Pokémon combined shipping one shots and stories

The bet- Pearl/Contest

 While revisiting the Sinnoh region, Ash, Dawn, May and Drew were out having fun. Ash had challenged someone to a battle, Drew was standing by tending to his Pokémon, and May and Dawn were chatting. Since the two girls met, they have been great friends.

"Then, Solidad said 'but at least he is better than a magikarp'." May giggled.

"Haha! That's priceless!" Dawn laughed.

"I know. I couldn't believe it myself." May remarked.

"Wow, any other funny stories?" Dawn asked.

"Hmmm, not that I can think of at the moment." May answered.

After a moment of silence between them, their attention was taken by the declaration of victory by their raven haired friend.

"Great job Pikachu! That was great!" Ash exclaimed to his Pokémon partner.

"Pika!" Pikachu squeaked happily.

"And thank you for the battle, your Wormadam is a really strong Pokémon." Ash congratulated his opponent.

"Same to you." His opponent grinned and returned his Pokémon. The trainer then walked off.

Ash walked over to a bench near by, continuing to congratulate Pikachu.

"He is such a good sport." May stated. She then glanced at Dawn, to see she had an affectionate look as she gazed at Ash. May smiled evilly and she added "And quite the catch."

"Yeah...Wait, what? No!" Dawn blushed, as she quickly realized what she just agreed to.

"Oh, calm down. I already know, so there is no denying it. I just don't understand why you haven't told him yet." May shrugged.

"You mean like you have with Drew." Dawn countered, hands on hips.

May too blushed. "Ok, ok, I see your point."

"I thought so." Dawn grinned.

Another few minutes passed without any words exchanged between the two. That is, until Dawn got an idea.

"How about we make things interesting?" Dawn questioned.

"What do you have in mind?" May asked, very intrigued.

"Let's make a bet." Dawn replied.

"Ok, what's the bet?" May quizzed.

"I bet I can win a battle with Ash, without using a single Pokémon. If I win, you have to confess to Drew, but if I lose, you get to decide my punishment." Dawn chimed.

"Oh, your on." May agreed.

"Great. I'll be right back." Dawn smiled and walked off. May watched, confident she would win the bet. Dawn approached Ash and said "Hello Ash."

"Hey, what's up Dawn?" Ash asked.

"I was wondering if you could do something for me." Dawn chirped.

"Sure." Ash responded.

"I challenge you to a battle, and I'm going to win it without using any of my Pokémon." Dawn smiled, confidently.

"You're on, but I wouldn't be so sure you're going to win." Ash boasted, taking a Pokéball from his belt. "After all, just because we're friends doesn't mean..."

Ash was interrupted in his speech, by a kiss on the cheek from Dawn. His face turned red at the affection. He was truly defenseless as he stood there, frozen, unable to comprehend anything else and dropped his Pokéball. Dawn pulled back, a satisfied smile, as well as, a slight blush dusted her cheeks.

"I win." Dawn stuck her tongue out at him playfully. Dawn then turned to face May, who's mouth hung open in shock. 'I win the bet too' Dawn mouthed to her. Before Dawn could rejoin May, Ash grabbed her shoulder, and turned her back to him. "Ash, I-"

Dawn wasn't given a chance to explain, for Ash had silenced her, with a kiss of his own. Although, this kiss, was on her lips. Dawn was definitely surprised by the action, but kissed him back nonetheless.

May just watched, her mouth hanging open in shock. 'I can't believe she won the bet! She even got him to kiss her. And now, I have to confess to Drew how I feel! I never should have taken that stupid bet!' May thought.

"Ya know May..." Drew closed her mouth, now standing next to her "...if you're mouth opens any wider, a Butterfree might fly into it. What are you watching anyway? Oh." Drew stated when he caught sight of the two kissing. "Well, good for them." He glanced back at May and gave a sigh. 'Of course. She is jealous. I should have known she liked Ash.' Drew thought, bitterly. "Well, I'll just leave you alone."

"Hu...what? Drew, wait!" May sounded, snapping out of the shock.

"What?" Drew asked.

"I...I need to tell you something." May replied, nervously.

"Ok, I'm listening." Drew stated.

"Well...I...I kind of..." May stuttered.

"Kind of what?" Drew questioned.

May began to blush a bright red, and tapped her pointer fingers together. She gulped before she continued, avoiding his gaze "Drew, I...I love you."

"You what?" Drew blushed, shocked.

"I love you." May repeated. "But, I get it...I'm just your rival and..."

Drew stepped forward and lifted her face to meet his gaze. "May, I love you too." Drew smiled. He then, suddenly, planted his lips on hers. When he pulled back, he couldn't help but smirk at her bright red, flustered face. "If it's not to much trouble, might I ask what made you confess so suddenly?" Drew asked, acting like he was going in for another kiss.

"Um...D-Dawn bet me....she c-could beat Ash in a b-battle w-without using a s-single Pokémon. I-if she won...I confess h-how I feel about you." May stammered.

"Well, then I guess I should thank Dawn. Otherwise, who knows how long it would have taken for us to be together." Drew remarked. He stole another quick kiss.

"Looks like May held up her end of the bet." Dawn commented, gaining their attention.

May and Drew turned towards Dawn's voice, to see Dawn standing there with Ash, his arm wrapped around her.

"Yeah...looks like." May muttered, still flustered.

"I have to thank you Dawn." Drew flipped his hair. "Without you, I wouldn't have the girl I love." He took May's hand and gently kissed it, earning yet another blush.

"No problem. I was happy to." Dawn smiled to Ash.

"So, what should we do now?" Ash asked the three.

"How about a double date?" May suggested, finally able to speak properly.

"Sure." They replied in unison.

So, the two new couples left to go have a double date.

THE END!!!