Well, here's my first Pokémon story! It is an Ash/May story and it'll be based off a song I really like - Alessia Cara's 'Stay'. This is set during episode 466 (AG192) - 'Home Is Where The Start Is!' As per usual, nothing you see here is mine! Without further delay...ROLL IT!
The sun is setting in Terracotta Town. 14 year old Ash Ketchum and 13 year old May Maple have just tied in the unofficial Terracotta Pokémon Contest and each have a half ribbon to show for it. Now they've both started planning for the next phase of their journey. May's next words will shock the young Trainer...
"I've decided to enter the Johto Pokémon Contests by myself!" she declared to her friends and brother.
'WHAT?!' Ash thought. 'I know she's come far as a both a Trainer and a Coordinator, but going out on her own? And to the Johto region, no less? Where Team Rocket still has strongholds? If anything happened to her, I don't know what I'd do! I gotta stop her! I gotta tell her I love her before it's too late!'
No one else knew what the young trainer was thinking. But he did. Something inside him went off telling him that May made a haphazard decision. Ash then realized that Max had gone missing. He quickly walked away from the picnic they were having to go talk to his genius friend. "Max..."
"Oh. Hey, Ash," Max greeted with a somber look on his face. "What's up?"
"Ever feel like something...or someone...is being torn away from you right when you need them the most?" Ash asked. Max knew he was talking about his sister.
"I knew it...you're in love with my sister, aren't you?" he asked.
"I am, Max," the Trainer confirmed. "Now I'm losing her and I haven't told her how I really feel about her..."
"Tell her, Ash. You can save her from making the biggest mistake of her life."
Ash smiled. Max agreed with him and Brock that May could be making a huge mistake by going out on her own. It was up to the aspiring Pokémon Master to tell May how he felt before she left and possibly made a huge mistake.
Now, thanks to Max's assessment that his sister could be making a huge mistake, Ash sprang into action, running to May just as the last call for the ferry back to Petalburg City was being made.
"MAY!" Ash called out.
May turned behind her and saw the jet black-haired Trainer coming up behind her. "Ash?"
'This is it, Ash Ketchum. It's now or never', he thought.
"May, I've got something to tell you..." Ash started. "Throughout our journey together, I've watched you grow as both a Trainer and a Coordinator. In turn, you've helped me grow as a Trainer. I don't know what I'd do without you. What I'm trying to say is...I love you, Maybelline Allison Maple!"
May blushed at Ash's confession. She smiled and kissed him before saying "Ash, I've been waiting for you to say that! Truth is that...I've been in love with you ever since I saw how you never left Pikachu's side on the day we met. I was so excited to travel through Hoenn and the Battle Frontier with you. Now that I know how you really feel...I can't wait to see where our journey takes us next!"
"OUR journey? Does that mean...?"
May smiled. "That's right, Ash. While I may head back to Petalburg City now, as soon as I find out where you're going next, I'll be right there by your side. I'm staying with you!"
"Guess that means we're..."
"Boyfriend and girlfriend."
Immediately, Pikachu climbed on top of Ash's shoulder. "Pikachu Pikapi! Pi Pikachu Pika!" (Translation: Nice goin', Ash! You finally got yourself a girlfriend!)
"She's more than just a girl, Pikachu. May's a woman."
As May and Max sailed away to Petalburg City, Brock came up to the duo of Ash and Pikachu..."Well, Ash...you finally did it. You finally have a girlfriend."
"I know, Brock. And I know I'll see her again real soon."
On the ferry back to Petalburg City...
May looked off into the distance to where Ash was standing. "What's got you so happy, sis?" Max asked of his sister.
May swooned. "I finally have the man of my dreams - and I know I'll see him again...when OUR journey continues."
Not 2 months later, she did rejoin Ash and later Brock alongside fellow Pokemon Coordinator Dawn as their journey through the Sinnoh region began. And all she had to do...was STAY.
"You know what the best day of my life was, Ash?" May asked of her new boyfriend.
"What was that, May?"
"When I decided to come to Sinnoh with you..."
Ash smiled and kissed May. "Everything couldn't be more perfect now that I'm with you, Maybelline Allison Maple."
So, when I heard 'Stay' for the first time, I thought back to the final episode of the Advanced Generation of Pokémon and figured that if the song was out during that time, there'd be no doubt in my mind that if Ash had sang it to May, she would've stayed. Anyway, I hope you enjoyed this one-shot!