It should be possible, but might require hand coding. It would start by adding columns to the cart to store length, width, and height.
Then you would have to set the shipping settings to "send each item separately" rather than assuming combined packaging.
Then I'm not sure if it would be as simple as assigning the length, width, and height to the cart columns you added or if some hand tweaking would be necessary from there, but if you get that far and send me the resulting page I can help more.
This is also something we could do together in a premier support ticket if you were interested.