Jay Wimp kneels and waits while Maitresse Madeline touches up her make-up, and she tells him of the plans she has in store for him. Maitresse Madeline has decided to use Jay to make some money by pimping him out to the nearby construction crew, and she reasserts her power over Jay by flogging him and slapping his face. Jay’s eyes fill with fear when Madeline describes in detail how she will turn him into a cock-sucking sissy whore while taking off Jay’s clothes.
Maitresse mocks Jay’s puny cock and shaves off his beard to try and make him more appealing to paying customers. Jay is made to put on women’s pink sheer panties, white stockings and bra, and Madeline ensures Jay’s obedience by caning his body and outstretched arms and hands. The domme puts lipstick on Jay’s lips and guides her gimp servant’s big cock into the sissy’s mouth. Mistress Madeline watches closely to ensure Jay’s technique is good enough so that construction workers will pay to fuck his mouth.
After making sure Jay’s dick-sucking skills are up to par, Maitresse Madeline uses her strapon to ensure Jay’s ass can take a pounding. She warms up Jay’s whore-hole with her fingers, sticking them one by one until Jay’s moaning fill the room. Madeline guides her plastic cock into Jay and widens him inch by inch, caressing Jay’s puny dick and laughing as Jay tries to control the mixed feelings that overcome him.