Ash stood at the bottom of the winding path leading up to the Cerulean City Gym, he smiled as he looked up to the huge Dewgong on the roof, he thought back about the call he had received from Daisy a few days earlier, Misty and the other sisters had been requested in Alola for some kind of emergency and Daisy was left looking after the Gym alone. She had asked Ash to come to the Gym immediately and more worrying, he was told to leave his Pokémon at home. He thought back to Pikachu being held by Mr Mime, it had been hard to leave it behind but if Misty's sister needed his help, he would do all he could. He sighed before pushing the door open and entering the gym. He walked through the halls and into the giant arena, "Hello?" he called out in front of the empty pool.

"In here, Ash!" was the response echoing from a room just off the arena. Ash walked towards the voice catching his reflection in the water, he noted just how different he looked from the first time he was here. He had grown noticeable taller and his hair was significantly longer, growing straight down with the help of his new love for product. He was still fresh faced, with small bags growing under his eyes. The evidence of his last few days sleeping rough on his way to the gym. He walked into the room and noticed Daisy hastily packing a suitcase.

Daisy looked up, her face turning from stressed to happy. She was quick to make her way across the room throwing her arms round Ash in a hug. "Oh, thank goodness you came." She exclaimed.

"Of course Daisy, I left as soon as possible just like you asked. So, what was this about, it sounded serious" He asked stepping away from the hug awkwardly.

"Please come in, I'll explain everything." She moved her hand gesturing to him to sit in a nearby salon chair.

Ash entered and followed Daisy into the Gym, "Hey, is Misty around?" He asked, "It's been a while since I saw her too."

"No, she's travelled to Alola to help out the locals there." She closed her suitcase and sat on top of it.

"Oh…that's right." He said, "So, how can I help you out, Daisy?" He asked eager to hear why he was there.

"Well, all my sisters have gone to Alola and I am also needed but I cannot leave the gym alone. That's when I thought of you. I need you to…" She paused slightly before continuing "run the gym while I'm gone?"

"You want me to run the Gym!?" He asked his mouth falling open, "Wow, I've never ran a Gym before Are you sure?"

"I know you've never ran a gym but you've been a trainer for a long time and I think you'll be great." She assured him

If you think I can do it then sure, I suppose I can act as a temporary Gym Leader" He said smiling.

"That's great!" She shouted in relief, jumping to her feet. "Now, I have been in contact with an old buddy of yours that will help you while we are gone."

"That's for trusting in me." He said, then he looked confused, "old buddy? Which old buddy?" He asked

She smiled to him, taking a Poke ball from the top of the cabinet, throwing it in the air. A familiar looking Squirtle wearing sunglasses popped out. "Squirtle, squirt!"

"Squirtle!" Ash cheered, hugging the little Pokémon, "How are you, old friend?" He asked with a smile.

"Squirtle, Squirtle squirt." It chimed happily.

"You can look forward to battling together a little later." Daisy said, returning Squirtle to its ball.

Daisy smiled and tilted her head. "Now, you can select five more Pokémon from our water type archives. I left some and there is also Misty's..." she sighed "Psyduck."

"Really? I'm surprised she didn't take him with her." He said, "Well, I think I can manage the rest on my own, anything else that I might need" He asked

"Emm, yeaaaaaaaaaaaaah. There is one thing." She moaned awkwardly.

"What is it?" Ash asked, "I'm sure I can handle it."

"Emm, follow me." She lead him to one of the rooms, and opened the door to reveal a walk-in wardrobe with lots of outfits, dresses, underwear, swimsuits and shoes.

Ash looked around "wow you sure have a lot of clothes. They are really nice." He admitted, letting his hand run through the fabric of one of the dresses.

"Thanks, Ash. I'm glad you think so... you'll... you'll be wearing one of them." She blushed, looking down to her feet shuffling them.

Ash's eyes widened looking at Daisy confused, "I'm sorry?" He asked, thinking he might have heard her wrong.

"Yeah, you have to pretend to be one of the sisters in order to run the gym. It's in the contract that only we may run it. I'm sorry I didn't tell you earlier." She sighed, looking apologetic.

"Oh…So you want me to be a Sensational Sister?" He asked, a small smile growing on his face, turning slightly red. He thought back about the days dressing up in his mother's clothes, parading around in front of the mirror, how awesome he felt, how comfortable he felt. "Okay!" He shouted suddenly, giving Daisy a slight scare.

