SISSY PUNISHMENT: Crossdressing, Sissification

After being unfairly targeted by the school principal, Ian decides to put on some dark clothes and egg the principal's house, one week before Halloween. But he gets the wrong house. The house he hits with his many cartons of eggs actually belongs to Jenna, a housewife who throws the town's biggest annual Halloween party.

When Ian's mom finds out about the act, she decides that Ian will be punished by spending the week at Jenna's house, helping her prepare for her big party. And Jenna's got an idea to make the punishment especially humiliating, with a bit of help from her college-aged daughter's closet.