Animated glove

I was asked to do some mockup for a SF creature.
The creature behaves like snail-eye on sticks.
limbs must be able to intract but also be poseable (limbs behave alike inflated gloves), a kindof a shapeshifter.

At first i thought to do it with with a shapekey and bones combo but then i realized that intracting moves the mesh inwards over the armature limb length and that kinda conflicts with bones. If the mesh moves backwards mesh position relative to the bone changes, so bended skin (inwards) is no longer at the edge of the armature while still responding to the bones on the edge.

any ideas on how to solve such skin morphing problems ?