When Jack arrives home, he finds his wife, Evelyn, and her boyfriend, Derek, waiting for him. Jack has been a cuckold for some time now, but this is the first time his wife has allowed him to meet her boyfriend or even be in the same room with them. He knows it's strange, but he has no idea what Evelyn has planned for him. Evelyn has been doing some thinking. While being a hotwife has been fun, she feels it has run its course—she wants something more. And lucky for her, she knows exactly what she wants—and she has a boyfriend who is ready to make her biggest fantasy come true. When Jack realizes that Evelyn wants to watch Derek have his fun with him instead of her, he cannot believe his ears. He's been a loyal cuckold, but he's also straight. How could he do anything with another man? And more importantly, how could he allow himself to be so emasculated as to let his wife's boyfriend have his way with him? But Evelyn knows her hubby will be loyal to his wife and put her enjoyment above his own. Sure enough, Jack goes along, but to his surprise he likes it! Jack was once a cuckold—but now he's a gay cuckold. And there's no going back.