This paper undertakes a critical comparison of two short stories by Rudyard Kipling (1865-1936) and Ruskin Bond (1934-) through which they negotiate the complexities of their divided identities in pre and postcolonial India. Despite being of British descent, Kipling, an ‘Empire Man,’ and Bond, a self-confessed ‘son’ of Indian soil, are linked by the common thread of Anglo-Indianism. They spent considerable parts of their childhoods in India where they were born, Kipling in his “Mother of Cities,” Bombay and Bond in Kasauli. Written almost a hundred years apart, Kipling's "Baa Baa Blacksheep" (1888) and Bond's "The Room of Many Colours" (1999) are two autobiographical, poignant and powerful short stories which feature young counterparts of the authors themselves. In addition to demonstrating how macrocosmic socio-political events can invade the personal world of impressionable children, the stories document a historical shift in the status of the Anglo-Indian community after the dissolution of the British Empire in India. Close readings of both texts underscore the similarities and differences which bind and distance young Punch and Bond from their native and adopted countries and blur the rigid boundaries of race and nationhood. Notwithstanding his reputation as a vehement spokesperson of the Empire, Kipling’s six-year-old protagonist Punch recalls his near idyllic childhood in India as he enters a harrowing phase of his life in a foster home in England’s Southsea. “A Room of Many Colours” reveals a seven-year-old Bond’s deep love for India even as their status as Anglo-Indians are increasingly threatened in a newly independent nation and his father prepares to return to their ‘home’ country England. My paper aims to explore the thematic connections of imminent orphanhood, surrogate parents, racial binaries, cultural assimilation, literary legacies and unlikely connections which define the conflicted childhoods of two writers who are so similar and yet distinct from one another. Furthermore, I explore how the short story, while being emblematic of the brevity of childhood, perhaps becomes a powerful tool to make an ironic comment on the lasting effects of childhood trauma and grief on adult minds.