Sonic Series Fan Fiction ❯ The Milkshake Challenge!!! ❯ Dressing in Drag ( Chapter 3 )

Disclaimer: I don't own these characters!!!!!!!!!!

THE MILKSHAKE CHALLENGE!!! 3

Ready for his turn, Shadow looked at the two cards in front of him and randomly selected the one on the far left. Taking the card he chose, Rouge looked at it and put the other away. Intrigued, she raised an eyebrow, then looked to Shadow.

Shadow returned her stare with an emotionless expression. "What is it?"

Rouge smirked and turned to face the rest of the group. "Everyone, you should pay close attention to Shadow on this. If he agrees to this challenge, you all are going to weep for your dignity!!"

"What?" Sonic exclaimed.

"Hmph!!" Knuckles scoffed and tightened his fists. "It doesn't matter what the challenge is!" he growled, narrowing his eyes at Shadow. "I'll take anything's that's thrown at me and knock over anything or anyone blocking my way! "

Catching Knuckles' threat, Shadow simply half smiled at him and crossed his arms. He didn't care if Knuckles had a grudge against him because he so far had the highest score, or if because Shadow was getting a bit too close to Knuckles' ideal lady. With a scoff, he turned his body away from Knuckles, but gave him a sideways glare. "Then, may the best man win."

Hearing his words, Rouge swayed her tail a bit and chuckled. "It's funny you should say that, Shadow, because for this event, you and the rest of the boys will have to strip down and dress up…like a lady."

"WHAT!!!?" Knuckles yelled.

"What?!" Sonic exclaimed.

"Strip?" Tails questioned innocently, scratching his head. "What's TO strip? We wear nothing but socks, shoes and gloves."

"Hey, Tails, that's our secret! " Sonic whispered to him. "No one has to realize we're naked, except us. It's a guy thing!"

Tails gave Sonic a bewildered look, but nodded. "If you say so Sonic!"

Knuckles, who was both angry and confused, ignored Sonic and Tails' words and pointed at the dark hedgehog. "Well, what will you do, now? Sonic, Tails and me are completely against what you've chosen!"

"Well…." Sonic trailed off.

With a start, Knuckles whirled around to face him with a shocked look on his face.

"Sonic--?!"

Sonic rubbed his nose, then shrugged. "Ah, it's no big deal. Dressing like a girl isn't a problem. Actually, I've always wanted to try it…as long as it was for fun only. Besides, it's kinda like the same curiosity you have when you get Kleenex instead of Cottonelle. You'll always wonder…what if…"

With an enraged expression, Knuckles growled and shook a fist at Sonic. "THIS…ISN'T…THE SAME! THERE'S NO COMPARRISON!"

"Oh Sonic!" Amy cried, running to him and throwing her arms around him. "I don't care if you have strange cross-dressing fetishes! I still want you to be my husba…er life partner!"

Sonic cringed and tried to gently pry her away from him. "Calm down Amy. It's not like that…!!"

"Really?" Amy asked almost innocently, then she narrowed her eyes. "You've dressed as a woman before haven't you…?"

"Er…well it's been an interest on my agenda to try sometime before I get old…"

Amy neared closer to him, her expression growing tense by the second. "Sonic…."

"Amy…would I ever lie to you…?"

Confused and a bit enraged, Knuckles shook his head and turned to Tails.

Looking at him, Tails shrugged. "What? I don't have a problem with it either. It does sound like fun, and besides, I look like a girl anyway. Sonic's told me so."

"Shhh!" Sonic shushed, while trying to get Amy off of him.

Looking at the commotion that had been caused by Shadow's choice in the next event, Rouge frowned. "Hey! I didn't say this was a 'coming out the closet' event…!"

Shadow scoffed. "I'm almost not surprised…"

Rouge half-smiled. "Hm. I guess heroes aren't as squeaky clean as they let on, after all. It's rather amusing."

"Hmph" Shadow replied.

"That's it, Sonic! I know you're hiding something, now just spit it out!" Amy pressed, shaking a finger at him.

"But!" Sonic retaliated, but it had no effect on Amy. Then he gave in. "Okay okay fine! I got locked in your bathroom one time when you had gotten out of the shower and left your clothes in there!!"

Rouge and Amy gasped as Shadow and the rest of them stared at Sonic.

"I knew I shouldn't have, but, I always wondered how that rubber dress of yours felt so I…."

"You put it on?!" Amy exclaimed, becoming both intrigued and excited and touched the hem of her dress.

"Well…" Sonic began, rubbing the back of his head nervously. "That was after I sniffed it…"

Amy gasped. "You SNIFFED it?!"

