Its In A Book: Literary-Inspired Characters For Your Game, Part 1

Hello, homebrewers and players!

Pitfalls and Pixies is going to be starting up a new series of creations for your playing enjoyment: It’s In A Book. Things made with a literary theme. from characters from famous characters, items, and other such topics pertaining to the presented material.

This time? Alice in Wonderland! Who has not ever wondered to see what lays at the bottom of the rabbit hole, have tea with a hatter and an insane hare and witnessing just why everyone is mad here.                           


                                     Cheshire Cat- small fey, Chaotic Neutral


AC: 16 (natural armor)

Move Speed 30 feet, fly speed 30 feet

Strength: –   Dexterity: +4   Wisdom: +2    Intelligence: +2  Constitution: +1   Charisma: +4

Hit Points: 85

Languages: Common, Sylvan, Elvish

Skill Proficiencies: Arcana +5, Insight +5, Persuasion +7

Greater Invisibility: The Cheshire Cat can turn itself invisible at will. Attacks that the Cheshire Cat makes do not break the invisibility. This can be removed with the spell Dispel Magic, as this ability acts as a spell or spell-like effect.

We’re All Mad Here: The Cheshire Cat targets the closest two creatures in a 30 foot radius. The target(s) must make a Wisdom saving DC 15 or take 2d6 psychic damage and gains a level in Insanity. At the end of each of it’s turns, the creature may make this save again. When the person affected is hit with an attack, they may roll to make the save with advantage.

Multi-Attack: The Cheshire Cat may make two claw attacks, one claw and one We’re All Mad Here, or one We’re All Mad Here and one spell.

Claw: +4 to hit, reach 5 feet. Damage upon hit is 1d8+4 slashing damage. This attack counts as magical.

Spells: The Cheshire Cat knows a small number of spells it may cast.

Cantrips: Friends, Magic Stone

1st Level: Magic Missile, Bane, Tasha’s Hideous Laughter, Dissonant Whispers (4 slots)

2nd Level: Heat Metal, Blindness/Deafness (2 slots)


                                       Jabberwock- Large Monstrosity, Neutral Evil


AC: 18 (Natural)

HP: 200

Strength: +7  Dexterity: +2  Constitution: +5  Intelligence: –   Wisdom: –  Charisma: +2

Move Speed: 30 feet, fly 45 feet

Skills: Intimidation +6, Stealth +5

Languages: Abbysal (understands it but does not speak)

Dark Vision: 120 feet

Snicker-Snack: The Jabberwock picks up a target, initiating a grapple. If the target does not make a Strength save DC 17, they are grappled and take 3d10 force damage. The Jabberwock then may choose to pick up said creature and throw up to 25 feet away or continue to grapple it. The Jabberwock may not move with a grappled victim.

Multi-Attack: The Jabberwock may make 3 attacks: two claw and one bite  or two claws and one Snicker-Snack.

Claws: Range 5 feet. +7 to hit. Damage: 2d8+7 slashing damage.

Bite: 5 feet, +2 to hit. 1d8+2 piercing damage.


                          Queen of Hearts- medium humanoid, chaotic neutral



AC: 16

Hit Points: 150

Strength: +3   Dexterity: +4   Constitution: +6  Intelligence: +1  Wisdom: +1  Charisma: +4

Move Speed: 30 feet

Skills: Intimidation +6. Persuasion +6, Investigation +5

Languages: Common, Dwarven

Off With Their Heads: The Queen of Hearts can rally her allies, causing them to have advantage on melee attacks and spells which require a d20 roll to hit. On a natural 20, either the Queen’s Strength of Dexterity modifier (based on the weapon type) is applied to the damage but this is not doubled by the critical roll.

Flamingo Croquet: The Queen of Hearts uses a flamingo to knock weighed ammunition at targets, as if created by the Magic Stone cantrip. Range 20 feet, +4 to hit. The ammunition is considered magical, and does 1d6 damage. Three pieces of ammunition are created, and she may choose whether to hit all three at a single target or each at a different one.

In addition, the flamingo may make a beak attack should a target be within 5 feet of it. +5 to hit melee attack. 3d4+4 damage. This can be used within range of the Queen of Hearts, as well as attacks of opportunity should a target be so close.

Multi-Attack: The Queen of Hearts may make two attacks: one Off with their Heads and one Flamingo Croquet, or 2 Flamingo Croquet.

Love is in the Air: Valentines Day in Your Game

Hello, fellow tabletop gamers!


School has been generally busy after it starting again after the long winter break and I haven’t put terribly much content out there. Hopefully, this post will fill that blank, dark void with the prospect of love in the air and Valentine’s Day!

For all of you DM’s out there, these can be some great plot hooks. Why is Cupid causing people to fall out of love out of nowhere? Is he plotting something when he makes two nobles from opposing houses develop feelings? How come there are hundreds of cherubs dying and falling from the sky? There’s a lot of possibilities!

Cherub- small Celestial

cherubsBlonde curly hair atop their heads, cherubs are the parrots of angels. Generally harmless, their gentle nature is off-setting to their larger and more powerful counterparts: the Solar, Planetar and Deva. With small fluffy white wings and pudgy bodies, they can be seen dancing amidst the low-hanging clouds and offering praise for struggling artisans. Oftentimes, they depict the forces which have blessed them.

