Sam wants to find out how Alan got out of his deal with the devil, but after they are attacked by two demons, Alan disappears and a demon takes an interest in Ben.
The Devil takes Sam to the police station and introduces him to Morgan, whom he calls his son. Now, Sam and the gang are tasked with hanging out with Morgan and showing him the ropes.
The Devil misleads Sam into thinking his next escaped soul is an easy catch and encourages him to take along the gang for a road trip. Unfortunately, when they arrive, they discover a tentacled beast has taken over a small town and is eyeing each of them as its next dinner. Meanwhile, Andi feels Sam is becoming too comfortable with this lifestyle, Ben struggles to not be so clingy with Nina, and Sock makes one last effort to sleep with his stepsister.
The Devil sends Sam to a tutor for proper training to be the Devil's right hand. Sam uses this as an opportunity to get information about the Devil in hopes of getting out of his contract.
Sam, Sock, and Ben go after their old high school teacher, Mr. Sprong, assuming he is the current soul they are trying to catch. The only problem? Mr. Sprong is still alive, and none too happy when the boys take him hostage to try to convince him not to press charges.
When Nina returns from Hell with the information Sam needs, he challenges the Devil to the game he's best at. However, when it comes to a draw, Andi is forced to make the ultimate sacrifice.