Desperate college sophomore, Michael, jumps at the opportunity to rent an affordable room, especially when he meets the stunning girl who answers the door, Taylor. He becomes infatuated with her and is determined to become her roommate and possibly more.
However, Michael is unaware that "Taylor" is actually Tyler, a college geek who cross-dresses at the hands of his domineering girlfriend, Anna. As Michael gets pulled into their world, he begins to develop feelings for "Taylor," still unaware of the truth.
And when Anna tricks Michael into a bet over whether "Taylor" is a real woman, or just Tyler dressed-up as one, Michael loses and is obligated to become another one of Anna's 'dolls,' per the rules of the wager.
Before he knows it, Michael is dressed as a beautiful woman alongside Tyler, and thrust into the world of cross-dressing in a wild and unforgettable way.
And as the night goes on, Anna reveals yet another a truly unexpected "tool" she plans to use on Michael for his initiation into permanent cross-dressing sissydom.