10/8/15 Edit: I'm going to be uploading this to ao3. When ao3 gets updated, this will also be updated in terms of the chapters being edited. When I get to where I left off, it'll continue!

Loosely based on "She's the Man."

Also inspired by the fact that Cloud cross-dressed in his game and was able to fool people.

"He's the Gal!"

by ShadowYin-Yang

(You are NOT authorized to copy and paste a.k.a steal my work. You are NOT authorized to copy and paste with a few changes here and there either. If caught, you will get no mercy.)

"Everything happens for a reason."

Tell that to all those who never got a chance to live out their lives…

Or to the lion who got left behind…

Not to mention the poor bird trapped against their will…

No, things are never fair in life.

However, every now and then, people can get lucky.

Is it bad if happiness can be obtained through sheer luck?

Well, things are never fair after all.

Yet people seem to forget that luck is a factor that is dependent on every single person's decision throughout their life.

-.-.-.-.-.-.-.-.-.-.-.-.-.-

With one swift movement of his arms, Cloud Strife swung his wooden sword upwards and knocked another sword out of its owner's hands. The weapon landed right into the grass of their backyard with a light bounce followed by a light cry of pain.

"Aaaah! Are you trying to kill me?! You could've slashed me!"

The taller one of the two sighed before waving his weapon slightly.

"You'd live," he stated, still waving the weapon, trying to emphasize the wooden part of their weapons. He lowered the item and glared slightly at the younger blond who held his hand as if he really was injured.

"Also, I'm more careful than that anyway. You have to pay more attention! You need to focus and face your fear!" The man only received a glare in response from the teenage boy.

"You do realize that you guys forcing me to use swords doesn't help my self-esteem…"

Cloud sighed again and shook his head, not able to really argue against something like that.

"You liked it when we were younger," Cloud said, not to guilt the boy but merely worry at the disinterest on top of other growing changes the young one have been displaying in recent years.

"Yeah! Until Roxas surpassed me! I'll never catch up!"

"It's not about catching up…it's about self-improvement…" Cloud responded and placed a hand on the boy's shoulder as he knelt down, "I apologize, Ventus, if we really are hurting your self-esteem. We want you to have confidence, not the other way around."

Yeah…not really great news to find out you're killing your own brother's self-esteem right before he's getting sent off to high school…

Not to mention the boy constantly giving you those big puffy blue eyes of sadness is a great way to guilt-trip anyone.

The younger blond eventually nodded in understanding as he stared at the ground and let his arms fall to his side,

"I'm sorry…but…Roxas is a jerk to me! And…we're all separating soon, right Big Brother? Aren't you leaving the house too…? Who's going to protect me from him and Sis?"

"Well I don't know…I haven't actually decided what college to go to," he responded and pulled the boy close as he stood up. They started to walk back into their house, Cloud tossing his weapon close to Ven's from earlier, "But I may take a year break, who knows? And this is why you need more confidence. Don't let your brother bully you!"

Even after 18 years of being alive and living…what? 90% of of those years with his younger brothers, he never understood how the older twin brother of Roxas is at the bottom of the food chain of his own family. He thought he was doing a great job at being a protective older brother…but apparently he wasn't good enough if this boy right here has such insecurities and entering one of the brutal parts of life for an ever growing boy.

Though before anything further could be said about it, two bright colored travel bags fell from the sky without warning, hitting both of them with a thud. What the hell was even in one of the bags (bricks?) that made it hurt so much?

"Whoops! Sorry guys!" Cloud groaned as he felt his head. He was surprised he didn't fall over…which couldn't be said for his younger brother who was lying under a pink bag.

"Ventus! Ven! Are you okay?" Cloud removed the bag off the boy and helped him into a sitting position,

"Ow…what happened?"

"Sorry guys!" the voice repeated and Cloud finally looked up to see a blonde ponytail dance energetically as Rikku waved with her whole arm from her window.

"Oh great, what is she up to…?"

-.-.-.-.-.-.-.-.-.-.-.-.-.-

Upon entering Rikku's room, Cloud finds her and Roxas trying to shove a whole luggage through the window. Now normally, these things aren't that abnormal. Especially since Rikku always seems to be getting in trouble and Roxas is the perfect sidekick for trouble. Although from what's being thrown outside, Cloud couldn't help but think they were running away from home if he didn't know better…which wasn't much…

"What the hell are you two doing?" he asked bluntly just as the luggage went flying out the window.

