Tippy Madison has a pretty big secret-she's a twenty-eight year old virgin. Thanks to her awkward teenage years, then a crazy college schedule, and, finally, her struggling bookstore, she simply hasn't had time to date. When her beloved bookstore burns down one night, she ends up having a confrontation with a cop that leaves her handcuffed in the backseat of his police cruiser. A cop who happens to be Brent Kingston, the hot former quarterback she tutored back in high school. Though she finds him infuriating, she also finds herself having some pretty wicked thoughts about him.
Brent had a pretty big crush on the opinionated redhead who helped him pass English class. Now grown, Tippy is even more stunning-and just as strong headed. A good turn over his knee and a sound spanking is exactly what she needs, but it's not enough for Brent. Tippy draws out his darker, kinkier, side, yet he quickly learns she is still a virgin. He worries that the feisty redhead won't be able to handle this side of sex, but she is full of surprises.
As their relationship grows so does Tippy's old high school insecurities. Can she overcome the shadows of the past, or will it drive them apart forever?