It was quite obvious that Robin had married Chandler for his money, in fact she bragged about it to everyone. And Chandler was swept away with love for the tall and beautiful woman so much so that he became an obedient little slave to her even though she treated him like a child, even sending him to bed with a stuffed bear.

But Robin’s selfish desire for keeping both Chandler and his inherited fortune under her domain was becoming an obsession and she needed a scheme to prevent Chandler from being stolen by her best friend Kelly.
Her idea was to dress Chandler as a female to humiliate him if front of Kelly in an attempt to hopefully discourage Kelly from hitting on Chandler. But the plan did not entirely live up to Robin’s expectations.