Masatora learned calligraphy from Tsunefusa INOO (since Tsunefusa INOO died in 1485, it was conjectured that Masatora actually learned from a man who was one of Tsunefusa's disciples), and he was one of the top grade calligraphers of the day from the Sensoji School.
正虎は、書を飯尾常房に学び（飯尾常房は1485年に没しているので、実際にはその弟子筋の人物に学んだと推測される）、世尊寺流の当代一流の書家であった。