"Oh! Well…I was hoping you and Ven were done so…uh…" Rikku only gave a smile without fully answering. So Cloud turned to Roxas who used to his hands to show him zipping his mouth and turning the key. Ven peered in behind Cloud a moment later,

"Are you going somewhere, Sis?" he asked innocently.

"Oh Ven…you're so CUTE!" she nearly squealed, which was almost a daily thing with her. Roxas gave a huff and looked away, at anything in the room but his siblings, as never understood why she only called Ven cute when himself and Ven are identical,

"Okay, okay, I'll tell you!" Rikku ended up exclaiming in excitement. Roxas let out a groan and face-palmed. He knew shoving things out the window was a stupid idea. Especially since even he knew Ven was so accident-prone that he wasn't even surprised Ven got hit. The worst part was still how easily Rikku caved; all that secrecy from the past week for nothing.

"Okay so…promise you won't tell Mom and Dad!" Rikku pleaded.

"Okay!" Ven immediately agreed and stepped in front of Cloud while Cloud just folded his arms in response. He hated being the responsible one around here and constantly debating if something is 'report worthy.'

"Fine…" Cloud muttered in response.

"Well see: Yuna, Paine, and I got this great gig!" Rikku gave a light jump, trying to restrain a squeal, "We're gonna perform at a Blitzball tournament!"

"Awesome, Sis!" Ven congratulated.

"…" Cloud only gave her a raised brow in response.

"And…it's all the way down at Destiny Islands!"

"Do I even want to know when this is taking place?" Cloud immediately asked after the revelation of the location. Rikku just grinned again, attempting the innocence she couldn't capture as well as Ven could.

"Next week!" she replied cheerfully.

"…And what are you going to do about school? That I should remind you is starting next week and you're supposed to watch over Roxas and Ven on their first year there."

"That's why I had Roxy help cover for me! I'm going to be out with the pneumonia! And as far as Dad's concerned, I'm supposed to be at Mom's place. And come on, Bro! They can take care of themselves!"

"…And when will you be back?"

Rikku held up two fingers,

"2 weeks max! Maybe. You won't tell, will you, Bro?"

"Rikku…I…"

"She's on her last year of high school," Roxas finally spoke, "I'm sure she'll catch up on her school work when she gets back."

"Ugh…alright, fine, but just this once!" Cloud was officially an adult now…he didn't want to stuck being babysitter. That job officially got passed on to Rikku. Yet here she is…taking off…

"Yay! Thank you, Bro!" Rikku cheered and gave the man an unsuspected hug. As soon as it was over, Rikku started to climb out the window, "I love you guys! Be good and root for your only sister! Oh! I wasn't supposed to be here so don't mention you saw me!"

"Well that explains why she's leaving through the window...she probably had to pack last minute as usual..." Cloud thought, the very idea of letting her get away with this was eating the growing urge that he should be putting his foot down.

"I love you, Sis!" Ven waved,

"Be careful!" Roxas added as they crowded around the window.

"Don't let anyone take advantage of you!" Cloud practically ordered, "Kick any guy's ass if they touch you!"

"Yeah, yeah, I know! You know I will!" Rikku replied when she got to the ground. She waved once more before she gathered her things and left.

As Cloud watched her leave, it only reminded him on how little he's done in his life. Rikku seemed to know: perform with Yuna and Paine. Plus, Rikku joined clubs and did many school activities in which Cloud just simply avoided them. Sometimes he wished he did do something in school besides get in trouble for beating up those that picked on his younger sister…although it didn't take long for her to start beating people up herself…

That was besides the point. What did he even do in school that wasn't just studying? After all…isn't school the only time one can date in the most innocent way possible and then go to tame dances? Not that Cloud really knew for sure...and probably will never know. Now Cloud lightly hit himself for even thinking that as he hated dancing. Well, with how dependent Ventus has always been on him, and how Roxas did look up to him, maybe he'll get to know the high school life for a boy after all. It's not like either really fell short on telling him various aspects of their lives. Plus it's with two very different people going through it. It should be interesting if anything. At least Cloud hoped it would, for the pair's sake more than his own.

