A stern trainer guides her sissy through rigorous feminization training, focusing on anal discipline and cock denial. The sissy, eager to please, takes a thick, veiny dildo deep into his ass, groaning as it stretches his tight hole. His trainer watches, instructing him to keep it in while she lubes up a huge, veined strap-on. She slaps his face with it, making him drool, before ramming it into his mouth, gagging him on her massive fake cock. All the while, he's wearing a chastity device, his own throbbing cock denied release.