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You can use your Disk (or any grayscale image) as an alpha channel:

img = ExampleData[{"TestImage", "Lena"}];

disk = Graphics[Disk[]];

diskImg = 
  ColorConvert[Rasterize[disk, ImageSize -> ImageDimensions[img]], 
   "Grayscale"];

face = ColorCombine[{img, ColorNegate@diskImg}, "RGB"]

Then you can use Inset to place it like other graphics primitives:

Graphics[{
  Table[
   Inset[face, {Cos[i*10 \[Degree]], Sin[i*10 \[Degree]]}*50, {256, 
     256}, 5 + i*1], {i, 10}]}]