Classical India is a multilingual area where Sanskrit and Prakrits live side by side. Sanskrit and Prakrit speakers are next to each other in the classical drama; Prakrit poetry composed in Māhārāṣṭrī, the literary Prakrit par excellence, is known from Sanskrit poeticians who quote it extensively. This contiguity provides situations for passages between the languages. They take the shape of translations, total superpositions producing one meaning, superpositions to be decoded as they correspond to more than one language and have different meanings in each one. These phenomena are possible only because the concerned languages have enough common features. The current linguistic usage, which we can access through the dialogues of the theatre, shows how linguistic closeness between Sanskrit and Prakrits occasionally gives birth to comic ambiguity or how total superposition is subordinate to disguise while enabling to respect the traditional linguistic distribution between Sanskrit and Prakrit speaking characters. Prakrit poetry in its own right, represented by the Sattasaī, does use the traditional stock of words with double-entendre (śleṣa) in connection with similes (upamā) which force the reader to consider distinct interpretations. These interpretations involve double meanings of words within Prakrit, or double meanings which are due to the merge of etymologically distinct Prakrit and Sanskrit words. But this usage is not pervasive. Rather, polysemic discourse is the main feature of this poetry which creates its specific codes. Thus Prakrit poetry needs to be taken into consideration in order to precise the history and progressive development of the Indian double-entendre.