity to David Bowie at the age of 13. [And s]he was Jimmy Page's steady girlfriend while still underage." But in a Thrillist post titled "I Lost My Virginity to David Bowie, Confessions of a 70s Groupie" (Nov 3, 2015), Maddox stated that she was actually 15 when Bowie "de-virginized" her, which she described as a "beautiful" event.

In terms of requited age-gap relationships, Mino (Domino Kirke), Lola’s then-15-year-old older sister, had a brief affair with a movie star. During the affair, Mino “fled” with the “movie star via his private jet.” However, after a “stern call” from Simon Kirke, Mino’s father, the movie star returned Mino “just in time for her Sweet Sixteen”. Lola wrote that the Sweet Sixteen was “celebrity packed”, but that Mino’s movie star was “banned from the event, [however] he sent sixteen dozen roses in his stead.”

Simon Kirke, in addition to being the father of Lola, Emi, and Mino, is the co-founder of the rock group Bad Company. On the “Nancy Spungen” episode of The C-Word podcast (July 8, 2021), Lena Dunham and Alissa Bennet said that 16-year-old Spungen bragged that she had sex with every member of Bad Company but that she only gave hand jobs (simultaneously) to two members of the rock band Aerosmith. As we wrote earlier, Lola wrote that when she was in the 7th grade, she “discovered a thread of secret emails” on her father’s computer, which revealed to her that “on the road, he led a double life”.

The Strokes' Julian Casblancas

Despite Lola's age, Emi appeared to have a thing for Lola and smoking. One evening while hanging out in the hot tub on the Amagansett estate of a “gorgeous” pre-teen “heir to a vast tabloid fortune”, 17-year-old Emi “slinked”, topless, into the hot tub with the heir’s older brother and asked, “Do you smoke?’ Lola replied, “No. We’re twelve.” “But the Strokes smoke,” Emi said. Consequently, 12-year-old Lola “urgently” reached for the cigarette, because she “loved Julian Casblancas” - the then-24-year-old lead singer of The Strokes. (By the 10th grade, Lola’s mother would “dangle a Marlboro Light before” her, and “sometimes”, they smoked together.)

Vincent Gallo

One school day, Lola mentioned at the dinner table that she needed help with her ninth-grade term paper on Charles Manson. Consequently, Emi exclaimed, “You have to interview Gustava [Vincent Gallo]!” Emi knew Vincent Gallo well, because when she was an (approximately) 18-year-old freshman at the famous Rhode Island School of Design, Emi had “willingly” taken time off from school to go on vacation with (approximately) 42-year-old Vincent Gallo. Unfortunately, Gallo was of little help to Lola, but after speaking on the phone for three hours, he offered Lola the starring role in a music video he was directing. Emi said no. 

Next, Lola asked Poppy, Bea’s grandfather, “Could I please interview you about Charles Manson? Lola wrote that, despite Poppy’s age, she “loved” him, he was her “dream man”, and she  “wondered if there was something romantic between” them. Lola wrote that Poppy was her “type”, because: “[...] he was dependably dressed in a three-piece suit and doused in Chanel No. 5. He loved to sing Marilyn Monroe songs, and he winked a lot. My dream man.” 

Eve, a famous actress, used to help Lola with her acting. Eve and Jude, Eve's 16-year-old son, lived uptown, and they lived on a “sprawling” Long Island estate; however, a divorce forced Eve and Jude to move to the West Village with Lola’s family. Soon after, Lola “[...] became Jude’s girlfriend.”

Blanche, “who was a bit older than” Lola, took 15-year-old Lola out for Manhattans after Lola’s performance in her “school’s neofuturist production of Macbeth”. At the bar, Blanche asked Lola, “What’s Jude’s penis like?” Lola lied, “I’ve never seen it.” Blanche must’ve sensed that Lola was lying because Blanche continued to ask Lola about the size of Jude’s 16-year-old penis. Eventually, Lola informed Blanche that Jude’s penis was “perfectly nice”, which apparently was an understatement, because “One dark winter evening later that year,” Blanche informed Lola that Jude’s penis was “huge”. Blanche had found out about Jude’s penis size from Emi. Like Lola, Emi had first-hand knowledge about Jude’s penis, because, per Blanch, that prior summer, (approximately) 19-year-old Emi performed oral sex on (approximately) 15-year-old Jude in the Kirke’s pool house. 