"…And…rubbed it…"

"You RUBBED it?!"

"And then I…tried to slip into it but…"

"But what???" Amy questioned, extremely interested.

Sonic blushed, and turned his back to all of them. "The inside was really tight and the more I tried to inch in, the harder it got me-"

"SHUT UP, SONIC!" Knuckles yelled, kicking him.

Sonic barely dodged it. "What?! I was going to say 'to struggle' before you cut me off, Knuckle-brain!"

Rouge raised an eyebrow. As much as she was interested in where Sonic's story was going, Rouge had to admit she was also glad that Knuckles cut him off. "Allright! We have an event to start! I'll go pick the outfits for all of you and you each have to strut your stuff down a runway and look convincing for your part. You each will wear three different outfits: Street, Evening, and Hoochie."

Shadow raised an eyebrow at her. "…'hoochie'…?" he spoke flatly.

Rouge tried to cover up her anticipation for the next event with a mischievous smile and winked at Shadow. "That one is just for fun!" She turned to the rest of the group and saw Knuckles' hand up. "And no, none of these outfits are mine, so you can forget about me dressing like that. This is drag material only."

Knuckles quickly put his hand down. "I don't like it, but I can't back down from a challenge when something worth my while is on the line." He glared at Shadow, then glanced at Rouge. With a frown, he risked a look at Sonic. With a mildly bashful expression, Sonic nodded. Tails, who was a bit distant from them stepped up and agreed, giving Sonic a placid look.

Sonic shrugged, trying to soften their intense gazes, but it wasn't working. "Fine, let's get this party stared!"

"Oh Sonic…" Amy lightly called. Before stepping upto the ramp-like stage, he looked back at her. "Y-yeah Amy?"

With an alluring stare, she sauntered upto him and pointed to his chest. "I'm not mad with you trying on my dress without my knowing, but…I need to know…Just…how did you get locked in my bathroom…? Did you do that on purpose?"

The room grew silent as everyone's eyes were on Sonic. He cringed and rubbed his head. "A…actually, Amy…"

"Yes??"

"I was um…messing around with Chaos Control and somehow ended up in your bathroom with the door locked."

"Yeah…?"

"The shower had just been used. You weren't in there though…"

"What?!" Amy shouted, taking his statement the wrong way and hitting him. "Oh so you were looking for me naked, is that it?"

"No! That's not it!"

She hit him again. "Oh! So I'm not attractive enough for you to want to see me in my purest form?!!"

"No! I mean…Yes! …Wait a minute…did I say that right?"

Angry, Amy clenched her fist and began to reach for her hammer. "SOOONIIIC….!!!"

"Whoa! Whoa!!" Rouge yelled, stepping between them and pushing them apart. "That's enough! I don't have much tolerance for this anymore! Sonic, go, get ready. Amy you…"

"What?"

"You…go put make-up on the guys, I don't care. Just get out of here and leave the contestants' odd fetishes alone!"

A little glad she had something FUN to do this time, rather than wait for a loser, Amy agreed and ran off to grab her make-up.

Watching her run off, Rouge sighed, and began to walk upto the stage to join the rest of them.

About fifteen minutes after the guys got their first outfit ready in a backroom.

"Okay" Rouge said, taking a seat. "The first outfit should be Street-wear. Sonic! You're first!"

The second he heard his name, Sonic rushed out from the backroom and slammed the door behind him. Panting, he rubbed his forehead, then tried to walk over to Rouge. "H-Here I am!" He breathed. "I…had to get Amy off me. That girl is even crazier when she's got a grudge. I'm definitely going to feel bad for her man!"

Rouge chuckled, and looked up from her notepad. Then she gasped. Sonic had on a pair of blue Parasucos, brown suede boots, a black and silver outlined corset with a long-sleeved suede brown mid cut jacket with tassels leading from the shoulders to the wrists. On his head, he wore a dark brown crimp-styled wig and had red lipstick with a touch of blush, mascara and rosy eye-shadow.

"Wow…" Rouge muttered, looking Sonic up and down. "You look fresh!"

"Er…Thank you!" Sonic replied, heightening his voice.

"You don't have to do that…"

Sonic sighed. "Whew. Good! So, do I look hot, or do I look hot?" he mused, striking a pose.

"Hmph!" Rouge smirked, then quickly jotted down a number for Sonic. "I wouldn't get so proud so soon." Glancing up at him, she noticed that the apple and orange he had wedged in the bust of the corset were pretty visible. "And by the way, your fruits are showing."

Sonic raised an eyebrow at her. "What? My 'fruits'? My legs aren't wide open, no one can see…" Then he looked down. "Oh!! These 'fruits'!"

