Jim Benson is a guy who seems to have it all, aside from a steady woman in his life. In his leisure time he enjoys writing spanking stories and watching videos. When his favorite website sponsors a contest asking for screenplays for an upcoming video shoot, he submits his best work yet, and wins! He and the other contest winner - the sexy Jennifer - are flown to London to meet the spanking stars they will be working with. As Jim spends time with Jen, the pair realise they are members of the same spanking website and actually know each other by their pen names, and when Jim admits he has never actually spanked a woman before, Jen has the perfect solution! The first day of film shooting goes well, with Jim getting into his role as he effectively spanks Amanda. Anna, one of the other models has the hots for Jim. She asks him to practice using a cane for the first time so he will be ready for their scene together the next day. He does a great job and is determined to get further practice in the hotel later that night with Jen.

The next day, Jim and Anna perform a scene for the camera and Jim realizes this experience is like a dream come true for him. He proves adept at ad-libbing the scene and keeping up with the professional actress bent before him. His caning skills leave the beautiful Anna stunned and aroused... and Jennifer experiences a pang of jealousy. On the last day of shooting, Jim's co-star is ill and unable to perform. Jenny quickly volunteers to be his bratty girlfriend for the scene and filming begins. Their on-screen chemistry is obvious when they perform a wonderful scene for the camera, leading to a successful video. After they return to the States, distance and work commitments keep them apart. But will they let this 'chance of a lifetime' pass them by?