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In a dimly lit room, a sissy man, bound and gagged, awaits his initiation into anal training. His master looms over him, a wicked grin on his face as he lubes up a thick, curved toy. The man's hole clenches as the toy is pushed inside, stretching his virgin ass. He moans, a mix of pain and pleasure, as his master fingers his prostate, making him squirt pre-cum. The man's body tenses as he's brought to the edge, then pushed over, his prostate milking onto the floor. His master watches, stroking his own cock, before unleashing his load onto the sissy's face, marking him as his new toy.