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I've only drawn this character once before but I'll give a bit of context. In our DnD game, SHE is the person Rupert is "protecting".

Princess Teari. Shes technically a princes of a Bear centric kingdom on a continent that her family conquered. Shes also the little sister of Mac and Bubba ( who you guys know... mostely without clothes) but you know shes clearly gunna take the thrown in their place. But shes all about being prepared and she ensures that he men as ALSO ready so she Trains them a lot of the time. a little tidbit, Rupert does have a crush on her so , NO... hes not trying...

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Lord Caesar

I am tempted to draw ship art of these two at some point

Digsby

she's so cruel <3 she needs to understand bear belly and muscles are much heavier to carrier around