Bailey Wilde, a vision of femininity in heels and a tight corset, is about to experience the ultimate sissification. Chisholm of Boston, a seasoned trans lover, has Bailey strip down to his lacy lingerie, admiring his feminine form. Bailey's amateur humps and grinds, fueled by humiliation and desire, only serve to excite Chisholm more. With a growl, Chisholm pushes Bailey onto the bed, ready to teach him the art of taking a thick, hard cock up his tight, virgin ass.