You can sort of do this with Carbide Create — it affords one V carving and textured toolpaths and will accurately model a cut made with a ball-nosed endmill — for that sort of thing it’s just a matter of patiently assigning toolpaths and previewing and adjusting until one gets the desired effect.
https://www.shapeoko.com/wiki/index.php/Carbide_Create_Photo_Tracing and Could use some guidance on creating a carve may offer some ideas / techniques
For more organic shapes, some sort of CAM intended for such work will likely be easier. MeshCAM has an option for this, and the other options are listed at:
- https://www.shapeoko.com/wiki/index.php/CAD#Image_Depth_Maps
- https://www.shapeoko.com/wiki/index.php/CAM#Images
- https://www.shapeoko.com/wiki/index.php/Commercial_Software#CAM_for_Images
Alternately, you can 3D model the entire shape and then use a 3D CAM package.
Usually you’d use a series of smaller ball-nosed endmills, but one can use any endmills which your software supports.