The Opposite Sex: Jamie's Story (2004)

Forty-seven-year-old Jim Alter pursued manly roles so successfully for so long -- playing football, starting a family, running auto-shop and construction businesses, hanging with the guys -- that the shock was total when he announced he would now cross-dress (and, eventually, undergo sex-change surgery) as a woman. Reactions range from his mother's earnest bewilderment to the scandalized fury of in-laws. Only wife of 25 years Brenda retrospectively sees signs she'd ignored of the cross-dressing, then hormone-taking "alter ego" he managed to keep secret for decades.