“So, you did not tell me that Jude’s penis is huge!” she said with a strange guttural laugh [...]

“Who told you that? I [Lola] replied, feigning nonchalance.

“Emi,” Blanche said. “You know she blew him, right? In your pool house? Last Summer?”

In a fit of advanced rage, Lola called Emi at Rhode Island School of Design and repeatedly called Emi a “cunt”.

In the chapter “Little Lolita of West Fourth Street”, Lola introduced the readers to Ray. “Ray had played guitar in a semi-successful ‘90s rock band,” but when the band disbanded, Ray did a “brief stint” as Lola’s live-in manny. 15-year-old Lola was often left alone with Ray; so, she “hosted sleepovers with [her] girlfriends every other night and smoked ceaselessly inside” while Ray flirted with Lola’s friends. 

One morning, Lola “awoke to find Zora blushing in her underwear.” Zora informed Lola that she was smiling because Ray had kissed her while she was (nude) in the shower. 

Zora said, “I was in the shower, and he came in, and he just…kissed me. Oh! And then he asked me where the rolling papers were.” 

And somehow, Ray had gotten hold of Zora’s bra, because: “A few weeks later, the housekeeper found Zora’s oversized bra stuffed in Ray’s sheets.” However, Lola did not say how Zora's “black lace” bra got into Ray’s bed. Of Zora’s bra, Lola wrote:

What do we do?” my mother asked [...]

“Probably give it back?” I suggested. 

“You’re right. It does look expensive,” she agreed. 

Very interestingly, Lola shared that as she was writing her 10th grade English paper on Lolita, she felt connected to the book, she shared that the Colombian seamstresses whom worked in her mother’s basement called her Lolita, and she related that when she was 13, her mother gave her “an original poster of the Kubrick film version.” And Lola wrote that she: “[...] thought it was a good thing to be a sexually precocious young girl, and who was more that than Lolita?” Thus, it appears that Lola agrees with novelist Robertson Davies' assessment of Lolita as: “[...] not [about] the corruption of an innocent child by a cunning adult, but [about] the exploitation of a weak adult by a corrupt child”.

Of Gideon, Lola wrote that he: “[...] had been a heartthrob movie star since he was a teenager, but he no longer looked like it [...] he was now almost unrecognizably bearded and fat.” One day, at Lola’s house, “Gideon was sprawled across a sofa”, and he announced to no one in particular, “I want pot.” Lola’s mother replied, “Oh, Lola loves pot,” which was true, because Lola shared that, at the time, she was “smoking at least eight times per day.” 

To fulfill Gideon’s request, Lola “ran upstairs two at a time”, grabbed her “stash”. Subsequently, Lola, in a “hot pink American Apparel catsuit”, and Gideon walked to Gideon’s loft where Lola “rolled a joint on the kitchen counter”, they smoked it “until it was gone”, and Lola “wafted to the center of his loft and began to dance for him” as she “considered what it would be like to kiss him.” 

Although, despite the fact that Gideon was a movie star, Lola still held the stance that older men should “on no occasion wear sandals.” Lola realized that her “seduction had worked” after Gideon said, while “patting his lap”, “Come sit here.”

During Emi’s second year at the Rhode Island School of Design, which was when Lola was “just starting high school”, Lola went to visit Emi, whom had a “large poster of a movie about a pretty child heroin addict” hanging on her off-campus apartment wall. After Emi “did a line” and Lola smoked (a cigarette), they went to a house party where Lola sat “on a twin bed, falling in love with [Gary] a local.” 

Lola wrote that Gary was like “the whole solar system”; however, at the end of their conversation, Gary wrote his number down on a piece of plywood with the caption: “Call me when yer [sic] 18”, which Lola brandished “like a trophy.” Later, at the party, Lola learned from Emi that Gary had recently broken into her apartment, but Emi reassured Lola that, “It was fine. We had sex.”

Like Paris Hilton and Julia Fox, Lola went to nightclubs in high school too. However, unlike Paris and Julia Fox, Lola went to nightclubs with her mother too. Lola wrote:

Being underaged, I’d discovered the secret to getting in wasn’t having a fake ID but looking like you didn’t give a shit.

