>>1830369>>1830485So this is basically gonna be a series of small stories instead of a huge overarching story? Alright.
For starters, perhaps checking out the previous Pokemon ENF story might give you some ideas if you haven't checked it out already?
https://archive.loveisover.me/e/thread/1780076/#q1783416As for starters, your second image seems to have already given the two Pokemon, but I'd still like to suggest Oshawott for Lavender and Snivy for Teal. Snivy's internet fame as "Smugleaf" would work well if Teal if half the jackass you imply. Oshawott, in a similar vein, always seems to go to the "underdog" trainers, like Bianca.
(Oshawott also learns Razor Shell, so he would fill both the "slicing move backfires and shreds Lavender's clothes" and "get Lavender soaked in thin white clothes with water attacks" roles.)
As for ideas... How about Lavender napping in or near Viridian Forest, as a Weedle nonchalantly munches on her clothes as if they were leaves. I remember a Pokemon artist who used to draw these types of pictures in the past, but I can't remember the artist to look them up. The artist's style wasn't really to my liking, but I enjoyed the theme.