I would like to talk about a certain fox friend. That's right, Tails! but what I want to talk about right now is, can a two tailed fox REALLY FLY?
Is it possible for a two tailed fox to fly Miles above the ground!?

"Get it? because his name is 'Miles'? Miles Prow... Oh, never mind!"

But in all seriousness... My answer, is NO.

The two tails would just wrap around each other, not to mention fox tails aren't flat like helicopter blades.