Prostate to the Limit: Milking Sissy's Chastity-Caged Cock

Enslaved in a chastity device, a muscular sissy student is brought to his Mistress' dungeon for an advanced prostate training session. She teases his caged cock relentlessly, making it swell and strain against its confinement. She then introduces a variety of prostate toys, from small to large, massaging his sensitive gland until he's squirming and begging for release. She binds him in intricate bondage, showcasing her expertise, before pegging him with a large, textured dildo. She fucks his ass hard, her dominance absolute, until he's screaming with pleasure and pain. Finally, she milks his prostate, drawing out a massive load of cum from his chastity-caged cock, rewarding him for his endurance.

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