Lola and Gael García Bernal in MOZART IN THE JUNGLE

Lola starred in Amazon Prime’s Mozart in the Jungle (2014–2018), but when she first learned of the role, she wrote that “the whole thing sounded dubious”; however, her “imagination went wild” after she learned that Gael García Bernal “was attached to star”, because she spent her adolescent masturbating to Bernal whom is 12 years Lola’s senior. 

One afternoon [...] my agent called [...] he told me how a website that typically sold books was now making TV shows. Except the TV shows would be played not on an actual TV but on your computer. The whole thing sounded dubious [...]

When he mentioned that a foreign film star I’d spent my adolescence getting off to was attached to star, my imagination went wild. 

Surprisingly, on the “Nancy Spungen” episode of The C-Word podcast, after Dunham said that 16-year-old Spungen bragged that she had sex with every member of Bad Company, Dunham failed to mention that Lola and Jemima’s father was a co-founding member of Bad Company. Of course, Dunham and Emi (Jemima) were co-stars on Girls. However, Dunham did write a blurb for Wild West Village:

Lola Kirke has captured more than just her own wild and specific New York upbringing. She has captured the yearning of a generation [...] She is a wise, witty, and unsparing writer.” - Lena Dunham

Netflix’s CHELSEA HANDLER: THE FEELING (2025) | Pre-Teen Autoeroticism and Teen Girl-on-Girl!

Liza Esquibias posted on People “Chelsea Handler Is Ready to Spill 'Lots of Tea' in New Netflix Comedy Special The Feeling” (February 17, 2025) In the piece, Esquibias wrote: “[…] while some topics she mentions are more controversial than pickleball, [Chelsea] Handler tells PEOPLE she doesn’t regret a thing.” And Chelsea confessed to Esquibias, “I shared lots of tea in this special, just when I thought there was no more tea to spill.” Here’s some of  the tea that Chelsea spilled:

The Feeling, the title of the comedy special, is in reference to when Chelsea participated in a pre-teen group masturbation session 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, “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 said, “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 shared that she masturbated insatiably and vigorously for 12 hours straight that night. So much so that when she left Jodi’s house, Chelsea had rug burns on her 8-year-old forehead, and she was dehydrated. 

“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”.

“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, a ruler during 8th grade math class, and a ladle during Thanksgiving dinner, which caused her to faint - at the dinner table.

The Wall

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

“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 for almost an hour upon her banana-seat bicycle.

“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

Interestingly, Chelsea opined that “masturbating as a young person is just like masturbating as an adult”. Consequently, during her elementary school math class, via a ruler, Chelsea climaxed - more than once. 

“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 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 her 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!”

In addition to admitting to pre-teen masturbation, Chelsea overshared that when she was 11-years-old, she had a girl-on-girl sexual affair. Chelsea related that during her summer break, she would visit a deli on Main Street in Edgartown where Martha McIntosh 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. 

“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, that’s why Chelsea didn’t have a daughter. 

“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.”

Unsurprisingly, by the end of the summer, Martha concluded that it wasn’t always better to give than to receive oral sex. 

“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.’”

On Rotten Tomatoes, Jimmy E gave Chelsea Handler: The Feeling  5 out of 5 stars, and Jimmy posted: 

Fans of Chelsea Handler will enjoy this special. She is witty as ever, sprinkling in her life experiences in a funny laugh out loud manner. She shares aspects of her life that made me like her brand of entertainment even more.

CRUEL INTENTIONS (2024) | TWO (2) Manchester College Students Seduce Professor!

 

Here’s IMDb’s synopsis for Amazon Prime’s Cruel Intentions (2024): 

After a hazing incident at their elite college, step-siblings Caroline and Lucien set about to preserve their power and reputation by seducing [Annie] the [18-year-old] daughter of the Vice President of the United States.

In the fourth episode of the series, which was based on the films Cruel Intentions (1999) and Cruel Intentions 2: Manchester Prep (2000), potential pledges were invited by members of Delta Phi Pi to “Heaven: An Intimate Night of Friendship and Sisterhood”. The event took place in the Delta Phi sorority house on the campus of Manchester College where the coeds shared “a sacred part” of themselves, which wasn't to be “judged” or “repeated”.

