NOT TOO DEEP!: Crossdressing, Sissification

It's rare that Randy and his stepbrother, Nathan, are left home alone. So when it happens one night, they make the most of it with plenty of video games, movies, and drinking. After Randy puts Tootsie on the TV, Nathan feels the need to prove that he can make a more convincing woman than Dustin Hoffman. So he goes up to Nathan's sister's room and gets himself dolled up. And he's right--he looks stunning in a cute little dress and a pair of heels.

A few drinks later, the boys get carried away and they wake up the next morning on the couch together, both knowing exactly what they've done. But instead of it being the awkward end to an awkward, drunken night, it turns out to be the beginning of a deep, dark secret, that must remain a secret, especially from Nathan's very conservative minister of a father.