Hong Kong writer Wong Bik Wan (1961-) wrote about her mournful attachment towards the colonial status of Hong Kong in an essay named "Colonial Touch" in 1987. Twenty five years later, the complicated discourse of colonialism is still the prime concern of the writer. Wong has been a political journalist of The Hong Kong Standard with acquaintances of officials in the British colonial government of Hong Kong. Her abundance of travel writing also gives rise to a lot of description of cultural encounters. Among this corpus of works, the bilingual novel Doomsday Hotel published in 2011 is the most complicated, far-reaching and profound work of colonial reflection. The novel is about Portugal settlements in Macau and their stories related to a hotel. It takes Wong Bik Wan ten years to write a novel again after Silence, Dimness, and Trivialness. The novel is published in Chinese with an English translation co-worked by the author and the translator. The act of writing a story of Macau Portuguese in Chinese and English by a Hong Kong writer shows the ambiguity of post-colonial writing of Hong Kong literature. The paper argues that the practice of writing Doomsday Hotel as well as the essays and fiction by Wong Bik Wan over the years can demonstrate the ambivalence and possibility of colonial discourse in Hong Kong literature in the three dimensions of the metaphor of hotel, the ambiguity of colonizers' image and the substitution function of language.