Works for some with the very same Version 53.0.2785.143 m (64-bit)

If I hold shift, I at least see the black arrow cross cursor to see where I click...

Can't repro it. Do you by chance have any custom mouse settings in Windows Control Panel?

Okay, so if I activate "Display pointer trails" in my Windows 10 mouse cursor settings, then it works. But if I disable that, the grey circle pointer does not show.

Update: So this seems to be related to some kind of Windows bug on my side. If I choose the inverted colours cursor set and have "Display pointer trails" ENABLED, then it behaves very strangely everywhere... while moving my cursor it has the right colours -the pointer trails do I guess- but when I stop moving it, the outline/border of the cursor/pointer will always be black, but the inside colour filling of it are sometimes right (the inverted colour of whatever is underneath -see screenshot) but sometimes simply transparent (the same colour of whatever is underneath -if you look at the screenshot, orange instead of blue in this case, but on a screenshot all of it simply invisible...).

Deleted: 2016-10-13_13-24-14.png 92.1 KB

	2016-10-13_13-24-14.png 92.1 KB View Download

I am also seeing this. Cannot see a mouse pointer/touch emulation circle at all when the dev tools are set to device mode. I can confirm that holding shift does show a black curses with 4 arrows though (the one usually used for 'move' actions).

Chrome 
- Version 54.0.2840.99 m

Windows 10 Pro 
- Version: 1607 
- OS Build: 14292.447

I have just seen this answer on Stack Overflow and can confirm it works:
http://stackoverflow.com/questions/36712750/how-to-show-mouse-pointer-in-responsive-mode

If you change the device type to one which is supposed to support 'touch' then no pointer appears (but it should show grey circle), but if you set device type to 'Mobile (no touch)' or 'Desktop' then the standard mouse pointer DOES show