Abstract: An electronic messaging contextual storefront system and application provides electronic and instant messaging with contextual graphical and textual content which corresponds with or is related to the subject matter of an electronic or instant message string or chat stream. Graphical and textual content for the contextual storefronts is retrieved based upon detected keywords, and presented in contextual storefronts which are associated with conversation and text entry boxes or other parts of an electronic message system display. Selected graphical and textual content can be placed directly in the text stream or elsewhere in the display either by user commands or automatically by the system. The graphical and textual content is stored by subject matter or theme or by association with keywords in a relational database. Access to contextual storefront content can be tracked, accounted for and controlled by a payments processing system.