Bailey Wilde, a stunning transsexual, takes a unique job application route, aiming to prove her worth as a maid. She's joined by Jake Grand, a naive and curious man, who's about to experience the kinkiest cleaning service he's ever had. Bailey, in her feminine glory, teases Jake with her sissified appearance, parading her assets in a sexy maid uniform. She dominates him, making him her bitch, and introduces him to the pleasure of anal stimulation. Jake's world is turned upside down as he's pegged by Bailey's strapon, learning the true meaning of sissy humiliation.