100 Impish Contracts with Twisted Clauses

For adventurers navigating the whimsical worlds of tabletop RPGs, impish contracts serve as delightful traps set by the mischievous denizens of fae realms and realms governed by trickster spirits. These agreements, characterized by their artful wordplay and unforeseen twists, are crafted to ensnare the unwary, offering a tantalizing glimpse of desires fulfilled while hiding layers of deception and humor. As adventurers embark on quests for power, wealth, or assistance, they may find themselves caught in webs where their dreams are tantalizingly within reach, only to be thwarted by the clever turns of a phrase. Whether an adventuring party is desperate for resources or seeking a shortcut through magical bureaucracy, these contracts promise to teach valuable lessons in caution and wit.

The presence of mischievous clauses can transform an ordinary encounter into a memorable adventure, adding both tension and levity as players navigate the labyrinthine language of these impish pacts. The contracts are not mere obstacles but opportunities for characters to demonstrate their cunning, testing both their insight and resourcefulness. In realms where magic and imagination reign supreme, these contracts may be viewed as a rite of passage, a test of mettle against the clever machinations of magical beings. Each agreement is a story waiting to unfold, bringing with it the risk of unforeseen consequences and the promise of laughter.


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Impish contracts have long enchanted players with their blend of whimsy and strategy, creating engagements that are as rewarding as they are challenging. Through clever twists and unexpected demands, they subvert expectations, encouraging players to think beyond straightforward solutions. In these worlds of storytelling and creativity, they become a canvas upon which players can paint their own tales of trickery and triumph, weaving narratives rich in humor and intrigue. These contracts light up any campaign with their charm and cleverness, ensuring that even the most mundane transaction becomes an adventure.

Whether players find themselves befuddled by a fae’s playful stipulations or outsmarting a demon’s cunning bargain, these contracts guarantee memorable moments that keep everyone on their toes. They are the lifeblood of a world where the line between ally and antagonist blurs, where a simple agreement can have rippling effects throughout the narrative. In a game defined by its possibilities, these impish contracts open doors to exploration and creativity, turning potential pitfalls into opportunities for growth and laughter. With their presence, every choice becomes crucial, every mistake a stepping stone for character development, and every victory an indulgence in cleverness and humor.

How to Use These Impish Contract Random Tables

The beauty of these impish contract tables lies in their versatility, each entry distilling the essence of deceitful charm into a mere 2โ€“3 sentences. Within this concise space, DMs will find the devilish humor and potential pitfalls that make each contract an adventure in its own right. Depending on the desired atmosphere, DMs can use themed d20 tables to conjure specific trickster realms, from the enchanting courts of the fae to the devious minds of cunning demons. For those craving the thrill of unpredictability, rolling on the full d100 table offers the ultimate randomness, ensuring no two encounters are ever the same.

These contracts can elevate a straightforward transaction into a tale of suspense and comedy, sparking a series of misadventures that test the players’ wit and creativity. By injecting a bit of impishness into the campaign, these contracts can act as catalysts for unexpected plot twists, challenging players to think on their feet and adapt to unforeseen changes. As narrative tools, they are invaluable, transforming mundane interactions into pivotal moments that can drive an entire storyline. Players may find themselves embroiled in comedic chaos, navigating pitfalls with humor and ingenuity as they attempt to unravel the contract’s hidden meaning.

Whether used as spice for a mundane trading session or as the centerpiece of a grand adventure arc, these tables offer endless possibilities for engagement and entertainment. Within each contract lies a narrative spark, ready to ignite the imaginations of both Dungeon Masters and players alike. These agreements are more than just words on parchment; they are living parts of the story, inviting exploration and interaction. By utilizing these tables, DMs can create a dynamic campaign environment that challenges players’ expectations and rewards their creativity.

d20 Contracts with Forest Fae (1 โ€“ 20)

In the heart of ancient forests, where sunlight dances through emerald canopies, the forest fae await with contracts that shimmer with nature’s glamour and mischief. Beneath their elegant and beguiling appearances, these contracts conceal cunning intent, offering gifts of forest magic that come with amusing obligations or unexpected transformations. Adventurers seeking the fae’s favor must tread carefully, for even the smallest oversight can lead to enchanting, albeit unforeseen, consequences. Every contract is a delicate dance of words, an opportunity for players to engage with the whimsical world of the fae, where nature and magic intertwine in a tapestry of challenge and delight.

