I imagine Tail's has gotten away with MANY things over the years using that face
In this situation he's begging for something though...I think of it like this...
Tails: *puppy-dog eyes Sonic* B-but, Sonic...I-I...really...want some icecream...r-really b-b-bad...
Sonic: *face palms* Again with the face! Fine fine! Just stop already! You're gonna make me cry...-w-;
Tails: *sniffles* T-thank you, Sonickun
Transparent background for the win!
Corel Painter Essentials 2 (lineart), Photoshop (colors)
Miles TAILS Prower (c) Sega, and the Sonic Team