Born in Kingston Jamaica in 1911, Bessie immigrated towards US. By Egli Diana Pinto of five, however, Bessie had been an orphan. She grew up by "an Irish woman" in Boston. This Irish woman, whoever title had been never discussed by Bessie in every interviews, spoiled Bessie by giving the girl any such thing she desired. At age 16, Bessie desired a motorcycle, and although "great women didn't drive motorbikes", Bessie was presented with a motorcycle, a 1928 Indian Scout. Bessie didn't have any classes or prior knowledge on the best way to run a motorcycle but just climbed on bike. She was an all natural - a present she attributed to "The Man Upstairs".