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d20Contract Descriptiond100
1The fae promises to guide the party safely through the forest, but they must sing a song of the forest’s beauty each dawn or be turned into woodland creatures until sunset.1
2In exchange for a favor, the fae grants a seed that grows into a tree overnight, gifting shelter and fruit. However, the tree speaks only in riddles, requiring answers before bearing fruit.2
3The contract offers a magical cloak that allows the wearer to blend into the forest, but the wearer becomes enamored with the fae and must compete in a dance competition at the next full moon.3
4A fae will enhance the party’s senses, allowing them to hear whispers of the forest, but they must never harm a plant while within the fae’s domain, or the enchantment will turn against them.4
5The fae offers to weave a path of moonlight that leads to hidden treasures, provided the adventurers promise to return and entertain the fae with tales of their journeys under another full moon.5
6For the gift of a golden acorn that wards off evil creatures, the party must perform a play for the fae once a season or risk being transformed temporarily into the play’s characters.6
7The fae provides a crystal vial to capture sunlight, which can illuminate even the darkest caverns, but the adventurers must leave a token of their laughter wherever they use it.7
8In exchange for a potion that grants a night of prophetic dreams, the party must spend a day following the whims of the fae’s youngest child, a mischievous sprite with an insatiable curiosity.8
9The contract grants the ability to understand animal speech, but the adventurers must spend one day a week aiding forest creatures in their daily tasks or lose the gift.9
10The fae will protect the party from storms within the forest, but only if they promise to host an annual picnic for the forest beings, who will judge their culinary skills.10
11A fae promises a map showing the safest paths through the forest, provided the adventurers plant a tree at each destination, nurturing it with songs of their home.11
12The contract blesses the party with swift travel through forest paths, yet they must leave a trail of flower petals, ensuring a path of beauty behind them.12
13In return for a flute that calms wild beasts, the party must serenade the fae queen under the light of the stars every month, or the flute’s magic will fade.13
14The fae promises a potion of youth to one, but the party must aid a fae child in a scavenger hunt, racing against time to return before the potion’s effect is undone.14
15The fae grants a night of safe passage in the forest, asking in return for the adventurers to recount their journey in the form of a poem when they return.15
16To gain the ability to sense the true intentions of forest creatures, the party agrees to craft and gift a work of art inspired by the forest to the fae each season.16
17A fae offers a charm that reveals hidden dangers in the woods, but the group must forsake any use of fire within the forest for the duration of their travels.17
18The contract provides a magical net to ensnare evil spirits, with the condition that they spend each dusk planting seeds of light around the forest’s edge.18
19In return for guiding the party to a grove of rare herbs, the fae requires a song that must be sung to every tree they pass until they leave the forest.19
20The fae promises to bless their weapons with a touch of forest magic, but they must feed the forest’s creatures with treats from each of their rations.20

With these fae contracts, DMs can introduce players to environmental challenges or whimsical transformations, making them perfect for light-hearted sessions. Whether players become temporary creatures of the forest or find themselves singing songs to please the fae, these contracts offer adventures filled with humor and heart. They allow players to engage with the magical world of the fae, where every interaction is a chance for laughter and a lesson in the unexpected.

d20 Deals with Cunning Demons (21 โ€“ 40)

Deals with demons are the siren calls of forbidden knowledge and corrupted power, tempting adventurers with the promise of immense capabilities cloaked in cleverly hidden pitfalls. These contracts are masterpieces of temptation, each word meticulously chosen to conceal loopholes that threaten to turn dreams into grim consequences. The allure of such deals is in their ability to offer what seems too good to be trueโ€”because it often is. As adventurers grapple with the seductive power of these offers, they must navigate a moral labyrinth where each decision weighs heavily on their souls.

