Of course, let's begin with I don't own Ed, Edd 'n Eddy nor any of the characters, Cartoon Network does I guess. Blah blah blah, onward to what I want to say.

For those of you whom have read my Rocky Road story, I apologize profusely for not updating in too long. Lack of motivation, time, and energy are my excuses for that not being worked on, though I am starting up again on it as you read this. Right! Well, this is someone completely different from that, it's not even in the same gender category. This story will be about the relationship that grows between Kevin and Edd (Double D) after a bet is placed. That's right, two guys, why not? I figured that writing something I don't normally write about would help me start back up.

Also, flamers that don't like this pairing... First of all, I don't know why you would be reading this, but hey, there's a chance. Second! I couldn't really figure out which pair I wanted to go with when I started this fic up, but as it went along, I figured that Kevin and Edd would be a bit more entertaining to do. That doesn't mean Eddy has been left out!

Chapter 1: Bet Your Bottom Ed

It was a beautiful October night in the small town of Peach Creek. The cool breeze of autumn washing away the memories of the heat of summer. The perfectly clear sky twinkled with hundreds of stars and a bright, full moon.

The wonderful night happened to fall on a Saturday, Halloween at that. The young Eds, now seventeen, found themselves walking together across the center of their neighborhood's small cul-de-sac in which they lived towards a very familiar house. Various colors of light flashed on and off within the home, a pulsing bass within.

"I can't believe the others would actually invite us to this costume party." Edd, or known as Double D to everyone who knew him, mumbled placing a hand on his chin.

"Yeah, well, I can't believe you're actually wearing that costume." Came the snide voice of one of his fellow 'Eds', Eddy. The short young man grinned a bit looking to his childhood friend, his sly looking light brown eyes scanning him over. "The kids are gonna start wondering about you."

The tallest of the three, Ed, dressed in a black cat outfit, laughed happily, wrapping his arms around the slim boy's neck. "I think Double D looks pretty!"

Blushing, the boy, dressed as a witch, attempted to extract himself from the rather strong Ed. "I'll have you know Eddy, my mother made this herself for me... Though... I do think she confused wizard with witch..." Looking down to himself, Edd blushed a bit more. The slim cotton cloth of his long purple dress outlined his slim body in the breeze. What he was wearing was essentially a long sleeved dress, a very flattering one at that. The sleeves flared slightly and the collar flared up around his chin. In place of his regular sock-like stocking cap, a witch hat of the same purple color hid his hair from the view of others, a few black strands hanging down at various lengths.

"Yeah, well, I still find it hilarious." Eddy smirked thrusting his hands into his pocket. Having grown up a bit, his slightly overweight form changed to being just a bit overweight, the baby fat now long gone. "And you, mister I-wanted-to-be-cute-and-cuddly!" Thrusting an accusing finger towards the redhead, Ed, Eddy frowned. "I swear, with you two, we're barely likely to get ANY chicks!"

"Sorry Eddy..." Ed mumbled as the neared the house. Edd could only sigh and shake his head.

When they stepped up to the door, Eddy paused a moment, snapping in the air. Behind him, Ed held up a small mirror which the narcissistic young man checked his hair in as well as his fake fangs. He dressed as swank as he could while still following the costume theme of the party. The result left him in a simple black suit with a billowing blouse under it and a long black and red cape, the classic vampire.

"Really Eddy, it's just the kids." Edd huffed, kicking at a small leaf near his foot with one of the black leather ankle boots on his slim legs.

"Yeah but..." Eddy mumbled fixing a few strands of his dark brown hair. "Nazz is gonna be there." His reasoning only made the second tallest of the three sigh in annoyance. "Ready then?" With a nod from the other two young men, he spun around and pressed the doorbell.

The door swung open to reveal the kids of the cul-de-sac all standing around having what seemed to be quite a good time. Before them, a tall young man stood before them dressed as some kind of zombie biker. The very noticeable bright red hair stuck out from under the skull-cap helmet noting him as the neighborhood jock, Kevin.

"Oh, it's you Dorky." The football player smirked. He looked to Ed who was looking inside curiously, then to the figure in the purple that he couldn't quite put his finger on. For a few moments, he looked at Double D curiously. "Double Dweeb?" He asked hesitantly.

The light blue eyes that the little witch owned flicked from the events inside to Kevin. "Salutations Kevin. Thank you for inviting us." The polite young man greeted.

Shaking his head a bit Kevin laughed lightly. "D-Didn't recognize you for a second, dork..." He moved aside as Eddy grumbled a bit at being left outside for far too long.

