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Alex Truelove is on a quest to lose his virginity, an event eagerly awaited by his patient girlfriend and cheered on with welcome advice by his rowdy friends. But Alex, a super gregarious dude, is oddly unmotivated. A magical house party throws Alex into the presence of Elliot, a hunky college guy, who pegs Alex as gay and flirts hard. Alex is taken aback but after a series of setbacks on the girlfriend front he takes the plunge and learns some interesting new facts about himself.

In 1955, young photographer Dennis Stock develops a close bond with actor James Dean while shooting pictures of the rising Hollywood star.

Teenager Deacon works at a video shop, and his buddies, Fred and Matt, sell the bootleg porno films he acquires. Deacon gets fired, but the pals have the bright idea of filming their own Internet porn flick in order to make money and become more popular at school. Hijinks ensue as they cast and create their movie, but porn industry player Vic Ramalot grows jealous of their burgeoning success and tries to put a stop to the project.

In 1972, a seemingly typical shoestring budget pornographic film was made in a Florida hotel: "Deep Throat," starring Linda Lovelace. This film would surpass the wildest expectation of everyone involved to become one of the most successful independent films of all time. It caught the public imagination which met the spirit of the times, even as the self-appointed guardians of public morality struggled to suppress it, and created, for a brief moment, a possible future where sexuality in film had a bold artistic potential. This film covers the story of the making of this controversial film, its stunning success, its hysterical opposition along with its dark side of mob influence and allegations of the on set mistreatment of the film's star.