Spoiler From last year's Pokeshipping Week on Tumblr. The prompt? "Their Relationship Through the Eyes of Others."
Spoiler Jigglypuff attacks: one of many things where you think “if they’d just gone 20% further in Johto after what went down in the Orange Islands…”
This is an illustration/concept piece for the long-running fanfic "AAML: Diamond and Pearl" by EchidnaPower, where Misty comes back for Sinnoh, Ash picks up a Riolu, and said Riolu (later Lucario) looks on Ash and Misty as, literally, Dad and Mom.
This is an illustration for the fanfic "Distortion," the fourth entry in Skylight Sparkle's The Road You Choose series (my favorite collection of Pokefics.) This illustration isn't of a specific scene from the story, but something that potentially happened just after it...read for context (The Riolu here is Ash's; like EP, Sky gave Ash a Riolu, but this one has a name, Ria, and is much smaller than normal.)
Another "The Road You Choose" drawing, though this one has no relation to any of the main stories. Sky maintains a Tumblr full of details, bios, and tidbits on her universe, and these include what sort of personality Ria develops. This is an illustration of her vanity.
Another drawing for "AAML: Diamond and Pearl." Not a specific scene from the fic, but something inspired by this Lucario's personality.
I love it whenever fans combine Ash's Sir Aaron get-up with Misty's mermaid costume, so I gave it a try myself. And wrote a fic around this picture, which you can find here.
An illustration of my favorite scene from the second entry in Skylight Sparkle's "Yesterday's Tomorrow" collection.
An illustration from Skylight Sparkle's series finale, "When the World Ends." I refuse to give context, as that might mean you all don't read the series