Magical item idea #1: A shirt that becomes slightly shorter every time you tug it down in an effort to hide your padding/peeking waistband.
Magical item idea #4: An ordinary-looking pacifier that acts different after you touch it just once. It teleports into your mouth any time you call somebody else a baby.

[I'm factoring other people's ideas into my item count, too, so check out responses in this thread!]
Magical item idea #6: An article of clothing that looks 100% average, but whenever your friends see you wearing it, they're STRONGLY compelled to tell you you're cute, often more than just once!

[Replies to this thread featuring item ideas are factored into my item count.]
Magical item idea #8: A washing machine or dryer that is perfectly functional, but every article of clothing that comes out of it looks almost unnoticeably more juvenile than before. Over many dozens of washes, clothes take on pastel colors, gain cute embroidered emblems, etc.
Magical item idea #9: An ordinary-looking sippy cup that a friend gave you. The more you drink from this cup, however, the more you uncontrollably ask this friend for a bottle instead in increasingly juvenile ways.

"C-could I get a bottle?"

"Warm milk, p'ease..."

"Baba, baba!"
Magic item #10: A seemingly average plushie. Whenever you hold it, you shrink and the plushie grows so gradually that you don't even notice either of these things happening. The longer you hold onto it, the more possessive you become of it and the more you don't want to let go!
... and as you shrink and the plushie grows, the smile on its face gets ever so slightly wider, not that you notice all that much. You're too focused giving special hugs to your soft new buddy!
Magic item #11: A wind-up pocket watch that behaves normally to whoever's using it. For every hour they turn it back, the PREVIOUS user of the watch regresses by 1 year and they can only regain their age as the hours pass. If it breaks or wasn't wound up beforehand, tough luck~
Magic item #12: A pacifier that really does silence you! You can't talk at all or even mumble while it's in your mouth!

[Replies to this thread featuring item ideas are factored into my item count.]
Magic item #13: A pair of pants that makes it look like you're padded no matter what. These pants mysteriously add visible bulk regardless of what you're wearing underneath, and if you're wearing a diaper underneath, they make it look even thicker.
Magic item #14: A pacifier which, once inserted in your mouth, cannot be removed until you do something extremely babyish in front of somebody else. There's no guarantee that you'll have control over what that babyish act will be, though~
Magic item #15: A diaper which amplifies ALL sounds that come from it. It makes everything significantly louder- every crinkle, every tape sound, every rub, every squish, every hiss, and so on!

[Replies to this thread featuring item ideas are factored into my item count.]
Magic item #17: An office chair which very gradually raises you up higher and higher as you sit on it, but your head remains stationary because it makes you shrink at the exact same rate! While you work, this happens so slowly that you don't even notice it in action!
Magic item #19: A pair of training pants that instantaneously makes you have an accident whenever somebody asks if you need to use the potty, regardless of how well trained you actually are.

[Replies to this thread featuring item ideas are factored into my item count.]
Magic item #23: A diaper that becomes thicker whenever it's pat repeatedly. This effect could range from hardly noticeable to almost comically dramatic.

[Replies to this thread featuring item ideas are factored into my item count.]
Magic item #25: A large, simple wooden crib. If you've been lowered into it by somebody else, the railings will rise up every time you try to get out. There's no escape without the help of a grown-up!

[Replies to this thread featuring item ideas are factored into my item count.]
Magic item #26: A fairly thick and ordinary-looking diaper. The more you potty in it, the more you're overwhelmingly compelled to cuddle with and cling to any trusted person who's close by.

[Replies to this thread featuring item ideas are factored into my item count.]
Magic item #28: A special type of cookie which makes people significantly more susceptible to being hypnotized. While eating these cookies, you can sense your eyes just barely defocusing.

[Replies to this thread featuring item ideas are factored into my item count.]
Magic item #29: A tear-resistant onesie which cannot be removed by you or anybody else once you've been put in it. The moment you use the diaper you're wearing underneath enough to need a change, the onesie's snaps dramatically and instantaneously pop open! The only way to-
-get out of this onesie while padded is to use your diapers to capacity. If you are not wearing a diaper when putting this onesie on, one will manifest taped around your waist.

[Replies to this thread featuring item ideas are factored into my item count.]
Magic item #30: An ordinary-looking, but cursed training potty. The closer you get to it, the more likely you are to have an accident.

[Replies to this thread featuring item ideas are factored into my item count.]
[1/2] Magic item #33: A sticker with your face on it! The sticker is inert by default, but if it's adhered to an object, your consciousness is bound to the sticker and your body is left as helpless and clueless as an infant. While your consciousness is bound, your sight, hearing-
[2/2] smell and taste all work through your sticker face and you can feel anything that touches the object. Being peeled off is the only way your consciousness can be transferred back to your body.

[Replies to this thread featuring item ideas are factored into my item count.]
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