Summary :: When best friend Ino bets Sasuke is gay during a slumber party Sakura just can't keep herself from taking on the dare. She'll even go so far as to cross dress and engage her childhood friend Naruto for help. After all, he owes the bastard anyway. Will Sakura prove the infamous Uchiha is strait? Or will she be left in the dust? Find out in this high school AU ficiton by yours truly -winks-

..Chapter One..




The room was filled with laughing girls of all the same age. All blissfully enjoying their final days of summer with a last minute sleep over. Next time they saw each other would be first day of school. Their final year and their first as seniors. And today they were ignorant to all the drama that came along with the final days of freedom. Excitement bustled about the room. Pillows were thrown and secrets shared.

It was large and adorned with all the colors of a fully hormonal teenage girl. Gone were the trappings of childhood and ever present were the colors of adulthood on the brink. It was a large room by many standards. Money did that to a girl. She wasn't what some might call rich by all that was holy. But she did lead a comfortable life. As comfortable as one could be with their parents always away on business.

"Ow! Cut it out, Yamanaka!" A girl with brown tresses cried out in laughter. Said girl picked up a pillow and thew it a the offender known known as Yamanaka.

"What are you gonna do about it, huh, Tenten?" She snickered and dodged the pillow swiped near her head with a giggle. In an instant she was running for her life around a couch.

"Oh, I dunno, maybe I'll call Choji and tell him you plan on dumping him for the infamous Sasuke Uchiha."

Ino's jaw dropped and she made a very unlady like noise. "You wouldn't dare!" When she said nothing she ran after the girl with her pillow, fully intent on making her pay for such a crime!

"Oi!" Cried a pink haired girl from her seat a the couch. "Relax, Ino. It's not like she would actually do it. She doesn't even have his phone number."

Ino stuck her tongue out at Sakura. "You're just saying that because you like him."

Sakura rolled her eyes and stood up. "Like a jerk? Psh... he's too stuck up for my tastes. I'd never date him. Even if he didn't go to that private boys school."

"You mean he wouldn't go out with you." She grinned and dropped the pillow on Sakura's bed as she flopped on to her stomach next to the cushy item. "He never dates."

Tenten laughed and joined her on the bed. "You mean he doesn't date women."

Hinata, who was quietly sitting on the couch walked over and joined her friends on the bed. "You actually believe those rumors? I hear he only dates college girls."

"Yeah right." Ino rolled her eyes and tossed back her long strands of perfect blond. "Don't you know all the unbelievably hot guys are gay? I heard he was dating that blond friend of his. What's his name?" She looked over at Sakura who was, at the moment digging through her mini fridge for a soda. "You know him don't you?"

"Know who?" She popped the top on her drink and took a sip.

"The blond bimbo who always hangs out with Sasuke like he'd glued to his hip? The soccer star."

"Ah," Sakura mused and sat down on the bed with her friends. "That's be Naruto Namikaze. And no, he's not gay. He's just super picky about his women." She took another sip.

"See," Hinata defended. "They're not gay."

"She said Naruto wasn't gay. That doesn't Sasuke isn't."

"I agree with Hinata." Sakura wrinkled her nose. "He doesn't date women or men. Just because he avoids his fan base like the plague and goes to a private boys school does not make him gay."

Ino pouted. "I say we find out."

Tenten blinked. "How are you going to do that?"

"Yeah," Sakura chuckled. "He wouldn't touch you with a ten foot pole."

"And Choji would get pissed," commented Hinata.

Ino stuck her tongue out at Sakura. "You're such a smart ass. You don't think he's gay but you don't want to help me either."

"No," Sakura scoffed, "I just think you're wasting your time worrying about it. He goes to an elite school that keeps him busier than hell. I know because I barely see Naruto. Even if we thought up a way to find out we'd never get the chance to put the plan in motion."

Hinata nodded. "See Ino? You're just being silly. It's was a fun idea though."

Ino was still pouting and thinking.

