A spy is captured and punished with feminization training, transforming into an anal-masochistic prostitute. Bound and helpless, he writhes in pleasure as his nipples, penis, and anus are touched, unable to resist. He is taught the joy of masochism, his anus twitching uncontrollably as he experiences repeated female-like orgasms. His disobedient ass is punished with enemas when he fails to obey, bringing tears of humiliation to his eyes. He performs penile servitude and is forced to vow loyalty to his masochistic training. Eventually, as a fully transformed anal-masochistic prostitute, the femboy is impaled by an extremely thick penis, driven to ecstasy by relentless anal pounding.