I got carried away…
I'd say these characters are aged up to about 18.
"Do I have to?!"
"Yes, you do! This place is girls only and you want to go in, right?" Dawn asked as she sifted through the fancy dresses on the rack.
"Yes…" Ash said dejected. He spotted a familiar purple mop of hair over in the men's section of the building and dashed over there.
"Come here," Ash said, grabbing Paul by the arm and dragging him towards where Dawn was.
"What are you doing?!"
"Dawn's making me dress up as a girl and I refuse to do this alone," Ash hissed at him so Dawn wouldn't hear him.
"Where's Brock then?" Paul asked through his teeth, seething.
"He bailed on me," Ash said, "he started chasing some girl."
"Well you'll have to find another sucker!" Paul said, yanking his arm out of Ash's grip.
"Oh, Ash~" Dawn called, having found a dress and was running towards Ash. She saw who he was with and looked at him confused. "Paul?"
"He wants to go in, too!" Ash said.
"Oh, well I guess I'm gonna dress you too!" Dawn said, practically throwing the one dress at Ash and going back to look for one for Paul.
"Thanks," Paul said in a deadpan, a look of murder in his eyes.
"Oh, come on!" Paul said when Dawn came back with the dress he was to wear.
"You have to wear it!" Dawn said. She was mostly excited about having two life-sized dress-up dolls to work with instead of just one.
"Fine," Paul said as he went into the dressing room to try it on, to his dismay.
"I look so frilly!" Ash shouted from his dressing room. Dawn ran over.
"Let me see!" Dawn said excitedly. The lock clicked open and Ash stepped out in a blue frilly dress that reached the floor.
"Is this necessary?" Ash asked, sweatdropping.
"It's formal dress, Ash, or should I say Ashley?" Dawn said with a big toothy grin.
"Ugh."
"IT DOESN'T EVEN FIT!" Paul shouted in anger.
"Need one a size up or down?" Dawn asked.
"If I have to, a size up," Paul groaned. Dawn fetched him a dress a size up and delivered it to him. Paul threw the first one over the top of the door and Dawn put it on the return rack.
"Dawn, I need another size up…" Paul said in a frustrated tone after a few minutes.
Five dresses later and one finally fit the poor boy. He groaned as he stepped out of the dressing room in an orange number with significantly less frills than Ash's, but with a lot of lace instead.
"Orange? Really?" Paul asked.
"They didn't have a purple one that wasn't super ugly," Dawn said. Paul huffed.
"Now, Paul's hair is fine, just style it a bit, but Ash needs a wig," Dawn continued. She found a black wig that was a bit wavy that would go down to the middle of his back. She put it on his head and examined how it looked.
"Great! Now for Paul!" Dawn said with a smile. She gathered his hair in a ponytail kinda high on his head and secured it with a hair tie.
"Ow! You pulled!" Paul protested.
"Oh, get over it you big baby!" Dawn said as she finished up his hair.
"So, what torture are you gonna subject us to next?" Paul groaned.
"Makeup!"
"Sorry I asked."
Dawn got the two boys into the makeup chair, Paul seething with anger at Ash for making him do this and Ash upset that Dawn's making him do this. Dawn went to work on Ash first, scolding him for not holding still. When done with Ash, she moved on to Paul, who actually stayed still as he knew there was no fighting her if he wanted to keep his eyeballs intact.
When Dawn was done she showed each boy their reflection.
"I look like a girl," Paul said in a deadpan.
"That's the idea, genius," Dawn said sarcastically.
"You look like a pretty girl," Ash said with a smile.
"So do you," Paul said, finally cracking a smile himself.
"You're ready!" Dawn said. "Well, almost!" She dashed off only to be back within two minutes. She was carrying shoes and something small that glinted in the light.
"Earrings! I got clip-on ones!" Dawn said excitedly. She affixed some blue dangles to Ash's ears and some orange ones to Paul's. Then she placed some white heels in front of Ash and some purple ones in front of Paul. Ash's fit but Paul sweatdropped as he realized Dawn had given him shoes that were WAY too small. He lifted his foot with the tiny shoe on it and Dawn got the hint.
"Oh," she said, dashing off to get some that were bigger.
"I'm a size 13!" Paul shouted in anger in her direction. Ash could only laugh. Dawn returned with some more purple heels that actually fit Paul this time.
"Now you're perfect! And it's my turn! Give me like 30 minutes!" Dawn said, dashing off.
"I can't believe you forced me into this," Paul said angrily.