"Get over it Ino. He'd never go for any of the chicks you sent his direction to find out anyway." Sakura got up and walked towards the mini fridge. She tossed her empty can in the trash and grabbed another.

"Oh? And you think you could do better?" She challenged.

"Uh oh..." Tenten muttered and moved in close to Hinata. "I think I feel something bad coming on."

"Like that time Ino dared Sakura to burn her bra from the top of the high school and shout out that she would not longer be repressed by the binds of men?"

"Eh..." Tenten started... "Yeah. I thought we agreed to never talk about that again?"

Hinata shrugged. "You asked."

"Of course I can," Sakura was replying. "I'm just not going to be roped into your stupid schemes."

"Yeah," Ino grinned, "But we all know how you can't say no to any of my dares."

Sakura grunted and placed a hand on her hip. "Put your money where your mouth is, Yamanaka. I so enjoy taking it from you."

"Fine, I bet you that you that Sasuke Uchiha is gay."

Sakura arched a brow. "How do you expect me to prove that?"

"You can make out with him public. I'd say sleep with him and video tape it but I'm not into porn." She smirked at her. "He has to like it. We have to know he wants you. He has to be all over you. Practically sleeping with you in front of people."

Sakura wrinkled her nose. "Fine, what's on the line here?"

"Hm..." Ino thought for a moment and moved to lay back against the head board. "If I win and he is gay... you have to..." She grinned evilly. "Flash the entire student body on graduation day."

Sakura rolled her eyes. "Kid stuff. I'd do that anyway."

Ino pouted. "Then you think of something then."

"Fine, I will." And so she went about pondering the worst thing possible that could be done to herself. Not the most horrifying, but definitely the most embarrassing. "I'll take Lee out for a date."

Tenten wrinkled her nose. "Oh... that is bad."

"Ok," Ino grinned. "What do you want me to do if you win?"

She smirked. "On prom you have to dress up like your favorite Sailor Senshi for the first thirty minutes."

Ino groaned. "Oh hate you. Fine, but I won't lose. You can count you date as good as done."

"Um, guys," Hinata waved her hand. "Just how are you two going to do this?"

"Yeah," Tenten added, "and what are going to do if Sasuke is bi?"


"Never thought of that." Sakura said. "Well, I guess the bet would be null and void."

Ino made a face. "Yeah, well, that won't happen because I know he's gay. And Haruno is going to lose."

"Say that when you win, Yamanaka." She smiled despite this. "So, any ideas as to how we plan on pulling this off?"

"Hm.. I want something to snack on. How about we order pizza and talk about it then?" Tenten jumped off the bed.

"Agreed," Hinata called out.

"Yeah, and maybe Haruno can flash the pizza guy." Ino laughed as she followed after the two girls.

Sakura just rolled her eyes and smiled. Ino could be such a dare devil. Most times she only lived vicariously through Sakura though. She could never turn down one of Ino's dares. It had always been fun as kids. When her parents had been around more often she'd put them through hell with the blond. Both would egg the other on. Ino would start in with some snide comment and then Sakura would charge right back with something equally snide. And then Ino would dare her into doing it. More often than naught Sakura won. But, lately Ino had been winning a few. The last one Ino lost was the bra incident. Ino never thought she'd do it.

"Hey! I ordered the pizza already. You got the cash, girl?" This from Tenten.

Sakura nodded and pulled a wad of twenties out of her pajama shorts. "How much?"

"Just thirty."

She handed her two twenties. "Let the driver keep the change."

Hinata plopped down at the island counter next to Ino while Tenten and Sakura went about talking. It was just thirty minutes later and they had their pizza.

"Jeeze, Haruno, I wasn't serious about flashing him."

Sakura grinned as she reached for a slice. "Yeah, I know. But the look on his face was priceless. I probably made his night."

"Or gave him a boner for the rest of the evening." Tenten scoffed. She was smiling though.

"So," Ino started after her first few bites, "I have a plan."

