There is special software and hardware available for this (suggestions, anyone?) but if you don't have access to it you'll have to get creative. After Effects has a feature for animated painting that could be overlayed on a video clip once you nailed down the timing. Depending on how simple your telestration will be, you could also pull frame grabs from your video into Photoshop, make all your lines and shapes on a higher layer, then superimpose that layer over your video in FCP, and use Mask filters to reveal the drawings in an animated fashion. I'll refrain from going totally insane and suggesting you pull a matte from footage of a white-gloved hand holding a black marker painted white, drawing on a thick sheet of white paper taped to a TV screen, through which your video is barely visible...
Good luck,
Zap