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Miles of Misfortune - #3 - One Knuckle Sandwich
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EmperorCharm
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Miles of Misfortune - #4 - Kiddy Potty Plus

Miles of Misfortune - #5 - Dizzy Day Dream

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Miles of Misfortune - #3 - One Knuckle Sandwich
Miles of Misfortune - #5 - Dizzy Day Dream
There was a knock on Cobalt's door the very next day.

With a worried expression and a thump in his heart, he got up from playing blocks with his baby brother Diesel, and shot towards the door. He tripped and stumbled a bit but managed to scamper and scramble his way to the doorknob before opening it up.

"Hello Master~! It's great seeing you again today!" Cobalt tried his very best to beam with happiness. His master, or Tails rather, looked down at Cobalt with an almost blank, half-open expression on his face. The fox saw the chipmunk, covered in sweat and jittering, and figured that he must be nervous.

Tails sighed and put a hand to Cobalt's head, smiling a bit to himself. "Hey there, Cobalt. How's it going today?"

Cobalt felt a sigh of relief escape his throat when he went to answer. "It's going great! Thanks!"

That was good. He was certainly rather worried that his master was still upset about what happened yesterday.

In truth, Tails kind of was. After he woke up from being knocked unconscious by his student, he found that Cobalt was the only one left. They apparently got tired of waiting for him to get up and left, thinking class was over... which, to be fair, it might as well have been. Still, it stood as a sign of great disrespect. He'd lost a lot of clout yesterday and it was going to take eons before winning it back.

Oh well though. The karate class maybe isn't one of those things he can brag about now but his stance as a babysitter had taken off. He was currently here to actually babysit both Cobalt and his baby brother Diesel. That's why Tails came prepared with a large bag of baby items and supplies. He had to get bulkier ones because Diesel, as it turned out, was a pretty heavy user of these diapers. Small ones just wouldn't cut it.

This was all rather frustrating considering that Diesel was supposed to be going through with potty training too. However, his parents weren't seeing a ton of success at the moment. Tails even less so. The only one that Diesel seemed to acknowledge in any sort of way was his older brother Cobalt. Perhaps he could surprise their parents today by helping Diesel finally take a big leap in his potty training and use Cobalt to do so. Yeah, that'd be a big shining star on his record.

When Tails settled in, he clapped his hands with a bright smile on his face before going into the living room and spotting the training pants wearing toddler playing with his blocks on the floor. "Heya Diesel! It's your bestest babysitter in the whole wide world, Tails!" The fox splayed out his arms, as if waiting for an applause.

The toddler merely looked up at him and blinked. Tails sighed. Cobalt had to giggle a bit.

"Alright, so I've got a great idea," The fox boy continued. "We're gonna finally get you potty trained! Won't that be swell?"

Diesel looked like he was pouting a bit.

Tails winced. "Uhm... d-don't you wanna be more like your awesome big brother Cobalt? He wears big boy undies after all!"

Diesel looked over at his big brother. Cobalt gave his baby bro a wink and a thumbs up. Diesel then turned back to Tails and gave a small nod.

"That's the spirit!" Tails grinned.

---

When in the bathroom, Tails got the new Kiddy Potty Plus set up! It was nice and shiny! All it needed was a baby to go on it for it to be perfect.

Diesel stood by, clutching his big brother's pants rather roughly. Cobalt was slightly embarrassed by this but chuckled and tried to comfort his baby bro with a pat on the head. "It's okay Diesel. Master and I are here for you. The potty may look scary but I promise it won't bite."

Tails glanced over at Cobalt and saw Diesel tugging at his pants a bit, exposing the waistband of Cobalt's blue boxers. Tails blushed slightly and looked to the side. 'Seriously? Not even regular Tighty whities but straight on Boxers? Here I am still wearing Super Mario underoos... but I can't help that. They're comfy and I like them. B-Besides underwear isn't the barometer for maturity. I-It's not like it makes me weaker than him or any-'

"Master?" Cobalt asked suddenly. Tails gasped.

"Huh? What ABOUT my underwear?!" Tails panicked, sounding rather defensive.

Cobalt blinked in confusion. "Uhm... no. Diesel looks pretty scared. He won't go on the potty unless... I think we're gonna have to show him it's safe."

