When sixth-grader Jeremy needs money to repair the damage he did to his father's boat, he and his best friend dress up as girls and infiltrate the Cupcake Cadet troop in an attempt to win prize money in the Windjammer Whirl model sailboat contest. When sixth-grader Jeremy Bender damages his father's prized boat and needs to come up with a lot of money to get it repaired, he and his best friend dress up as girls and infiltrate the Cupcake Cadet troop in an attempt to win the Windjammer Whirl model sailboat contest, and the prize money that comes with it.