In the busy streets of Coumarine city, a sky battle tournament is currently being held there. People from all around the world, will come and participate this glorious event. Among them was a beautiful woman with long purple hair that is all tied up, she wore a sky blue flight suit. The side of the woman's hair sticks up at the side in two tufts, representing feathers. She wore a helmet and a pair of goggles, the woman is none other than the Fortree city gym leader, Winona. She was ecstatic about this tournament, why? Because this tournament was only held once every 3 years, and flying type from all over the world will be there. So there is no way she was going to miss it.

'I wonder what flying type pokemon does Kalos have to offer?' Winona put her hand beneath her chin as she looked at graceful flying type pokemon around her, the cafe in Kalos was amazing, it felt so warm and cozy. Her train of thought was interrupted by the sound of her shiny swellow chirping next to her.

"Huh? What is it swellow?" Swellow pointed its wings towards a group of people out of the window, Winona stood up from her seat and saw a familiar face, a boy in a cap with a pikachu on his shoulder. Winona found herself smiling when she saw Ash.

'Ash? He is in Kalos? Well might as well say hi." Winona stood up and exited the cafe with her swellow behind her.

With Ash

"So I heard that there is this tournament being held here." Clemont said as he trying to stop Bonnie from asking other woman to 'take care' of him.

"Really? What kind of tournament?" Serena looked at her pokeguide. (Yeah I'm calling it that)

"It says that it is sky battle tournament." Ash's eyes instantly gleamed as he quickly step next to Serena, causing her to blush.

"Really? All right I'm in!" Ash shouted in excitement.

"Oh it says that only flying type pokemon are allowed to battle, I think it's a sky battle." Ash looked at fletchlinder's pokeball and smiled.

"Don't worry, with me and fletchlinder, we will win the it!" Ash says as he looked at pikachu.

"Pika-pika!"

"Ash?" Ash turned around and saw a familiar face.

"Winona? Is that you? Wow long time no see!" Ash said as he walked towards the purple haired beauty.

"It's been a long time since we saw each other, how have you been?"

"I've been great! Are you here for the tournament?" Winona smiled and nodded.

"Yeah I am, I assuming you are travelling at Kalos?" Ash nodded and pikachu waved a cute hello.

"Aww hello to you too pikachu!" Winona petted the electric mouse pokemon who nuzzled Winona's hand.

"Hello! Will you take care of my big brother!" Bonnie said as she knelt down.

"Bonnie!" Clemont shouted in horror at what his sister is doing.

"Err?" Winona sweatdropped as she looked at Ash.

"This happens all the time." Ash scratched the back of his head as he smiled.

"Bonnie! How many times did I call you to stop doing that! You are embarrassing me!" Clemont grabbed her sister gently as he pulled her to the fountain.

"Hope you reconsider une belle femme!" Winona nodded slowly before she noticed Serena.

"Oh hello and who are you?" Winona asked politely.

"My name is Serena, and I'm travelling with Ash through Kalos."

"Oh that's nice, say Ash are you entering the sky battle tournament?"

"Me? Of course I am, I look forward to battle you again Winona."

"Me too Ash, I'm sure you got a lot stronger now, but so have I." Ash grinned and held fletchlinder's pokeball.

"Say Winona, how many flying type pokemon does Ash need to participate the tournament?" Serena asked Winona as she put her hands behind her back.

"Well every participant needs 3 flying type pokemon." Winona said as she looked at Ash, he has grown taller and his voice is deeper now. His still looks the same though, more muscular and more handsome.

"3! Aww man, well I guess I have to bring my old flying type pokemon with me." Ash tapped his chin as he though who could he bring.

'Hmm let see here, there is swellow, unfezant, staraptor, noctowl, oh I could bring charizard, but that will be overkill though." Ash was still thinking of his pokemon when he felt pikachu tapping his paw against his face.

"Huh? Oh sorry pikachu, I was trying to think of who should I bring to the tournament."

"Well I'm going to the tournament now, see you later Ash." Winona hopped onto swellow and they flew in a incredible speed towards the direction of the tournament.

"Wow her swellow moves fast! Pikachu, I think I know who to bring for this tournament." Pikachu looked at Ash with a confused look.

"Pika?"

It was evening and trainers along with their pokemon stood proudly at the stadium, thousands of people were witnessing this tournament, cameramen and news reporters and snacks were everywhere.

"Oh right folks this is the tournament we've all been waiting for, are you ready to be blown away!?" Thea announcer shouted loudly, the crowd screamed and shouted in excitement, claps and cheers were being thrown at every direction.

"For the first battle we have Sarah Liliums from Sinnoh!" A girl with long black hair appeared with her staravia next to her.

"Versus the graceful and beautiful, Winona Nagi." The crowd erupted into cheers as the flying type gym leaders waved her hand towards the crowd.

