In October 1998, Benjy Nelson, a 45-year-old former athlete and Air Force airman, underwent a sex-change operation. He had been cross-dressing for five years, initially at home and then in public, eventually doing so full-time for the last five years. His wife of seventeen years, Debbie, fully supported his decision to cross-dress and then transition. However, their three teenage sons struggled with and reacted to their father's choice. This documentary explores the impact of that decision on the family as a whole, prompting viewers to consider the complexities involved.