"Yes, the most fabulous, sensational sister there is!" She smiled and pulled out a tape measure. "We just need to get your sizes!"

Ash blushed a little deeper, then, surprising Daisy, he smiled, "Ok…That sounds fun" He said

"R... really? That's great!" She threw her arms in the air and rushed Ash, she pulled the tape measure across his body in numerous places, she wrapped it around his chest, then waist. Nodding every now and then.

Ash stood still as Daisy measured him, "Yeah…I guess you're surprised I'm going along with this." He said blushing

She got on her knees in front of him and looked up. "Yeah, actually. I thought I was going to have to lock you in here and tie you up get you into the clothes by force but this is easier." She moved the tape to the floor and guided it up his leg, just grazing his crotch.

Ash blushed, "Well…the truth is…I like it. I like dressing like a girl. It's a secret of mine that no one else knows" He admitted

She was halfway round his ankle measurements when she stopped, dropping the tape. "Aaaaaah!" She screamed in her typical girly fashion. She grabbed his hand and dragged him to the clothes. "While we are gone, these are all yours. Your measurements are the same as Violet except the breast region." She motioned to Ash's flat chest letting out a short laugh. "We also have this." She opened a small locker, revealing an assortment of hair care products. Ash's eyes light up, his gaze floating over all the products he could ever want or need. "You can use any of these to make your hair look perfect. I'm so glad to decided to grow it long."

Ash blushed "Wow, I can't believe you're letting me have all this. There is one thing though you need to promise me you won't tell anyone?" He asked sweetly.

"Of course not. It's between you and me" She smiled "and Violet and Lily" She added under her breath.

He blushed at that, "Well…I don't suppose you'll have time for a little makeover?" He asked hopefully.

"I was hoping you'd asked. No time to waste, sit in the chair." She pointed to the makeup chair in front of the lighting mirror. Ash smiled as he sat back on the chair.

Daisy pulled open the makeup chest and started matching makeup to Ash's skin tone. "This is going to be so much fun."

"Oh yes…I can't wait to be Ashley again" He said smiling before his face fell, realising what he had just said.

"Ashley. I like that." She smiled. "Don't worry. Your secret is safe with me." She assured him, catching a look at his worried face. She quickly got to work, applying makeup all over his face, giving some fake eyelashes to top off the look. She was quick to pull his hand forward giving him a manicure before adding brown nail polish to match his eyes, she repeated the action with the other hand and stood back to admire her handy work.

"Perfect if I do say so myself." she laughed at her own words spinning the chair round to let Ash see himself in the mirror.

"Wow, I can't believe it's me. I look just like a girl!" He said happily looking at himself, seeming to finally feel like his true self.

"Can I change out of my clothes?" He asked hopefully

"Of course, of course. You have a large range to choose from. Pick your favourite!"

Ash smiled as Daisy left to give him some privacy. He looked around just to make sure he was alone before taking everything off. Since most dresses doubled as swimsuits, he was free to wear those alone. He looked around thinking of how the Sensational Sisters looked in their dresses, he decided on one that was light blue. Not wasting any time, he quickly slips the dress on. He opened a small drawer blushing a little at the selection of panties that he found. He picked one that matched the dress perfectly, slipping them on and blushing even deeper.

Ash giggled and did a little twirl as Daisy entered the room again "Oh Daisy, I feel…well…Sensational" He said in a girlish tone

"I love it Ash-ley" She added, "You're a real Sensational Sister now." She picked up a suitcase from the floor and smiled. "Well, I've got a Lapras to catch."

Ash smiled with gratitude "Well, I guess this so goodbye" He hugs Daisy, "Thank you so much."

"You are going to fool everyone, you look perfect!" She hugged Ash and put on her stylish coat. "Good luck and call me if you have any problems." With that she headed to the front door.

Ash now had the gym to himself. after choosing the Pokémon and explaining to them everything that was going on and a special explanation to Squirtle, Ash was free to do what he…or rather, she pleased. He had set his six poke balls in their spot by his battle area and was humming a song with his feet dangling in the pool. A sound of the front door opening gave Ash a shock. He quickly stood up, heading to the entrance to the arena, waiting on his first possible opponent. A knock came at the arena door and Ash took a deep breath and opened the door.