Ash wakes up in Gary's cheerleader harem

Ash's return to consciousness was slow. She could feel her head against a pillow and a sheet atop her. She brought her hands up to her face to try rubbing her eyes. "Oh man, I dreamed that Gary kissed me," she said to herself irritably.

"It was more like a dream come true."

Ash stopped rubbing her eyes as she heard the response. Eyes snapping open and sitting straight up in surprise, she found herself sitting in some hotel room with Veronica and Rachael. Both girls had changed out of their sexy cheer outfits into their day to day clothes. Veronica wore a aqua blouse whose top buttons were undone to show off her chest, white shorts that clung tightly to her rear, and pink heels. Rachael wore a pink dress that hugged her figure, emphasizing her cleavage and legs, with a bright yellow jacket and red heels.

Ash stared at the two trying to figure out what was happening. "Uh...what happened?"

"Your plan worked sweetie," Veronica answered. "Putting yourself out there in those super tight clothes won you Gary's approval."

"Probably not the brightest to not bring any spare clothes," Rachael followed up, "but don't worry, we got you covered."

As Ash thought about what they said, it all came rushing back at once: waking up, running to the labs, bumping into Gary, and the revelation of her new body. Taking a look down confirmed her worst fears, she had boobs. She was a she.

What she also found was that she no longer wore her old, ill-fitting pajamas. Now she was clad in the same sexy cheer outfit that she often saw the two girls before her wearing. And she looked every bit as desirable now.

Ash's thoughts were a whirl of thought before she found her voice. Of all the surprises, it was a subtle one she voiced. "They fit."

"Yep. Good thing too," started Veronica. "Seems we all have the same general sizes."

"And don't worry," said Rachael. "That's not one of the ones we were wearing. It's one of our spares."

The girls had packed a few spare outfits just in case. They knew that someone with Gary's popularity would attract more girls seeking to garner his favor, and they were open to inviting more to join their group. Though, they hadn't expected to pick someone up before leaving Pallet Town.

It was at this moment that Gary and Taylor came in through the room's front door. Taylor had switched into a black skirt and blue top that, like her friends, emphasized her assets. She was also carrying a shopping bag with her.

Gary smiled at the sight of his newest girl, looking all nervous and cute in her new uniform. "Hope you enjoyed your rest beauty, because I want to welcome you to the first day of the rest of your life," Gary said.

"Sorry we couldn't be here when you woke up, but we were out getting you some new clothes," Taylor said, holding up her shopping bag for emphasis.

Ash starred at them and the bag for a moment. "Okay look," she started, "I'm still processing all this-"

"Don't worry," Veronica interrupted, "we got you covered. Girls!"

And just like that, the trio got to work. They quickly pulled Ash out of the bed, and started stripping her. So surprised by their actions that she could barely make any sort of protest before the quickly got her dressed in her new outfit. But it was more than just that, Ash felt her hair being pulled and objects getting shoved in her face. Gary for his part watched in delight as his new babe got dolled up for him.

When it was done, Ash was placed in front of a mirror. "Say hello to the new you!" Taylor exclaimed in pride. Ash took a good look in the mirror and her first thought was how purple her outfit was. Purple dress showing off her new tits. Purple heels. Purple hair band holding her new ponytail. Purple choker. Purple makeup. It was very purple.

Her second thought was just how hot the girl in the mirror was. And her third dreadful thought was how that girl was her.

Gary gave an appreciative whistle, which brought Ash back to reality. "I gotta go," she said, trying to rush to the door. But her new unfamiliar heels caused her to stumble right into Gary's chest, allowing him to wrap the new girl (his new girl) in a tight embrace.

"What's the rush babe," Gary said giving Ash a seductive smirk. She gasped when she felt him firmly grab her bubbly ass. "Why don't we just take the time to get to know each other."

Ash was feeling very uncomfortable. Her new gender, her new look, and Gary's unwanted advances were all too much for her. "We can't!" she blurted. "Because, uhm... I need to see the Professor."

"Gramps? Why?" Gary asked, loosening his grip so Ash could stand on her own.

"I was..." Ash started before thinking about how she should answer. If she told them she wanted to see Professor Oak because she was a man last night and a woman today and he might be able to help figure out what was going on, they'd wouldn't believe her. Or worse, they would and she would die of embarrassment. So she settled on a half truth. "I wanted to get my first pokemon."

"Well I hate to break it to ya babe, but I got the last one," Gary said. "Besides, we're already long past Pallet Town. No point in turning back." Gary shrugged in indifference.

"What!" Ash exclaimed. "But-but-but-" Ash wasn't sure how to take all this. She woke up a woman, got dragged into a makeover, suffered Gary's flirting, and now she couldn't get her first pokemon? This journey was starting all wrong.

"Don't worry babe," Gary said, placing his arm over Ash's shoulder, unaware of the discomfort it caused her. "Since I'm such a nice guy, I'll take you out and catch you one as a welcome present. Teach you the ropes."

"Oh, he's so generous," Veronica said as she, Rachael, and Taylor gushed off to the side.

Ash cringed at the whole display. While on paper it was generous, she knew Gary was only looking for the opportunity to show off and score with what he saw as his newest trophy girl.

But it was still the promise of a pokemon.

If Ash had to pick between putting up with Gary's ego or going home without even having gotten the chance to try, it was no contest. A moment of humiliation for the first step of her journey.

So, taking a deep breath and letting it out, she faced Gary. "Thank you, Gary, I would...appreciate that."

"Of course you do. It's how I roll. I always keep my babes happy." Gary held his head high at his own boast.

Ash rolled her eyes only to be pulled into a hug with the other girls. "How lucky are you. Any pokemon Gary catches is sure to be a winner," said Taylor.

"Gary's going to make you feel so welcome," said Veronica. "But we should really introduce ourselves if we're all going to be friends. I'm Veronica, that's Rachael, and this is Taylor." She gestured to his friends. "What's your name."

"I'm Ash." Ash immediately winced after answering. It was automatic to just say his name, and now that it was out there, he could only hope they wouldn't put together who he really was.

Gary quirked and eyebrow. What were the odds that this babe would have the same name as his childhood idol.

The girls were likewise perplexed. "Your name is Ash?" Taylor reiterated.

"How unfortunate," Rachael said.

Ash gave a frustrated look at her before Veronica cut in. "You should really go by your full name instead of abbreviating it. Ashley is so much better."

"Yeah! Ashley is so much prettier," said Rachael.

Ash was relieved that they didn't recognize her, but was annoyed by their changing of her name. "I'm not going by Ashley."

"Don't worry Ashley, stick with us and you'll be comfortable with yourself. You'll see how much better it is being Ashley over Ash," said Veronica.

"Okay girls," Gary interrupted, "let's head out so we can get Ashley her first pokemon. I'll make sure it's as lovely as both her and her name."

"Yeah!" exclaimed the trio of girls. Gary turned about and headed out the door followed immediately by his cheer squad.

And so it was with an irritable sigh that the newly christened Ashley took her first proper step to begin her pokemon journey.