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Tristan Taormino has dished out advice to Howard Stern, Dr. Drew and the Playboy Advisor, but she finally meets her match when she approaches John "Buttman" Stagliano to produce the video of her bestselling book, "The Ultimate Guide to Anal Sex for Women". Buttman challenges Tristan to pop Ruby's anal cherry to earn his support, and she does - right in his office! When Tristan invites her favorite porn stars to an anal sex workshop, Buttman's camera captures an incredible mix of true confessions and intense escapades. Before class even begins, Nacho can't wait to get his huge dick inside real-life girlfriend Jazmine's delicious ass. After an enema skillfully administered by Ernest Greene, Chloe seduces Kyle into f**king her ass until she comes.