It is difficult to write about and may even be considered family heresy, but in view of some of the records and the life grandmother Annie led after Charles Pfieffer left her in California in 1914, we have to consider other not so pleasant possibilities. I always felt my mother disapproved of my grandmother's life style every time we visited in California. Also the 1900 census shows conflicting information.
1900 Census (Taken June 18, 1900) Shows:
Note the difference in the facts and the census record:
It was rumored, Belle ran a Brothel in Fort Smith. It could be true, Susie Stewart said she has one of Belle Starr's original cards from the house of ill repute. Susie's attorney gave it to her. The card has a Plum, an ostrich feather on it. The card says, "Let Us Tickle Your Fancy." On the other hand, maybe it was Pearl's card that said, "Let us tickle your fancy".
Pearl Starr (right) and unidentified girls

It is possible Annie was alone after her parents died. She may have been despondent after she found out how difficult it was to raise her daughter alone. Pearl Starr, who knew her in school, might have convinced her to move to Fort Smith and live in the girls boarding house. This would get her away from her relatives in Porum. Maybe she even became a prostitute for a while to take care of her child.
Sometime around 1893. Belle's daughter, Pearl, opened a girls boarding house in Fort Smith. It was decorated with a large red star draped with a string of pearls and outlined in electric lights. ("Electric lights" in Fort Smith in 1893, very modern, Edison's 1st incandescent bulb in 1879, electric arc lamps in Philadelphia 1878).
Pearl's boarders were pretty young girls willing to sell themselves at two to five dollars a night. It is even possible Anna met Charles Pfieffer in the brothel. Charles may have conceived Bessy May there, felt guilty because of his religion and married Anna. This might account for the animosity he had for her and Dora when he left them in California.