In vintage, long-lost footage, Tianna (also known as Buttwoman) spiced up the office of a porn company by filming her coworkers Heather Lere, K.C. Williams, and Missy Warner's attractive asses and legs. With her camera in hand, Buttwoman saunters around the office, excitedly recording their attractive posteriors as they sag out of form-fitting miniskirts. Before long, everyone in the group is bending over for action and lewdly masturbating at their workstations. In this anally obsessed mass lesbian lickfest, the attractive office whores reach climax with prodding fingers, toys, and tongues.

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In the 1990s, pornographer Melanie Moore calls Tianna, also known as Buttwoman, to film a girl-girl action scene. She brings two models, Suzie Matthews and Tawny, with butt acne, and Tianna takes over with her video camera.

Teens Vanna Bardot, Veronica Leal, and Lina Luxa are excited for a sleepover and bring a bag filled with the largest dildos they've ever seen. They take turns sucking on a rainbow-colored cock, playing tonsils with it, and removing a gigantic pink dildo. They admire each other's boobs before loading themselves with the monster cock. They eagerly await to get into each other's naughty regions.

Dominno is disgusted by the scattered erotic toys on the couch. Alysa, a small-framed rectal stuntwoman, is eager to use her skills on Dominno to obtain her massive, organic knockers. Alysa shows Dominno her jugs, ass, and gadgets, licking his knuckles with delight.

Dana Vespoli, an exotic tattooed woman, meets blonde booty queen Phoenix Marie for a private lesbian ass play session. They engage in a playful exchange of wet tongues, causing Dana to receive a spanking for her large ass.

The narrator expresses their shame over past sexual decisions and the difficulty in recognizing their own. They seek advice from their stepmother, Cherie, who is more experienced and trustworthy. They discuss their experiences with Cherie, who becomes horny and eager for their first anal experience. The narrator gets two fingers and a powerful orgasm, practicing on her anal toy. Cherie praises their progress and asks them to make her cum again. Cherie offers them a pink glass of dildo, and the narrator is eager to become an expert.

Phoenix Marie trains Abella Danger, a young woman, to become a voluptuous and powerful woman. She uses various devices to soothe her sore butthole, including a pink dildo, vibrator, strap-on, and other gadgets. Abella uses these devices to worship her boobs and phat, resulting in a sexually explicit scene.

Puma Swede, tired of his stepdaughter Bree Daniels' sour attitude, uses sexual dominance to change her. He physically confronts Bree, smothers her with butt plugs, and threatens to send her to school if she doesn't suck the $10,000 worth of tits. Puma takes pictures to keep Bree in check.

Dana Vespoli, an exotic tattooed woman, meets blonde booty queen Phoenix Marie for a private lesbian ass play session. They engage in a playful exchange of wet tongues, causing Dana to receive a spanking for her large ass.

In Joey Silvera's studio, Laela Pryce and Sarah Shevon engage in anal playtime, using various devices to invade Laela's rectum. Laela uses tools to drill her asshole, while Sarah's rectum prolapses, resembling a sensual rose.