An unemployed pilot is offered a career and relationship saving job, with one catch - he must work as a woman. Follow the tale of self-discovery, as our pilot (our sissy pilot), with the help of his loving fiancée, discovers, much to his surprise, that he likes working as and living as a woman. And follow the tale of his relationship with the love of his life, his fiancée, too, as he discovers no matter how much she loves him as a woman, deep inside, she still craves a man, and both wonder, if she will, if she should, cuckold him.