This study targeted a total of 181 pages of prostitute-related documents, including all prostitute-related documents for [Records of Gisaeng and Prostitute] and 3 pages of [Agenda on Gisaeng and Prostitute Regulation Enforcement Instructions] that did not exist in the original copies and were newly discovered during the preliminary research. Then, this study examined each document and reorganized them based on the time sequence of documentation for a precise and detailed clarification on the details and process of changes in the policies that the Resident-General enforced on the prostitute, who was a professional prostitute during the late Korean Empire. First, the Resident-General ordered a head pimp to make a petition in June to July 1908 to establish the Gyeongseong Gisaeng and Prostitute Association as a preparation step to implant a licensed prostitution system to the Korean Peninsula. However, the “Petition on Foundation of Gyeongseong Gisaeng and Prostitute Association” ended as an agenda without official approval. Secondly, in September 1908, the Resident-General enacted a series of prostitute-related laws and regulations, including the “Prostitute Regulation Law” and “Terms of Compliance Regarding Prostitute Business,” to establish a legal and political system to control and manage the Korean prostitutes in a modern way. Third, in October 1908, the Metropolitan Police Department of the Resident-General reminded the laws and terms of compliance to the prostitutes and people related to the licensed prostitution system and reported to Resident-General Ito Hirobumi and Vice Resident-General. The Resident-General of Korea also enacted the guidelines and detailed guidelines to be aware of and conducted by the Japanese police officers of each local police station. It also arranged and confirmed the formats for reporting operation, closure, address change, etc., of prostitutes. Fourth, the Resident-General commenced the establishment of system for “Hanseong Prostitute Association” as the first legal prostitution organization of the Korean Peninsula from April 1909. In August and September 1909, it intensively invested legal and political intentions, including “Order and Approval on Hanseong Prostitute Association,” “Final Approval of Hanseong Prostitute Association Regulations,” “Composition of Hanseong Prostitute Association Directors and Its Approval,” and “Composition of Hanseong Prostitute Association Clinic’s Japanese Doctor, Nurse, Accountant, Clerk, and Interpreter and Its Approval,” to complete the system of “Hanseong Prostitute Association”as the beginning of the licensed prostitution system in the Korean Peninsula.