I don't think I'll be able to do something like this manually, because I'm using a touch pad and I don't have 100 % control with it.
And I don't understand how I would make this even if I had a regular mouse :-)
Edit:
I'm trying out the second link, Alpha Masking, but I need some help here. How do I name layers (only know how to name the whole file), and how do I use a combination of line/curve tool and paintbrush? Should I just use line/curve, then paintbrush, then line/curve again etc?