Here I’m a bit less certain on the order

  Tygon
Tygon was there when I told the others, but I’m not sure if Trask and Ryu got in first. It’s interesting how it’s at exactly 10 that my memory get muddy.
Tygon’s ’sona at the time was Mikia the lioness, who always wore a mariner’s cap and tank top, so here is Caterpie with those clothes!
I spent the whole time thinking: what is this level of anthropomorphism? I guess the right thing to do would be to claim it’s a Pokémon Mystery Dungeon character, but when have you seen these kind of clothes in Pokémon Mystery Dungeon? ( MRZoet 's comic series notwithstanding…) So instead I'm going to claim it's from the YouTube series Starter Squad. Viva la caterpievolution!
^{I started this drawing overworrying about getting the hat right, and that was before I realized it would need ear-holes/antenna-holes! I guess antenna holes make more sense since bugs are practically blind without their antennas so yay? As for the rest of the body, I spent the whole time thinking about how horrible my last attempt to draw Caterpie had come out.}

  TraskFox
#011 Metapod goes to TraskFox. Trask the Toymancer (at least that's how he was known back then) is a plush fox who loves plushifying others with his magic needle. Having seen the adorable Metapod plush they sell at The Pokémon Center, I doubt Trask would miss the opportunity of having a real-live one.
Trask was probably the first watcher I gained “organically” (everyone else I knew from somewhere else) that wasn’t a mouse (Zc456 was organic but was a mouse at the time; I had this weird idea that only mice would follow me). We just both shared a love for cute, wholesome toy scenarios and the comments showed that.
^{This was my first time ever drawing a "living plush". It was unexpectedly hard! I will probably be told a lot of things are more fitting to the “pooltoy” type but it’s a really difficult balance to strike. I also intended for the metapod to be about as big as Trask to emphasize how small a plush he is, but I was having a hard enough time drawing already.}

  Ryuuie
Ryuu, as we called him, I also knew from elsewhere. I don’t know if he can, canonically, fly but I wanted to draw a scenario only possible in an anthro world: racing your own Butterfree through the skies. I also don’t know if he has pads on his feet but I didn’t knowhow else to indicate that they were feet
^{This may be my first properly toony drawing. I usually try to avoid it, borrowing only what I strictly need to, but here it was inescapable. The clothing was fun to draw. I was very deliberate about making this butterfree different from the last one I drew; namely, this one is female, the last one was male. ...I may have overdone it, though. The body is not very "Butterfree-like"}

As with the twitter sketches, if you want yours colored, or if you want me to edit you in to somebody else's, I'll happily do it for $5 (not counting shading)