d20Contract Descriptiond100
1The demon offers vast knowledge of the arcane arts, but in exchange, the caster’s spells are whispered during sleep, manifesting in random mischief each morning.21
2In return for strength beyond measure, the adventurer must wrestle a shadow each night or face waking to find a token of their power missing.22
3A demon grants the power to foretell misfortune, but the bearer is compelled to share these prophecies in verse, often leading to social awkwardness.23
4The contract promises a map to untold riches, provided the party can endure a day where they can only speak in cryptic riddles.24
5For the promise of eternal youth, the adventurer’s reflection vanishes from mirrors, replaced by the visage of a trickster.25
6The demon plants a seed of courage in the adventurer’s heart, but fear of the mundane becomes larger-than-life, turning rats into dragons in their mind.26
7A pact for the ability to fly temporarily binds the adventurer to manifest wings made of shadow in moments of doubt.27
8The demon offers a sword that cuts through lies, but each truth revealed leaves the wielder’s tongue tied until sundown.28
9The adventurer is promised a charm of protection, but must forsake all sounds of laughter, lest the charm shatters.29
10In exchange for unlocking an ancient chest, the seeker must face a day where their own voice echoes another’s thoughts aloud.30
11The demon offers memories of another life, but each memory costs a daydream of the adventurer’s own, lost to the ether.31
12A pact grants the ability to commune with shadows, which occasionally whisper cryptic secrets that require solving before pursuing their tasks.32
13For night vision, the adventurer becomes blind to daylight colors, seeing only the world’s silhouettes until nightfall.33
14The demon promises a coin of infinite value for one day, but the adventurer must give it away before their shadow becomes a part of the void.34
15The adventurer is given the power to walk through walls, but each step taken echoes in the demon’s realm, requiring a toll of secrets each week.35
16The demon offers insight into another’s heart, but the adventurer’s own heart becomes a whispering echo only heard when solitude finds them.36
17A contract for charisma requires agreeing to animate their own shadow, a playful yet occasionally irritating mimic.37
18The demon grants the power to summon a storm, but the adventurer hears the storm’s fury as a constant, distant argument until it passes.38
19The contract bestows the ability to taste truth, but the adventurer finds they are compelled to speak of imagined flavors when asked of lies.39
20In exchange for a demon’s treasure, the adventurer must forgo their name until the next full moon, facing the risks of a nameless existence.40

These demonic contracts infuse a campaign with moral dilemmas and the palpable tension of decisions that echo beyond immediate effects. They challenge players to consider the cost of their desires and offer rich storytelling potential, prompting introspection and character development. It is through these encounters that adventurers learn the peril of greed and hubris, facing consequences that may alter their fate or offer redemption through clever choices. These deals with demons invite players to confront the darker sides of ambition, unfolding stories steeped in intrigue and moral complexity.

d20 Agreements with Trickster Spirits (41 โ€“ 60)

Trickster spirits, known for their love of jests and riddles, craft contracts that are as vibrant as they are unpredictable. These agreements, filled with humor and cleverly veiled demands, are designed to spiral into delightful chaos, offering players a rich tapestry of challenges that test their wit and ingenuity. Their contracts transform ordinary encounters into riddles and playful games, where the lines between friend and foe blur in a dance of cleverness and fun. Adventurers must be prepared to engage with the unpredictable nature of these spirits, turning each task into an opportunity for laughter and cunning solutions.

d20Contract Descriptiond100
1The spirit offers a bowstring of lightning, yet it demands the adventurer tell a new joke each day before sunrise or face static shocks.41
2For agility of a cat, the adventurer must navigate obstacles with feline grace, while meowing at every misstep until sunset.42
3The spirit guarantees a day’s luck, but requires the adventurers to walk backward until they share an embarrassing tale.43
4In exchange for a trickster’s mask of disguise, the wearer must mimic a different animal sound each hour while disguised.44
5An agreement grants a pouch of endless feathers, but they can only be spent while having a feather fight with the nearest ally.45
6The spirit blesses the party with the ability to levitate, provided they travel in hopscotch fashion until the sun sets.46
7The adventurer gains a staff that whispers secrets of the wind, but only if they can rhyme with every sentence spoken.47
8In return for a map to the spirit realm, each adventurer must sport mismatched socks and switch the dominant foot for marching.48
9The spirit offers a cloak of invisibility for one night, but the wearer must remain still when hearing a knock from the spirit’s realm.49
10A contract delivers a stone that glows during danger, provided the adventurer accepts a ticklish phantom presence when danger is afoot.50
11The spirit lends the power to mimic voices, but insists the voice of songbirds is sung each dawn by the adventurer’s campfire.51
12A borrowed cap of suggestion grants mental persuasion, yet forfeits the power if the adventurer sneezes more than thrice in a day.52
13The spirit grants a talking compass for navigation, but the compass insists on being serenaded with sea shanties at dusk.53
14An agreement allows borrowing an imp’s curiosity, but compels the adventurer to answer all questions with a question when asked.54
15The spirit offers a bag of endless jingling coins, but requires a dance in a circle whenever the moon is seen.55
16The adventurer gains the ability to conjure echoes, but must perform a joke before wielding such mimicry.56
17For the talent of mimicry, the adventurer can’t repeat any word more than twice a day without the mimicry’s power failing.57
18A spirit-blessed flute enchants listeners, but the player must laugh heartily before each melody is played.58
19The adventurer receives a monocle that reveals hidden paths, but must blindly trust a partner’s guidance during each use.59
20The spirit grants the trick of teleportation within sight, but the adventurer must honk like a goose whenever startled.60

