Sissy Slave's Femdom Feminization: Fucking Machine Anal Training

A svelte femboy, his manhood caged in chastity, is led by his stern mistress to a room filled with whirring machinery. His red hair cascades down his back as he timidly walks, his eyes darting between the looming fucking machine and his domme's heels. She orders him to strip, revealing his slim body and hard, confined cock. She releases the chastity device, allowing his length to spring free. She applies lube, rubbing it onto his hole, preparing him for the machine's BBC attachment. She positions him, his face pressed against the cold table, and turns on the machine. It grinds into him, filling him, stretching him, as he cries out in pleasure-pain.

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