A nervous, inexperienced sissy is led by the dominant hand of a hung shemale to his first ever anal experience. His ass, virgin and tight, is about to be stretched and pounded by a thick, throbbing shecock. The sissy, dressed in lacy panties and a push-up bra, is made to service the shemale's cock, sucking and licking it to hardness. The shemale then forces the sissy onto his back, lifting his legs high to expose his pink, puckered hole. The shemale teases the sissy, rubbing her cockhead against his ass, making him beg for it. Finally, she slams her cock deep into the sissy's ass, making him cry out in a mix of pain and pleasure. The shemale fucks him hard, making him call her 'Mistress' and humiliating him in the process.