Hugh doesn't know anyone is watching him when he slips on a skirt. Not until Kelsey tells him that she thought it looked cute on him. Kelsey is Hugh's sister's best friend, and she's over at the house hanging out with Rachel when she goes to Hugh's room to ask him if she can borrow some tape. Kelsey never expects to see Hugh in a skirt, but thankfully, she closes the door before Hugh hears her. As much as Kelsey tries to forget what happened, she can't. Kelsey wants to see just how far Hugh will go, so she offers him some help to become the pretty girl of his dreams. Caught Red-Handed is a sweet and steamy feminization romance about a guy who needs a little push towards femininity by a kind and understanding girl.