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headcannon: Bagheera and Baloo used to work respectively a Pan Am pilot and flight attendant and that's how they met like 40 years ago~
They made outta the golden age of flying services so they retired early. Nowadays Baggy is that cool old man who attends community college and Baloo is the perfect house-husband

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True North

God I love this man so much.

Boozin Bruin

Chonk bears the best

Off

The amount of happiness I experienced from this headcanon is probably illegal

Caudle

This is SO cute, I'm going to explode