Below are my girlfriend and my two cats, Misser and Popkorn. If you hover the images you will see a slider for each image which you can slide to the right to reveal the characters I created from them: Gobber and Cob.
You can find a ton of different character portraits I have made, including these ones, in my D&D Character Portraits post. You are free to use any of them in your own personal games (but not for commercial use).
Foundation for the Two Characters
While a goblin and a bugbear might not sound like the most flattering choice of races, a lot of thought actually went into the choice (and a lot of the thought manifested by chatting about it with my girlfriend!). Also I have always had an affinity towards goblinoid races and used to collect and paint Orcs and Goblins Warhammer in my youth. While Warhammer and playing a lot of Warcraft 2 has shaped my mind into a "orcs and goblins are green" shape, I understand that is not how it is (generally) in Dungeons & Dragons thus I went for a more reddish hue for Gobber. But I am getting ahead of myself. Let us start looking at the pairing of races and how it relates to the cats.
Misser is a 10 years old cat my girlfriend had when we started dating a little more than half that time ago. Popkorn is a 2 years old cat my mother found which we adopted a little more than a year ago. Misser is to the smaller side, very clean and is not very happy with Popkorn although he tolerates him for the most part. Popkorn is an absolute unit of 8kg. He is not too bright and he really wants to befriend Misser. He often walk all the way up in Misser's face which usually results in Misser hissing or slapping him in the face and then walking away. Popkorns reaction is usually to stand and look confused or instantly drop and lie down on his side. Popkorn is also not very good at cleaning himself.
Anyway. They have a dynamic. Small, clean angry fella and big, dumb boy. This dynamic I wanted in the characters, and I found it fitting that their races would be either the same or related. While tabaxi would have been the easy choice, I feel that some of the traits of the goblin and the bugbear lend themselves a bit more to their respective personalities, plus the size difference between the two races makes a perfect caricature of Popkorns towering size compared to Misser while still maintaining the relation.
From Popkorn to Cob
Popkorn is a big cat. Even when he was a much smaller kitten, he had large paws and ears and you could tell from looking at him, that he would become quite large. That combined with his white color truly makes him live up to his name "Popkorn" (the "k" is intentional, Danish spelling).
While bugbears are most often illustrated as being coarse and spiky (see image below from Monsters of the Multiverse, for example), traits I left out of my final portrait of Cob, they also have a bunch of traits which I really felt fitted Popkorn. "Long-limbed" and "powerful build" lend themselves to his frame; "darkvision" and "sneaky" match him being a feline; he is very much a hunter which makes "surprise attack" a good fit and while he loves snuggling up it is very much on his terms, so even avoiding being charmed with "fey ancestry" makes some sense.
But Popkorn is also a very happy cat and not the least mean spirited, so I wanted the Cob character to reflect this and look like a kind being. I started by cutting Popkorns eyes and nose from an image. I think having the same eyes is an easy connection point, and I though the nose even fit a bugbear pretty alright. From there, I tried to give him a big and strong-looking face with a lot of opportunities for "fur" (beard, hair...), which of course had to be white. As part of this, I also gave him some big, dominating eyebrows - from googling bugbears, this seemed to be a recurring element of the race. I also made sure to give him visible teeth and a big-but-friendly mouth. I made sure to give his actual skin a slightly more yellow-tinted color, just to pull a little bit more in the bugbear direction, and of course gave him some fitting ears as well.
Popkorn has a tendency to get dirt in his face and isn't as good as Misser at removing it and if he weren't an indoor cat I'm sure it would be a lot worse - so as a final design move, I ended up adding a bunch of dirt to him.
As of the time of writing this, I haven't made an actual D&D character using this portrait. But hopefully I will sometime in the future, in which case I'm going to incorporate Popkorn into his being. He will not be too clever, he will have a tendency to step too close to people when he is speaking to them, and he won't like to eat without someone watching his back. He will be a good-hearted character, that's for sure. Probably a fighter, even though he prefer not harming anyone.
His character name, Cob, of course alludes to his cat name though the loose reference of "corn on the cob".
From Misser to Gobber
Misser is a smaller cat than Popkorn. He keeps himself very clean and have the softest fur. His voice has a tone that makes him sound like he is complaining all the time (sometimes he is, but mostly not). He doesn't generally like lying on your lap, but he is very social and usually try to be close by us.
So why does the goblin race fit Misser? Well, other than the traits shared between the bugbear and the goblin, what really sold me on using this race is "fury of the small", as Misser has a tendency to slap Popkorn repeatedly on the forehead if he comes too close. No claws, just slapping. He also, pretty much from the first time I met him, hate my feet and likes to attack them. That's with claws. After showcasing his fury, he normally retreat and hide, so "nimble escape" fits perfectly too! And then, of course, he is comparatively small, so it works for the dynamic between the characters as well.
I chose the name Gobber because "Misser" in Danish is pretty much the same as simply calling your cat "Kitty". So much in the same vain, I wanted the name to be very derivative of his species. Like with Cob, I worked from Misser's actual eyes and incorporated them in the design. I gave Gobber an ochre/red coloration, which isn't really derived from Misser in any way. He has a few brownish areas of fur, but that didn't have any say in the choice. But a couple of important visuals from Misser did make their way into Gobber's design:
A) On Misser's cheeks he has a 2-line pattern I really love (I also borrowed it for my Tiger of Vigor digital painting), which I translated into scars on Gobber.
B) Misser has a small, cute, furry chin. I made sure Gobber also have a similarly small chin with a few whiskers of hair.
Misser takes good care of his fur, keeping it all nice and soft. While a goblin is much less furry, I made sure to give Gobber a neatly brushed tuft of hair to care about. I also gave him nice clothes (at least by goblin standards), to showcase some of his orderliness.
Like with the Cob portrait, I haven't played a character using this portrait as of yet. But I can clearly visualize how I will play the character: A little fella often complaining just to complain and keep people at a distance, but a softie on the inside who really like the company of those he think of as friends. He will have anger issues and probably be a dual class rogue/barbarian. He will probably be pushed into adventuring from his dislike to other goblins, as they will not live up to his level of cleanliness. And he will always push for visiting the bath house of the cities he visit.
And that's about it. Gobber and Cob, two potential characters of future D&D sessions I can look forward to play. Even if not, it was fun imagining them as characters.