can you post and image so we can get a better idea of what you are doing.
it sounds like you need to make a compound path ... a shape like the letter "O" or "A" where there is a hole in the middle. to do this you need to make your outer path... then make an inner path.
- you might want to look at some tutorials on using the pathfinder tool at this point
then use the path finder tool to make a compound path. once this is done you need to select that resulting compound path and the image and right click for a Clipping mask. this should result in a image with a mask with another mask in it as you asked... please let me know if this helps.