"What did you think I was talking--"

"…." Sonic said nothing and blushed.

Rouge shook her head. "Nevermind. Allright, step over to the side. Knuckles! You're next!!"

Silence.

Looking around, Rouge cleared her throat. "Ahem! You listless echidna! Come out here, it's your--"

"I'm right here!" Knuckles called, bursting out the door.

Looking to him, both Sonic and Rouge gasped.

Slowly, stepping out on one foot at a time, Knuckles graced the stage in a manner neither Rouge or Sonic had seen before.

"Well now…I've never seen him so…focused before..." Rouge commented.

Sonic shrugged. "Nah, he's only trying to focus, but he'll mess up sometime. He's pretty annoyed."

"…Is he?" Rouge watched as Knuckles tried to put one foot in front of the other and then nearly trip over them twice. She then narrowed her eyes. "…He is…"

"Dammit, I need to get this right!" Knuckles growled under his breath. With a focused frown on his ebony laced lips, he tried to walk without wobbling in platinum colored 3-inch pumps with criss-crossed ties that laced up his legs. He wore silky gold capris with a diamond-studded black belt that encircled diagonally around his waist and thigh. He wore a sparkling platinum triangle halter around his chest. On his head was a long jet-black wig with pink and blonde streaks in the bangs, and a sideways platinum cap. The outfit was complete with thick gold bracelets on each arm and two gold and platinum diamond studded rings on both hands. Standing close to Sonic, Knuckles glanced at him, then Rouge and tried to smile.

"Wow Knuckles. Your outfit is very impressive! I barely recognized you, Gold Diggah! So, tell me, how do you feel?" Knuckles frowned, which made him look very much like a cute girl. "Dammit, I hate these heels! But I'm going to win this event no matter what the cost!!"

Rouge chuckled. "That's nice to hear. I like a man who knows what he wants."

Knuckles winced. "Even…even when I look like this…?"

With a sigh, Rouge nodded. "Yes…even a man dressed like a woman can entice a girl's imagination…"

"Wh-what?!" Knuckles exclaimed, blushing a bit.

Warily, Sonic looked to him. "Don't get so excited. What she's really saying is that she'd use you for weird experiments while you're still 'prime' "

"Wha..?"

"Think about it..." Sonic whispered "Just why do you think Amy is so bent on claiming me…?!"

Ignoring them, Rouge continued on. " Next up is Tails!!"

There was a soft bump against the door, before it finally creaked open and Tails' curiously stuck his head out. "Um…Allright, I'm ready!" With that, the little fox stepped out onto the ramp wearing a short blonde wig and a netted black shirt with a red tube-top halter underneath. On his legs, he had black and red rose embodied capris, followed by red and black loafers. He also wore a thin red bracelet on one arm. With a meek smile, he waved to all of them on stage as he walked by and stood next to Knuckles. "So…how am I, this time?"

Rouge raised an eyebrow at his words having double meaning, then returned the act with a playful smile. "Mmmm, you're the best, Fox-Boy. I never would have known that so much potential and creativity was being held inside that delicious little body of yours."

Quickly, Sonic and Knuckles caught on.

"Hey…Hey!!" Knuckles called. "I didn't walk all the way out here in heels to hear you say that to an under-aged minor!"

Rouge scoffed. "Oh, and I suppose you'd rather me say it to you?"

Knuckles blushed and stumbled on his words. "W-well…I…"

"That's what I thought. Anyway, Fox-boy here knows I'm just toying with him, don't you?"

Tails nodded. "I sure do!"

Rouge chuckled at his enthusiasm. "Keep that up, and you'll be a fine young beefcake, indeed. Allright! Shadow! You're up! …Shadow?"

After three seconds of silence, the backstage door was slightly ajar. There was a grumble before it opened completely, and Shadow reluctantly stepped out. On his head was a lush and sleek black wig that reached his waist. He wore a black and red studded belt around his neck along with a white halter-top with silver lining. On his waist, he had a black belt with silver studs, a short blue-jean skirt and his normal black and white air-shoes. For accessories, he had dangling diamond earrings and had black and red bracelets covering most of both his arms.

Stepping over to the rest of them with crossed arms, Shadow ignored the stares from the guys and put his attention on Rouge. "…Hmph." Was all he could say.

With a giggle, Rouge nodded to him. "Not bad." She then jotted down a number. "I'd lose the shoes, tho, but…what's done is done! Allright, I've evaluated all of you for this round. Sonic has a 4, Knuckles has a 4, Tails has a 4 and Shadow… has a 4!"

