Tawara Chikatsura was an adopted son of Tawara Chikakata.
According to the writings of Jesuit Luis Frois, at age 14, while in Usuki with his father, Chikatsura encountered some Christians and was seized by desire to convert to Christianity. His father Chikakata, along with Chikakata's sister (Ôtomo Sôrin's wife "Jezebel"), then forbid him from any contact with the Church, and removed him to another location, placing a guard over him to keep him from seeking to join the Christians. However, while under guard for the next two years, he maintained a secret correspondence with the Jesuits, and read Christian materials, and was eventually baptized in 1577 and given the name Simão.
He was then placed under house arrest by his father again, during which time he again engaged in secret communications with the Jesuits. Chikakata meanwhile wrote a lengthy letter to the Jesuits explaining how Chikatsura's conversion would ruin the Tawara family, and beyond, as the family had a responsibility to serve Hachiman and other gods (and the associated shrines, and the people affiliated with those shrines), and to serve their daimyô, who would not allow Christians into his armies. Chikakata offered some five thousand men to convert in place of his son, and threatened to destroy both his son and the church if the Jesuits did not un-baptize and return his son. This ended with Chikatsura being disowned, though "Jezebel" continued to write letters to the Jesuits demanding that they end their association & communication with Chikatsura, and that Chikatsura had a duty to the traditional gods which the Christian God represented a conflict against. Sôrin even offered that if Chikatsura could pretend in front of his father to not be Christian, he could convince his own daughter (Chikatsura's fiancee) to convert, and could otherwise make a peaceable end to the entire incident. In the end, however, seeing Chikatsura's resoluteness in remaining (openly) Christian, Sôrin stopped pursuing the issue.
Chikatsura lived with the Jesuits for a year, but never pursued priesthood, and continued to be contacted by his aunt "Jezebel" and others who tried to bring him back from Christianity. Ultimately, he fled to Iyo province, where he married another woman. In 1581, Alessandro Valignano came across the couple in Sakai, and tried to bring Chikatsura back to the Church; instead, Chikatsura and his wife fled back to Iyo, and there is no further record of him in Jesuit documents. Chikatsura's father forbade him from returning to Bungo.
- Haruko Nawata Ward, Women Religious Leaders in Japan's Christian Century, Ashgate (2009), 117.