Abstract The Swahili Community, was, by and large, shaped, influenced, and affected by slavery. From African hinterland to Bagamoyo on the coast of Tanganyika (now Tanzania) and later to Zanzibar en route to outside Africa, the influence was immense. Using the Intertextuality theory, the paper examines how Swahili creative writers have portrayed the experience of slavery in the span of fifty years. It analyses three Swahili texts: Uhuru wa Watumwa (1934), Maisha ya Tippu Tip (1966) and Tendehogo (1984) in an attempt to see the conceptualization and challenges of slavery in Swahili society in that timeline and duration. In particular, the paper attempts to address and find answers to the following queries: How did the prior textual memory of slaves contribute to the realization of their slave-hood at any given material time? Conversely, how did such realization help or become a hindrance in negotiating slavery on one hand, and antislavery in public and private spaces? This article will be looking into forms of resistance to slavery as depicted in Swahili literature. Putting the concept in a contemporary scrutiny, the article attempts to find out if there has been a change in the conceptualization of slavery in the Swahili world. Has the concept of slavery in the Swahili literature gone beyond classical slavery to embrace other forms of slavery in and outside Africa? Key words: Swahili, slavery, servitude, darkness, Intertextuality, textual memory,