After decades of silence, Hefner's former number one girlfriend Sondra Theodore shares her story detailing how she was groomed by him to participate in his increasingly abusive sex life. Sondra's testimony shines a spotlight on Hefner's mechanisms for controlling and breaking women.

The Playboy corporate world was billed as a welcoming place for women, but Playmate and eventual Director of Playboy Promotions Miki Garcia and Bunny Mother PJ Masten reveal the rampant sexual harassment they faced within it.

Playboy hired the most attractive women in the world by promising an environment where they would always be protected, but outside of the Playboy Mansion, the Bunnies faced dangers and abuses that were covered up by the Playboy “cleanup crew.”

Even in the earliest parties at the mansion, celebrities like Roman Polanski and Bill Cosby are a big part of the allure of the Playboy brand, but Hugh Hefner keeps some Hollywood A-listers happy at the expense of the women.

The sports world is often criticized for not only underpaying and undervaluing female athletes, but these women are also notoriously sexualized. It is something investigative journalist and former Playboy cover model, Lisa Guerrero has personally experienced during her time as an NFL cheerleader and sports reporter. Lisa talks with three athletes who made the controversial decision to pose for Playboy, and the backlash they received from appearing in with the magazine.

This episode explores the 1970s DEA investigation into Hefner, Playboy, and drugs through the lens of two women who lived and worked at Playboy: Hefner's right-hand woman Bobbie Arnstein, who committed suicide while being investigated for drug trafficking, and Playboy Bunny Adrienne Pollack, who died of a drug overdose in 1973.

While Playboy usually featured a specific standard of beauty in its magazine, it occasionally disrupted that norm by showcasing models not typically seen within its pages. Those decisions often created controversy. Investigative journalist and former Playboy cover model Lisa Guerrero talks with three Playboy models who were not the traditional women readers were accustomed to.

Playboy has long been known for its pictorials of working women. Perhaps none of these features were more tantalizing to their readers than those of women in uniform. Playboy cover model and investigative journalist Lisa Guerrero sits down with a former NYPD officer and a former US Air Force Training Instructor to discuss the highs, and lows, of their fateful decision to pose.

After a divorce in the late 90s, Hugh Hefner became a bachelor again, and the era of the seven girlfriends emerged. For some, being one of the seven girlfriends was a highly coveted position that was as much a job as it was a relationship. Hef's girlfriends were not only supported by him, but they were used to publicly promote the Playboy brand during lavish events and club outings. But being a girlfriend was not all glitz and glam. The inner-drama that ensued among the girlfriends played out on the public stage.

Former girlfriends of Hugh Hefner Karissa and Kristina Shannon, discuss their experience with Hefner and the hit television series "The Girls Next Door," which introduced a new generation to Hefner and the Playboy lifestyle. Telling their emotional story for the first time, Karissa and Kristina reveal that beneath the sugar-coated exterior was a darker world led by Hefner with increasingly stricter rules designed to control the women in order to maintain the Playboy image.

Sondra Theodore and her daughter Katie explore their dramatically different versions of life at the Playboy Mansion as they work to heal the trauma in their complicated relationship.

In 1977 Playboy introduced pictorials featuring often barely-legal college women. Playboy went to university campuses across the country and hosted auditions for female students to pose and represent their school. While some of these women jumped at the chance to audition, others protested the magazine's presence on campus. For those that were selected, the choice to pose for Playboy sometimes resulted in unanticipated, far reaching consequences, in their personal lives and their careers.