These contracts with trickster spirits inject humor and quick thinking into any session, inviting players to embrace the absurdity and ingenuity required to navigate these playful pacts. The challenges presented by these agreements encourage creativity and adaptability, allowing players to revel in the lighter side of adventuring. With each contract, players are reminded that even the most serious quests can be filled with laughter and joy, transforming obstacles into moments of camaraderie and clever solutions.

d20 Bargains with Enchanted Merchants (61 โ€“ 80)

Enchanted merchants, purveyors of rare treasures and whimsical goods, offer bargains that blend enchantment with risk, inviting adventurers to partake in transactions bound by peculiar conditions. These contracts may involve unusual trading customs, bizarre payment methods, or eccentric clauses that add an element of unpredictability to the campaign. The merchants’ contracts are as beguiling as their wares, promising wondrous items that challenge adventurers to think creatively about their acquisitions and the costs associated with them.

d20Contract Descriptiond100
1The merchant offers an enchanted quill that writes secret messages, but only if the buyer’s name is penned backward each dawn.61
2A potion of fleeting invisibility is exchanged for a dance performed atop a barrel to entertain the shop’s spirits.62
3In return for a powerful amulet, the buyer must trade a nonsensical riddle answered each week without repeating a question.63
4For a mirror reflecting alternate futures, the adventurer must supply a bottle of laughter from each place visited.64
5The merchant grants a pair of shoes that never wear out, but the wearer must switch shoes every hour lest they become uncomfortable.65
6A telescope showing the nearest dreamscape is offered, but the borrower must choose an unusual hat to wear whenever stargazing.66
7The buyer receives a bag that turns rocks into loaves of bread, but the bread must be shared with whispers of stories before eating.67
8The merchant offers a wand of small illusions, but only if traded for a night’s performance of shadow puppetry by the campfire.68
9For a cloak of silent steps, the buyer must trade a dance with the merchant’s pet poltergeist at the peak of each solstice.69
10A compass that locates lost items is exchanged for a pledge to collect abandoned dreams and return them to the merchant.70
11The buyer receives a bottle of wind-sent whispers, but only if they promise to celebrate each new moon with a new melody.71
12An enchanted scribe stone is offered, but requires the adventurer to compose nightly haikus on its surface to remain functional.72
13The merchant trades a scarf changing colors with emotions for a collection of bedtime stories heard at campfires.73
14In exchange for a box of fleeting wishes, the buyer must promise to speak in rhymes each dawn until noon.74
15The merchant grants a glove that sees through illusions, but insists on a riddle swap between adventurer and merchant weekly.75
16A book that chronicles the past of any object is offered, but the borrower must engage the merchant in monthly debates of history.76
17The buyer receives a locket holding a fragment of silence, requiring a moment of reflection paid weekly in thoughtful silence.77
18An enchanted horn summoning helpful creatures is exchanged for a poem composed nightly under starlight until the next full moon.78
19The merchant offers a ring of fleeting protection in return for whimsical tales shared each morning until the ring’s power fades.79
20For a goblet of unending fables, the buyer must gift a new bedtime story to the merchant’s magical library each month.80

These bargains with enchanted merchants introduce peculiar items and quests that enrich a campaign’s economy, adding depth and variety to the adventurers’ interactions and acquisitions. Through these deals, players gain access to unique treasures, each with a story and challenge all its own. The contracts offer an opportunity for adventure beyond the battlefield, inviting characters to engage with the world through creativity and storytelling, where every trade has the potential to be a tale of its own.

d20 Pacts with Celestial Beings (81 โ€“ 100)

Pacts with celestial beings offer tremendous boons to those who prove worthy, yet they come with similarly lofty commitments. These contracts are often steeped in divine riddles and carry the weight of purity of intent and heart, challenging adventurers to navigate a realm where virtue and desire must be carefully weighed. The rewards provided by celestial contracts are immense, yet they demand sacrifices and choices that may test the very core of one’s character. In these agreements, players explore the boundaries of their virtues, embarking on journeys of moral exploration and growth.

