Scott has been living a lie most of his life. He has a secret part of himself that he has not shared with anyone, not even his wife. Scott's life is changed the day that his wife catches him dressing in her clothes. The crossdressing is only the tip of the iceberg that is Scott's secret. Scott has other desires as well, darker desires, and so it turns out does his wife. In A Sissy Diary we follow Scott as he becomes immersed in these darker desires with the help of his 'Auntie Lois' and 'Uncle Cliff.'