In Jared Hitches a Ride artist Vanessa and college-girl Mallory pick up Jared when they see him hitching on the Interstate. Vanessa flirts with Jared, but refuses to have sex with him unless he conspires with her in a seduction of Mallory; the college girl is unhappily engaged to her feckless high-school sweetheart and Vanessa sees this as an opportunity to wake her up to other opportunities. Jared employs all his cunning in breaking down Mallory’s resistance, culminating in a wild motel-room tryst with Vanessa which eventually draws in an aroused and enthusiastic Mallory. He secretly records part of the encounter on Mallory’s fiancé’s voicemail, as a result of which Mallory is forced to confront her doomed relationship and with Vanessa’s encouragement to embark on a new chapter in her life.
In Jared’s Roller Coaster friends Sasha and Libby meet Jared while he works at a funfair in England. Libby is beaten to a date with him by the pushy patronizing friend who always leaves her in the shade. She finds herself seduced by him, however, behind Sasha’s back, and while resisting his advances, embarks on a scheme to tease him, showing him what he turned down without actually giving in to him. The plan backfires at a Halloween costume party however when she encounters a naked Jared in one of the house’s bedrooms. Almost caught in this compromising position by Sasha, she hides and watches from a closet as he fucks her friend, becoming progressively more aroused. When Sasha passes out Jared completes his seduction of Libby and has torrid sex with her, fucking her more or less on top of the sleeping Sasha. As a parting shot Jared handcuffs her to the bed, writing ‘Trick’ and ‘Treat’ in lipstick on Sasha and Libby respectively, so that once Sasha wakes up the girls will have no choice but to face painful truths about their friendship.
Finally in Jared Teaches a Lesson Jared is met by his former high-school teacher Sylvia Steele at a gig where he is playing. She has come out of a dull and disastrous marriage and is tempted by him, recalling how she come close to abandoning her professionalism with him when he was only eighteen. They flirt and, unable to resist, she accompanies him to his apartment. He seduces her to the point of submission, then stops, insisting that he will only have sex with her if she returns another night in her teacher guise, so they can enact the teacher/student fantasy which remained unfulfilled years before. She fights the urge, but ultimately gives up all her scruples regarding sex with ex-students and returns to him for a fiercely erotic and bdsm-tinged encounter. In the aftermath a fondness is established between them and she advises him to pursue something meaningful with Vanessa from the first story, with whom he has stayed in touch. The encounter with Jared ultimately shakes her out of her work-obsessed lifestyle and sets her on the road to rebuilding her life.