Dynamic Lighting to block sight without blocking the inside of the shape used?

Hard to explain what I'm asking, best way I can say it, is there a way to draw say a circle, and block sight past it like normal, but not block what is INSIDE that circle.

So for instance, you could draw a circle on a pillar or a tree trunk, and it would block line of sight, but you could still see the pillar or tree trunk on the map, just not whats past it? As right now if you put a load of trees down with tree trunks blocking line of sight the map looks quite ugly with all the black circles blocking the middle of the tree.

Draw an 'X', or just a line if they won't be going around it (like trees in the background).

I ran into this situation with my first home-brewed game. I had an ancient abandon temple complex in a clearing, but surrounded by a dense forest. Part of the game was the struggle by the PCs to make their way through the trees from a near by road.  Here is what I found worked best:

1) Dynamic lighting was turned on, but the Daylight setting was turned off.

2) I created a number of light emiting objects, e.g., small rocks, paving stones (in the road), statues in the open, etc.  A few I kept as 360 degree emitters, others I restricted to 180 degrees or 90 degrees.  I then shrank the rocks down to a small size that wouldn't be noticed.

3) The light rocks were placed around the clearing so everything except the forest and the buildings were fully lit.  The paving stones had their light distance tweaked so they only showed the first rank of trees and bushes along the side of the road.

4) This left the forest completely dark.  So I then made each PC token a light emitter of about 10ft, with very dim light that fell off quickly.  This was to simulate not being able to see very far.

5) Things that I really wanted the PCs to see, but not see behind, I used carefully shaped lighting curves tracing around the back of the object, so from the direction the PCs were likely to view it from they could see the whole image, but not beyond.  I did this with all the trees and bushes immediately along the road.  The long dark columns vanishing into total darkness gives it a really eerie feeling.

6) For PCs that had Dark Vision I made sure to turn on the tinting of their token's vision (generally either gray or dark red).  I then set the distance to 60ft, but had the light intensity low (about 40%) and dimming past 10ft.

I have run the game several times this way, and the Players as a whole love it!  They really like the feeling on edge of not being able to clearly see things.  Especially when they are chase 'sounds' in the forest.  All they see is a ping coming from somewhere in the darkness of the trees beyond their visual range.  Even the PCs with dark vision find it hard to get around confidently.

The one limitation is that they will still be able to see any 'brightly lit' area on the map.  But in my case, my map is huge, and they would have to scale out to about 40% to see that far....

You could try placing a transparent token with sight inside the circle, that was controlled by all players. Note that Ctrl-L will not show this properly, but if you use a dummy account (perhaps in another browser) you can see what it would actually look like to the players.

I've never actually used this technique (I usually just make the blocking lines slightly smaller than the light-blocking objects so they can see what is doing the blocking), but it seems like it kinda works? YMMV