ROOMMATE DARES (Crossdressing, Feminization, First Time)

Aaron's roommate, Jake, has a gambling addiction. He's always betting on everything, and from time to time, Aaron can't help but get in on the action. But soon enough, Jake runs out of money, so he starts getting more creative with his wagers.

One afternoon, Jake and Aaron find themselves betting on a hockey game with the biggest stakes yet: the loser has to be the winner's slave for a day, and do whatever the winner wants within the confines of the house.