-.-.-.-.-.-.-.-.-.-.-.-.-.-

"Big Bro!" Roxas called and Cloud paused in his walk towards the kitchen. It's been a day since Rikku left and the day was just as normal as it's always been but just minus Rikku. Which meant fights between Roxas and Ventus happens and Cloud doesn't have back up this time...

"What is it, Roxas?"

"Phone! Your girlfriends!" Cloud strolled over to Roxas and took the house phone, ignoring the 'girlfriends' comment.

"Yeah?"

"Hey Cloud, it's Aerith."

"And Tifa! We're on speaker!"

"Er, hi guys, something I can help you with?" he resisted the urge to groan as he leaned against the wall.

"Yes!" they both responded at once, loud enough that Cloud pulled the phone from his ear for a second.

"Rikku is supposed to be our third roommate!" Tifa exclaimed, "But she has taken off…" Aerith added with a hint of sadness.

"Rikku has to be present when we get our rooms or we can't get a room for 3!" Tifa exclaimed.

"...And? What do you want me to do about it exactly?" Cloud asked, not sure how Rikku's absence involved him in any way. It took only a moment's pause for his little friend-being-evil-radar went off as he could just imagine smiles spreading across the girls' lips at that moment…

"Cloud, remember our junior high school's play?" Aerith asked as casually as possible. And as Roxas stood there, waiting to have the phone back, he didn't expect that he'll get to hear Cloud say so much at once, and with a louder voice. Not to say Cloud doesn't speak often or get upset, but it's not like he usually has to say more than what he needs and he doesn't often have to re-emphasize...

"Not over my dead body! I will never again, in a million years, EVER, do it! Not again! Never! Ever! Ever! And that's final!"

-.-.-.-.-.-.-.-.-.-.-.-.-.-

"I hate all of you…" Cloud murmured as he sat in his room with his arms crossed and unable to budge in the chair he was placed in.

"Well, you're not straight right? So accept your inner flamboyant-ness?" Tifa shrugged as she was finished up taping around Cloud's waist to the chair with duck tape. With the legs already taped down, that should be all, and she tossed the roll to the corner of the room after she was done.

"That has virtually no correlation…" Cloud stated. He knew he should've just struggled with his life when the two showed up at the door…but the moment he gave up, Tifa had him down and now he just gave in. Oh where has his willpower gone?

"Now, now, Cloud, we just need you to be there for a day. Two days at most. Then you can go back to deciding what to do with your life now that you're out of high school," said Aerith with a smile and she kept that smile as she held up a wig with braids, "Now let's see if this still fits you."

"Promise me I'll have less make-up this time, no lipstick, and one cup smaller," Cloud requested as he pointed. That lipstick was disgusting last time and he was pissed at himself for even letting the girls decide his fake-breast size.

"Hmm…okay but only if we can dress you up! And we can lighten make-up on everything but your eyes!" Tifa suggested instead.

"No!"

"What if we promise to stay in your comfort zone for the clothes and we just want to make your beautiful eyes stand out," Aerith added.

"You're already forcing me out of my comfort zone!" Cloud argued, "But it's a maybe on the make-up."

"You can wear leather…boy that's an odd image: 'Rikku' in leather…" Tifa murmured the second part.

"…Deal," Cloud muttered and sat back, waiting for the torture to begin.

-.-.-.-.-.-.-.-.-.-.-.-.-.-

"Big Brother! Save me!" Ven cried as he ran through the hallway and opened Cloud's door as he ran in.

"Get back here now so I can pound you into the ground!" Roxas shouted as he chased his twin. Upon running into Cloud's room, he crashed into Ven who suddenly stopped and the two tumbled to the ground. When the two looked up, they had the most…well they couldn't think of a word for the image before them.

"Gah! Get out you twerps!" Cloud shouted and was about to stand up and cover himself if he wasn't taped down to the chair that was taped to the wooden floor, "Why the hell didn't you two lock the door?!" he shouted at the two young women.

"We thought the two had better things to do then bother you," Tifa answered with a shrug before she held out the eyeliner, "Now hold still!"

