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 

ACADEMY X: A Prep School Student Seduces Teacher for Princeton

Here’s Amazon’s synopsis for Andrew Trees’ Academy X (Bloomsbury, 2006):

[Mr.] John Spencer, an English teacher at the elite Academy X, is struggling through the final weeks of the spring semester [...] Pushy parents demanding higher grades lurk behind every corner and a favorite pupil suddenly reveals a cunning and sophistication far beyond her years [...] John digs himself deeper into trouble, until his very career is at stake. [...] Academy X is a priceless peek into New York City's top private schools [...] where parents risk all for their child's academic resume and no price is too high (or pressure too great) to achieve a coveted admission to Harvard, Yale, or Princeton.

It may be beneficial to read my recap of Academy X with the knowledge that Trees wrote the novel while he was an English teacher at the Horace Mann School - a New York City prep school whose most infamous alumna is inarguably Swiffer Girl. 

In Academy X, 18-year-old Caitlyn Brie, the antagonist, was “attractive and slim”. Her “six-hundred-dollar haircut and three-hundred-dollar highlights [...] gave her a glamorous, tousled look.” She was “handsome, clever, and rich” and “sophisticated beyond her years”.

Mr. Spencer admitted that Caitlyn was “incredibly attractive”, but he blamed his attraction on Caitlyn’s outfits that “fell somewhere between skimpy and obscene.” For example, during class: “Caityln stretched her arms above her head and managed to make her top, which was already verging on the theoretical, nearly disappear altogether.”

To keep his “libido firmly on the straight and narrow”, Mr. Spencer stopped walking around the class during discussions. Why? Mr. Spencer shared:

“[...] I had stopped doing that because each day I was confronted with another of Caitlyn’s wispy thongs - at least on the days that she decided to wear any underwear at all.”

 

Phil Snopes, the head of college counseling department, was re-named Mr. Ivy by the Academy X students. Connectedly, he was “rumored to be the highest paid employee at the school.” 

Snopes told Mr. Spencer that Caitlyn had been accepted to Wellesley, but that she preferred to go to Princeton. Consequently, Snopes asked Mr. Spencer to write Caitlyn a recommendation letter. Mr. Spencer had already written Caitlyn “a very strong letter of recommendation”, but Snopes requested, indirectly in exchange for courtside Knicks tickets,  “another letter, a stronger letter.” 

Subsequently, during class, after Mr. Spencer asked, “Does the boy always have to be the one to ask [for a prom date]? Caitlyn replied, “I think that, if you know what you are doing, you can make a boy do anything you want him to [...] and by boys I mean all men.” 

After class, Mr. Spencer entered the cafeteria, and Caitlyn decided to tease her English teacher with some sexual innuendos and kino, which began by Caitlyn implying that her Mr. Spencer wanted to eat her. 

“Mr. Spencer,” said Caitlyn, “you are looking at me as if you haven’t eaten in three days.”

She laughed, and the other girls laughed with her. 

“I mean, looking at my food,” she said with a giggle.

The girls around her exploded in shrieks and screams.

“Save my seat. I need to talk to Mr. Spencer,” she said. 

After joining Mr. Spencer, Caitlyn placed her hand on his arm and implied that she wished there was a way that she could repay him for writing her (another) recommendation letter.

“I just wanted to say thanks. Mr. Snopes told me about your letter. And I really appreciate it.” 

“I hope things work out for you,” I said, pretending not to notice her hand.”

“I wish there was something I could do to show you how much I appreciate it,” she said.

While Caitlyn “fingered her bra strap”, Mr. Spencer encouraged her to be an empathetic classmate and prevent bullying on campus to which she replied with an innuendo:

“Are you trying to mold me now?”

“Never mind,” I said. “I’ll see you tomorrow.”

I turned away before she could begin fingering some other undergarment [...] 

For an assignment, Caitlyn wrote an erotic essay. Consequently, Mr. Spencer was “appalled” yet “a little turned on”, and he found it difficult to stop “dwelling on the sexual details of her essay”. 

Günter, another Academy X student, advised Mr. Spencer to ignore the erotic essay, because Caitlyn had an agenda, which was to provoke and get a reaction out of her teacher. 

