Chrissie, the seasoned sissy trainer, transforms a curious young man into her latest sissy slut. She starts by feminizing him, transforming his appearance with makeup, wigs, and provocative clothing. Then, she introduces him to the world of pleasure and pain, using toys and tools to explore his newfound femininity. Chrissie teaches him to take a cock like a true sissy, using her strap-on to pound his boy pussy until he's begging for more. She trains him to serve and please, ensuring he's ready to fulfill the desires of his future mistress.