"As if I was going to do this alone!" Ash said.
"If it makes you feel better, Dawn did a good job on you," Paul said.
"Same to you," Ash said with a grin. "I'm sorry I dragged you into this."
"Don't worry about it. I think I kinda like it now that Dawn's not trying to stab my eyeballs with a pencil," Paul said, eliciting laughter from Ash.
"I do too," Ash said. "You make a beautiful girl."
"So do you," Paul said. He stepped closer…
…only for his ankle to twist under him, sending him to the floor.
"Oh my Arceus, are you okay?!" Ash said, helping Paul up off the floor.
"Yeah, I'm fine. Dawn's just strapped these death traps to the bottoms of my feet," Paul said, dusting himself off.
"I'm kind of used to them by now," Ash said. This caused Paul to look up, startled.
"What? Dawn's not the first one to force me into a dress and heels," Ash said.
"For some reason, that doesn't surprise me at all," Paul said with a smile.
"Wanna try that again?" Ash said, stepping closer to Paul. Paul tentatively took a step forward, gripping Ash's arm for balance, before falling into his arms.
"I didn't expect you to fall for me so soon," Ash said with a smirk. Paul blushed and smiled sheepishly.
"Sh-shut up, Ashley," Paul said. Ash helped him up onto his feet.
"Not a chance, 'Paula,'" Ash said, closing the gap and kissing the other boy. Paul's eyes went wide for a minute before he melted into the kiss.
After a minute, they heard a light snicker from behind Ash. They broke apart to see Dawn, dressed in a pink gown far fancier than both of the boys' dresses combined.
"I'm ready, lovebirds," Dawn said, leading the boys outside, Paul holding onto Ash for support until he got the hang of the shoes. He then moved his hand from Ash's shoulder to his hand, holding it as if his life depended on it.
"Welcome to the Ladies' Ball," Dawn read the sign. She lifted her skirt enough to clear the steps to the ballroom and ascended.
"You wanted to go to a lesbian dance?" Paul asked.
"Dawn told me it was a Pokémon gym!" Ash said, clearly upset.
"Might as well enjoy ourselves," Paul suggested, leading Ash inside.
By the end of the night, Paul's toes were in pain, and Ash fell like fifteen times.
"I didn't know you were so bad at dancing," Paul said.
"Well…"
"Never mind. I need to ice my feet," Paul said, his voice giving away just how bad his feet were hurting him.
The two boys went back to the Pokémon Center to where Paul was staying, Paul holding a bag of ice and Ash holding a couple of buckets they got from Nurse Joy. The boys kicked off their shoes, sighing in relief.
"Oh, man, those things were painful!" Ash groaned. Paul filled the buckets with water and Ash dumped half a bag of ice in each one. Ash took off his wig and threw it on the table.
"Hopefully these will help," Paul commented as he drug the buckets towards the bed so they could sit there while soaking their feet. They finally dunked their poor feet in the water, shivered, then sighed in relief.
"It feels better," Ash said, lying back on the bed.
"It does," Paul sighed, mimicking the other boy. He pulled the hair tie out of his hair, wincing when it pulled a few strands out on the way.
"I'm not sure how I feel about this," Ash said.
"About what?" Paul asked.
"The whole… kiss… thing that happened earlier," Ash elaborated.
"Well…" Paul blushed, "I've, uh, kind of had a crush on you for a while…"
"R-really?"
"Yeah."
"What a coincidence, huh?"
"What?"
"I like you, too," Ash said with a big grin. Paul stared into the other boy's eyes for a minute before he rolled over and kissed him. Ash melted into it, accidentally kicking over both buckets in the process, but neither boy cared as only the other mattered.
KNOCK KNOCK KNOCK
"Ash, are you here?" Dawn called. "Nurse Joy told me you'd probably be in here!"
No response.
Dawn tried the handle and found it unlocked. She slowly opened it and was greeted by an interesting sight.
Two dresses lay crumpled on the floor, one blue and one orange. Two pairs of shoes lay abandoned by the door, one white, one purple. A black wig lay haphazardly placed on the table. There was a pair of boxers draped over the lamp and another one about to fall off the dresser. Then she saw them. Two bodies under the blanket, both fast asleep, a mop of purple hair and a mop of black hair visible on the pillow.
"I'll leave you alone…" she said, slowly closing the door.
"So?" Brock asked.
"Looks like they got lucky last night," Dawn said with a smile.
"Finally," Brock said with a laugh.