Homebrew Cheshires (Underland) Species Details

𝓒𝓱𝓮𝓼𝓱𝓲𝓻𝓮𝓼

The Ones Who Smile Between Moments

“If you see the grin before you see the cat, you should probably run.”

𝓘𝓷𝓽𝓻𝓸𝓭𝓾𝓬𝓽𝓸𝓻𝔂 𝓟𝓪𝓻𝓪𝓰𝓻𝓪𝓹𝓱

Cheshires are mysterious catlike beings who exist somewhere between creature, fae, and living anomaly. They are deeply connected to the strange fabric of Underland, possessing an uncanny ability to bend reality around themselves. A Cheshire might vanish in the middle of a conversation, step into a shadow and emerge somewhere entirely different, or simply float several feet above the ground because they have decided that gravity is being terribly inconvenient today.

Their appearances vary wildly. Some resemble ordinary cats enlarged to humanoid proportions, while others possess mostly humanoid bodies with feline ears, tails, eyes, claws, and unmistakably feline features. Their fur, hair, skin, or markings commonly appear in shades of pink, purple, blue, cyan, black, and grey, sometimes shifting between colors when their magic is active.

Not every Cheshire embraced the madness that swept across Underland. Some surrendered themselves to it, becoming increasingly unpredictable creatures of chaos. Others resisted, preserving their minds and becoming quiet wanderers who travel the world helping those they deem worthy.

Most of the time.

Cheshires are said to be descendants of the first creatures who learned how to smile between moments. Whatever that means, no Cheshire seems particularly interested in explaining it.

𝓟𝓱𝔂𝓼𝓲𝓬𝓪𝓵 𝓓𝓮𝓼𝓬𝓻𝓲𝓹𝓽𝓲𝓸𝓷

Cheshires possess feline characteristics, but there is no single appearance that defines them.

Some have digitigrade legs, paws, whiskers, tails, and fur-covered bodies. Others look almost completely humanoid, possessing only catlike eyes, ears, claws, and a tail. Some appear to shift subtly between these forms depending upon their emotions or surroundings.

Their eyes are often unusually bright and may glow faintly in darkness. Their pupils can change shape independently of the surrounding eye, and some Cheshires have been known to possess mismatched eyes.

Their most famous feature is their grin. A Cheshire's smile can be perfectly ordinary one moment and impossibly wide the next. When a Cheshire is frightened, angry, or using its magic, its grin may remain visible even after the rest of its body has disappeared.

𝓒𝓸𝓵𝓸𝓻𝓲𝓷𝓰

Common colors include:

• Pink
• Purple
• Blue
• Cyan
• Black
• Grey

Rare Cheshires may possess stripes, spots, gradients, glowing markings, or colors that do not appear entirely natural.

𝓐𝓰𝓲𝓷𝓰

Cheshires mature at roughly the same rate as humans, but their aging slows considerably once they reach adulthood.

No one agrees on how old a Cheshire can become. Cheshires certainly aren't telling.

𝓢𝓲𝔃𝓮

Cheshires range from Small to Medium, though most are Medium.

𝓢𝓱𝓲𝓯𝓽𝓲𝓷𝓰

A Cheshire's appearance may subtly change when they experience strong emotions or use their reality-bending abilities. Their eyes may change color, their fur may appear or disappear, their tail may become translucent, or parts of their body may briefly fade from existence.

𝓐𝓽𝓽𝓲𝓽𝓾𝓭𝓮𝓼 𝓪𝓷𝓭 𝓟𝓱𝓲𝓵𝓸𝓼𝓸𝓹𝓱𝓲𝓮𝓼

Cheshires are difficult to generalize. They tend to be curious, observant, playful, secretive, and difficult to predict. Many enjoy riddles, games, strange conversations, and asking questions whose answers they already know. Cheshires rarely believe that reality is as simple as everyone else claims.

𝓣𝓱𝓮 𝓜𝓪𝓭𝓷𝓮𝓼𝓼

The Breaking affected the Cheshire people deeply.

Some Cheshires embraced the madness, allowing their reality-bending nature to become increasingly unstable. These Cheshires may act erratically, speak in riddles, or perceive different versions of reality simultaneously.

Others resisted. The uncorrupted Cheshires became mysterious wanderers, appearing in places where they are needed and disappearing before anyone can properly thank them. They sometimes help travelers, rebels, children, lost souls, and those caught in the path of the Ink. But only if they deem them worthy.

What makes someone worthy?

Ask a Cheshire.

You will probably receive a riddle.

𝓒𝓾𝓵𝓽𝓾𝓻𝓮

Cheshires have few permanent settlements. Many prefer to wander throughout Underland, appearing wherever curiosity, fate, or some invisible thread pulls them.

