Fortunately, it has! Not with hair as sexy as yours but with four different women.....although not at the same time...unfortunately..hehe

A few times with women of rather short hair, many times with a g/f with elbow length blond hair, and many times with a g/f of waist length brown hair. With her I was lucky enough to do her loose hair, ponytail, braid, french braid, and bun. I think she liked to power it had over me.