In this amateur fetish scene, a crossdressing sissy kneels before his stern mistress, eagerly awaiting her command. She orders him to insert a large, black butt plug, stretching his tight hole. The sissy moans, sensations coursing through him as he obeys. His mistress then attaches a milking machine to his bound cock, the rhythmic pulsations drawing out his humiliation and pleasure. She watches, smirking, as he's milked dry, his body quivering with debased ecstasy.