A femboy's anal journey begins with a harsh pegging session. His mistress, clad in latex, lubes up a massive dildo and pushes it deep into his virgin ass. He cries out, but she silences him with a gloved hand. She fucks him hard, humiliating him, making him call her 'Mistress' and 'Goddess'. His ass stretches, accommodating the toy, as he's taught the hard way that pain and pleasure can intertwine.