AC: 13

HP: 50

Strength: -1  Dexterity:  +3    Constitution: –   Wisdom: +2    Intelligence: +2  Charisma: +3

Move speed: 10 feet, fly 30 feet

Languages: Common, Celestial

Skills Persuasion +4, Stealth +2, Arcana +3, Insight +3

Condition Immunities: Charmed, paralyzed, frightened

Multi-attack: The cherub may make two attacks: one with a short bow and another with Puppy Love OR two with a short bow.

Puppy Love: spell-like effect. Range 60 feet. The cherub targets a single target it can see and causes them to become temporarily infatuated by them. The target must make a DC 14 Wisdom saving throw or be charmed by the nearest person to them. They also move within 5  feet of that person, and move within that distance at the end of their turn if movement speed is left.

The person has disadvantage on melee attacks and spells that require an attack roll. They may make the saving throw again whenever they are attacked with advantage, and at the end of their turn with disadvantage.

Short Bow: Range 20 feet, +5 to hit. 1d6+3 piercing damage.


Cupid- medium Celestial


Alternatively known as Eros, Cupid is a god of love and passion. Never does he prefer to take the appearance of his cherubs, who serve him and spread his messages and heralds on the wing: he is very much a striking man, with none of the infant cuteness his attends seem to always have.

AC: 18

HP: 179

Move speed: 30 feet, fly 60 feet

Strength: +2  Dexterity: +3   Constitution: +2    Wisdom: +3   Intelligence: +2   Charisma: +4

Languages: Common, Celestial

Skills: Persuasion +6, Stealth  +5,   Arcana +5,  Insight +4

Condition Immunities: Charmed, paralyzed, frightened

Multi-Attack: Cupid can make two attacks: one Heart Seeker and one Bardic Bliss, two Heart Seekers, or one Heart Seeker and one spell.

Damage Resistances: Psychic, piercing, slashing, and bludgeoning from non-magical weapons

Bardic Bliss:  Range 60 feet cone. Spell-like affect. Time: 1 round of combat. Cupid sings an enrapturing song, charming and delighting those in the area when he wishes this. Targets must make a DC Wisdom saving throw 17 or be charmed for the duration of the effect.

In addition, while playing this song, he can choose up to two allies and give them a Bardic Inspiration die of a d6. He cannot do this upon himself.

Heart Seeker: Ranged attack, range 150 feet. +5 to hit. Cupid lets loose a single red-tipped arrow at a single target, poised and precise. If Cupid hits with a critical 20, they take an additional 2d6 psychic damage. This is not added to the normal damage of the critical 20. Damage: 3d6+3.

At Will: Magic Stone, Friends, Comprehend Languages

3/ Day: Bless, Comprehend Languages, Cordon of Arrows

1/Day: Moonbeam


Artifact: Red String of Fate


The Ties of Affection: some say this strand of fabric was made by a Bard, grieving for the loss of those he held closest. Bolstered by the magic of love and his strong emotions, the fabric became enchanted and led him to the one person he could spend the rest of his life with.

When you become attuned to this artifact, the fabric becomes either a ring, a choker or a bracelet of red woven fabric (your choosing). Only you see that, coming from it, is a faint red trail that leads into the distance: this shows you to someone who you are meant to be a kindred spirit with either friend-wise or romantically.

Others with a Red String of Fate can see the line cast off of you. You can do the same, and see the ties that people have severed willingly or forcefully.


Choose one from each table as listed.

Minor Beneficial Properties:

You have advantage on Charisma saving throws and gain proficiency in it as well.

You learn Celestial.

You learn the spell friends and can cast it at it’s lowest level once per day.

You gain proficiency with the Persuasion skill.

People find it easier to trust and confide in you. Your DM dictates how.


Minor Detrimental Properties:

When you fail a Wisdom saving throw, you take an additional 1d4 damage.

Food spoils around you when you touch it. Eating said food causes 1d4 damage but is regained upon a short or long rest.

You find yourself crying at random moments. Your DM rolls a d100 to see when you start crying: 50 and under you cry and over 51 you do not.

People have a harder time trusting you. DM determines how.


Major Beneficial Properties:

Once you become attuned to the artifact, you may choose one person in your party to give a twice-a-day Bardic Inspiration (d6). You regain this at the start of the next day.

You become immune to being charmed.

You have proficiency with two weapons or two skills.

You learn Cure Wounds as a spell that you can cast three times a day. You regain this trait at the start of the next day.

Those around you are calmed by your presence. You have advantage on Persuasion checks.


Major Detrimental Properties:

You gain a random enemy, someone who has feelings for a loved one and sees you as an enemy.  They actively try to end your life and cause you misery. The DM keeps this a secret.

Once you become attuned to this artifact, you take 3d10 psychic damage. You regain your hit points on a short or long rest.

You have disadvantage on all Charisma saving throws, as well as no proficiencies with Charisma based skills.

The god Cupid comes forth, challenging you to one-on-one combat in order to show that you are worthy of love from others. No one else can participate, however Cupid may summon up to d10+2 cherubs for the others to test their mettle against. You gain 2d10 temporary hit points and your Charisma goes up by 1, and your maximum Charisma score goes up by one to a maximum of 21.


Well, I hope that filled the darkness that is infrequent postings. If anyone has had a chance to play with these, please let me know. And as always, may you always roll 20!