Shockingly, Caroline, the Queen of Delta Phi, shared that she was “painfully insecure” and “felt like a disappointment” to everyone, including her mother, but not Adrian - Caroline’s “gorgeous” tennis coach. Caroline said:

This might be a surprise to all of you, but I wasn't always the person I am now. Growing up, I was actually painfully insecure. I felt like a disappointment. To my mother, to everyone really, except for Adrian. He was my tennis coach. A man in tennis whites. You can imagine. But it wasn't just that he was gorgeous. I could also really talk to him. You know? 

Caroline went on to add that “one day after practice”, she and her tennis coach kissed before he took her virginity on a couch in his office. Caroline admitted that she wanted that “happen for so long” and that it was “all so perfect.” Caroline shared:

Anyway, one day after practice, he brought me back to his office. He had a couch in the corner of the room. All of a sudden, I just knew what was gonna happen next. He kissed me. It was just. I had wanted it to happen for so long. Next thing, we were having sex. It was my first time. I remember looking up at him. It was all so perfect. 

However, Caroline related that her mother paid the “man in tennis whites” to have sex with Caroline, because Caroline’s mother wanted to “boost” her (teen) daughter’s confidence. 

Caroline, “The only reason he had sex with me is because my mother paid him. She was just trying to boost my confidence, because I told her no guys would ever like me. She thought she was trying to help.”

As for the main student-teacher affair in the series, in the pilot, after Professor Chadwick caught Celeste “Cece” Carroway, a senior at Manchester College with a recent nose job, rummaging through his office, she got on her knees and begged him to allow her to be his TA. 

In episode 04, Cece went to a book reading at Lowe’s Books that was given by Dr. Deidre - Professor Chadwick’s ex-wife where Dr. Deidre read from F*ck Your Trauma, which was a bestseller. Dr. Deidre advised, “Through sex, the body finds new rhythm. So we must not be afraid to give in to our desires, no matter how shameful or taboo,” which caused Cece to look lovingly upon Professor Chadwick. 

After the book reading, Cece read F*ck Your Trauma at a bar on campus before Professor Chadwick joined her for a drink. During their conversation, Cece said, “[...] fuck my mom for paying my tennis coach to fuck me.” Professor Chadwick, “[...] I’m sorry that happened to you. Cece, “No. No, it’s really - it’s not a big deal.” Thus, streamers learned that it was Cece’s mom and not Caroline’s mom whom paid the tennis coach for age-gap sex with her daughter; however, per Cece, it was “not a big deal.”

In episode 05, due to the stress of being attracted to her professor, Cece fainted in Professor Chadwick’s office. Subsequently, Professor Chadwick stayed with Cece in the “infirmary all evening”, taught her how to breathe, and fed her cookies. After a battery of tests, Cece was discharged and Professor Chadwick drove her back to her sorority house where Lucien surmised that Cece was in love with Professor Chadwick. 

In episode 06, Caroline informed Cece, “You have been distracted, you have been late to things, and you are constantly talking about him [i.e., Professor Chadwick] [...] Is there some medication you should stop taking?” Inconceivably, Caroline suggested that Cece resort to drugs to get over her love for Professor Chadwick. 

Cece, “Prozac won’t help this.”

Caroline, “Try lithium.”

Cece, “Lithium doesn’t work on love.”

Caroline, “Cece, this is not love. This is a manic episode.”

“No, I’m telling you. That’s why I was so sick. A roving ne’er-do-well [i.e., Lucien] confirmed it’s definitely love.”

Caroline surmised that Cece was obsessed with Professor Chadwick and that Cece was fixated on Professor Chadwick like Cece was fixated on the “man in tennis whites”. Consequently, Caroline came to the conclusion that the only way that Cece could get over Professor Chadwick was to seduce him and “[f]uck him and be done with him.”

Caroline, “This is an obsession. Just like that fixation you had on your tennis teacher [...] We need to take care of this right away. Get him out of your system.”

Cece, “Like a juice cleanse?”

Caroline, “Fuck him, Cece. The sooner the better [...] So go. Seduce him [...] Fuck him and be done with him.”

Following Caroline’s advice, Cece locked Professor Chadwick’s classroom door before she attempted to (unsuccessfully) seduce him by goading him into discussing the sex lives of fascists. 

