Tools such as MeshCAM can take a photo or other image and convert to a 2.5D engravings rather easily. You won't have much control over results. They tend to come with a price tag. You might be looking for something a little cheaper, as in free (or nearly free) ...
Two software came up through my searching for tools not specific to CNC. The first, free, is for Windows : FotoSketcher. The 2nd, nearly free (5$) is for the Mac OSx : Photo Sketcher. Almost the same name, but different all across.
FotoSketcher for Windows, a sampling :
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Photo Sketcher for Mac OSx, a sampling from original photo and 5 pencil sketches :
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Yes, you could use Bender, PhotoShop and a slew of others. But you might need to burn some midnight oil trying to figure out the necessary process / steps and then tweaking the results... The above tools seem to simplify the process to a few clicks : choose photo, choose conversion effect, optionally tweak a few parameters, and GO. You don't have to be or become an artist.
I have not used either at this point in time. I am still uncertain how these would help, beyond taking a colour photo and turning it into pencil sketch which could then be converted to Gcode for your CNC. Their cost is key ... (nearly) free !
Note FotoSketcher, will do a lot more than pencil sketching your photos. a very recent update exists as well. While the other seems frozen to its 2012 release, yet still quite capable to get pencil sketchs out of full colour photos.
First one to make use of either could inform the others of the successes, a failure or the pain points within a CNC context ?

Convert photos to pencil sketches, drawings or even paintings
Looking to convert photos to sketches to etch, burn or engrave ? These two tools will do the trick.