Anal Apprenticeship: Sissy's Surrender

A timid sissy submits to his dominant mistress, his anal initiation a rite of passage. He's dressed in lace and heels, his ass plugged and primed. As he's ordered to his knees, he tentatively takes his mistress's massive cock into his mouth, gagging as it hits the back of his throat. She guides his head, fucking his face, before pushing him down onto her thick, veined shaft. He squeals as she stretches his virgin ass, his cries of pain morphing into pleasure as she pounds him, his sissy cock leaking pre-cum.

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