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How about modeling a "folded" bag, make it a Cloth, add a pin group set to the top vertices and apply some simple shapekeys? Here is a quick example:
With more geometry and some experiment a bit more details can be added...
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The only way how you can do that (at the moment) is to actually join them togeher. Select all of them, the Shift-click on the one you want to be the center and press Ctrl+J. This way they are all one mesh and you can sculpt away.
If you need them to be separate again at some point, go into Edit Mode, press P and select By Loose Parts.
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You can Mask the part of the mesh you want to separate
and then choose the Mask -> Mask Slice to New Object menu option
Which will give you two new objects (the Blender pseudo-equivalent of SubTools).
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If you don't want to do any texturing, you can use vertex paint. It's like painting on the surface of your 3D model. It's not the most advisable method of coloring, texturing usually is, but if you don't want to have to deal with retopo and just want an idea of what your colors are going to be, vertex painting is an great tool. I'm not that great at teaching,...
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Answer - you can import your head by going to File > Import > Wavefront (.obj). If your model isn't a .obj file, select the other option that matches yours. Sculpting tools are in the sculpt panel, top of the screen under Sculpting.
Advice - do not start with a head. If you're new to Blender, start with something simple. Human head is a really complicated ...
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I had the same problem and found in the top left drop down menu "sculpt" there is a check box for show mask. The hotkey is CTRL M
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