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A sissy-boy, hungry for new sensations, introduces an anal probe to his training regimen. As the toy's thick, curved tip pushes against his prostate, he moans, his cock swelling within its chastity device. The vibrator's hum intensifies, driving him to the brink of a sissygasm, his ass clenching around the toy, desperate for release. Finally, with a shuddering cry, he cums hands-free, his prostate milked dry, leaving him a trembling, satisfied mess.