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Juvenile Jenga - #11 - Chance Encounter
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Carol of the Christmas Dare

The Wedgie Night Before Christmas (Commission)

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by SDCharm
"Christmas dares? That's a strange idea." Tails said as he sipped on his hot chocolate.

"Come on! It'll be fun!" Charmy smirked. "I do this with Vector and Espio all the time."

"And you always lose." Sonic said quickly, sitting over on the nearby chair. Charmy blushed and turned to face the hedgehog.

"What?! Who told you?! Did Espio blab his big stupid mouth off again?!" The young bee stammered.

Sonic shook his head. "Nope. I guessed because it's just how you work."

Charmy pouted and got even redder.

It was Christmas Eve and the only people who would agree to staying over at Tails' place was, Sonic, Charmy, and Shadow. Shadow was a shocker but it only really happened because he and Sonic were in the middle of a fight. Sonic promised to clear it up at Tails' place and here he was. Whatever though. The more the merrier.

"Whatever you want to do is fine with me," Shadow stated, sitting with his arms draped over the back of the couch where he sat. "I'm game for anything. I won't lose to anyone in any competition. Try me."

"HAHA! AWESOME!" Charmy stood up with his fists raised. "And so what if I always lost to them, that won't happen here. Not with you scrubs! Let's do it!"

"How do you lose?" Tails asked. "You get dared and you do it right? I doubt someone as crazy as you refused the dares..." Tails said.

"I didn't refuse any of them. I just couldn't finish them because they'd ask me to do something they knew was too hard for me to do." Charmy said defensively. "It's not a matter of will. It's a matter of strength... which I TOTALLY have! I just messed up before! That's all!"

"Fine, fine. I get it." Tails waved it off. "Well, if that's the case, let's each decide on a dare for each of us to do." Tails stood up and dusted off his hands. "If what Charmy said is true, than this'll be decided by how well the dare is constructed as well. Let's go for it."

"Right." Sonic nodded.

"Already ready." Shadow said, arms crossed and eyes closed.

"Haha! I'm an expert at this. You won't beat me!" Charmy smirked and licked his lips.

With that, the dares were laid out by each person to the next.

Sonic was to dare Shadow, Shadow was to dare Charmy, Charmy was to dare Tails, and Tails was to dare Sonic.

We now take you to the current scene of the dares already in progress. This is a depiction of what transpired.

DARE #1 - Shadow - Wear a Sissy Girl outfit, complete with exposed toddler girl panties!

"Is that all?" Shadow smirked. "HA! That's easy, Sonic. You're losing your touch."

Sonic raised a brow. "Am I? Well, you're super confident. I wonder what makes you so sure..."

Charmy butted in. "He's only saying that because he's used to wearing panties."

Shadow shot Charmy a glare which made the bee giggle and shuffle back. Either way, Shadow managed to do it. Sonic added the addendum that he had to strip in front of everyone too. THAT made Shadow blush, finally. He even growled a bit. However, he complied and began stripping down, tossing his pants, shirt, and plain white briefs aside before taking the items out of the "PRANK BAG" that Charmy had brought along with him. Of course there were panties in there, as well as a bow-tie, a girly shirt, and pink socks. This kid was a treasure trove when it came to pranks.

When the outfit was on, Shadow stood with his fists by his side, face blushing, and cheeks puffed out like a huffy little girl. He had to stand there and take it as the other three laughed and took pictures of him.

DARE #2 - Charmy - Punch yourself in the face repeatedly for five whole minutes and don't pass out.

"WHAT?! THAT'S A DUMB DARE!" Charmy snapped.

"Come on. It's not as humiliating as being stuck in this outfit. You've got on your festive Christmas clothes still. I'm stuck in this for the rest of the night so quit whining." Shadow said with a mutter.

"Hmph...!" Charmy growled and stood with his arms crossed. He then grinned. "Hahaha~! Alright. I guess that's fine. Sure. What's the worst that could happen. Alright me, GIMME YOUR BEST SH-!"


Charmy flew right out of his pants and smashed against a standing present as he punched himself only once! He slid down it and slumped there, tongue out, eyes rolling, and stars circling his head. He looked happy but he was well and truly unconscious.

"Oh. He passed out. Guess he lost again." Sonic said, shaking his head in disappointment.

"Nice Christmas briefs." Tails commented.

Dare #3 - Tails - Drink a ton of water and wear a diaper and baby clothes. Try to hold it for 10 minutes.

"WHY IS IT ALWAYS DIAPERS!" Tails snapped, immediately upon reading the dare Charmy left behind for him before he passed out. "He's getting revenge on me for beating him up back at the daycare..."

"Probably. But you can still prove you're better by doing the dare and completing it, unlike him." Sonic said with a wink.