Mr. Spencer complained to Günter that if the parents couldn't prevent the students from writing erotic essays, they should, “[...] at least impose some control on wardrobes” to which Günter advised Mr. Spencer to enjoy the scantily clad schoolgirls, which reminded Mr. Spencer that a number of the Academy X nymphets were in age-gap relationships:

“You should enjoy it. Other men your age do,” he said. “There are girls here who date men in their twenties and thirties.”

He was right, of course. That year, one senior girl was dating a man in his fifties. He was famous, an artist, and French - each quality apparently taking about decade off of his age.”

During class, Caitlyn shared with her classmates that she wrote about, “You know, sex.” And she defended her choice of topic by stating that even the New York Times [and the Washington Post] wrote about (middle school) sex.

“But you can even read about it in the New York Times,” Caitlyn said. “Remember that article about how middle school girls give boys blow jobs as a way to have sex but keep their virginity?”

And Caitlyn looked at Mr. Spencer “intently” and advised him to be more comfortable with his sexuality, because humans are inherently “deeply sexual”.

And speaking of school sex. Since it was the spring semester on Academy X’s campus, “[s]ex was in the air”; thus, Mr. Spencer: “[...] tried to avoid using any out-of-the-way stairwells in the afternoon.”

And, per Günter, the Academy X schoolgirls were having unprotected teen sex and were, consequently, on antibiotics. Günter encouraged Mr. Spencer to read the next issue of the school newspaper, which would be a “double-page spread” that connected the “[...] sexual dots among the senior class.” The piece would analyze “[...] an array of drunken one-night stands, dances, overnight trips, and summer flings”. Günter stated that the piece would be a “testament to the flagging sexual ardor” of the Academy X senior class. 

After class, Caitlyn informed Mr. Spencer that Mr. Snopes informed her that it appeared that Princeton was going to accept her off the waiting list. Mr. Spencer informed Caitlyn that Laura, another Academy X student, “insisted” that he check Caitlyn’s essay for plagiarism. The paper in question had been submitted to the Turbridge Student Essay Prize committee. Fearing that plagiarism could prevent her from going to Princeton, Caitlyn attempted to seduce her Mr. Spencer slash Turbridge Student Essay Prize committee member.

Caitlyn “leaned forward and slid her hand” up her English teacher’s thigh and said, “You know I think so much of you…” Caitlyn smiled, took her teacher’s silence as “acquiescence and confidently”, slid her hand higher towards her teacher’s penis, and she shared that she found “[...] older men so much more … interesting.”

“Stop!" I shouted, pushing her hand off my leg.

As my fragilely maintained view of student innocence came crashing down, I couldn't help imagining Günter saying that he told me so.

"I think you'd better go," I said.

"But, Mr. Spencer, I find older men so much more . . . interesting." She looked at me like I was a particularly tasty ice cream cone that she intended to lick.

“Go!”

She stood up reluctantly and left. 

Subsequently, Mr. Spencer learned from Snopes that Caitlyn had been officially accepted to Princeton. Consequently, Mr. Brie attempted to bribe Mr. Spencer into overlooking Caitlyn’s plagiarism with a hundred thousand dollar (fake) advance on a novel. 

The readers learned via Caitlyn’s lawyer’s “confidential notes” that Caitlyn opined that Mr. Spencer was cute, but she wasn’t sure if she was attracted to him, but she did enjoy provoking him, because teens tested boundaries and explored. 

“I’m I attracted to him? I don’t know. I enjoyed provoking him. I guess I thought he was cute…To be honest, I feel like I am more of an adult than he is. I obviously have more life experience [...] I guess you could say some of my behavior was inappropriate, but I’m only a teenager. Isn’t this what we are supposed to be doing? Testing our boundaries? Exploring?”

Due to the (seemingly) unsuccessful bribe, Caitlyn, seated across from Mr. Spencer and dressed in a “flimsy” miniskirt, took off her t-shirt to reveal her bra “[...] that seemed to be in the planning stages of construction.” Then she donned a torn t-shirt from her Prada bag, said, “I just want you to know that I didn’t want to do this,” ripped the torn t-shirt to reveal “double-barreled trouble”, and screamed. Lastly and unsurprisingly, Mr. Spencer was accused by the Head of, “Groping a student in a sexual manner,” and he was asked to resign. 

