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In this kinky role-play, a femdom milks her sissy's prostate until he can't hold back any longer. She challenges him to orgasm without direct penile stimulation, using only her expert anal play. With a determined look, she pegs him deeply, curving her strap-on to hit his sweet spot. The sissy squirms and moans, his chastity device a constant reminder of his submissive role, as he finally succumbs to an explosive, prostate-driven orgasm.