Stop and Smell the Roses: Tails encounters an odd flower which sprays mind-and-body-transforming spores/pollen.
The Jealous Lover: How about one of Sonic's myriad love interests decides to turn Tails into a girl, so that he won't hang around with Sonic anymore, and the girl can get her way with the hero?
A Best Friend's Gift: A gender-bent Sonic turns Tails into a girl in the same way she transformed, to give the 'gift' of femininity to her adoptive little brother. (Soon to be sister.)
A Powerful Mix-up: Tails uses his powers on Moebius, but the weird energy affects cause them to backfire and gender-bend him.
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