"Hell no! Get those two out now!" Cloud pointed to his younger brothers. Cloud still held one of his arms over his near-bare chest, as Aerith was trying to stuff his bra with pudding-filled balloons. But this was still enough time for the twins to stare and continue staring at the eldest child of the family grew two long braids hanging over his shoulders...

The pair didn't move as they stayed on the ground while they continued to look as if Cloud himself just hypnotized them. Ven was the first to speak and move.

"You look really pretty, Big Brother!" he said with a smile and giggle. He started to stand up and walked closer to the now-red-faced-Cloud, "What are you dressed up for?"

"Oh just a favor," Aerith replied a smile, "Now Cloud, hold still so I can put these in," she shook one of the balloons to indicate her point.

Roxas got on his knees as he continued staring, still trying to wrap his head around this. After about a minute of registering the sight before him, and because he needs to play his role as the 'brat' as he's so often called, he pulled out his phone and snapped a picture.

"ROXAS!" Cloud shouted while Roxas scrambled to his feet to escape, but nearly choked when Tifa grabbed him by the collar when he ran by.

"I'll give you 20 bucks to delete the picture," she offered and Roxas looked up in thought,

"I don't know…this is great blackmail material," he said with a smirk.

"50," Tifa offered again before leaning in to his ear, "And I'll personally make sure I dress up your twin too later."

"Okay!"

Cloud's hand met his face again, not believe what was happening.

"Will you be in a dress, Big Brother? Can I see when you do?" Ven asked excitedly, "Will you wear lipstick? Oh! Are you FINALLY going on a date after all these years?"

"VEN! ROXAS! GET OUT! NOW!"

-.-.-.-.-.-.-.-.-.-.-.-.-.-

"I can't believe he kicked us out…" Ventus pouted as the two sat outside the bedroom since they both want to see the finished results.

"I can. He always kicks us out…well this time Tifa did since he couldn't move," Roxas stated, "Oh yeah, I'm still mad at you for deleting my game file," Roxas announced and without warning, punched Ventus in the arm.

"OW! That hurts! You jerk!" and in turn, Ventus shoved Roxas.

"You shove like a five year-old!" Roxas returned the shove and Ven punched his brother's arm.

"And you're a bully!"

"Wuss! That didn't even hurt! You can't even beat me in a sword match!"

"…BIG BROTHEEEEERRR!"

Cloud groaned upon hearing Ventus call for him again.

"I'll handle it," Tifa stated and left after she cut Cloud free so he can put on outfits. Aerith started to pull everything out of the bags she and Tifa brought and laid them out for Cloud.

"Okay Cloud…I say, those shoes with black leggings, and that skirt. You can pick your top and…oh! You wanted leather. I'm sure Tifa will let you borrow hers," said Aerith and picked up a leather jacket from the bed. Cloud sighed, not sure why he can't just keep the pants he still has on while throwing the jacket over him.

"Okay…I rather have those brown boots instead, I'm okay with the leggings, I want knee-length dress, and I'll take that purple top, and yes," Cloud took the jacket from Aerith, "I'll take the jacket. I'm also taking that red belt."

"Oh my Cloud, you really can dress yourself! Or perhaps it was just good luck," Aerith lightly giggled while Cloud rolled his eyes as he picked up the pieces of his outfit. Just one time. Well, two, as Cloud still had to go with them when school started. Still. Just two times. Two times and it never has to happen again.

-.-.-.-.-.-.-.-.-.-.-.-.-.-

"You look so pretty," Tifa said as she drove. With the perfect outfit picked, Cloud not getting himself out of the plan, and the school year starting, it was time to put the plan into action. Aerith sat beside Tifa, the pair couldn't help but let out giggles every time they took a glance at Cloud through the mirror.

"Shut up, you've said that at least 10 times!" Cloud growled.

