I haven't had the chance to read
Gregory H. Williams book,
Life on the Color Line: The True Story of a White Boy Who Discovered He Was Black, but I believe that it addresses this question in a unique way.
The current President of CCNY, Dr. Williams, grew up thinking that he was white. When he was 10 or so, his father came back into his life, as his father. His father is black. They moved to Indiana, to be near his dad's family. He then lived life on the other side of the racial divide of that time.
The book sounds fascinating, and I'll probably read it before the year is out.
ETA
QuickTime interview with Dr. Williams is
here
Life on the Color Line: The True Story of a White Boy Who Discovered He Was Black
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