Allen Salkin reported in the New York Times piece “Private School, Public Fuss” (Nov. 18, 2007) that, due to writing Academy X: “Andrew Trees had been informed that his contract at the Horace Mann School, one of the nation’s most academically respected high schools, would not be renewed.” However, the Washington Post opined that Academy X was: “Smart, on-target and very funny.” [Emphasis added]

GLAMOROUS DISASTERS: A Fifth Avenue Teen “Porno Druggie Queen”

Here’s part of Amazon’s synopsis for Eliot Schrefer’s Glamorous Disasters (Simon & Schuster, 2006)

Noah rose from humble beginnings and [...] got himself through Princeton. Now staggering under the weight of massive student loans and dazzled by life in the big city, Noah enters the rarefied field of SAT tutoring in Manhattan, working one-on-one with the spoiled, gorgeous children of the American aristocracy.

He takes on the considerable academic challenges that are Dylan Thayer [...] and his waifish sister, Tuscany. [...] Tuscany is avidly pursuing her own downfall via drugs and relationships with men more than twice her age. 

[...] Glamorous Disasters is an incisive portrayal of a small and privileged world, a cautionary tale written by a Harvard grad who was once an SAT tutor himself -- an outsider who became a magnificently observant insider.

That’s correct. Schrefer’s a New York City based 2001 Harvard alumnus and former SAT tutor. Autofiction?

In terms of Tuscany’s drug use, the reader learned from Dylan that Tuscany used to steal pills from their mother - Dr.  Susan Thayer, the pediatrician. Dylan, “I mean, Tuscany and me [sic] used to go into my mom’s office and her bedroom all the time and steal her shit.” 17-year-old Dylan smiles crookedly. “She has all this crazy shit.” 

However, Dylan did not say exactly when 15-year-old Tuscany started stealing her mother’s (prescription) drugs.

Tuscany, “a fifteen-year-old beauty”, was expelled from Moore-Pike Girls Academy, which some referred to as “Whore-Like Girls Academy”. Why was Tuscany expelled? She sexted her teen nudes, and she was found with a number of tabs of Xanax. Consequently, Noah and his  “Hamptons-tan” was hired to prepare Tuscany for the ISEE boarding school exam. 

For their first tutoring session, Tuscany wore “tiny purple pants'' that didn’t “[...] quite make it to the top of her exposed hipbones.” “The majority of her shirts sit on only one shoulder, and her pants all require thong underwear.”

Tuscany beckoned Noah into her bedroom while she played with a strand of her “white-blond” hair - twisting “it around an orange, fake-baked finger.” (i.e., an indicator of interest).

In a bit of age-gap relationship foreshadowing, Tuscany displayed a poster of Josh Hartnett. The actor was over her bedroom desk and encased in an “ornately gilt eighteenth century frame”. Before the tutoring began, Tuscany shared with 25-year-old Noah that her boyfriend was “so much older”: 

“My boyfriend is so much older than you.”

“My mom thinks I should hang out with guys my own age.”

“[...] But guys my age are so dumb.”

And before offering Noah one, Tuscany placed a cigarette between her lips, which her mother allowed, because, as Tuscany stated, “[...] She knows I’d be eating if I wasn't smoking.” Connectedly, a pillow placed in the center of Tuscany's bed read: “Boys Like Girls Who Look Neat - When in Doubt, Just Don’t Eat!”

On the way to the next tutoring session, Noah spied Tuscany on 86th street. Tuscany and Monica,  Tuscany’s “Really tall, really skinny” friend, were observing a Victoria’s Secret “pink teddy on a waxy pale mannequin”. It appeared to Noah that Tuscany was: “[...] recounting something that recently happened to her, probably involving a boy, or [more likely] a man.”

An hour later, Noah entered Tuscany’s cigarette smoke filled bedroom where “at the sight of her swaying hips”, Noah was “overtaken by a sudden burst of nerves.” And Tuscany shared with Noah, “I’m grounded again.” Why? “This man,” she replies. “My mom is crazy.” Thus, it appears that Tuscany was grounded for participating in some salacious activity with a man whom Tuscany described as, “[...] pretty nice. And loaded.” Unsurprisingly, Tuscany opined that her mother was “crazy” for disciplining her for having an age-gap affair. 