Before any of them could protest, she continued on. "Now, you'll change into Evening-wear. So hurry back to your stations, boys. You'll be rated on poise. And you've got to be silent!" she said, glancing between Sonic and Knuckles, then she smiled. "Allright, the next set will begin in 30 minutes!"

30 minutes later…

One by one, the guys came out and showed Rouge how well they could walk in a dress. They all kept the same wigs on.

Sonic was the first. Clad in a purple bell dress, he tried to keep his balance while walking down the runway, then ditched the idea and tried to speed things up. He aimlessly spin-dashed off the stage.

On Knuckles' turn, he showed up in an orange and black prom dress and made himself try to strut down the runway in 5-inch heels. Needless, to say, he fell off the stage after taking two steps.

When Tails' turn came around, he happily did the runway in a dual layered blue and white bell dress without falling over even once, and struck a cute pose at the end.

For Shadow, in his black spaghetti-strap dress, he nonchalantly sauntered down the runway and crossed his arms at the end.

Quickly jotting everything in her notes, Rouge looked up at all of them. "Well, this was embarrassing. Anyway, hopefully things will straighten out in the last round." With a chuckle, she clapped her hands. "Allright, here's the last one. I want you boys to go back there and come out dressed like places where the sun doesn't shine! Come back out in 15 minutes!"

Once the guys left, Rouge evaluated her scores.

Sonic had a 1, Knuckles had a -2, Tails had a 5, and Shadow had a 4.

15 minutes later…

All four contestants came out of the backroom at the same time and stepped onto the stage.

Watching them walk out in nothing but their wigs and heels, except for Shadow who still wore his air shoes, Rouge winced at them, then angrily placed her hand on her hip. "What are you all doing?! You're not wearing anything!"

With a nod, Sonic spoke up. "Yeah, but we still kept the look with the wigs…"

"And the damn heels…" Knuckles added with a growl.

"And the make-up too." Tails chimed in.

"But, why?!" Rouge demanded.

"Well…" Tails began "We talked it over, and decided that we didn't want to offend anyone, so we came out naked!"

Shocked, Rouge stared at them, then she burst out laughing. "I swear, Fox-boy, you really have a way with words."

Tails blushed. "I-I do?"

"Mmmhmm" Rouge mused with a wink.

"Ahem!" Knuckles cleared his throat. "coughcoughminorcoughcough!! coughcoughunderagecoughcough!!"

Annoyed with his blatant hinting, Rouge glared at Knuckles. "Do you need a lozenger for that oh so OBVIOUS cough of yours?" she asked sarcastically.

Knuckles returned her glare. "Oh no, I'm fine. coughcoughjailbaitcoughcough!!!"

With an icy stare, Rouge twitched her wings, then turned away from him. "Allright…Moving…on!" With that said, she posted the final scores of this event are on the marker-board again, and this time, she added nicknames based on their opening outfits.

Sonic (The Philly) had a 5.

Knuckles (Gold Diggah) had a 2.

Tails (Lil Clubbah) had a 9.

Shadow (Gothic Chick Next Door) had an 8.

"What?!!! Knuckles roared. "A 2 again!?!!! This thing must be rigged!"

"No Knuckles, I'm afraid you just happen to fall short of an average score."

Shadow scoffed.

Looking at him, Knuckles snorted. "And you…you didn't win this round either, so we're even."

Without a word, Shadow turned and walked off the stage.

Rouge watched him go, then walked over to Tails. "Well done, Fox-Boy! I knew you had it in you!"

Tails grinned. "Well, like you said, Miss Rouge, I'm just full of surprises!!"

Caught by his way with words again, Rouge tried to give him a straight smile. "Ah…Ahem! And since you won this event, you get to choose the last one in the category. There's only one care left, so, here you go." She stated, handing him the remaining card.

"Just you wait…" Knuckles murmured, eyeing Shadow "This is far from being over! Next time, when it's on my turf, you'll be sorry…!"

"Give it a rest, Knucklehead!" Sonic said, passing by Knuckles and slapping him on the back, causing Knuckles to lose his balance in the heels and fall off the stage.

"DAMN HEELS!!!" he roared.

--

Sigh Poor Knuckles. I like the guy, really, I do. But he's always in the way of odd comical relief. Oh well…He'll get his better luck…next time! And is it me, or does this sound kind of like a "Touge"? I'm surprised myself. Who knew the little Fox-boy would be so innocently alluring…Anyway, I'm a little unsatisfied with the way this came out. Too many ideas came together clashing into one mass. The request was fine. But the collaboration of it, on my part, is what I'm not too thrilled about. Still it was funny, but…a bit too detailed, maybe. Oh well. The next one may be better.

Thanx for tuning in.

-Mel