Later, due to Cece being unusually quiet, Caroline concluded, “So, you didn’t fuck him.” As an alternative seduction technique, Caroline suggested that Cece “get him out of the classroom.” And Caroline reassured Cece that she would be able to “fuck” Professor Chadwick because, “He’s a man, Cece. And men, beyond all reason and above all else, want one thing. To fuck.”

Cece, “I tried, I swear. I mean, I did everything right. I got him alone. I’m telling you, I used everything I knew. I put the moves on him in a major way. All he did was tell me to make a syllabus.”

Caroline, “He probably had no idea what you were doing.”

Cece, “No. Trust me, he knew. He just didn’t want to have sex with me.”

Caroline, “Not possible [...] You just have to make it more painfully obvious [...] Just get him out of the classroom.”

Cece, “What if he rejects me again?”

Caroline, “He won’t [...] He’s a man, Cece. And men, beyond all reason and above all else, want one thing. To fuck.”

Subsequently, Cece tricked Professor Chadwick into coming to a party where, to his shock, she kissed him. Professor Chadwick responded, “This can’t happen.” Cece apologized and explained, “I’ve just been so distracted lately and completely preoccupied, and I was sick last week [...] but then I realized I have these feelings for you, and I thought that if you didn’t find it completely repulsive, we could just have sex [...] I totally understand. You don’t have the same feelings for me [...]”

Unsurprisingly, Cece’s love was requited and Professor Chadwick wanted to have student-professor sex too, but he suggested their age-gap attraction be put on hold until after Cece graduated from Manchester College. 

Professor Chadwick, “I do [...]”

Cece, “Wait. You do what?”

Professor Chadwick, “I think you’re amazing.”

Cece, “Okay. Sorry, I’m just really bad at this stuff. Does that mean you did or didn’t like the kissing?”

Professor Chadwick, “It doesn’t matter. These aren’t the type[s] of feelings that we can get rid of by sleeping together.”

Cece, “So you didn’t like it?”

Professor Chadwick, “Cece, we can’t do this. I’m a professor. And your boss. It’s a power imbalance [...] Which means we need to keep things professional [...] we can get to know each other better. And after you graduate, we’ll see what happens.”

“You want to see what happens?”

“Yes. I really do.” 

Consequently, Cece related to Caroline, “You were wrong. About Professor Chadwick. He’s not like Adrian [i.e., Cece’s tennis teacher]. He’s not something I can just fuck out of my system. Not that Adrian was something I fucked out of my system. But, Caroline, he loves me too. We just have to wait until graduation and then we can be together.” And Cece shared with Annie, “There’s this guy, a professor actually [...] Our brains are connected but our bodies are supposed to stay strictly separate until after graduation.” 

Later, Cece, the Rush Chair, informed Caroline that she couldn’t reside over pledge night, because she was invited by Professor Chadwick to “the poli-sci department meeting”. After Cece asked Caroline if she should attend the department meeting in a “bra or no bra”, Caroline said, “Cece. He’s grooming you [...] He’s a predator [...] You have a history of making sacrifices for men who aren’t who you think they are.” Cece responded, “Oh no. Professor Chadwick is nothing like Adrian.”

Annoyed that Cece was neglecting her duties to the sorority, Caroline set out to seduce Professor Hank Chadwick. Caroline initiated the seduction by ramming her vintage convertible into the professor’s Prius. Next, she informed the professor that the sorority girls on campus were “collecting men like trophies.” And that, “One of them [i.e., Cece] actually performed fellatio on a boy with ice in her mouth so she could take pictures of his shriveled penis [...] You know, I heard whispers of them seducing professors too. You know, for grades or just to ruin their lives for fun.” 

Shockingly, seventeen minutes later in the episode, Lucien happened upon Caroline and Professor Chadwick having age-gap professor-student sex. Lucien asked, “Fucking the faculty, Caroline? Is that really the best you can do?” Caroline replied, “I like to fuck people.” However, to complete her agenda to punish Cece for neglecting her duties to the sorority, Cece filed an anonymous sexual misconduct complaint against Professor Chadwick.

Professor Chadwick assumed that Cece filed the sexual misconduct complaint; however, Cece informed the professor, "You think it was me? That reported you? [...] Why would I report you?” 