"About Sasuke?" Hinata inquired and bit into her slice for the fourth time.


"Lay it out," Sakura said and took a sip of her drink.

Ino grinned. "You're not going to finish school at Suna this year."

"I'm not?" Sakura arched a brow.

"Nope." Her grin got wider. "You're going to go to Konoha this year."

Sakura frowned and set down her can. "I don't know if you haven't noticed yet or not... But, I'm still a girl. At least I was the last time I checked. It's an all boys prep school. Regardless of my grades they won't let me in."

Ino waved her hand dismissively. "I know that. That's why you're going to go as a guy."

"What kinda crack are you on, Ino?" Tenten looked at her like she'd grown a third eye.

"Don't look at me that way." The blond shot her a glare. "If Sakura dresses up like a guy and enrolls she can close to Sasuke. It's the only way."

"Hm..." Sakura mused. "Ok, let's say I go along with this. And we know I will because I don't have much of a choice it seems. How am I going to get in? Where are the false documents going to come from?"

Ino smirked and turned her blue eyes back on Sakura. "Oh that's simple. I just happen to know a guy can get you some made up real quick. Authentic too. All you have to do it convince Naruto to help you out."

Sakura sighed and placed her pizza down on her paper towel. "You want me to bring Naruto in on this? That's kinda risky, yeah?"

Ino shrugged. "He's his best friend. And from what I hear he's been looking for a way to get him back for that incident last year."

Sakura frowned. True... from what the blond had told her Sasuke had accidentally given his number out to some random girl at a party. Sasuke had been wasted at the time and didn't think too much about it. But the girl had turned into a major stalker and would not stop calling Naruto. It wasn't until he changed his number that she heard the end of it.

"Sounds good enough. I'll give him a call tomorrow and we can start setting things up."

Hinata frowned. "I still think this is a bad idea, guys."

"Yeah," Tenten grinned and at her. "But won't it be fun to watch it blow up in their faces?"

Both the pinkette and the blond glared at her.

"It's not going to blow up for me when forehead loses."

"Try saying that to me when you lose, pig."

Hinata smiled slightly and blushed a bit. "Guys..."

And then everyone was laughing a smiling. All three girls could think about was how interesting this year was going to turn out for them. Would the infamous Sasuke Uchiha turn out to be gay? Would Ino win the bet? Or would Sakura make him fall despairingly into her sexy clutches?


"I still don't see how me dressing up as a guy is going to prove he's not ga.y Actually," Sakura said as they rounded the corner towards the salon. "This kinda works more in your favor than mine."

Ino rolled her eyes. "Hey, if he fucks you after he find out your a girl then you know he's not gay."

"How are you going to know I'm going to be honest with you about it?"

Ino made a face. "You've never lied to me before. Why would you start now?"

Sakura sighed. "True... I should still get some kind of evidence though."

Ino shrugged. "I guess." She pondered for a while. "Bring the used condom as evidence."

Sakura wrinkled her nose. "You're sick."

"You're the one wanting proof. I say that's proof enough."

Sakura grumbled. "So now I have to fuck the guy? What happened to just kissing him?"

"If he kissed you while you're a guy then it's pretty much proven he's gay or bi. But, if he goes further and you guys actually have sex? Then we know he's not into men."

Sakura sighed long and hard as she opened the glass door to the hair dresser. "I'm sure I won't even enjoy it. Stuck up guys like him are only after making themselves happy. He's probably a total prick."

Ino walked past her as she held the door open for her. "Naruto doesn't talk to you about him?"

She shrugged. "Sometimes." She nodded to the stylist. "I need it all cut off today, Mercedes."

"All of it?" The man behind the counter gaped her her, his mouth hung open. "But, cheri...! You're hair is lovely! Why would you cut it?!" His French accent was thickly laid in.

Sakura smiled wryly. "Don't ask. It's for a bet with the pig here."

