The first time they encountered a shootout with the law, they were around 14 years old. By this time, they were already entrepreneurs, selling whiskey illegally to the Osage Indian tribe. By the way, Little Britches often disguised herself as a young, boy for various ruses.
Little Britches and Cattle Annie were excellent riders and sharpshooters who dressed in men's clothing. The two women evaded law enforcement and became known for their daring pursuits throughout the region. The pair sold whisky to the Osage and Pawnee tribes and engaged in stealing horses.
Note: Anna Emmaline McDoulet, known as Cattle Annie, died at the age of 95 in Oklahoma City, Oklahoma, in 1978. I couldn't find when or where Jennie Stevenson, known as Little Britches, died. She was born in Kansas in 1879. Both women only served a few years for their crimes which weren't murder but other violations instead including their illegal whiskey operation. They both were married about three times each and had children.