During his days in middle school, Roger’s favorite pastime is to daydream about life as a pirate. One day during history class, Roger notices outside that his crush, Lila, has gotten caught in a nasty storm that came out of nowhere. Roger’s knowledge of the confidence and bravery it takes to be a pirate leads him to run out and save her. The storm gets the best of him though, and he collapses on the ground. When he wakes up, he finds himself on a beach. Confused as to why he is here, he begins to investigate. He notices he is surrounded by people who an evil ruler seemingly leads.
Interestingly enough, this ruler looks a lot like his middle school principal. Still trying to grasp what is happening around him, he notices Lila has become a princess and has been captured by the evil ruler. He decides to try and rescue her and everyone under his rule. Suddenly, another storm breaks, and Roger finds himself once again back in his classroom. Confused by all that has happened, he wonders if it was all just a dream or if he really was a pirate saving his princess.