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A dominant woman educates her eager student on the finer points of anal pleasure, comparing the sensation of a toy penetrating his ass to the feeling of his own cock cumming. The lesson begins with the submissive male, locked in a chastity device, worshipping his mistress' feet while she teases him with a vibrator. She then demonstrates the art of prostate massage, bringing him to a hands-free orgasm before comparing the feeling to the anal penetration.