[Toitoikai (Toitoi)] Yankee Shounen Josou Mesu Ochi [mysterymeat3]

A cocky young delinquent slips into a skirt and off-shoulder top to test out his first onahole, only for an older man to come home and catch him mid-thrust. Instead of a scolding, the suited man takes charge, pressing a vibrator against the boy's slick hole and coaching him on how to grind against his own prostate until he's gasping and trembling. By day eight the tomgirl is completely fallen—strapped into frilly lingerie, teasing his nipples and chasing toy-induced bliss while his tutor's lessons go utterly ignored.