Hi Dave,

Currently that feature does not exist.
In general it may be possible.

There could either be a transparent gif,
preferably a png as an overlay on which to draw.

That would need some custom macro / widget, though...
and some experimenting as to creating a blank transparent image of a given 
size.

At image tiddlers, rather than directly drawing over them
— which doesn't seem a very practical idea anyway —
you would have a "draw on me" type of button
creating another tiddler with the ability to draw on that overlay instead,
showing the related image below in a see-through manner.

I have created an issue here...

https://github.com/Jermolene/TiddlyWiki5/issues/1377

...maybe someone skilled with image files takes a shot at it.

Best wishes, Tobias.

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