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In the early 17th century, there was widespread male and female prostitution throughout the cities of Kyoto, Edo, and Osaka. In , due to the need for space as the city grew, the government decided to relocate Yoshiwara and plans were made to move the district to its present location north of Asakusa on the outskirts of the city. The old Yoshiwara district burned down along with much of the city in the Great fire of Meireki of ; it was rebuilt in the new location, when it was renamed Shin Yoshiwara New Yoshiwara , the old location being called Moto Yoshiwara Original Yoshiwara ; eventually the "Shin" was dropped, and the new district became known simply as Yoshiwara.
Yoshiwara was home to some 1, women in the 18th century, with records of some 3, women from all over Japan at one time. The area had over 9, women in , many of whom suffered from syphilis. If she was lucky, she would become an apprentice to a high-ranking courtesan. When the girl was old enough and had completed her training, she would become a courtesan herself and work her way up the ranks. The young women often had a contract to the brothel for only about five to ten years, but massive debt sometimes kept them in the brothels their entire lives.
One way a woman could get out of Yoshiwara was for a rich man to buy her contract from the brothel and keep her as his wife or concubine. Another would be if she managed to be successful enough that she was able to buy her own freedom. This did not occur very often, though. Many women died of sexually transmitted diseases or from failed abortions before completing their contracts. In these cases, the advanced payments their parents received could be used to fund her dowry.
There was no stigma against marrying a former prostitute. Social classes were not strictly divided in Yoshiwara. A commoner with enough money would be served as an equal to a samurai.
Though samurai were discouraged from entering the Yoshiwara area, they often did so. The only requirement on them was that all their weapons had to be left at the town's entrance gate. By law, brothel patrons were only allowed to stay for a night and a day at a time. Like all official policies for Yoshiwara, this was rarely enforced.