Tails winced. "Hmmm... well how kind of you. What an awesome big brother you are, doing something so embarrassing for the benefit of your baby bro. That's so sweet."

"Well... actually..." Cobalt blushed a tiny bit. Diesel would NOT let go of Cobalt. He was stood there, frozen solid. "H-He won't let me go. I think he wants me to stay with him... I think you're the only one who can do it Master."

Tails' face flushed red. He began sweating and then pursed his lips while looking to the side. "Hmmgh... mmmggh... I-I can't because I'm... too big. I wouldn't fit."

Cobalt looked the potty over and smiled. "I bet you could."

"Fine. MAYBE I could but there's no way seeing me do it would reduce his fear of the potty." Tails snapped a bit. "In fact, you said you wanted to make it a bet? If it works from me simply doing this then you can put ME in a diaper... but if it doesn't YOU wear one so your brother can at least feel more at ease."

Really, he just wanted an excuse not to be the one wearing the most babyish undergarments between the two of them. Cobalt was none the wiser.

"Okay. Sure. Deal." Cobalt gave a thumbs up, blushing slightly at the image of him being in a diaper. He'd been potty trained for a few years now so that'd be weird. If it made his brother more comfortable, he'd do it though.

Tails then examined the faces of both his charges before sighing. "... Alright. Fine...! Be warned though, I got a girly package of diapers by mistake...!"

Cobalt winced. "Th-That's fine..." It wasn't fine. That sounded humiliating.

Tails looked the potty over and examined it a bit. He turned over and sat down with his pants still on, feeling rather dorky and weird. However, what he noticed was that his size was so incompatible with it that he almost sunk into the thing and got stuck. He needed to give it more leverage so he could sit more comfortably on it.

Looking around the place he eventually found a small rolling cart. He lifted the potty and set it down on the thing to keep it more elevated. That should help with his feet sitting more comfortably on the floor but the danger of his butt getting stuck was still there... and if he got stuck and whined about not being able to get out then it would make Diesel way more afraid of this thing...!

He had to do this in a way that didn't make Diesel terrified of the potty but still didn't see the issue being resolved from HIM sitting on it, specifically. What a tightrope to walk.

Tails then bit the bullet and realized what he had to do. "Don't the two of you look. I mean it." He said this with narrow-eyes glaring at the two of them as he went to unbuckle his pants.

Cobalt nodded and closed his eyes. Diesel didn't let go of his brother but mimicked what his big brother did by shutting his eyes too.

Tails sighed and tugged his pants and underwear down. With them pooled around his ankles, he sat on the potty with his arms crossed. "There. Open them and take a look...!"

Cobalt and Diesel both opened their eyes.

What a sight.

Tails was sitting on the Kiddy Potty Plus looking SUPER embarrassed. He was blushing and pouting like a toddler himself.

"So? Did it work?" Tails asked, sweat beginning to form on his brow. He hoped it didn't...

Cobalt looked down at Diesel. "Well? It's safe right?"

Diesel kept gripping the side of Cobalt's pants. He was still scared.

"Aha!" Tails smirked. "Looks like I won the bet. Guess we'll have to get you fitted for a diaper Cobalt...!"

Cobalt blushed and nodded. "S-Sure..."

Tails grinned and was about to get up but gasped when he found he couldn't. Oh no. His big butt was too huge for this thing. Despite removing his pants and undies he still got stuck!

The fox grunted and tugged at the potty, unable to get loose. He then yelped as he began rolling forward, jerking about the bathroom in an attempt to stand up. The two confused kids stood back and watched at the fox rolled his way towards the door and ended up exiting the bathroom, kicking his legs down the small hallway as he did. "COME... ON! OFF! GET OFF!"

Cobalt picked up Diesel and followed after him. "M-Master! Maybe you should stop moving about and let me get the potty off that roller before you-!"

"AGH!" Tails yelped, suddenly skidding back when he reached the stairs. He screamed as he bounced his way down the steps! "AAAAAAUGH! NO! I'M GONNA SMASH INTO THE FRONT DOOR!"

