XashXdawnX - This is going to be my attempt at a multichapter story focusing on Gary and Leaf as the main couple/ship. So it'll be OldRivalshipping with some Pearlshipping thrown in. This will also be an attempt on a high school fic, since I haven't done many...or usually delete them, due to the fact, I never like how it's going. Hope you enjoy!

I don't own anything, all rights go to the respective owners.

Gary Oak sat on the bleachers, looking at someone he had once been close friends with. They had been best friends. Who was he staring at? Her name was Leaf Green. Once upon a time they had been best friends, never a part from one another. That was until she moved in the ninth grade and when she returned during the summer before junior year, she was completely different. They were no longer friends, no longer best friends, now they were just familiar faces, strangers.

He watched as she talked animately to one of her friends.

She had changed so much. Freshmen year she had been short and slim. Her dark brown hair had fell to her waist and her green eyes hadn't been covered with makeup. Her skin had been pale and her figure hadn't really developed. Now, she was tall and slim with her figure filled out nicely and boy did she flaunt what she had. (Her short plaid skirt accented her legs and the tied white shirt accented her waist, boobs, and toned stomach, but add the leather jacket that was beside her bag, it only added to her looks.) Her hair was now a caramel color with blonde highlights, her eyes were surrounded by dark eyeliner, her lips painted dark red, and her skin was now tanned.

She laughed and smiled with her friend.

Even though she was known as the bad girl, she didn't act as rude as one would think. She was known for cutting class and hanging out with college guys, then there was a rumor that said she was messing around with these college guys.

Gary didn't believe that she was that type of girl, but he wasn't sure anymore. The girl she once was had vanished and had been replaced with this girl.

"Stop, staring before she catches you." a voice said.

Gary looked over and saw one of his closest friends, Dawn Berlitz. Dawn was younger than Gary, but was in the same grade due to her starting early in school. She was short and slim. She had long sapphire blue hair and eyes to match that were accented by eyeliner, and her lips were light pink with her lipstick. She was wearing a yellow sundress with white wedges and a white cardigan was across her arm since she had it for inside for class.

"You were staring."

"I can't help it."

"She's not the same girl anymore, Gary. You can't expect her to become who she once was." another voice said.

Looking over he saw his other best friend, Ash Ketchum approaching. Ash was the same age as Gary and the same grade. He was tall and slim. He had messy black hair and dark brown eyes or "chocolate brown" according to Dawn. He was wearing a plain white tee with some jeans.

"I just wish I knew what caused her to change." Gary muttered.

"So do I..." Ash replied.

They had all been friends with her, but when she returned she had made it clear she didn't want anything to do with them. So they had left it alone.

Gary walked through the halls after the final bell rang, heading towards his locker to get his books.

He heard muffled voices coming from the far hallway.

"I said stop!"

He knew that voice all too well.

Without thinking he hurried down the hall and turned the corner quickly.

Leaf was pinned against a locker, looking uncomfortable as a guy named Red, Gary believed that was his name, was kissing on her and his hands were roaming.

Before Gary knew what was happening, he was walking towards the two. His step was confident and he felt his eyes setting into a glare.

"...You should get off my girlfriend before we have a problem." he said, snaking his arm around Leaf effortlessly.

"Girlfriend? Since when does Green have a boyfriend? And since when does Green date someone like you, Oak?" he asked, looking at the two unconvinced.

Gary scoffed. "Beat it before I beat your face in for feeling up my girlfriend."

"She's just a piece of ass anyways."

Gary snapped and threw a punch at Red, hitting him right in his nose.

"That's it!" Red yelled.

Gary was quick and grabbed Red and slammed him into the lockers, pinning his arms behind his back.

"Don't ever call Leaf that again, got it?"

He shoved Red once again and faced Leaf as Red walked off.

Leaf was fuming.

"I'm your what?!" she screamed.

Gary held up his hands in defense. "I was only trying to help."

"I don't need any help, Oak." she muttered, grabbing her bag from the floor and stalking off.

Gary could only watch her walk away. That was the first time Leaf had spoken to him since she just dropped him as a friend.

Gary walked towards the bleachers the next day to find Ash and Dawn already there.

"So Gary, anything to tell us?" Dawn asked.

"What are you talking about?" Gary asked as he made his way up to where they were sitting.

"Oh no you don't." a voice said.

Gary's wrist was grabbed and he was yanked down the bleachers. He almost fell, but regained his balance to find himself face-to-face with Leaf.

"We need to talk." she muttered, glaring at him.

Today, she was wearing a red crop top, white short shorts, and converses. Her hair was pulled into a high ponytail. She dragged him away from the eyes of their peers.

Once she stopped, Gary yanked his wrist out of her grip.

"What the hell?" he questioned, raising an eyebrow.

Leaf just glared at him and crossed her arms.

"That whole stunt you pulled yesterday after school is the fucking talk of the school. I'm now known as your damn girlfriend."

"So?"

"We aren't dating, Oak. So here's what we're going to do. We're going to go back out there and break up in front of everyone. Understand, Oak?"

Gary laughed.

"This isn't funny, asshole."

"Oh, but it is."

Leaf quirked an eyebrow, waiting.

"This relationship was announced yesterday. If you were to break up with me, it would allow everyone to see that it wasn't real. You'll lose your reputation."

"No, I wouldn't. I'm the bad girl, Oak. I'm known for not staying committed."

"So it's not even a day...not like you." Gary replied, smirking as he saw her expression change.

"Ugh!"

"Gotcha..."

"Okay...so how about we make this interesting."

Gary looked at her.

"How so?"

"You just inserted yourself as my boyfriend. We can play the boyfriend girlfriend gig. Here's the catch, it's going to be a bet. I bet that you'll actually fall in love with me. If that happens you lose and I get to humiliate you."

"Hmm..."

"So, how about it? You get to be known as the bad girl's boyfriend."

"How about I add to the bet?"

Leaf raised an eyebrow. "Make it interesting and maybe I'll allow it."

"IF I fall in love with you, you get to humiliate me OR if you revert back to the girl you once were, then you lose."

She scoffed. "You're losing, Oak. That girl's gone."

Gary stepped closer to her, causing her to step back slightly.

"She's still there, because I saw her yesterday."

She shoved him.

"Okay. So this is the bet. I bet you fall love with me before I change back to who I used to be."

"Yep,"

"Okay then, it's a bet." she said, holding her hand out.

Gary shook her hand.

"You're going to lose, Oak."

"I think it's going to be tougher than you think, Leafy."

He heard her gasp softly, it was barely audible, but he heard it. He smirked to himself.

This is going to be interesting. he thought to himself as he wrapped his arm around her waist.

Please R&R