Can you provide an existing activity that may be a model similar to what you want ?
A windows game that comes close to what you want?
As a reminder, the Memory Activity allows for the easy creation of custom "flashcard" type games with pictures and sound. Do a search on "flashcard" on this and other forums.
Browse allows for book marks to lead a user through internet documents.
Scratch allows for story telling.
Can any of these rudimentary tools meet your need ? I would guess no for middle school, but one never knows.