John is a college student who is a classic under-achiever. He s falling behind in his studies, letting his body get flabby, and most importantly allowing his relationship with the beautiful Laura to stagnate. Fortunately she isn t ready to quit on him and she s convinced by her housemate, Christine, that John needs some tough love to help him get his life in order. In fact Christine suggests that imprisonment in a male chastity device is exactly the thing that will focus John s attention while he is away from Laura at college during the week. When presented with an ultimatum by Laura, John reluctantly agrees. Of course, Laura has her needs, and it seems that the gorgeous and totally evil Christine is quite ready to satisfy them which only adds to John s frustration as he s forced to witness their nightly love making over a videoconferencing link from his dorm room, with his poor cock almost exploding from its plastic prison. And this is only the start of his Journey. As he struggles to meet Laura and Christine s goals for his life John submits to ever more cruel challenges, but along the way he discovers the joy of bringing pleasure to both of his Mistresses.