Taylor would do just about anything to finally get a girlfriend. And when the hottest girl on campus starts to pay him a bit of attention, he thinks he might finally have a chance at love. But Kelsey is dating Jason, a football jock. And despite Taylor's best attempts to get Kelsey to leave her boyfriend, he can't seem to convince the pretty girl to drop him.
Taylor soon understands why, when Kelsey lets a big secret slip. Turns out, the hot girl needs a 'tiny favor' from Taylor. The nerdy boy cannot resist--not when he thinks he might have a chance with Kelsey if he just helps her out. Taylor's obedience is tested when Kelsey asks Taylor to dress up as a girl and be her 'moral support' when Jason drops by for a visit. Because Taylor soon learns that Kelsey's boyfriend wants to explore a naughty backdoor kink, and Kelsey wants no part in it.
Little does Taylor know, he's about to be used by the cruel girl. Before the afternoon is over, Taylor is going to end up bent over and taken by jock Jason. But it's OK, because, oddly enough, Taylor is starting to feel prettier as a girl than he ever did as a guy...