Author 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 round ass. After an enema skillfully administered by Ernest Greene, Chloe seduces Kyle who fucks her ass until she comes, then makes her come again. Always the naughty schoolgirl, Chandler arrives late to class, but Sydnee reviews what she learned as the two girls go at it with enough sex toys to satisfy an army. Tony takes on blonde beauties Inari and Jewel in a jam-packed threeway, complete with butt-licking, eight fingers in one asshole, and gapes galore. After a day of difficult assignments, Tritans' students surprise her with an "extra credit project". It doesn't take long for the teacher herself to surrender; she makes her porn debut - as the object of a ten-person anal gang-bang! When the pros get their hands on their teacher and each other, what follows is a wild orgy with no holes barred.