Hello @FattyBull ,
To add to what @tobor8man said, there are several different concerns here.
You are using an IMM brush to attach a 3 dimensional mesh to what appears to be a 3D surface. Clipping is inevitable in this scenario. If you merely want to displace the surface you might consider using an alpha-based brush instead of the actual geometry of an IMM brush. See the Stitch Basic brush for an example of this.
OR
Work on the sack as a closed 3d volume. This produces the best results when combining geometry and is required for the use of features like Dynamesh and Live Boolean. You can then fuse the geometry together using either of those features. Both features will remove the overlapped interior geometry, and you can always remove geometry after the exterior surface is constructed to return it to an open 2D volume.
OR (recommended)
Work on the sack as a closed 3D volume as above, use IMM brushes for whatever surface effects you want to create, and then use Detail Projection to project the detail to a cleanly retopologized multi-res version of the mesh as simple surface detail. Eventually you want to simplify the geometry on the surface of the mesh as much as possible to eliminate complicated overhangs and undercuts, and so that all the normals of the surface geometry are all facing outward from the surface of the mesh. The more you are able to consolidate the geometry on the surface into a single piece of geometry, the better it will perform in displacement and detail projection scenarios.
A multi-res mesh in this form with good quality base topology is going to be the end goal for many workflows, as it provides the best results for projecting detail from mesh to mesh, as well as for sculpting ultra fine detail,posing, painting, UV unwrapping, Texture creation and export.
