This article re-examines from the perspective of “urban narrative” the philandering writing of the Ming-Qing period and the significance it bears on the development of modern Chinese literature especially during the late Qing period. By re-presenting the spatialtemporal context in which the narratives were composed, the paper investigates how the genre, when imported into Japan, cast its influence on modern Japanese literature and Kanbun novels. Yu Huai’s Banqiao Miscellany, highly acclaimed in the Shanghai literary circle, was particularly noteworthy for the way in which Yu recounted the transformation of brothel-houses on the Qinhuai riverside in Nanjing. Among many of its imitations, Wang Tao’s Sea-corner Philandering Record was widely acknowledged as an exceptional work. Wang depicted the change of Shanghai brothels in a language that also evoked great sentiments for his native country as well as his own life. Banqiao Miscellany was very well received in Japan. It is believed to have a considerable bearing on Narushima Ryūhoku’s Ryūkyō Shinshi, an account in which Narushima also reported the transformation of Yūri, a Japanese brothel area in Yoshihara during the Edo era. Ryūkyō Shinshi gives the reader an opportunity to observe how Kanbungaku was transmitted or transformed during the late eighteenth century when Westernization was taking place. It also allows us to appreciate how controversial and accommodating, both at the same time, modernity found its way into Japanese culture. In short, works by Wang Tao and Narushima reveal the deep reflection that engaged the intellectuals at the turn of the twentieth century when they were faced with the quick and menacing approach of Western civilization.