Prep School Sexcapades Fall Flat on Their Faces

“Her skin wasn’t soft. She had weird moles. She wasn’t delicate, and she wasn’t even built in the sexy way that Josh liked. This girl was ugly. So he did what he thought he was supposed to do: He reached for her vagina.”
Welcome to Milton Academy, an exclusive boarding school where the students are wealthy, the parties are wild, and the parents are woefully oblivious. It’s the subject of Abigail Jones and Marissa Miley’s fact-based book, Restless Virgins, a steamy, eighth-grade-reading-level exposé that dares to peer behind the glittery veneer of prep school in order to share the groundbreaking observation that kids in high school are totally doing it.
That “it” isn’t necessarily what you think it is. As is immediately apparent from its purposefully eye-grabbing title, the main topic of Restless Virgins is sex—but not the missionary kind. Jones and Miley conducted 280 interviews with Milton students, faculty, and parents to try to get to the bottom of a scandal that rocked the academy’s community in 2005: on January 24 of that year, a sophomore girl was discovered in the locker room of the boy’s hockey team, performing oral sex on five separate players in turn.
The most shocking thing about Restless Virgins is that the events of the supposed scandal weren’t actually out of the ordinary for Milton. Jones and Miley, Milton alumnae themselves, repeatedly make the point that Milton is a place where, at least for the members of the god-like boy’s hockey team, “group sex acts were just like showering together after practice.” According to Restless Virgins, relationships between guys and girls at Milton are entirely one-sided—the girls go down on the guys and the guys tell each other about it afterwards.
The book also features stories of real-life occurrences of the kind of sex acts you thought they only wrote about on the Internet. There’s the ski-pole, in which a girl gives two boys simultaneous hand jobs; the Dub Saw, in which “two boys penetrate a girl simultaneously, one in her vagina and one in her anus”; and the Eiffel Tower, “when a girl performs oral sex on one boy and simultaneously receives vaginal or anal sex from another boy.” The Blow Job Club, which “serviced guys in public locations,” also gets a passing mention. It’s a wonder that Milton students have time to apply to college in the midst of all this debauchery.
Restless Virgins wants to be more than a litany of unorthodox sexual terms. Jones and Miley try to give their story some heart by telling it through the eyes of seven Milton seniors who graduated in 2005. This style, reminiscent of Alexandra Robbins’ 2004 bestseller Pledged, has its pros and cons. On one hand, readers can see how members of different social groups reacted to the locker room incident and get an extra voyeuristic thrill by reading excerpts from IM conversations and diaries. On the other—more important—hand, it results in a disjointed, unbalanced, and ultimately unfocused narrative.
It’s unclear why Miley and Jones chose the students they did, since many of them represent stock characters that can be found in every media representation of high school—the popular mean girl, the awkward outsider, the alpha male athlete. Puzzlingly, none of the main players in Restless Virgins were directly involved in the events of January 24, so we never learn anything from the book that hasn’t already been reported by newspapers like the Boston Globe.
It’s easy to imagine Milton students and grads pouring over the book and gossiping about it with each other, trying to guess which pseudonyms match up with which real former Miltonians. For everyone else, though, Restless Virgins is all sex and no substance.