SissyBoy, dressed in skimpy lingerie and stockings, is subjected to a rigorous training session by MrsAnnette. She begins by humiliating him, making him worship her feet and lick her heels. Then, she commands him to lie on the Sybian machine, inserting a massive dildo into his ass while he's forced to wear a chastity cage. MrsAnnette uses a pussy pump to inflate his balls, causing him immense discomfort. She switches between anal fingering and fisting, and pegging him hard with strap-ons, all while degrading him verbally.