Celestia gets to lose first, all too easily. She seems to adore having an excuse to pad around with no shoes to obscure her huge, juicy size 26 feet, and positively basks in the attention this attracts from all the regular ponies. The older Princess had way, way, way more time to get fed up with being prime and proper and uses any opportunity to do something outside the box. If anyone is complexed about their smooth, thick, meaty soles and dexterous, ring-adorned toes, it’s not her. It’s almost suspicious she lost this one so easily…
Luna still somehow manages to lose, and finds much disappointment in her sister’s adoration of what was meant to be thorough humiliation. Still, perhaps it’d be unfair to the universe not to rake the poor socially awkward cutie through the coals. Always more self-conscious and embarrassed, she’s taking her barefoot ordeal far worse, even if going out at night should have its own benefits. She’s wracked with paranoia, feeling every last glance, giggle and murmur turned at her feet, and not even going out in casual urban wear will help her blend into the shadows and avoid the attention a Princess like her deserves. She can hide all she wants, but her shoeless night will be as remembered as Celestia’s day was. Especially because Luna tends to get rash under pressure, and boy is she under a lot of pressure…
There’s probably room for Celestia to top her barefoot adventures, and for Luna to find more things to blush at once all is said and done. Equestria isn’t exactly a place where its rulers are too busy to tease and prank one another… This lengthy description is actually a very highly compressed summary of a short story written by this picture’s commissioner, ExTor. You can read the full thing on DeviantArt and FurAfiinity. It’s a happy accident borne of an inability to stop layering on details, so, enjoy!