Ashton Arlington is a rich kid that follows the order of his father well, but he is hiding a secret: he wears women's panties and craves other men's throbbing members inside of him. When his father sends him to spy on an old rival by working there, he's quickly called out as the sissy he is by the boss's wife… whose package is almost as large as her husbands. Ashton becomes the willing slave to his new boss and his ladyboy wife and loses his virginity, agrees to wear a chastity belt, and desperately tries to hide his dirty secret from his strict father.