A sissy's anal training reaches new heights as his trainer inserts a thick plug, pushing it in and out while massaging his prostate. The sissy's cock is milked, pre-cum leaking as he's denied release. The trainer's hands work magic, coaxing intense pleasure from the sissy's body. The scene culminates in a anal orgasm, the sissy's body convulsing as he's filled with pleasure, yet no milking of his cock, leaving him yearning for more.