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