Kelsey Masters, a femboy in chastity, is a tempting prize for Jake Grand. After being edged for days, Kelsey's anal virginity is about to be taken. Jake grinds his thick cock against Kelsey's ass, making her whimper in anticipation. With one swift thrust, he breaks through her tight ring, making her gasp. Jake fucks her slow and deep, savoring her tightness, before picking up the pace, slamming into her, claiming her ass as his own. Kelsey, overwhelmed with pleasure, can't help but call him daddy as he fills her with his hot cum.