That's a very creative use of tentacles. I think the paintbrush cable looks a bit like a pen though, because it has the same width all across. Also, if it had more than one color (most paintbrushes have a silver end next to the brush and then either a black or a wooden cable) it could also help making it look a bit less like a pen. The brush itself looks quite nice though, as does the ink splatter.

Goodbye, my chances of winning! 

 That's original and very creative, nice!

very good concept

Cool Idea!

 Anyone else getting mildly trypophobic looking at this?

Nope. Only a rude sketch of my own hand. 

I like the tentacles. It would be cool if the hand was holding a fountain pen instead of a brush though :-)

Any references used?

The hand is quite pillow shaded I think. Think in terms of the planes of the hands.