All items made by prompts from the WTF Is My Ridiculous Magic Item Generator.
The False Serpent of True Sight
The False Serpent of True Sight began as little more than a parlor trick for drunken royalty. When released from its ink-filled container, this enchanted coil of iron will slither across whatever is before it, be it the bare ground or canvas, and produce a black and white sketch of what it can see. The drawing has limited details and is panoramic, which leaves scale up to interpretation at best.
What started as a curiosity to entertain drunken guests evolved into a tool to counter espionage when the serpent sketched the image of a looming figure that was invisible to all others in the room. Unfortunately, the party trick mantel still lingers within the enchantment, and the item will only work when the attuned owner is inebriated.
Prompt: A thick metal rope that will sketch a picture of the scene whenever you are drunk or high.
Hellish Never-Emptying Wine Bottle
Gluttony isn’t a demon in the traditional sense. Like its six siblings, it’s a living idea that never dies, no matter how many pieces of it you vanquish. A part of itself will branch off or break away, infecting a creature, object, or idea with a little portion of gluttony that is sure to grow.
In this case, a bottle of wine that never empties or ever stops insisting people drink from it. When not being observed, it will move itself within reach of people or give itself a prominent place on a dining table. Its soft calls and gentle suggestions can be heard in dreams and are often mistaken for one’s own thoughts.
Its only true redeeming quality is its sensitivity to any demonic presence. It will rattle and emit a shrieking noise when any demon draws near, and the noises are loud enough to wake a slumbering person. However, this noise is not a warning. The bottle simply cannot contain its excitement when seeing an old friend.
Prompt: A super evil never-emptying wine bottle that wakes you up whenever a devil is close.
Never go to sleep angry. Gilmits believed that more than anything. So when he enchanted his friend’s bedroll that could make her fall asleep instantly, he added his own twist to it. Despite both adventurers parting long ago, this gift continues to live on.
Catnap will only activate once a creature is inside the bedroll. If anything other than their head is uncovered, the enchantment will not trigger. When encased, the act of smiling will cause them to instantly fall asleep, regardless of other conditions. Catnap does not aid users in staying asleep or waking up if there is danger.
Prompt: A dusty bedroll that lets you fall asleep whenever you smile.