Jess Sparkhill is a relatively small time shoe manufacturer who has ecked out a pretty good living taking over his Fathers business. He has a somewhat open relationship with a fellow entrepreneur, Mary Belanger, but his interest in her young protege, Allison MacGruder, is piqued when he first sees her as someone he might not have a chance with. As her story unfolds he begins to find she may be just the thing to solidify his life. But first he must deal with Mary, his "friend with benefits."
Transgender teen Alexandra Plessy moves to Masons Peak to complete her senior year and escape her sex addicted uncle. She keeps her transgender identity secret and has to navigate the challenges of being 'the new kid'. She piques the interest of 'The Karens', three middleclass, self-centered, overly entitled bullies who are determined to put her in her place. She has to satisfy her uncle's sexual appetite whilst trying to have a stable relationship with her boyfriend.