Cobalt panicked. He couldn't let that happen. With Diesel clinging to his back, Cobalt jumped and slid down the banister, past his master, and reached the front door before Tails did. He quickly unlocked the door and sprung it open. "There!"

"NO! YOU IDIOT!" Tails screamed as he just rolled right out into the front yard.

"...Oops." Cobalt blinked. Perhaps he should have thought that through a little more...

Tails screamed as he rolled down the porch and into the street, finding that the potty was filling up with an accident as his fear overtook his body. The scared fox then found salvation when the roller smacked against the curb of the sidewalk and shot him off the potty with a wet POP!

The fox then smashed his face against the large telephone pole before sliding down it onto his front. His butt naked booty stuck out for the general neighborhood to bare witness too. The potty had stopped, now smelling faintly of pee.

Cobalt stood with Diesel in his hands and gasped. That's when the toddler in Cobalt's hands started to laugh and point at the potty.

Cobalt was confused for a second before Diesel tugged on his arm and pointed at the potty again.

"Wait... you... you wanna go on the potty? Did that... look like FUN to you?" Cobalt asked.

Diesel nodded, giggling like a baby.

"OH?! AWESOME!" Cobal beamed with joy. "Master! We did it! He wants to go on the potty thanks to you...! Oh... I guess that means I actually won the bet... but still, this is great!"

Tails laid on the sidewalk, eyes swirling and stars circling his head. His tongue was sticking out the side of his mouth and the bottom part of his fur was wet.

Seems like the "good news" didn't quite reach his ears just yet on account of being unconscious.

Oh well. He'd find out soon enough.

---

Read long chaptered stories over at my Patreon, every single week, for just a buck a month. Go for $10 a month and you get an exclusive colored picture every month too! Check it out: http://www.patreon.com/SDCharm

Keywords
cub 249,390, fox 231,857, butt 105,589, naked 104,371, boy 74,010, sonic 58,638, sonic the hedgehog 56,669, wet 28,758, booty 22,315, cubs 17,665, tongue out 17,365, tails 15,609, miles tails prower 14,020, embarrassed 13,151, chipmunk 12,022, humiliation 11,216, boys 10,686, male/male/male 8,690, embarrassment 4,071, kids 3,475, babysitter 2,060, potty 1,860, public humiliation 1,764, tongue sticking out 1,687, embarrassing 1,661, babysitting 1,510, humiliated 1,329, chipmunks 1,164, role reversal 991, derp 943, humiliating 893, unconscious 847, dizzy 671, potty training 555, cobalt 533, ko 530, knocked out 475, loser 472, passed out 312, dazed 305, unconsciousness 178, fainted 175, seeing stars 161, roles reversed 157, babied 153, knocked out cold 143, out cold 103, cuckoo 92, wet himself 76, cartoon ko 54, pottychair 47, kiddy potty 2
Details
Type: Picture Series
Published: 4 years, 9 months ago
Rating: Mature

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Nintendoman82
4 years, 9 months ago
Tails pulled a 'George of the Jungle'!
EmperorCharm
4 years, 9 months ago
Tails as George of the Jungle would be adorable. He'd crash into everything and it'd be the cutest thing ever.
Nobody14
4 years, 9 months ago
Super mario briefs! Tails is a traitor! Nah I'm just playing XD
EmperorCharm
4 years, 9 months ago
They're pretty much friends with the plumber nowadays anyway. Mario and Luigi probably have some Sonic merch of their own.
Nobody14
4 years, 9 months ago
I really hope it's either shirts or plushies
CuriousKit
4 years, 9 months ago
Haha, Tails on the potty! You're a person after my heart,
EmperorCharm
EmperorCharm
.  Tails though, seriously... a rolling cart?!
EmperorCharm
4 years, 9 months ago
It was all he could find I guess.
CuriousKit
4 years, 9 months ago
I'm sure a true master would find something else like a small step or a pile of books!  Still, time to make him an initiate again and see him all cute and child-like on the potty! *giggles* (To me, they're the cutest things!)
SolarisBlazer
4 years, 9 months ago
Sigh, Tails for a smart kid  you're a fool to get into another mess.
DrHojo123
4 years, 9 months ago
Whole new meaning to potty train.
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