Help with Track Mattes (I think)

Hello there,

So I'm basically trying to find the best way to place a layer on top of a map and find a way to have that layer tranform to look identical to the map underneath.  

In other words, if I were to zoom in Sicily, for example, and place a rectangle shaple layer there, how could I get it to look like Sicily, without having to manually move every piece to fit.  That's very tedious and I believe there's a way around it.  I'm rather new to AE, but track mattes sort of do what I'm talking about, but I can't get it to look just right.

If you've ever seen a historical video on Youtube where they move the borders around, that's basically my goal for the project I'm working on, just can't quite figure out how to do that.

Thanks,
Michael