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Is it possible to create resizable-rotatable brush in photosphop and/or gimp, that is sharp on one side and feathered on other side (and brush can be rotated to when required)?

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    Yes. Custom brushes can be made in both Photoshop and GIMP. A custom brush can be anything you want. Both applications have ways to rotate a brush. – Billy Kerr Feb 23 '18 at 13:15
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For Gimp:

Technically, yes:

brush

But it's quite hard to control the actual opacity gradient, since the overlap between successive copies of the brush depend on the curve radius:

enter image description here

Maybe your problem has a solution which doesn't involve such a brush?

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For Photoshop, pretty much any image can be converted to a brush. And all brushes can be rotated around their center axis.

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