A sissy boy, desperate for his mistress's approval, cross-dresses in lacy underwear and stockings. She teases him, pegging his ass with a thick strap-on, making him moan and beg for more. The humiliation and pleasure mix, driving him to the edge. She commands him to squirt, and he does, his cock pulsing as he showers her in his warm cum. She milks his dick, making him lick his own cum off her fingers before pushing him to his knees and feeding him her own load, gagging him with her huge cumshot.