The two slowly entered the reasonably sized house that Kevin's family owned. All the kids that they've grown up with were there. Ed's sister Sarah, her friend Jimmy, Johnny and Plank, Rolf and all the others. They stood about chatting as music played and lights flashed. Eddy was in his element.

Eddy grinned widely to himself as he began to attempt to schmooze his way into the crowd leaving Edd and his cat clothed friend Ed to move about uncomfortably. Not wanting to simply stand in the doorway all night, the two made their way towards the rather large sprawl of snacks set about the room on several tables.

The Ed dressed as a witch sighed a bit as he watched his chinless friend go off to aid his sister in a few party games. Edd wasn't sure why he always hoped to be invited to these parties along with his two best friends. He assumed it was just because of that, he wanted to be with them and make sure they didn't get into trouble. While he did enjoy the atmosphere, he always felt a little left out, not completely sure of what to do at such events. Instead, he chose to silently watch as he sipped some of the punch he got for himself.

"Hey dork." The deep voice came from beside Edd. He hadn't noticed Kevin walk up to him, he was busy watching Eddy who did his best to mingle with his peers, most of them just laughing along with him.

"K-Kevin!" The slim young man jumped up from his position leaning against the table. He blushed a bit as the table rustled a bit, he free hand straightening out his dress. "W-What is it?"

"C'mere, we're gonna start up a game and we need you in it." The redhead grinned, moving towards the group was motioning for him to follow. Curious, the young man refilled his drink then quickly shuffled to follow after him.

Edd took a spot beside his friend Eddy and sipped his drink a bit. His brilliant mind began to race through the games he knew about that teenagers often played at gatherings like this. As the group settled down into what was more or less a circle, a terrible conclusion played out in his mind.

"Okay guys!" Cheered a young blond girl standing before them. She was dressed as a stereotypical 'sexy-nurse', and she played it well. Nazz had on a tight fitting white dress with all the various accessories one would expect to see with a nurse including a stethoscope around her neck. "We're gonna play Truth or Dare!" A variety of responses came from the group including cheers, groans, and indifferent mumbling.

Saddling up beside the girl, Kevin grinned a bit placing a large glass jar on the coffee table before him. "To make it interesting, there's a twist. If you don't do it, you have to put a dollar in. If you do, we all have to put a dollar in. Truths don't deal with this. At the end, we'll have a very good reason for the jar." Perhaps he was being paranoid, but Edd could almost swear that Kevin looked at him when he said that. "Also, feel free to make bets on if someone will or wont do something." Behind him, Nazz had brought out a large marker board with everyone's name on it, 'will' and 'wont' written beside them.

"Let the games begin!" Nazz cheered.

After several humiliating rounds later, everyone knew far more about each other than they ever wanted, as well as did things they probably wished they didn't. Ed had drank nearly two gallons of gravy, Eddy found himself stripped down to his boxers, and Edd had revealed that under the dress were a simple pair of black boxer-briefs. The others all had their own expressions of guilt, shame, or embarrassment on their faces as well as a feeling of emptiness deep in their wallets. The jar before them overflowed with lost bets and 'coward money'.

Adjusting his witch hat a bit, Edd glanced to Eddy who could be seen figuring out on his head how much money could be in that jar. For a brief moment, the bookworm had to admire the large amount of math going on in the shorter of the two's head.

"Okay okay... I know you're all practically broke now, but we have one more dare to be given out by yours truly, and then we'll reveal the point of the jar." Kevin announced as he spun the lid about on his index finger. "Double D..." The young man snickered looking to the purple clad boy who let out a soft 'eep'. "There is no choice in this... I dare you to show everyone what's under your hat!" A large grin was plastered on the jock's face.

The entire group turned to look at the feminine boy who blushed terribly, turning to look at Ed and Eddy who both simply grinned at him. Bets began to fill the air loudly as the children began to wager the rest of their money. Not a one thought he would.

Edd puffed his cheeks in frustration. He would teach them all a lesson for thinking so little of him! Standing up quickly, the blue eyed boy looked around, eyes trained on him.

"I..." He began, sighing a bit gripping the rim of his pointed hat. "I'll... I'll show you." He mumbled. Audible gasped came from his every side, the sounds of chairs being scooted closer making him close his eyes.

In one swift movement, his hand pulled the hat from his head, another reaching a under the hat to pull something out.

Raven black hair spilled forth from under the royal purple witch's hat, falling past his shoulders to dangle just a little above the middle of his back. It was noticeably thick and strongly unkempt.