"Alright altaria fight with grace and style!" Altaria appeared and it looked at it's opponent fiercely.

"Alright, this would be a one on one battle, no one hit K-O moves or using items, got that?" The referee shouted, the 2 trainers gave a curt nod and the referee blew his whistle.

"Staravia take to the skies and use wing attack!" Sarah's staravia sped across the battlefield with it's wings glowing.

"Altaria take flight and use dragon breath!" Altaria immediately flew to the sky and unleashed a beam of draconic energy at staravia.

"Dodge with quick attack and use aeriel ace!" Staravia narrowly avoided dragon breath and it's eyes gleamed before it became a blur.

"Safeguard!" Altaria was too late as the attack landed on it causing it to fall on the ground, though Altaria managed to levitate on the ground. Altaria shook its head, the aeriel ace didn't hurt that much considering that it is much stronger than staravia.

"Hah take that!" Sarah said as she smiled cockily. Winona gave a small glare and looked at her altaria, that's it, no more misses nice gal,

"Altaria quick use your own aeriel ace!" Altaria rose up from the ground and one hit K-O the weaker staravia.

"Staravia is unable to battle, this match goes to the Fortree city gym leader, Winona!" Sarah jaw dropped and quickly took her staravia and rushed towards the pokemon center. Winona smiled and petted her altaria.

"You did great girl." Winona said softly towards her altaria before she recalled her.

Meanwhile at the stands.

"Whoa did you see that guys!" Ash said as he witnessed Winona's altaria one hit the opponent's staravia.

"Yeah, wow she's strong." Clemont said in disbelief.

"Don't worry Ash, you'll beat her." Serena said as she looked at him.

"Thanks Serena." Ash smiled her her causing her to blush, but Ash of course didn't notice it.

"Hey Ash isn't your match next?" Bonnie said as dedenne was sleeping in her bag.

"Oh yeah! Thanks Bonnie, I'll see you guys soon, catch ya later!" Ash then took off as he ran out of the sidelines, only to realized that he doesn't know where his next match will be held.

"Oh man, I should have ask Bonnie." Pikachu sighed and shook his head.

"Hey Ash!" Ash turned and saw Winona walking towards him.

"Oh hey Winona, I saw your match, man your altaria was awesome!"

"Oh it's nothing, you looks worried, something wrong?"

"Huh? No no no, It just that my next match is in a few minutes and I don't know where is it held." Ash scratched the back of his head while smiling sheepishly.

"Well I can show you, I saw it on the board earlier."

"Great!" The 2 then walked in silence as Ash followed Winona's lead.

"So Ash, who are you using? Are you using your swellow again? My swellow was hoping that he can have a rematch with him."

'Yeah don't worry I'll be using my swellow, but I won't use it during our match though." Winona got curious on who would Ash use, but decided not to ask, after all she wanted to be surprise.

"Well this is the field, good luck Ash." Winona walked to the stands as she gave Ash a thumbs up. Ash nodded as he walked towards his opponent from afar. The referee noticing Ash sighed in a breath of relief, afraid that he won't show up.

"It's about time you get here young man." Ash rubbed the back of his head while replying.

"Sorry I got a little lost." The referee shook his head and looked at Ash's opponent, who wore a black jacket with brown hair.

"This would be a one on one battle, you are not allowed to use moves such as one hit K-O moves. You are also forbidden to use items during battles, is that clear?"

"Very." Ash's opponent said coolly.

'Something tells me that he is serious and smart, better not underestimate this guy.' Ash thought to himself as he gripped on one of his pokeballs.

"This battle is between Ash Ketchum from Pallet town versus Victor Tersa from Luminose city, are the trainers ready?"

"Ready!" Ash shouted in determination. His opponent merely nodded as he took one of his pokeballs out.

"Begin!"

"Go fletchlinder!" Fletchlinder appeared and he squall at his opponent. Victor threw his pokeball and it revealed a honchkrow.

"Fletchlinder use flame charge!" Fletchlinder covered himself with a cloak of flames before diving straight into honchkrow.

"Honchkrow use night slash." Honchkrow wings turned into a blackish brown colour before it slash fletchlinder with it. The 2 were pushing at each other, but with fletchlinder's amazing speed, he was able to overcome honchkrow's night slash and hit the big boss pokemon. Honchkrow gritted as it tried to stay at the air.

"Payback!" Honchkrow was covered by a black aura before it rushed towards fletchlinder with a trail of black streak behind him.

'Razor wind! Fletchlinder flapped it glowing wings as air blades started to circle around his wings.

"Steady... steady." Ash waited for honchkrow to come closer, however, Victor has other plans.

"Charge at it!/ switch to dark pulse!" A bright streak of light and a large ball of darkness collided, however fletchlinder barely managed to pierce trough the ball of darkness and hit honchkrow.

