Back in the early 50's, Dad had a painter who did wheel stripes freehand with a long-bristled camel hair stripe brush. He would mount the wheel on a front spindle, and spin it with the brush applied to the right spot. He was so alcohol-addicted that it took about three drinks for him to get steady-handed enough to use the stripe brush, but once he was well-lubricated, he was a master at his craft!
Jerry