Cece surmised that someone saw her kiss the professor and reported them. Cece informed Beatrice, a sex tape leak victim and a student activist whom was working “against the coalition of sex criminals [...] that make up Greek life on campus”, “Look, I know you think you saw me and Professor Chadwick kissing at Lucien’s party. But what you actually saw was me throwing myself at Professor Chadwick at Lucien’s party, and Professor Chadwick, very professionally, I might add, completely and totally rejecting me.” Beatrice responded, “I have no idea what you’re talking about.” 

But Beatrice added that that Professor Chadwick, “[...] must have fucked some other student [...] because that’s what the complaint was about.” Cece said, “I guess men really do suck.” Subsequently, while crying, Cece naively informed Caroline, “You were right. About Professor Chadwick. He was everything you said. A predator. He was grooming me. But not me. He didn’t want me. Caroline, he had sex with some other student. Like maybe even hundreds, maybe even thousands. The point is you were right.” Caroline, while hugging Cece said, “Oh, God, I’m so sorry, Cece. Oh, I really didn’t want to be right about this one [...] You’re my best friend. My sister. You must know that by now.”

After that pledge ceremony, Annie asked Cece, “Oh, did something happen with Professor Chadwick?” Cece replied, “Yes. Something did. He didn’t want to sleep with me, which is not usual for me, that’s par for the course. But, as it turns out, he did sleep with at least one other student. Maybe even hundreds.” Annie, “Oh, my God. I’m so sorry.”

Then, to Annie’s dismay, she learned from Cece that Caroline lied at the Heaven event about having sex with her tennis teacher. 

Cece said, “Oh, didn’t I tell you about my [...] tennis teacher. A thrust is a thrust is a thrust?”

Annie replied, “I thought that Caroline said she lost her virginity to a tennis teacher named Adrian.”

After Cece learned from Annie that Caroline stole her tennis teacher sex story, Cece was able to surmise that Caroline was the anonymous source of the sexual misconduct complaint against Professor Chadwick and that Caroline was the student whom had sex with Professor Chadwick.

It may be worth noting that, in addition to Cece’s age-gap affairs with her tennis teacher and professor, at Caroline’s request, Cece performed non-age-gap oral sex on Blandsman. In episode 03, in an effort to blackmail Blandsman into dropping out of the race to be his fraternity’s president, Cece arrived at Blandsman’s frat house room in her underwear, pushed Blandsman onto his bed, and asked, “Have you ever had a snow job?”. Then she stuffed her mouth with ice before and gave Blandsman a “snow job’. Consequently, in episode 05, Cece shared with Caroline, “[...]  there was ejaculate everywhere. I mean, a lot of [Blandsman’s] semen on a lot of surfaces.”  

-----

It’s not uncommon for media that depicts age-gap relationships to depict (teen) girl-on-girl sexual scenarios and masturbation by teens and coeds as well; thus, it was no surprise to us that after Annie shared at the Heaven event, “I’m 18 years old, and I’ve never even been kissed. And when it finally does happen, he’s probably gonna know just because I’ll be so bad at it,” Caroline seductively and sensuously (tongue) kissed Annie and informed her, “You were perfect.”

As for coed masturbation, Lucien had a “camera thing” (e07). In other words, Lucien could not have sex unless he was making a sex tape; thus, every time he had sex on campus, it was recorded. And Lucien shared the sex tapes with his step-sister Caroline. Ergo, before the credits rolled in episode 5, Caroline masturbated in her sorority house bed while she watched one of her step-brother’s sex tapes on her MacBook. 

Cruel Intentions 2: Manchester Prep 

In episode 06, streamers learned that Cece broke her hymen on a “Gorgeous palomino named Lucky.” Cece’s confession may have been inspired by Cruel Intentions 2: Manchester Prep where Cherie Claymon, a freshman at Manchester Prep, was forced to masturbate, to orgasm, while posting upon a horse - 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 commaded Cherie, “Up and down. Back and forth. Faster! Faster!” And Kathryn asked Cherie, “How does that feel?”  (In addition, in the film, Kathryn had an age-gap affair with Steve Muller - Manchester Prep’s Assistant Headmaster,)

And in a bit of “Life imitating art”, on the “They’re Just Not That Into You” episode of the Hot Girl Talk podcast (Aug 4 22), one of the Hot Girls shared, “You can also pop your cherry 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.’”