"End it with flame charge!" Flecthlinder's body was engulf by fire and it charge at honchkrow causing it to ne burned by fire and to be flown back to the walls and faint.

"No!" Victor shouted weakly as he watched his honchkrow crashed and burned.

"Honchkrow is unable to battle, this match goes to Ash Ketchum from Pallet town!" Ash fist pumped to the air as fletchling flew towards Ash with a smile on his face.

'Wow Ash has really improved since we last battle, and that fletchling of his was really fast. So graceful, so swift...' Winona eyed Ash's fletchling.

Ash smiled as he stroke fletchling but frowned when he saw Victor's glare, he recalled honchkrow wordlessly and left the arena. Ash recalled fletchling and went out of the arena.

"Ash that was awesome!" Bonnie squealed as she tugged Ash's arm, Ash chuckled and ruffled Bonnie's hair in a brotherly manner.

"Aww thanks Bonnie, I think someone wants to see you." Fletchlinder appeared out of his pokeball and he chirped upon seeing Bonnie.

"Yay!" Bonnie gave fletchling a hug and gentle strokes.

"Ash that was great! Your coordination with your fletchling is amazing!" Winona put her hand on her goggles as she bend down.

"Thanks." Ash gave a toothy grin and a thumbs up. The co and Winona hung out till the last day of the tournament, their bond were closer now, especially the bond between Ash and Winona. Though on the last day of the tournament, it was cancelled due to team Rocket's interference, as usual they wanted to kidnap pikachu but it was fail, again. Though this time with Winona's help, the trio were arrested by the police due to Winona's swellow.

"Man thanks for your help Winona, team Rocket has been following me around for years! Thanks for taking care of them." Ash said as he looked at the huge pleadging tree with lights on it, it looks like Christmas came early.

"You're welcome Ash, I'm glad they are behind bars. They were very annoying. Though it's a shame that the sky tournament has to end because of team Rocket." Winona said with a sigh, the sky tournament only held once every 3 years. She took off her helmet, revealing her full appearance, she placed her helmet on the table next to her. Ash looked at Winona and blushed a little on how pretty Winona looked, with the moonlight shining on her skin.

"So uh, I'm really glad that you're here Winona, it's been awesome." Ash said while scratching the back of his head.

"Thanks Ash, it's been fun, I'm glad that you're here too." The 2 remain in silence as they looked at the huge and magnificent tree.

"You know...it's getting late, we should get back inside. I'm sure pikachu and the rest is getting pretty worried about us." Ash said awkwardly, he never been into situations like this before, well maybe he did, but maybe he never realized it.

"Oh yeah we should." Winona looked at Ash and played with her long locks in nervous manner.

'Kind, energetic, sweet, determine, loyal, caring, dense, reckless and brash." Winona looked at Ash and walked closer towards him, she never actually met a guy like Ash before, sure Wallace and Brawly were nice guys, but they have tried to flirt with her and wanted to date her, though she always turned them down ( for obvious reasons). Ash though, treated her like there were friends, not just a gym leader or someone famous but as a friend. The fact that Ash didn't flirt with her and with his endless love for pokemon made her heart race, even though she only met Ash for a short time, she could tell that he cherish the moments with his travelling companions, as well with his pokemon, he valued freedom and wanted to reach for the stars. No goal is too high or too low and she admires Ash for that, he never doubted his dreams, and Winona likes that, a lot. Ash was one with the bird pokemon, he just doesn't realized it.

"Ash." Winona said suddenly with her hands shaking skightly.

"Huh? Yes Winona?"

"I know this is sudden and all, but would you want to go out? You know just the 2 of us." Ash blinked his eyes and looked at Winona.

'Just the 2 of us? Err wait! Does she means a date? A date, date!? Man Brock would be jealous.' Ash looked at Winona as she flutter her eyes.

"Well I guess we could, I mean why not? Uh I'm totally fine with it, I mean if you're find with it I'm find with it." Winona giggled to herself, finding Ash's stuttering cute. She went closer to Ash and gave Ash a peck on the cheek, causing the raven hair boy to blush furiously.

"Great! So 7 o'clock tomorrow night?" Winona said shyly, Ash dumbly nodded in response. Winona smiled softly and wore back her helmet and she stares at the stars while humming a beautiful tune.

Ash look at Winona and looked at the sky before he smiled and scooted closer to her, unknowingly making Winona smile.

'Winona Nagi, never in my wildest dream would I thought that I get to date her.' Ash continued to looked at the star and smiled softly, wondering what the future would bring.

Well guys, I'm try one-shots, so I know I'm bad at it so I'm giving it a shot, I wanted to make this longer but if I do it will turned out more of a battling story rather than a you know story. Err so yeah, not many people do Winona so I decided to give it a shot. Tell me if you like it or not.