As he stood with his hat in one hand and a hair-tie in the other, he could feel his face heating up more and more as a stunned silence filled the air. Slowly, he let one of his eyes open, looking around at the group before him.

"Aw man! There goes all my cash! Thanks a bunch Double D!" Eddy cried in a huff throwing up his hands.

"Double Dweeb! You looked like a girl before, but wow!" Kevin laughed slapping his knee. He was grinning ear to ear in success. It didn't sound mean to Edd, but it made him blush worse, fidgeting with his hat.

"It's so cute!" Sarah squealed hugging Jimmy who nodded in agreement.

"Oh Sarah we must style it for him!" The blond boy giggled in his terribly girly voice.

The black haired boy began to place his hat on his head once more, his long hair still hanging down freely. What was the point of trying to hide it anymore if everyone knew about it? Thus, with that done, Edd began to sit back down, his hands going to smooth out his dress under him out of reflex.

"Wait wait Double D... We have one more thing just for you." The redheaded jock stated putting the cap on the glass jar once the rest of the money was stuffed into the container. Edd gulped lightly as he stopped in mid-sit to stand back up once more. "Everyone, what do you think about Double D in a dress?" Kevin asked leaned back in his chair slightly.

Edd could only look mortified as he looked towards Kevin who simply smiled as he looked about as the positive reactions to the black haired boy's cross dressing.

"Well then. Since we all think that Double D could pass for a girl, here's the deal, dork." Standing up, the taller and stronger boy held up the jar grinning. "If you can dress like a girl for a whole month, you'll get all this money..." Kevin turned to Eddy. "Which is how much Dorky?"

"Almost five-hundred dollars..." Eddy mumbled, nearly drooling.

Nodding, the redhead looked to Edd once more. "Whatcha say?"

"What do I say!?" The long haired by roared as much as he could with his light voice. "You expect me to degrade and humiliate myself for what? Money!?" Edd felt his cheeks heating up in anger, his fists clenched tightly. How dare they insinuate that he should do such a thing? Everyone watched the boy in the dress leave the circle, his half-full cup of punch falling to the floor as he made for the door.

"D-Double D wait a sec!" Eddy called rushing after him. "C'mon Ed!" The boy in the cat suit gave a crumb filled laugh as he ran after them, an armful of cookies and chips.

Grumbling to himself while walking across the street in the center of the cul-de-sac, Edd held the bottom of his dress up to keep from tripping over it as he stomped away furiously. "How dare they? Those... Those... Vitiated imbeciles!" He glared to his right as Eddy caught up to him a placed a hand on his shoulder. "Here to try and talk me into it?" He grumbled.

"...Kinda..." Eddy grinned shyly but squeezed his friend's shoulder as he followed beside him. "But really Double D, you should see it as a compliment." Seeing his friend's rage subside a bit, the dark brown haired smiled a bit. "C'mon... It's only for a month... Really, it's not half as embarrassing as some of the stuff we've been through Sockhead."

Mulling over that statement, the boy in the dress stopped on the sidewalk crossing his arms over his slim chest. "It's true but..."

"We wont ask anything too terrible of you Double D, just to go through with the dare." The short boy watched closely as the thoughts ran over the pretty features of the teenager's face. Eddy had to admit, he did look like a girl in the right light. A sly grin ran over his lips as he concocted an idea. "Listen..." He let his closer hand slowly reach out to hook a few of Edd's fingers making the long haired boy blush and look down quickly. "It'll give you enough money for that new telescope I know you've been eying." Eddy said as sweetly as he could, knowing that talking about science with this androgynous young man was enough to get him fired up to do anything. "Or maybe a bigger ant farm... Or a new microscope?"

Edd puffed his cheeks a bit and looked up from the hand a bit, feeling it being swung back and forth just slightly by the shorter boy.

"I'll do anything you want Sockhead, just name it after this whole thing is done." Eddy promised as he glanced over to the tallest of the three, laying on the grass in one of the yards. "Right Ed?" Only a light gurgle.

"Eddy..." Edd mumbled in a weakening voice. The black haired boy blushed feeling the hand slip from his. "I... I guess I can handle it..." His slim body was gripped tightly by the shorter boy who grinned up at him.

"I knew you could do it buddy! Ed! C'mon you lump!" The brown eyed boy called.

"I don't feel so good Eddy..." Mumbled the redhead in the grass, the armful of snacks long gone.

It seemed the party was still going smoothly when the Eds reentered the small home. No one seemed to pay them much mind as most of them were deep in conversations or dancing to the thumping music. The boy in the purple dress looked around sheepishly with a small blush on his cheeks, doing his best to spot Kevin. Behind him, he listened as Ed mumbling something terribly gurgled as he began half stumbling, half charging towards the bathroom.