Mercedes frowned and tisked a few times. Aside from that he said nothing more. He knew all about the girls bets with one another. Although until today one of them never involved cutting off his most prized customer's hair.

"Very well, cheri. Go sit yourself at my chair and I'll see what I can do with it."

"I need it as masculine as possible."

His eyes bugged out of his head. "Are you trying to kill me, blossom?"

Sakura laughed. "No, not at all, luv. This is important. I promise." She reached out and pat his hand a few times to try and sooth his horrified nerves.

He sighed and gave in. "Very well, do you have anything in mind?"

"Not at all. You work your magic on me, hun." She spread her hands wide and took a model's pose. "I am your canvas, do with me as you please." She smiled.

He scoffed. "Now you're just trying to suck up to me, cheri."

"Perhaps," she replied with a grin and moved to the chair offered. She kept that same smile as he got to work on her. Through the entire process she sat patiently and waited. He jerked her head left and right. Sometimes he pulled it back and sprayed on more water to cut more strands. She watched as bits of wet pink clippings fluttered to the floor like a rain of hair. He went about blow drying her it and then some gel was slicked through. In the end she looked slightly aristocratic. The back had a little length to it and so did the front. Long bangs that reached her nose fell freely in her eyes. The rest of it was a short bed head mess. In truth she almost looked nothing like man. She imagined with her breasts bound she'd look more androgynous than anything else.

"Good, you're work is flawless as always, Mercedes."

He gushed. "Thank you, cheri. You are a rose among women."

"Feh," she got up and tossed the hair dressers cover off of her. She handed it to him. "Now you're sucking up to me."

"Perhaps," he allowed with a smile as she paid for the hair cut.

An hour later she was waving goodby to Ino. She'd love to hang out more with the girl but she had to meet Naruto at the mall. Because really? She didn't trust her blond best friend to pick out her clothes. Not that she was going to let Naruto do it all. I mean who would with a guy who had orange stuck to his wardrobe like it was his own personal banner?

And well... she had yet to tell him of her little plan. She certainly didn't want Ino around to goad her in front of him. Hoooo... would he be shocked? Probably. But not entirely surprised. He'd known about her pranks before and the level she'd go to win. But... would he play along with her and help her out with Sasuke?


"What did you do to you hair?!"

She winced and joined him at the small cafe table just outside of Borders. "Yeah, well, that's why I called you here."

The blond haired blue eyed teenager stared blankly at her. He could be so adorable sometimes. Really. Especially with those tight jeans that hugged him in all the right places and the gray shirt that showed off his defined upper form. If she hadn't been such a good friend to him as a kid and didn't look up to him like a brother... and well if she didn't know Hinata had a thing for the guy she'd probably be practically married to him already. Her parents loved him and vise versa. He already had a scholarship to UNLV (University of Nevada Las Vegas), one of the best schools in the country for soccer. He wasn't always the brightest crayon in the box, but he did have brains despite his dimwitted moments of stupidity about what was going on around him.

Right now being a prime example as she explained the whole plan to him. The blank expression never left his face. In face, it got worse if you could believe it.

"So, are you going to help me?"

He blinked a few times. "Huh... " Another blink. "You know, Sakura, you've done some pretty strange stuff in your day with Ino... but this has got to top the charts." He grinned. "Of course I'll help you. It'll be fun to put that bastard in his place."

She grinned back. "I was hoping you'd say that. I need you to help me pick out clothes today. I know the school isn't uniformed."

He shook his head. "Nah, it's not. How are you getting in though?"

"Ino's got a guy who's going to falsify some documents for me. I should have them by tomorrow since school starts the day after on Monday."

"Cool beans." He stood up and dropped some cash on the table with the ticket for their meal. "Well, let's get going then. Any particular style you looking for?"

She shrugged and walked with him. "Anything that'll make him want me I guess."

Naruto laughed. "I hate to say this, but even I don't have a clue. I'm not even sure if he's strait myself."

