Penny (Kyler Quinn) arrives at the beautiful home of Charlie Foster (Brad Newman). However, the man who greets Penny at the door is not Charlie but Jack (Rion King), who doesn't seem too fond of Penny. As Jack leads Penny through the house and explains the rules, it is revealed that Charlie likes to rescue homeless girls by inviting them to join his harem. Charlie is into family roleplay, so he requires that the girls in the harem refer to him as a parental figure and refer to each other as siblings, even though none of them are actually related. Jack is the eldest 'sibling', who helps to watch over the girls. Penny is the newest one. In fact, Penny is the 100th girl.As the tour of the home continues, Penny meets some of her fellow siblings (Nadia Noja, Paris White, Hadley Haze, Rebecca Vanguard, Sage Foxx, Penelope Woods, Kate Bloom), who all seem to like Penny. Jack becomes jealous, and insists that Penny needs to prove herself. Eager to please, Penny takes off her panties to fit in with the home's dress code, and tries to show off a bold, sexual side, which includes kissing Jack.Although Jack likes Penny's initiative, he's still not convinced. Penny offers to have sex with him in order to convince him. Jack agrees, insisting that the other girls watch. They have sex on the couch, with Jack taking charge and trying to humiliate Penny in front of the others. However, the sex is eventually interrupted when Charlie enters. He's unimpressed with Jack's attitude, and scolds him. Charlie then has sex with Penny and eventually invites Jack to join them, in order to give Penny a proper welcome into this growing 'family'.