And where did 15-year-old Tuscany meet men? “At a bar, a club.” “Sometimes” the men would buy Tuscany drinks, but she preferred to keep her options open.

During a subsequent tutoring session, Tuscany wore: “[...] denim shorts that have been cut so high that the white cotton pockets hang to midthigh.” And a “tiny pink “Wild Girls” T-shirt”. Noah surmised that Tuscany was: “[...] probably planning her next date with an older man [...]”

Noah described Tuscany as a “hot girl in tiny shorts” ; thus, it was his “[...] job to look at her as little as possible.” But admittedly, it took “[...] resolve to keep his gaze averted.”

During the tutoring session, Noah asked Tuscany about It’s All You - Tuscany’s glossy teen fashion magazine. Here’s the headline on page 8 with Tuscany Thayer’s byline: “Hewitt Hos and Nightingale Nymphos: The Sluttiest Manhattan Schools Exposed”

And what did Roberto, Noah’s Albanian roommate, exclaim when he saw Tuscany on the cover of It’s All You? 

“Wow,” Roberto says libidinously

“This bitch is hot,” Roberto adds. “Seriously, Noah, you have to let me meet her.”

“No,” Noah says, his eyes flashing. “Absolutely not.”

“You’ve got to be shittin’ me. Why not [...]?”

“She’s a kid. Stop it.”

However, that night Noah was “alarmed by his [own] flicker of attraction” to Tuscany whom reminded Noah of his age-gap tutor-tutee attraction to Monroe. 

After Monroe he promised himself never to be drawn to another student. He stuffs It’s All About You under his mattress.

He thought he had banished Monroe from his mind, thought he had healed, but suddenly he feels the shame and guilt afresh. The depth of his feelings for her was inappropriate, he knows. His intense affection led him to consider doing things he should never have done, for which he can’t forgive himself. He distrusts his own feelings toward Tuscany, second-guesses himself: surely he isn’t repeating history, allowing attraction to distort his sense of duty?

Do you remember Monica, Tuscany’s “really tall, [and] really skinny” friend? Well, Cameron, another tutee, shared with Noah, “Well, they’re totally not friends anymore.” Why? Tuscany disappeared with Monica’s “totally hot doorman”.

“Monica has this totally hot doorman. Like, a little like Colin Farrel. And this one night Tuscany goes to Monica’s but, well, the doormen call up from the desk to say that she arrived, but she never makes it to Monica’s apartment”

“Whatever, I’m not going to say what I think, I’m sure she’s totally nice, but my friends say she’s a slut.”

Eventually, instead of going to boarding school, Tuscany: “[...] got into Choate, began the spring semester, and was removed from classes three days in [...]” Consequently, Noah was upgraded from tutor to teacher with teaching being done between Tuscany’s riding, ballet and piano lessons. 

After Noah became Tuscany’s teacher, Roberto suggested that Noah have a student-teacher sexual affair with Tuscany, whom Roberto referred to as “the bitch from the magazine”. But Noah replied, “She’s my student, Rob. And she’s fifteen. That’s not going to happen.”

However, Roberto persisted, “Just do things, don’t worry about what’s gonna happen, you know?” And Roberto suggested that Noah stick his hands in Tuscany’s pants or as a last resort, Roberto suggested that Noah kiss his student. 

On the first (home) school day, Noah: “[...] was nervous about entering the bedroom of a sleeping hot fifteen-year-old.” However, Dr. Thayer had Agnès, Tuscany’s assistant, prepare the dining table as Dr. Thayer deemed that it was “improper” for Noah to spend all his time in Tuscany’s bedroom.

Tuscany attended their first class: “[...] wearing a clubbing shirt emblazoned with a sequined martini glass, the neckline dipping to the tops of her breasts.” And “skin-tight denim”. Why? Per the narrator, Tuscany “[...] draws focus to herself whenever she can.” Consequently, Noah reprimanded himself: “[...] stop looking at the slender fingers playing with her bra strap, the butterfly wings of her breastbone.”