They value freedom, curiosity, secrets, and individuality.

𝓢𝓮𝓬𝓻𝓮𝓽𝓼

Cheshires are collectors of secrets. They remember things others have forgotten, including fragments of Underland's history that disappeared during the Breaking. Some Cheshires claim to remember Underland before the kingdoms existed. Some claim to remember the world before Underland. A few claim to remember things that have not happened yet. Whether these claims are true is another matter.

𝓣𝓱𝓮 𝓖𝓻𝓲𝓷

The Cheshire grin is more than an expression. It is an ancient part of their magic. Certain Ink creatures instinctively recoil from a Cheshire's genuine grin, as though something about it reminds the Ink that it does not belong. Among Cheshires, smiling is sometimes used as a form of protection.

𝓡𝓮𝓵𝓪𝓽𝓲𝓸𝓷𝓼 𝔀𝓲𝓽𝓱 𝓞𝓽𝓱𝓮𝓻 𝓡𝓪𝓬𝓮𝓼

Other peoples of Underland often find Cheshires unsettling. They have a reputation for appearing without warning, knowing things they should not know, and disappearing whenever someone asks too many questions. Cheshires generally find this reputation amusing. They are particularly difficult for enemies to track, making them natural spies, scouts, messengers, and infiltrators.

𝓣𝓱𝓮 𝓑𝓻𝓮𝓪𝓴𝓲𝓷𝓰

When the Ink Master escaped the Library of UM, the fabric of Underland began to warp. For most creatures, this meant madness, destruction, or mutation. For the Cheshires, it was something more complicated. They were already creatures capable of slipping between reality's seams. The Breaking simply made those seams easier to find. Some Cheshires became corrupted by the spreading Ink, their ability to bend reality becoming dangerous and unstable.

Others became strangely resistant. These uncorrupted Cheshires now wander Underland, occasionally intervening when they encounter someone they believe might influence the future of Underland. Nobody knows how they determine who is worthy.

𝓡𝓮𝓵𝓪𝓽𝓲𝓸𝓷𝓼𝓱𝓲𝓹 𝔀𝓲𝓽𝓱 𝓽𝓱𝓮 𝓘𝓷𝓴

The Ink does not affect every Cheshire in the same way. Some corrupted Cheshires have become almost indistinguishable from Ink creatures, their bodies constantly flickering between forms. Others seem capable of resisting the Ink entirely.

The Cheshire grin appears to have a strange effect on certain Ink creatures, causing them to hesitate, recoil, or flee. No one knows why. The Cheshires aren't telling.

𝓡𝓪𝓬𝓲𝓪𝓵 𝓣𝓻𝓪𝓲𝓽𝓼

𝓒𝓻𝓮𝓪𝓽𝓾𝓻𝓮 𝓣𝔂𝓹𝓮

You are a Humanoid.

𝓐𝓫𝓲𝓵𝓲𝓽𝔂 𝓢𝓬𝓸𝓻𝓮 𝓘𝓷𝓬𝓻𝓮𝓪𝓼𝓮

Your Charisma score increases by 2.

𝓢𝓲𝔃𝓮

You are Small or Medium. You choose your size when you select this race.

𝓢𝓹𝓮𝓮𝓭

Your walking speed is 30 feet.

𝓒𝓪𝓽'𝓼 𝓖𝓻𝓪𝓬𝓮

You have proficiency in the Stealth skill.

𝓒𝓱𝓮𝓼𝓱𝓲𝓻𝓮 𝓖𝓻𝓲𝓷

You can manifest your supernatural grin as a bonus action. When you do, your grin remains visible even if the rest of your body becomes invisible or enters darkness. You have advantage on saving throws against being frightened.

Additionally, when you encounter an Ink creature for the first time, you can use your grin to ward it away. The creature must succeed on a Wisdom saving throw against a DC equal to 8 + your proficiency bonus + your Charisma modifier or be frightened of you until the end of your next turn.

Once you use this ability, you cannot use it again until you finish a long rest.

𝓢𝓱𝓪𝓭𝓸𝔀𝓼𝓽𝓮𝓹

As a bonus action, you can magically step into a shadow you can see within 30 feet. You teleport to an unoccupied space within 30 feet that is also in dim light or darkness.

You can use this ability a number of times equal to your proficiency bonus, regaining all expended uses when you finish a long rest.

𝓘𝓷𝓿𝓲𝓼𝓲𝓫𝓵𝓮 𝓑𝓮𝓽𝔀𝓮𝓮𝓷 𝓜𝓸𝓶𝓮𝓷𝓽𝓼

You can magically become invisible. As a bonus action, you become invisible until the start of your next turn, or until you make an attack, cast a spell, or force another creature to make a saving throw.