"Okay, well you look silly too…" Tifa added and the two girls went into another wave of laughter. Cloud's frown only stretched further down. He just wanted to go in and get out. He could've sworn that he, well, swore on his LIFE that he'd never put on feminine clothes again. It's not his fault he has a feminine-face! At least that's what everyone kept telling him…

If that's true, why the heck has he not gotten a date yet? Oh right…most of the people that confessed to him are either:

1. Fans that only go for his looks and "mysterious" or "bad boy" persona that gave off.

2. Not his type.

3. They're desperate in the creepy way. He even had to fake-date with Tifa to keep people off his back.

"I think he's more pretty than silly," said Ven, sitting on one side of Cloud. Okay, that was a nice thing to say, Cloud will admit. Roxas, sitting on the other side of Cloud, only broke out laughing…again. Which was the only thing he's done every 5 minutes every time he's reminded that Cloud's dressed up like this.

"I hate you guys…all of you!" Cloud grumbled and pouted at the inevitable fact he's going to be seen like this upon arrival. He will confess that only 2 people can get him in a dress due his personal soft spot for them…and those 2 people were already taken.

"Well this is our first year at this school," Ven reminded, "We need help since Sis it gone right now."

"Ugh…I know…" Cloud was just glad he graduated. The last thing he wanted was to be in the same school as all his siblings.

When they parked, they all slowly piled out. When Cloud stepped out, he nearly tripped on his boots. He patted and straightened his the knee length skirt as he regained his position. Cloud turned to face the van to check his reflection and gave a light jump to make sure his fake breasts are well covered by the leather jacket and not unrealistically jiggling around. Not that his top was that tight but the test run had one of them falling out and spilled pudding all over his floor. He tossed his braids over his shoulder and walked with his arms crossed but he quickly changed and put his hands into the jacket's pocket as folding his arms across his chest just felt weird thanks to his pudding-filled balloons…

Cloud remained looking down and away from anyone's gaze in their general direction, his mind constantly worried that there was no way people will believe this disguise. The blond merely remained quiet while Aerith and Tifa did all the talking to get their rooms. The only time he had to speak was when they asked for his name in which he muttered 'Rikku' and only just remembered to change his voice a bit. Still no one called him out on this so it's working right? The man also prayed no one here here recognized him from last year. Though as he helped move furniture and luggage, he still hasn't gotten called out.

Cloud only just realized he had to move almost everything up to the girls' new dorm room…as well as his brothers.' Why does he so easily cave in to his friends' requests? Not to mention his insecure brother and cunning brother?

-.-.-.-.-.-.-.-.-.-.-.-.-.-

"Thank you, Cloud," Aerith smiled upon Cloud bringing in her remaining plants and flowers into the room.

"No problem…"

"Aerith!" a voice echoed from the hall.

Oh no…

Cloud wanted to die at that moment as he looked for a place to hide in this dorm. He knew that voice! After all, it was his first crush! He practically stalked the man! Not that he was ever caught or he admitted it…

Still, the guy coming in was his: old crush, first crush, best friend, and the guy dating one of his girl friends. With all that in one package, he doesn't want the guy seeing him like this! Or he'll never let it go! So Cloud dove behind the bed closest to the window.

"My beautiful Aerith!" Zack exclaimed as he bounced into the dorm room with open arms. Aerith merely smiled as she approached her boyfriend.

"Oh Zack." The two embraced for a moment and Zack planted a kiss on her forehead.

"Hi Zack," Tifa greeted when she came out of the bathroom but she stopped when she noticed someone was missing, "Hey I thought Cloud brought everything up already." Cloud wanted to curse so badly at that moment! If he didn't know better, he would think Tifa's out to get him!

"Cloudy's here?" Zack asked with interest, "Where is he?"

Aerith couldn't help it, but she let out giggles that she couldn't hold in.

"Oh he's in here, isn't he?" Tifa asked, catching on and she looked around.

"Cloudy! Come out and give your bestest bud a hug!" Zack called out. Cloud started to crawl under the bed at this point. Like he's actually going to willingly come out of hiding. What normal person would do that in this situation? Then again…he's not even sure if any 'normal' person could even end up in this situation to begin with…

"Ah ha!" Cloud felt himself being pulled by the legs and instead of gripping whatever he could get his hands on, he was forced to keep his skirt from going up as his leggings started riding down at some point…

And now that Zack saw him…he will never hear the end of this…

Oh great, and now that he heard Zack's camera phone go off…he knew he will never hear the end of it with about 5 other people too…