d20Contract Descriptiond100
1The celestial offers guidance through visions, provided the adventurer writes a daily reflection to share with the light each dawn.81
2A blessing of serenity is granted in return for a vow of peace upheld until the next solar eclipse.82
3The adventurer gains a talisman of truth, but must promise to speak only truths until the next equinox.83
4The celestial offers a crystal of foresight, provided the adventurer meditates at sunrise and shares the vision with the stars.84
5A divine shield is granted, but requires a promise to guide three strangers to safety before the next full moon.85
6The adventurer receives the strength of ten, but must perform a daily act of kindness for each burden lifted.86
7A boon of angelic wings is offered, but the adventurer must shelter a lost soul until the wings fade into memory.87
8The celestial promises insight into the divine, provided the adventurer composes a hymn of gratitude for each celestial aid.88
9The gift of celestial healing is granted, but requires vigil over the sick until the next celestial event is witnessed.89
10The adventurer is given a divine sigil, but must spread the teaching of wisdom learned each week.90
11A celestial compass guides the path of righteousness, provided the adventurer engages in silent contemplation each day.91
12The adventurer gains the voice of a seraph, but must speak only in blessings and songs until the next waxing moon.92
13A celestial mirror reveals the soul’s truth, but the adventurer vows to act with utmost honesty for each reflection seen.93
14The celestial offers a chalice of purity, requiring a pledge to cleanse a tainted place by the next heavenly convergence.94
15The adventurer is blessed with the wisdom of the ages, provided they share a story of courage with each stranger met.95
16A celestial song grants the power to inspire, but requires nightly odes to the stars in gratitude.96
17The gift of prophecy is offered, but the adventurer must promise to guide a lost soul toward their destiny.97
18The celestial blesses the adventurer with divine armor, but requires an oath of protection for the innocent until dawn.98
19A celestial map of the heavens is provided, but one must chart the travels of kindness before the stars fade.99
20The adventurer receives the light of the cosmos, but must promise to illuminate the darkest paths with hope.100

These celestial contracts are ideal for moral exploration and character development, offering enormous power entwined with tests of virtue and integrity. They encourage players to consider the weighty implications of their choices, shaping their journeys with narratives that challenge their values and desires. In these agreements, adventurers are invited to reflect on their place within the universe, crafting tales that elevate their campaigns from simple quests to profound explorations of character and morality.

Final Reflections on Impish Contracts

Impish contracts are far more than mere transactions; they are a gateway to enriched storytelling and gameplay, offering players a myriad of ways to engage with the world. By infusing their campaigns with these clever agreements, DMs create opportunities for character growth, a deeper exploration of morals and motivations, and the delightful spice of humor. Whether players learn from their mistakes or find ingenious ways to outwit their cunning counterparts, these contracts bring creativity, depth, and laughter to any campaign, ensuring that every choice has consequences that resonate throughout the story.

Adventurers navigating these contracts face challenges that test their wit, resourcefulness, and decision-making, providing a fertile ground for character development and narrative complexity. Each contract serves as a narrative device, weaving tales of cunning, intrigue, and humor into the broader tapestry of the campaign. They challenge players to think beyond the immediate goal, engaging with the world and its inhabitants in ways that are both imaginative and profound. These contracts are not just hurdles, but opportunities for creativity and connection, where every signature marks the beginning of a new adventure.

Through impish contracts, DMs lay the groundwork for sessions filled with comedy, suspense, and moments of genuine surprise, inviting players to embrace the unpredictable nature of the game. These agreements ensure that every session is vibrant and alive, transforming simple interactions into grand adventures with unexpected outcomes. The playful twists of these contracts encourage players to collaborate, problem-solve, and develop their characters’ abilities, emphasizing the collaborative nature of tabletop RPGs. The journey through each contract becomes a testament to the players’ ingenuity and their ability to navigate a world full of complexities and wonders.

In realms defined by their enchantment and mystery, these contracts serve as catalysts, breathing life into the characters and their stories. They enrich the narrative by adding layers of meaning and humor, keeping players engaged and eager for what comes next. As players unravel the intricacies of these agreements, they discover new dimensions to their characters and the world around them, highlighting the integral role of storytelling in tabletop RPGs. By weaving these contracts into their campaigns, DMs offer players an experience that is as challenging as it is delightful, ensuring that every session is a memorable journey of discovery.

Ultimately, impish contracts are a celebration of the imagination and creativity that define tabletop RPGs. They capture the essence of storytelling, inviting players and DMs alike to embark on adventures filled with whimsy and wonder. Each contract holds the promise of something extraordinary, be it a lesson in humility, a tale of redemption, or a moment of pure joy. As these agreements unfold, they become a testament to the power of storytelling, turning every encounter into an unforgettable adventure where the only limits are the bounds of one’s imagination.


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Paul Bellow

Paul Bellow

Paul Bellow is a LitRPG author, RPG game developer, and old school webmaster. He's been playing tabletop games since the 1980s. He started Random Tables RPG as a way to give out free D&D and Pathfinder content to the world. Enjoy!