Sissy's Intimate Anal Initiation

In the quiet of his home, a sissy cross-dresser delves into the forbidden. Clad in frilly lingerie, he strokes his chastity-caged cock, desperate for release. But not today. Today, he's training his ass, preparing it for his Mistress' impending arrival. He slips on a thin, black latex glove, coating his fingers in lube. He teases his pucker, then inserts one digit, gasping at the taboo pleasure. He adds another, stretching himself, ready for his anal lesson.

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