Benny

He does that already

Ash in Awe of Sonic's super form.

Merry Holidays

Chara doesn't fully know what Christmas is but wanted to show his festive spirit in his own way.

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Movie Sonadow, but Sonic becomes a Werehog. Shadow has declared Cat Law now; Sonic cannot move until cuddle time is over

Aw, cute idea!

Don't know if what I pictured is exactly what you had in mind but I enjoyed doing it anyway. Happy Halloween!

Perfect opportunity to introduce my Headcanon that of all the members of Sonic's family, the one Shadow warms up first to and gets along with better is Ozzie. To the point that he sometimes comes unannounced to sleep or hang around him.

SLAUGHTER HOUSE