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Create another layer (solid) directly above your finger layer and using a mask trace the area around the hole in the sharpener then from the track mat pull down menu (to the right of the finger layer) choose alpha matte. This will the use the mask of the layer above to hide the finger as it goes in.
As Nic said, use a matte. You could also pre-compose bits and pieces which would allow you to use a different stacking order. Probably that's part of the problem, as you seem to be trying to do it all in the same comp and thus cannot easily re-use matte elements. Also do not forget about guide layers - you could just drop your footage in another comp, designate it as a guide layer, then build your effects on top of it and use the result as a separate layer in your main comp.
Thanks a lot, I got it working. I guess I've got a lot to learn.