All prompts came from the WTF IS MY RIDICULOUS MAGICAL ITEM GENERATOR at RexiconJesse.github.io
There’s over 5 billion other items it can instantly make for you. Go get some.

5 magical items PDF here. Text below.

Stephon he Tiny, Deformed Pony

Like with many cursed items, it started with a drunken bet. Two bets to be exact. The first was that Frans’ deformed, raccoon-sized pony didn’t have the ability to kill anyone under any circumstances. The second was that prophecies were pony poo. When the two mages woke up from being blackout drunk, neither was sure what spells they cast the night before. A few months later, a sea monster-worshiping cult found the portal to their promised land. The night before that happened, Stephon the tiny pony no longer had an owner.

This deformed, raccoon-sized pony has a curved, S-shaped spine. While knowing a prophecy is about to come true can be useful, the pony’s owner must be aware of the pony’s power to utilize it. If able, the tiny pony will stomp on its sleeping owner’s face while they sleep, pushing its hooves into their eyes. If two days pass and Stephon hasn’t killed his owner, he will stop trying. That is, until the next prophecy is about to come true.

Prompt: curved tiny pony that attempts to murder you whenever a prophecy is about to become true

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The Magical “Shut Up and Keep Moving, Don” Briefs of Speed

“Do you think Don would walk any faster if you lit his ass up with lightning?” was meant as a joke. Jonavia had a thousand gold burning a hole in her purse, and she knew the artificer in the next town over. The rest is history.

Whenever a creature wearing the Magical “Shut Up and Keep Moving, Don” Briefs asks any rhetorical question, the briefs jolt the wearer with a powerful burst of lightning. The jolt supercharges them and allows them to move at double their normal walking speed for one minute. This does not increase any other speeds (fly, burrow, drive, etc.).

Prompt: lightning-producing pair of underwear that doubles your traveling speed whenever you ask a rhetorical question

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Jealous jelly nail polish

Thick, resistant to chipping, and gorgeous, Julia finally found the only nail polish that could survive a dungeon run. Not only did the nail polish look fabulous, the bottle itself was enchanted. If she kept the floating bottle somewhere on her, she could never fall fast enough to get hurt. She unintentionally tested this from 500 feet, and found it still kept her safe. Unfortunately, the previous owner was a bitter bachelorette, and it audibly mocks anyone who shows affection near it.

So long as the Jealous Jelly Nail Polish is on a person, they cannot fall fast enough to be hurt. However, they cannot speed up the falling process, making them an easy target for the entire fall. In addition, if anyone kisses within 1d20 feet of the bottle, it produces an overly loud and dramatic slurping noise. It lasts for several seconds after the kissing has stopped.

Prompt: gravity-defying bottle of nail polish that makes a slurping noise whenever people within 1d20 ft kiss

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The Ever-Burning Helm of Gruolgl, the Riverside Terror

While rare, it is possible for items to become enchanted without magic. Strong emotions over a long enough time can imbue items with compassion, hate, or even fear.

Gruolgl was the terror of the riverside clans. He’d lead his clan through the river, breathing through straws so they could sneak up on riverside villages. The moment he surfaced, he’d ignite his massive, troll face helmet and lead his clan in the raid. He was gruesome and said to be fearless. But every single time he swam, he feared the serpents that slithered beneath the surface. Whenever he felt something touch his foot, his fear would consume him, forcing him to swim faster leaving his clan behind. It was that very fear that brought about his untimely end and caused his helmet to wash downriver to a place that knew nothing of his legend.

The oversized, troll-shaped helmet is well insulated and keeps the wearer safe from the constant flames that engulf it. It deals fire damage to creatures that touch the flames, giving the wearer a unique effect when head butting something. When submerged in water, the flames will vanish but reappear when no longer submerged. Its additional magical ability comes from doubling the wearer’s swim speed for 10 minutes after they touch a snake, even if they are not in water when the snake touches them.

Prompt: ever-burning troll face helmet that doubles your swim speed whenever you touch a snake

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Petrie’s Perfect Paint Set

An empty ribcage didn’t stop undead Petrie from having the biggest heart in his party. He would use his artistic talent to make mini, colorful comics for his mates while they slept. He’d slip them into their bags next to their rations. When they found the comic, they’d laugh, look at Petrie, and Petrie would point back at them, since his fleshless skull couldn’t actually smile. The interaction always boosted everyone’s morale. The love and effort he poured into his comics infused the supplies themselves with power.

When the owner (requires attunement) uses these supplies to paint an image, they do not need to roll to succeed. The image is always looks recognizable as to what they were
attempting to paint. In addition, undead within 100 feet gain a morale boost whenever the owner makes finger guns at someone.

Prompt: brightly painted set of paint supplies which always create an accurate portrait that buffs undead in the area whenever you make finger guns

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