"... Alright... FINE!" Tails snapped and began stripping down. He blushed as he got down to his He-Man briefs and then stripped those off, wiggling his naked butt out for Sonic and Shadow as they giggled at him. He then put on the diaper and baby clothes in the bag. They looked really similar to the outfit Charmy wore when they were in that daycare as well. This was definitely still on his mind.

In the middle of chugging a ton of water he realized that Charmy's dare didn't require him to strip in front of them...

After mentally kicking himself for not realizing that sooner, he was eventually left standing with a big little plump water belly in front of them. Tails burped and moaned as he rubbed his stomach. He then immediately felt his bladder ache. "Oh... no... I think I should have gone to the bathroom BEFORE I chugged all that w-water... gughghh...!" Tails winced and began wiggling and dancing in place.

Dare #4 - Sonic - Get a continuous painful wedgie for 15 minutes.

"Fifteen minutes...?!" Sonic gulped. "Uh... that's... isn't that a bit long for a wedgie?"

"Perhaps but who cares. I'm the only one currently able to give you that wedgie so turn around and bend over." Shadow ordered.

"That sounded really wrong du-OW!" Sonic yelped when Shadow slapped him, making him spin around. Shadow than reached into the back of Sonic's shorts and yanked his briefs upward, giving him a tremendous wedgie!

"AAAAAYEEEEEEEK~!" Sonic screamed, instantly feeling his bladder break before Tails' did. His shorts got rather soaked.

"Phew. Look at you. Sporting kiddie briefs like a pro." Shadow said, pretending to be impressed, but blushing still due to remembering he had on panties.

Charmy drooled as he laid in his dizzy stupor, babbling nonsense about cake, birdies, and rockets. Tails hopped on by, holding himself and scrunching up his face as he tried to keep his bladder in.

This was a very unorthodox way to spend Christmas Eve, but this, honestly, should have been expected from these jokers by now.


Merry Christmas everyone~! Hope you enjoyed the story and the picture. I know these guys probably aren't enjoying those dares. XD

Check out my Patreon for more cool stuff. Even $1 patrons get stories every week: www.patreon.com/SDCharm

fox 144,448, male/male 61,772, hedgehog 50,071, sonic 36,472, diaper 33,482, sonic the hedgehog 31,562, erection 27,932, panties 20,231, underwear 18,768, christmas 10,702, shadow 9,588, diapers 9,502, shadow the hedgehog 9,320, tails 8,307, hedgehogs 6,878, boner 6,751, miles tails prower 6,598, undies 6,546, embarrassed 5,938, humiliation 5,311, briefs 4,953, sissy 3,636, diapered 3,016, fight 2,885, fighting 2,690, embarrassment 1,888, nappy 1,707, bee 1,652, girly boy 1,096, omorashi 943, underwear bulge 942, embarrassing 876, desperation 760, underpants 749, humiliated 556, punch 414, humiliating 390, diaper fur 378, tighty whities 358, erection under clothes 328, unconscious 289, bet 240, diapering 228, charmy bee 223, nappies 171, charmy 167, underoos 160, loser 160, slapstick 120, cartoon briefs 101, cartoon underwear 97, chaotix 87, seeing stars 75, cartoon undies 68, eyes rolling 62, swirly eyes 56, sissified 55, eyes crossed 47, potty dance 38, see stars 37, team chaotix 30, crossed eyes 27, losers 26, rolling eyes 18, punched 17, punched out 6, hold it 1, sissied 1
Type: Picture/Pinup
Published: 4 months, 4 weeks ago
Rating: Mature

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4 months, 4 weeks ago
I love seeing tails in a diaper, and the whole premise for this picture is adorable <3
4 months, 4 weeks ago
4 months, 4 weeks ago
I would say Shadow won here in the end out of the four, even when they all lose
4 months, 4 weeks ago
Yeah, you're right. It doesn't seem to look like the others are doing so hot compared to him.
4 months, 4 weeks ago
This is the pic I was waiting for, the one where Shadow stand's tall in the end
4 months, 4 weeks ago
Yeah. He also had the least childish undies on too. Before the panties at least.
4 months, 4 weeks ago
Super-cute! Dare-y Christmas~ ;P
4 months, 4 weeks ago
Ah! Puns! I love em.
4 months, 4 weeks ago
Wow, one little thing led to so much.
4 months, 4 weeks ago
Charmy, you lose, but at least you didn’t lose alone
4 months, 4 weeks ago
A perfect christmas hehe. Sonic acting like a tough guy but immediately peeing his shorts the minute a wedgie is given to him. lol.
4 months, 3 weeks ago
Am I the only one noticing the lump in Charmy's briefs? Lol
4 months, 3 weeks ago
It would seem so.
4 months, 3 weeks ago
I love this so much. Tails' pose is especially cute and funny! LOL and the story that goes along with it is pretty funny too. Great work as always.
4 months, 3 weeks ago
Thank you, thank you, thank you!
3 months, 3 weeks ago
You'd think Sonic would have briefs that are a little more mature.
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