You can use this ability a number of times equal to your proficiency bonus per long rest.

𝓦𝓪𝓵𝓴 𝓽𝓱𝓮 𝓦𝓪𝓵𝓵𝓼

You have a climbing speed equal to your walking speed. You can climb difficult surfaces, including upside-down across ceilings, without needing to make an ability check.

𝓣𝓱𝓮 𝓐𝓫𝓼𝓾𝓻𝓭 𝓖𝓻𝓪𝓿𝓲𝓽𝔂

A Cheshire does not always feel obligated to obey gravity. You can float a few feet above the ground. While floating, you can move horizontally as though walking, though you cannot rise more than 10 feet above a solid surface using this trait.

You cannot hover higher than 10 feet using this ability, and you descend safely if you are incapacitated.

𝓢𝓮𝓬𝓻𝓮 𝓚𝓮𝓮𝓹𝓮𝓻𝓼

You have proficiency in either Investigation, Perception, or Insight.

Additionally, when attempting to recall information about Underland's history, forgotten places, strange magic, or ancient events, the DM may allow you to know information that another character would not reasonably possess.

The exact nature of this knowledge is determined by the DM.

𝓢𝓱𝓲𝓯𝓽𝓮𝓻 𝓸𝓯 𝓕𝓸𝓻𝓶

As an action, you can magically alter your physical appearance.

You can change your feline features, fur, hair, coloration, facial structure, apparent age, and other superficial characteristics.

This transformation does not change your statistics, equipment, size, or creature type.

You cannot duplicate another specific creature's appearance perfectly unless the DM allows it.

You remain recognizable as a Cheshire to those familiar with your true form unless you deliberately disguise yourself.

You can remain in this form indefinitely and revert to your normal appearance as a bonus action.

𝓕𝓪𝓶𝓸𝓾𝓼 𝓒𝓱𝓮𝓼𝓱𝓲𝓻𝓮𝓼

𝓣𝓱𝓮 𝓖𝓻𝓲𝓷𝓷𝓲𝓷𝓰 𝓦𝓪𝓷𝓭𝓮𝓻𝓮𝓻

A mysterious Cheshire who appears whenever travelers become lost.

Some claim they have guided hundreds of people home.

Others claim they deliberately lead people somewhere far stranger.

Both may be true.

𝓣𝓱𝓮 𝓘𝓷𝓴𝓮𝓭 𝓒𝓱𝓮𝓼𝓱𝓲𝓻𝓮

A corrupted Cheshire whose body constantly shifts between feline, humanoid, and dripping Ink.

They are believed to have completely surrendered to the madness.

Some Cheshires refuse to speak their name.

𝓐𝓭𝓿𝓮𝓷𝓽𝓾𝓻𝓮𝓻𝓼

A Cheshire might become an adventurer because they:

• Want to uncover a forgotten secret.
• Are searching for another Cheshire.
• Were sent to watch over a particular person.
• Want to understand the Ink.
• Lost something during the Breaking.
• Believe the party is somehow important.
• Are running from a prophecy.
• Simply became bored.
• Know something about Underland that nobody else remembers.
• Were told by another Cheshire that they must go.
• Have begun remembering a place that supposedly never existed.

𝓝𝓪𝓶𝓮𝓼

Cheshires often have unusual names. Some use traditional names, while others choose names based on colors, emotions, riddles, places, objects, or concepts.

𝓜𝓪𝓼𝓬𝓾𝓵𝓲𝓷𝓮

Caspian, Corvin, Jasper, Silas, Salem, Cosmo, Milo, Orion, Felix, Poe, Indigo, Sterling

𝓕𝓮𝓶𝓲𝓷𝓲𝓷𝓮

Nyx, Vesper, Ophelia, Lyra, Azalea, Elara, Sable, Celeste, Iris, Fable, Echo, Luna

𝓤𝓷𝓲𝓼𝓮𝔁

Whisper, Wink, Cheshire, Shadow, Smudge, Midnight, Riddle, Dream, Echo, Velvet, Moon, Grin, Dusk, Mischief

𝓣𝓲𝓽𝓵𝓮𝓼 & 𝓔𝓹𝓲𝓽𝓱𝓮𝓽𝓼

The Grinning One, Between-Moments, Shadowtail, The Vanishing, Keeper of Secrets, The Smiling Stranger, Moonpaw, The Unseen, Walker Between Worlds, The Last Cheshire

Cheshires (Underland) Traits

Cheshires possess strange abilities inherited from creatures who learned to smile between moments. Their connection to Underland allows them to slip through shadows, disappear from sight, climb impossible surfaces, and float above the ground. Though unpredictable by nature, their gifts make them exceptional scouts, spies, and travelers.