Drawing pen being weird

So I have a drawing tablet and pen. Whenever i start drawing with it the stroke doesnt show up but when i pick the pen up the stroke appears. for the rest of the strokes are fine and draw normally. Though when I click undo or erase the strokes the first stroke I draw always does this. I cant really show you guys since I cant screen record with my pc plus I dont have permission to place video in posts yet.

For me the cursor is positioned as far as the pen reaches ~1cm above the surface and clicks and strokes are fine… But it may be a good idea to mention a bit more details for such a specific question as your OS and the brand/type of you tablet… and the software (of course blender but any other) where this happens?
(Does the pen use a battery? Then maybe the first move is to establish a wakup function in the pen hardwae??)