Later, Noah learned from Dr. Thayer that Tuscany had dated “forty-year-olds”, but Dr. Thayer didn’t “think” that Tuscany was still dating older men; however, Dylan referred to his sister as the “porno druggie queen”.

At Pangaea’s, a Manhattan night club, while Noah was at the bar, Dylan entered with an entourage:

Two are long-haired and handsome [...] Upper East Side twentysomething aristocracy; the other is an eyebrow-pierced Asian kid about Dylan’s age.

Noah learned from an aristocrat that Tuscany patronized Pangaea “all the time” - with the aristocrat. And, to Dylan’s dismay, Noah learned that Tuscany was the aggressor in the age-gap affair with aristocracy. 

“Hey, Dylan,” Roberto asks, “where’s your sister tonight?”

“My sister? She’s like fifteen. She’s at home.”

“Come on, Dylan,” an aristocrat says. “You know she’s here all the time.”

“Yeah,” says the other aristocrat to the first. “Here with you!”

“That had better not happen ever again, asshole.” Dylan says darkly. “Don’t ever let me hear about you touching her.”

“Dylan, Dylan.” The aristocrat over enunciates, bathing the group in beer vapor. “Don’t you remember? Maybe you were too coked up. She was touching me.”

The Asian kid shared some more details about Tuscany, Pangaea and men. The Asian kid pointed out a man “thirty-five, one hand against his belly and the other holding an unlit cigar” whom Tuscany had been “with for a while”. 

Interestingly, the Asian kid opined that Tuscany was too hot, and he related that Tuscany knew that there was a positive correlation between being skinny, being hot and being the center of attention at Pangaea. Consequently, she got “eaten alive” before turning eighteen due to men offering her drinks and drugs in exchange for teen sex. 

And it was the Asian kid who revealed to Noah why Tuscany was expelled from prep school. 

Asian kid: “What were you tutoring her for, the SAT already?”

Noah: No, no, the ISEE. She wanted to go to boarding school.”

Asian kid: “Oh right. I forgot, she got busted for sending naked pictures to some guy and having like forty bajillion tabs of Xanax.”

Later in the novel, Noah chaperoned Tuscany and Octavia, Tuscany’s teen friend, on a field trip to France. Octavia carried herself with a “voluptuous sense of sexual possibility”. On the Air France flight, 15-year-old Tuscany imbibed a miniature bottle of wine. And after landing, Tuscany and Octavia “developed an instant crush on Benoît” - the French tour guide and father of two. 

After returning to Tuscany’s Fifth Avenue bedroom, for being such a credible chaperone, Tuscany gifted her teacher:

A pink oxford. The fabric is sail-thick, as if made from the very stuff of yachts. The sleeves can be rolled up when watching a regatta or worn down for cocktails on the lawn.

While changing into the pink oxford in Tuscany’s bathroom, Noah’s “thoughts leap to horrible places” like the “bliss he would feel should he have ducked into the bathroom after having slept with Tuscany.”

After emerging from the bathroom, Tuscany, braless and with her lips inches away from her teacher’s, seductively adjusted the pink oxford. Tuscany’s young fingers skated across her teacher’s pectorals and lingered on his chest. Ergo, Noah was tempted to embrace his student, but he opined that Tuscany did not need another man “holding her”. And Noah was not like Roberto whom did not fear the potential consequences of having an age-gap affair with a 15-year-old.  

Later, at a dinner party for Mr. Thayer, Tuscany was dressed “like a fairy-tale princess” in a “red silken dress, ribbed in a darker red” - crisscrossed in the front and tied low in the back. Consequently, a group of men in business suits with names like “Solomon X, X Lidden III, Powel X, Peter X Stockton, and a half dozen Andrews” formed an “admiring circle” around the nymphet where Tuscany received “admiring glances”. 

After Octavia arrived “wearing a very short dress” “with lips glossed and erotically parted”, the two nymphets faced “down unsuspecting thirty-year-old bachelors are in arm, giggling and laying their hands on the unwary men.”

In the end, Olena, Noah’s Albanian immigrant tutee, fittingly said, “Perhaps we have fallen into a type. Student and teacher fall in love. It happens all the time, no?”