Kim is not as excited as Kris to do a Playboy photo shoot. Kim is concerned that Playboy will want her to pose nude, and she tells her mom/manager to make sure there is no nudity involved. Another issue on Kim's mind is the dreaded sex tape. She does not want to continue the negative image so many people have about her. Kim's sisters are all for Kim doing the photo shoot, her brother Robert doesn't seem to care either way, and step-dad Bruce is not happy about it at all. Kris and the family remind him that he shouldn't be against Kim posing for Playboy. Why? Because of Bruce doing Playgirl in the late 70's after he brought home gold from the Olympics. He didn't pose nude in the magazine, only the cover and an article. He reminds them he didn't pose nude, but looses the argument anyway. He does help Kim work out and get into shape for the shoot.
The day of the photoshoot, we see a brief cameo appearance of Holly Madison in the dressing room talking with Kim. On the set, the photographer wants Kim to take her top off, but she refuses. Kris lets us know that she's always wanted to pose for Playboy, and she doesn't understand why Kim is being uptight. Kim takes her mom up on the offer to switches manager/model roles. Kim sets up a nude photo shoot for Kris with an Olympic theme in honor of Bruce. Kris is delighted with the whole process and looks forward to the final prints.
A little while later, Kris gets another call from Playboy telling her that Hef wants to see some more shots of Kim-with nudity. Kim and Kris drive to the Playboy Mansion to meet with Hef in person, and he persuades Kim into going topless by reminding her that the December issue is very important to him. He tells Kim that he started Playboy with Marylin Monroe on the cover of the December 1953 issue. Kim figures if Marylin can do it, she can too.
Kim is much more relaxed at the second shoot, and she agrees to be nude as long as she can be draped in long strands of pearls and diamonds. That shoot turns out beautiful, with Kendra Wilkinson agreeing that Kim "looks hot".
At the end of the show the family gathers for the unveiling of a large framed photo's. The cloth is removed and much to everyone's surprise, it's Kris' nude "Olympic" photo! Bruce finally gets happy in this episode and takes the framed photo and Kris to the bedroom…to hang the picture?