Based on Lily's Manly contest for RAGS

Every year the coolest and bravest men in the world compete in a contest to see who the is the best. The winner gets ten million dollars and the official title of manliest man in the world! If you enter however, you better be the best, because the losers lose their manhood forever!

The rules of the contest is simple, five men enter the arena with one hot woman. Any time one of the men ejaculates he is turned into a woman, when only one man remains he is declared the winner.