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For day 1, with the prompt "kobold", I present to you my kobold ranger, Chupchik.
She was rather friendly and naive, but very efficient with her beloved longbow, "twig". And she would do anything for her people's leader, the copper dragon Nilollothnat the Bedazzling (Nils for short).
Aspects of her are modeled after the wonderfully named satanic leaf-tailed gecko.

A sketch of a slightly derpy-looking creature with lizards features, holding a longbow, staring absent-mindedly off into a random direction. She looks proud and content with her lot in life.

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Unfortunately, I fell behind a bit with as I had to travel, then I spent an entire day sleeping, and then an entire day with a migraine.
So here we have number 3:
I haven't encountered any in a recent campaign, really, so here's the first shapeshifter that came to mind: a

A rough pencil drawing showing a werewolf. We are looking over its shoulder as it gazes pensively at its left paw.

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Unfortunately, I fell behind a bit with
So here we have number 4:
We had an encounter with one of these when we explored the mansion the mayor had just gifted us ever so kindly. It turns out the place was haunted. (Mayor did not warn us.) And the worst of the lot was Runchard, the evil head of staff, who had turned the rest of the staff into undead to serve him. He drained our poor rogue of his life force! Not a nice guy.

A shadowy creature with talons for hands and a skull-like face. He has tattered remains of a waistcoat and tuxedo. He's just come out of a dark room.
A shadowy creature with talons for hands and a skull-like face. He has tattered remains of a waistcoat and tuxedo. He's just come out of a dark room.

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number 5. Still catching up. This one is dedicated to the time when all the tables in the dungeon library tried to eat us. It is the
It's one I think I would be more comfortable doing in ink, but I've decided to stick to pencil for now. I might revisit some of these and redraw them with pen or ink.

A Gothic-looking table with an open book on it. The book has a drawing of a skull. The table looks like it has clawed feet, teeth, and menacing eyes.

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finally all caught up! Today's word is
So here's Granny - a terrifying barbarian dwarf grandma who would make Chuck Norris quake in his boots.
With apologies to the character's owner, Joy, for my shoddy version of her superior character portrait.

A fierce elderly Dwarven lady holding a very big ladle. She's wearing very reasonably clothing, including comfortable pants and shoes, an apron and a fluffy cape.

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I really struggled with today's drawing! I should have started it earlier in the day, but I didn't, so I'm sorry for how it looks. Istruggled with what to draw, but the one theme which stuck with me for the prompt "Natural 20" was the trope of the bard charming the dragon with her natural charisma, so here you have my tiefling bard doing exactly that. This is not something that has happened to me (yet).

A young tiefling with braids and ribbons in her hair and curled back small horns winks and blows a kiss at a visibly confused smallish dragon.