She arched a brow and adjusted the purse on her shoulder. "Really? Did he ever make a move on you or make a comment about gay men?"

He shook his head. "Nah. I mean, I know we're close and all. But, Sasuke has always been pretty withdrawn. He's never even dated any of the girls in his little group of fans. He's never invited one to the school on holidays. I've not seen him dance with one of them before either at the dances our school host now and then."

She pouted. This could be a problem if his best friend didn't have a clue. She had been hoping Naruto could give her some insight. "Don't you guys talk about women?"

He shook his head again and stuck his hands into his pockets. "I do but all he ever says about them is how annoying they are. If he has ever had a relationship he doesn't tell anyone. But hey?" He grinned. "Who knows what that bastard does during the summer. He's never around then. For all I know he could off with a hot model from his brother's company."

She grumbled. Well, it was better than knowing he was gay. At least if she didn't know for sure she still had half a chance, right?

"Thanks anyway, Naruto."

"No problem, hun." He pointed to a shop. "Let's go in there. The shop owner is a friend of mine. Alright?"

"Sure." She nodded with a smile.

"Oi!" Naruto called to the man behind the counter. His had a bright white mane of hair that cascaded down his shoulders and over the leather vest tapering down from there. His lips twitched as he spotted Naruto. "Old man! I need you to close the shop up for about an hour."

"Oh!" Gasped Sakura. "You don't have to do--"

"What the hell do you want, mut?" The older male grunted with a grin.

Naruto beamed. "I've got the story of a lifetime for you. If you wan it you'll close the shop up for me." He leaned on the counter and all but ignored Sakura.

The 'old man' arched a brow. "Oh? I can write about it then?" He frowned. "Is it that good?"

Naruto nodded. "You bet, Jiraiya." He motioned to Sakura. "This is your story."

Sakura blinked. "Can someone please explain to me what the hell is going on?"

Naruto chuckled sheepishly at her. "Sorry, hun. This here is Jiraiya. He's my uncle and a writer. He runs the shop but his real passion is being a novelist. I want him to write your story in exchange of giving us a private shopping experience. You don't mind do you?"

She blinked a few times and looked over at Jiraiya. She wasn't sure if she should be upset or honored that Naruto had tried to rope her into being the star in a book. "What kind of book?"

Jiraiya grinned at her and waggled his brows. "Romance. What else?"

"Ah," she smiled. "I guess it's alright then."

"Give me the low down, Naruto and I'll think about it, eh?"

So he did. With some help from Sakura he laid out the whole idea for the old perv.

"Hm," he rubbed his chin and thought. "Sounds good. I love the idea. You'll have to keep updated, ok?" He glanced over at Sakura.

She smiled. "Sure."

"Alright, well I go ahead and close the shop up and you can look around till you're ready to check out. Hey, Naruto."

"Hm?" He turned his eyes on Jiraiya.

"I got that new book for Kakashi. Can you pass it on to him for me? Plus I need to ask your opinion about the next installment."

"Sure." He looked over at Sakura. "You go on ahead. When you're ready to try some stuff on let me know and I'll come look."

"Ok," she smiled and dashed off by herself as the two men locked up and chatted. The store was enormous. She had to wonder what he paid in rent. Although, if he was a writer... well... he could probably afford it, right? She heard the 'Come! Come!' series sold billions of copies world wide. Not just in the US.

She began flipping through the clothes in her size. There were so many styles in the shop. Some of it was punk, some of it was very preppy and others still seemed really goth. She frowned. As a woman she had a distinct style all her own. Much of it was very girly tomboyish. Lots of tank tops, shorts, mini skirts, sneakers and mid drift tops. It couldn't be helped. She was a sporty girl. One of her biggest hobbies was extreme sports like motocross or skateboarding. Her personal passion was gymnastics. She grinned. Last year a scout had come to her private trainer's building at Tsunade's request. After high school she had a scholarship to a Asa University in her hometown. It was a prized school that focused on extreme sports... but most of all gymnastics. It had started off as strictly a camp many years ago. But after a man named Iruka had taken it over he'd turned the place upside down and inside out. It was just her type of school.

