Use an image editor.
Create your map, add the items you wish to the image, then save and bring the new modified map into PD.
Also, there is a handy little item called Route Generator, it's freeware, and an excellent tool for a number of things.
http://www.routegenerator.net/#download
You can use this with maps, or "live" drawing animations for X's & O's in sports videos, "live" circling of objects to point them out, be creative.
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