I don't own Pokemon. This is for the Serebii Advanceshipping contest.
"Aip!" A voice made May come out of her thoughts. She felt something slightly heavy on her shoulder, as she turned to look a red rose came into view.
"An Aipom?" May questioned as the Aipom had given her a rose from her three-fingered hand on the end of its tail. May noticed the hat on Aipom's head. "Wait, are you Ash's Aipom?"
The playful monkey Pokemon smiled and nodded.
"Yep, definitely Ash's!" May grinned but then she went back to sighing.
"I guess it didn't work!" A male voice said. May jumped slightly but relaxed when she saw it was Ash. Aipom gave a happy grin and she went on her trainers shoulder.
"What didn't work?" May asked. Ash laughed softly and sat down next to May.
"Cheer you up!" Ash said. "I asked Aipom to pick me a rose so I could give it to you, but she decided she wanted to give it to you herself!"
"What do you mean?"
"Ever since your battle with Drew you've been kind of sad lately." Ash explained. May sighed. "Like that."
"Well," May suddenly shivered. Ash took off his hoodie and gave it to May.
"But you'll be cold…" She said as she hesitantly took it.
"But you'll be warm, and that's what matters.." Ash shrugged. "Now, tell me what's wrong?"
May slipped on Ash's hoodie and sighed in warmth. "Ash, after the Battle Frontier, where are you going?"
"Sinnoh." Ash replied. "Gary wrote to me saying that there's new Pokemon there, you should come too, I'm sure they have Pokemon Contest-"
"Woah!" May said. "Slow down, I don't think I want to go to Sinnoh!"
"Why not?" Ash asked.
May blushed. "I just don't know what I'm going to do after the Battle Frontier!" May said. "I was thinking of following my rivals, to Johto…"
"Oh," Ash looked at his Aipom as the monkey Pokemon was playing in flowers.
"Alone…."
"Don't you like travelling with me?"
"Of course!" May said. "But I just want to see how I'll be able to make it on my own, to develop my own battling style and not having you, Brock and Max to bail me out!"
"Have you told Max yet?" Ash said. "If you go alone, that means he has to go home…"
"I know," May looked away. "I hope he will understand, I haven't made any decisions yet, but I think it'd be good for me, finding my own battle style and not copy yours…"
"About that, I'm sorry I failed you…"
"Failed me?"
"Yeah, If It wasn't for me being your mentor you might have won the Grand Festival!" Ash growled. "A trainer should never mentor a coordinator!"
"Now you stop right there Ash Ketchum!" May shouted. "If it wasn't for you I would have still been afraid of Pokemon, if it wasn't for you I wouldn't have made it so far and if it wasn't for you, I wouldn't have become the coordinator I am today!"
"Thanks May," Ash smiled.
"So, roses huh?" May blushed. "They're beautiful but why did you think it'd cheer me up?"
"Well, Drew usually gives you a rose, I noticed when he left he didn't and you get all inspired and fiery whenever he gives you one, so I thought if I got you one you'd get your spark back!" Ash shrugged. "Stupid idea.."
"No, it was sweet and very thoughtful…" Tears welled up in May's eyes. "I didn't know you cared so much…"
"Of course I care May!" Ash placed his hands on her shoulders, May blushed remembering the first time he did that. "You're very important to me, I'm so proud of how far you came along, you're not the same girl I first met who didn't know how to battle…."
"Thanks Ash!" Aipom came back to the group. On her tail was a crown of flowers. She took off May's bandana and placed the crown on her head.
"Wow, you look like a Princess May!" Ash grinned.
"I guess I do!" May laughed. "So where's my Prince?"
Ash smirked. He kneeled before May and took her hand. Aipom curtsied. "Greetings, fairest of maidens, may this Prince take you on a magical ride?"
"You're no Prince; you're nothing but a Pauper!" May raised her eyebrow. "But what magical ride do you mean?" May huffed playfully and turned away.
"Go, Charizard!" Ash shouted releasing the monster. Charizard gave Ash a flamethrower. May covered her mouth as she giggled.
Charizard lay down on his claws and folded his wings. Ash climbed on his neck. He held out a hand. Aipom went more on Charizards head. May looked unsure.
"Ah Ash, Is this safe?"
"Of course it is!" Ash pulled May more towards him. "Don't you trust me?"
"Of course I trust you!" May wrapped her arms around Ash's waist.
"Let's go Charizard!" Ash commanded. Charizard gave a growl as he flapped his wings. May felt wonderful as the breeze lifted up her hair.
"This is wonderful Ash!" May sighed as she snuggled more into Ash's back.
"I'm glad you like it!" Ash blushed. "If you do go to Johto, I wanted us to do something together, alone, just like the day…"
"We first met!" May finished for him.