Wearing latex and a corset, Mistress Kendra James trains her femdom slave to be a sissy so she can pimp him out on the street to strangers. Kendra puts make-up, a wig and pink frilly dress on her servant, and he accepts it with the obedience that is expected of him. When his mistress orders he get on all fours, he obeys unquestioningly. Mistress James uses her gloved hands to prepare the submissive’s ass for his first pegging, slipping her fingers in and out of the sissy’s virgin asshole.
The feminized submissive can’t hold back the moans of pleasure Kendra’s anal fingering rips out of him. Kendra works her pink strapon into the sissy’s tight asshole, giving him advice on how to take her cock for the first time. After struggling to endure the pegging, the sissy learns to relax and discovers the pleasure of giving into his mistress’ desire, and begs Kendra to fuck his ass deeper and harder.