"Poor Ed." The black haired boy mumbled as he turned around to look at Eddy who was watching their tall friend sway back and forth as he moved further and further away. Putting his hands to his cheeks, Edd looked to the redhead throwing up within the small bathroom. "M-Maybe I should go see if I can help."

"Oh no you don't! You already said you were gonna go through with the bet! Go find Kevin, I'll deal with Ed." Eddy forcefully stated poking the slim boy's shoulder. He grinned as the long haired boy sighed in defeat and began looking around the children once more.

Walking towards the blond bombshell of the cul-de-sac, Nazz, Edd tapped the girl on the shoulder. "N-Nazz?" He stuttered with a growing blush. The girl turned to look at the boy with her light blue eyes, smiling sweetly.

"Oh hey Double D, glad to see you're back." She greeted turning a bit to face him. "Everything okay?"

Nodding, Edd smiled nervously rubbing the back of his neck. "J-Just fine... Um... I um-"

"Kevin's in the kitchen." The blond simple explained with her ever sweet smile. Edd mumbled his thanks as he turned to the entranceway across the room. Watching him walk away, the slightly older girl grinned a bit turning around to the group placing a finger on her chin in thought, biting her lip lightly.

The sounds of rustling chip bags made the boy dressed as a witch poke his head around the corner. He spotted the tall jock tossing 'Party Sized' bags of snacks from plastic shopping bags onto the counter. Just as he thought he was finished allowing all the blood in his body into his cheeks, he began to blush again as he approached the stronger young man, clearing his throat lightly.

Jumping in surprise, Kevin spun around quickly, ready to say something witty to whomever it was that decided to sneak up on him. The words came to a screeching halt as he looked at the androgynous young man before him, Edd playing with the rim of his hat a bit as he looked to the tiled floor under their feet. Kevin would never say it aloud, but dressed up like that, and with his hair let down, Double D really did look kinda cute... Completely in a platonic way of course though. Puberty seemed to have a strange effect on the effeminate teenager. Instead of making him more chiseled and manly looking, it seemingly made him even more waif-like then he was before.

Noting the silence between the two and Edd's obvious reluctance to begin, the jock grinned a bit crossing his arms. "What is it Double Dweeb?" Kevin asked in a knowing tone, making Edd bite his bottom lip in embarrassment, his soft blue eyes looking around a bit.

"I... I would like... T-To... Accept your dare." The sheepish boy mumbled, trying to pull the witch hat down over his head in order to hide from the stare of the older teenager. His mind mulled over a few things before her looked up at the slightly taller boy who simply grinned, his arms still over his chest. "What must I do?"

"Just wear chick's clothing for a full month." Kevin state as if it was nothing. "If anyone at school hassles you about it, I'll deal with them personally." He grinned at the shocked look from the bookworm.

Sighing a bit, the black haired boy toyed with the flared end of his right sleeve. "At school too?" A light hum from the boy before him making him sigh lightly. "I see..." Looking up, he offered a small smile. "You're sure I don't look like a fool in a dress like this, correct?" Edd asked doing a slight turn around before Kevin.

Geeze dork! You already act like a girl! Kevin thought with a growing grin. "Nah, you look fine." Putting an arm around the boy's shoulder while leading him out of the kitchen, Kevin walked with Edd back to Nazz. "Now, to get you set up with something to wear, you and Nazz are gonna do some shopping tomorrow. As soon as you put on the first outfit, the bet begins."

"This doesn't count?" Edd grinned a bit tugging on the dress' collar.

Kevin and Nazz snickered a bit, the young man in the zombie outfit looking down to the blond girl who was still in her sexy-nurse costume. "No, but I'm pretty sure we need to have you wear something like this when you're the nurse's aid again." The two older teenagers laughed as Edd blushed deeply, looking appalled.

Watching Edd walk off to tell Eddy and a visibly greener Ed the news, Nazz looked up to the jock who watched the slim boy walk off. "If I didn't know any better Kevin, I'd say you're enjoying this already."

The football captain simply smirked a bit watching Edd get flustered over the swaying lump named Ed, the waif boy trying to get him to sit down.

Sorry for the (possibly) many mistakes littered throughout. I just wanted to get this posted before I start on the next chapter. I'll be sure to fix it up a bit later. Reviews greatly appreciated.

Also, I would like to thanks the artist I only know as chidoriashi on Deviantart. A great artist, her pictures of the Eds dressed up for Halloween gave me the idea for how to start out this fic. Go check out the arts!