Hm... now back to style... what could she go for? She was creating a whole new personality here. All Ino was getting for her was a name and personal documents to legitimize who she was for the school officials.

She frowned and flipped through some shirts. She supposed she could just go for a more manly version of herself. Very surfer punk. She grinned and grabbed some outfits. If she tried changing herself too much the whole thing might blow up in face.

Very well.

An hour later and pile of clothes after that she had picked out her selections. With a sharp grin she showed Naruto her choices, plus the one she was wearing.

Naruto whistled at her. "Wow, did you bind your breasts?"

She nodded. "I brought the wraps in my bag with me. I had to get the right feel for the clothes as a guy. Look good?" She turned around in the loose but tight fitting jeans. Her top was a simple blue Henley with long sleeves that fit her form just enough to make her look boyish without really hinting at her bindings. "It's a good thing I'm mostly flat chested, eh?"

Naruto grinned. "I can't tell the difference. You're voice is pretty even too. I'd have to take a double take on you if I didn't know you better. Hell, if I weren't strait I'd got for you, sexy." He waggled his brows.

Sakura punched him in the arm with a grin. "You're hopeless."

He stuck his tongue out at her. "Yeah, but you love me anyway."

"Yeah, yeah, let's get out of here. I have entire wardrobe now."

He nodded as she stepped up the counter hand handed Jiraiya he pile of clothes and tags for the outfit she was wearing.

"You going in that?"

She nodded. "Yeah, I need to get use to the part if I plan on winning this thing."

Jiraiya grinned as he rung up the items. "Pretty serious about this aren't you?"

"Oh yeah." She nodded. "That pig is going down. She has no idea what she's gotten herself into."

"Ho...ho... remind me never to get on your bad side, pinky."

She smirked. "You don't want to. Trust me."

As Naruto and Sakura headed out of the now reopened shop with bags in hand he turned to look at her and asked. "You bought a wallet, right?"

She shook her head. "I don't need to. I have one at home already." She smiled and tossed back a few errant strands in her eyes. "My dad bought it for me during a tournament a few years back. When you've got a lot of people running around one place for the same thing it's best to travel light with your money."

"True enough..." He blinked as he stared strait ahead. "Say, how do you feel about testing our your new disguise?"

She arched a brow at him. "I guess it could be fun. Why?"

"Because," he pointed, "your target is coming right for us."

Sakura jerked her head in the direction of his finger. Sure enough, Sasuke Uchiha was walking down the long mall corridor and intently heading towards them. "What is he doing here?" She hissed.

He grimaced. "I told him I would meet him around this time at Gamestop. I completely forgot about it. And well, I didn't plan on you dumping this on me today when I invited him."

She frowned. "It doesn't matter." Shes stuffed her purse into a shopping bag with clumsy haste. "If he doesn't buy it now then there's no point in doing this at all. We'll call it a test, ok?"

He nodded. "What should I say your name is?"

Ah shit, she hadn't thought of that. Whatever name they chose was bound to be different from the one Ino got for her. "We'll just go with a nickname. I'll be..." she furrowed her brow in quick thought as the ebony haired senior got close to them. "Vince."


She grunted. "We'll say it's something you made up for me as a kid. Because..." she fought for thought. "...Because I loved Vincent from Final Fantasy Seven when we played together."

"I guess that's party true..." he murmured.

"Shut up and go with it, you idiot." She glared.

"Fine," he hissed back. "Get ready because here he comes."


AN: Ok, I have the be asking for the biggest ass kicking in the world to start another story. What is that, five now? Jeeze. And one of them is on hold for lack of ideas. I must be a glutton for punishment. I really couldn't help it though. I mean, this idea just flashed in my mind and I HAD to do it. I love cross dressing anyway. And how fun is this? I hope you liked it. Review please! -grins-