Daily Free-Write October 11, 2022: Boo, Bradley and Skrodgor Crusher of Souls in Halloweentown (Patreon)

Author's Note: It's 11 days into October and I realize I haven't put out enough spoooopy content yet! As I work on the hypno diaper curses, enjoy this silly little story that I dreamed up as I typed. A true free-write. The mind sure does go to some interesting places! 

"I've got the pumpkin pie pumpkins!!!" yelled Bradley, setting two small pumpkins on the kitchen counter.

"You don't have to yell," scolded Boo, "I'm right here. Remember: Indoor voice!"

"Sorry!" Yelled Bradley, before giggling and running out to the car to grab more groceries.

"That boy, I swear," said Boo, shaking their head as they hefted a big container of pumpkin spice into the spice drawer.

"I've got the candy corn!!!" yelled Bradley, dropping two big bags of candy corn on the kitchen counter next to the sugar pumpkins.

"Brat!" yelled Boo, getting down off the step stool and chasing after the bigger Bradley.

"Ha! Can't catch me Booboo!"

"Oh yeah? You just wait," said Boo, pulling out their wand. Try as he might, Bradely couldn't outrun magic. With three flicks of Boo's wrist, Bradley began to shrink, his legs growing smaller than his body even as he tried to run. "Oh no, not again!" he said as his clothes fell off of his body.

"Oh yes again," said Boo, smirking. "You're going in the playpen until I can finish putting groceries away. Why can't you be like your brother?" said Boo, pointing to Bradley's Twin, Skrogdor, Crusher of Souls, who was quietly humming and putting away the groceries like a good boy.

"Because," said Bradley, giggling and sticking out his tongue as Boo gathered him up in their arms.

"Oooh.. you're lucky you're cute, little one!" said Boo, carrying Bradley over toward the playpen. They turned back toward the kitchen as they walked. "You got the groceries handled, Skrogdor, Crusher of Souls?"

Skrogdor, Crusher of Souls smiled and shot a thumbs up gesture. He had his headphones on, and was bobbing his head to probably some Halloweencore, but always seemed to hear Boo when they talked. Boo turned his attention back to the little terror whom he laid on his back, so that he could take off the last of his big boy clothes.

"You're the terror of Halloween Town, you know that?"

Bradley nodded and giggled as Boo picked up their now too-large diaper and tossed it aside in favor of a more age-appropriate one.

"Looks like that one needed to be changed soon anyway. That means I should probably check your brother next," muttered Boo. Boo had taken care of the twins for a long time, and Boo knew that the best way to keep a couple of unruly demon brothers docile and obedient was some well-timed regression, and a lot of diapers. Bradley seemed to be a tougher nut to crack than Skrogdor, crusher of souls, however. "You never take anything seriously, do you, little one?" asked Boo, as they picked up the giggling tot and set him in the playpen. Boo shook their head and crawled over to some blocks in the corner to continue where he left off last time he got in trouble.

"Alright, alright. Skrogdor, Crusher of Souls! Get in here!" called Boo, who was surprised to see the demon man appear beside them even before they finished stating their request. "Holy water! How many times to I have to tell you not to apparate beside me like that? Just walk like a normal person."

Skrogdor, Crusher of Souls cringed at the mention of holy water. That was the equivalent of dropping an F-bomb here in halloween town.

"S-sorry, master Boo..."

"That's alright, Skrodgor, Crusher of Souls. Just try to be more mindful next time, hmm? Now drop your loincloth and let's check the damage."

Skrodgor blushed and gave a bashful little smile as he dropped his loincloth. He was well endowed, and even through the thick and obviously sodden diaper, the huge bulge showed. Even the outline of the massive mushroom tip could be seen through the yellow tinged padding.

"Jiminy crickets! You really do need a change. Down on the floor with you, good boy."

Skrogdor crusher of souls obeyed.

"Alright, now as you know we have to take some precautions, so please assume the position of the infernal martyr."

Skrogdor Crusher of Souls stuck his arms out and his legs went wide to touch the points of the pentagram that glowed in the floor as Boo chanted. Chains burst forth from the carpet to wrap around Skrogdor Crusher of Souls' extremities, and only when Boo was sure that Skrogdor of Souls was secure did they proceed with the diaper change.

"You know I don't like to do that," said Boo as they undid the top tapes of the demon's massive diaper. "It's just, well, you know..."

As the diaper came off, Skrogdor's eyes began to fade, the blue glow disappearing to give way to a deep, empty blackness with the smoldering flames of ever-burning charcoal deep within their depths. Suddenly, the whole atmosphere of the room began to shift as the smell of oily smoke began to emanate from a direction not quite known on any earthly plane. Then, it was as if Skrogdor Crusher of Souls awakened from some slumber suddenly. He snarled and pulled at his chains.

"YOU! Release me now, or suffer my wrath."

"Sorry, but you haven't earned release," said Boo, smacking Skrogdor Crusher of Souls' balls sharply and causing a roar from the demon. "I'm helping you, so you should be a little bit nicer," said Boo, as they began to wipe around Skrogdor Crusher of Souls' belly and thighs with the demons' delight depilatory wipes, designed to keep your demon baby smooth at all times.

Boo continued their work wiping off Skrogdor Crusher of Souls' dick and balls, and even butt with the wipes as the demon thrashed and made more threats.

"Don't worry, sweet pea," said Boo. "You'll be back in a diaper in no time. You always make such a big fuss during diaper changes. Why can't you be more like your brother?" asked Boo, nodding toward the cute baby demon playing in the playpen.

"Hey! Don't you dare put that diaper on me!" growled Skrogdor Crusher of Souls as Boo began to slide the diaper under his butt. "I don't need your comfy womfy, lovely crinkly diapees... I... uhhhhh....." Even before the diaper was completely secured, Skrodgor Crusher of Souls' speech became a little bit cuter and less threatening. Then, he simply spaced out, his eyes regaining their life and blue glow as the diaper was finally secured around his waist. "Uh... what was I saying?"

"You were thanking me for the nice diaper change," said Boo, snapping their fingers so the chains disappeared along with the glowing pentagram beneath them.

"Oh yeah!" said Skrogdor, Crusher of Souls, rubbing his wrist. "Thank you. These ones feel extra comfy today." he added, rocking side to side on his butt to emphasize the crinkle and thickness of the bulk between his legs. "Shall I finish putting the groceries away, master Boo?"

"That would be lovely," said Boo, smiling and patting the front of Skrogdor, Crusher of Souls' cursed diaper. "You've just about earned a nice release into your diaper, good boy. If you keep this up, you'll get to have creamies in no time. Won't that be nice?"

"Oh, yes, very!" said Skrogdor, Crusher of Souls, who couldn't remember the last time he'd had a release like that. His bulging and low hanging balls were a testament to that, as their outline showed even through the thickest of diapers.

"What good boys I have," mused Boo, fingering their magical ring and smirking. "The best boys in all of halloween town." It was their favorite month: October, and they were gearing up for the big festival with all sorts of sweet treats to offer to the infernal masters. Boo couldn't wait to show their diapered demons off once again. It was a Halloween tradition, after all!