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Peter and Joe help Quagmire pick out a new computer. Quagmire calls Peter for help to find his pictures and ends up frying his computer. Taking it in for service, Sonja the clerk discovers his tastes in porn and they end up on a date. Out to eat, they find they have a lot in common but Quagmire wakes up the next morning handcuffed to the bed and discovers he was drugged to have sex, and decides that he has finally found his true love. Telling the guys at The Drunken Clam, they caution him to be careful. They engage in a variety of sexual acts including having sex with his father. At the Clam, Peter and Joe discover Quagmire hiding blackened eyes but he dismisses their concerns. Leaving the Clam, Sonja meets him outside, beats him and shuts him in the trunk of his car claiming that she is satisfying his fantasies of being dominated and humiliated as she drives away with him.
Ida shows up at Peter's door and expresses concern that Quagmire hasn't been seen for days and Joe is also aware that Quagmire hasn't been seen either. The guys search for Quagmire by going to all his usual haunts. Wandering into a seedy area, they find Sonja has a reputation and are directed to a storage container. Finding Quagmire, they are cornered by Sonja who takes Joe's gun. He calls her bluff and closes in. She pulls the trigger without result and Joe tackles her, admitting he keeps his gun unloaded following an incident the previous April. Quagmire admits later that he'll need to be the really kinky one in his future relationships as he worries about his dad being pregnant.
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Meanwhile, Lois and the kids prepare for Halloween. While going though storage, Lois finds Stewie's first teddy bear, Oscar. Stewie rejects it until he finds himself wavering between Oscar and Rupert. Brian discovers Stewie in the attic playing “tea” with Oscar and he begs Brian not to tell Rupert, claiming he is suicidal. Later, Stewie stomps downstairs claiming to have had a fight with Rupert, and gives him to Brian. Spending time with Oscar, he finds Brian humping him and takes him back. Rupert is forced to choose to pick between Stewie and Brian, falling over towards Stewie which Stewie takes as a sign of choice. As he rejoices with Rupert, he worries about how Oscar will take the news. Oscar is seen having apparently hanged himself in front of a painting of Stewie.
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