Critical concern with infantilisation practices—i.e. the tendency to treat older people as if they are dependent children—has for the most part concentrated on the negative associations between infantilisation and dependency in later life. Infantilisation is usually defined as an unwelcome imposition on older men and women who are often portrayed as relatively powerless to resist. Whilst the negative consequences of enforced infantilisation must not be ignored there are also occasions when infantilisation may be regarded as a voluntary or chosen mode of resistance on the part of older people to the decrements and external impositions of later life. The concept of infantilisation may therefore be enlarged to include modes of resistance involving processes of mutual identification of the old with the young; in certain instances even as a form of conspiracy between these two age groups against the wider society. This paper therefore pursues fictional images of such rapport as they occur in a selection of the ‘William’ stories written by Richmal Crompton during the period from 1919 up to her death in 1969, and with an appeal which continues up to the present day. The argument is that these stories of alliances between boyhood and ‘elders’ may be regarded as vivid examples (a repository of positive images) of what may be described as ‘positive infantilisation’: that is to say, of consciousness of the independence of subjective selfhood from the ageing body in the face of the misperceptions and misleading stereotypes of the ‘mature’ adult world.