For some boys, looking like a girl would be a blessing. For eighteen-year-old Sam Kent, however, it’s a curse. Already shy with girls, Sam can’t see how his girly looks can get him a date with his best friend Heather, on whom he’s had a crush for years. Heather sees potential in Sammy’s soft features, though, when her father’s country club announces an upcoming costume party. She’s sure that Sammy, dressed up as a beautiful bride, will win the $2000 Grand Prize.
A monkey wrench is thrown into Heather’s plans, though, when her brother Billy decides to blackmail his sister and her beautiful “girlfriend” into going on a date with and performing sex on him and his friend Alex. If they don’t comply, Billy will publish photos of Sammy at his feminine best to the Internet and ruin his reputation. Reluctantly, Sammy complies, not realizing that Billy has no intention of letting his sexual extortion end after one night.