Cross-Dressed Lover

The Sailor Maid Dress

  You know what I realized? Ash didn't have to cross-dress in XY or XYZ. We must remedy this situation at once. This takes place after the crap with Lysandre and everything is A-OK. Don't take this too seriously, it's all in good fun! Pairing is Megabondshipping, meaning Ash x Alain. 

... 

"Serena! Are you serious?!" shouted Ash, clutching the poster Serena had given him. He was staying Lumiose City with Clemont and Bonnie to learn more about Mega Evolution and his bond with Greninja. Serena had come back from Hoenn one morning during breakfast to visit and showed them a poster about an upcoming showcase in a few days. He thought she wanted to ask if they were interested in watching, not being a part of it! And what did it mean by girls-only?! Serena clapped her hands together pleadingly. She was practicing hard for Pokémon Contests in Hoenn and didn't have much of a budget for the great clothes her competitors wore.

"I'm sorry! But the prize was free performance clothes for a year and I couldn't let it pass me by! Please, just for a day?!" Clemont looked like he was going to pass out holding onto his table as a life support.

"But you want us to compete too? Why not take Bonnie?" Bonnie was giggling to herself as she swung her feet from her chair.

"I'm not a trainer or a performer!" she reminded them singingly, tapping the requirements on the poster. "It should be so much fun!"

Before Ash and Clemont could reject, Serena snatched the poster and pointed at the fine print on the bottom.

"'The host will also be bringing her Mega Evolved Ampharos and will accept challenges,'" she read, grinning when she saw Ash freeze. "'Performers must pass the Theme Performance of bonds and a select few will proceed into the semifinals and face each other in a Pokémon battle to test bond strength. The winner will face the host!"

She danced victoriously in her head when Ash got up with a fire in his eyes. He raised his fist to the air. "I'm entering! It doesn't matter if I suck at dancing, right?!"

She giggled. "At least do okay so there's still a chance for me to get clothes! As long as we all make it to the semifinals, we have it in the bag!"

He nodded vigorously. "Fine!"

They all looked at Clemont, who began to sweat under the pressure. He looked around wildly for an excuse.

"I-uh, need to watch the gym-" Clembot, who was taking their dirty dishes to the sink, interrupted enthusiastically.

"I will watch it for you!" he offered. Meyer, who was silently listening on the couch, laughed when his son began to sob at the loss of excuses.

"Think of it as giving Bonnie an older sister for a day! Besides, Serena needs your help and you're always gonna help a friend, right?" Clemont sobbed at the table, finally agreeing with a shaky nod. Everyone cheered over his groans.

...

They were in a dress shop to find Ash and Clemont the perfect disguises for the showcase. Clemont hid in a corner while Bonnie and Serena were discussing what colors would work well on the boys. Ash sighed, finally regretting saying yes to this stupid idea. He would've rather ask the host to battle their Pokémon rather than humiliate himself. He shouldn't have agreed so quickly.

But he was sort of used to cross-dressing, having done so in the past numerous times. He even wore a maid outfit. Ugh. Pikachu, sensing his trainer's sadness, gave him an encouraging pat on the head so he could cheer up.

"Light blue for Clemont!" announced Bonnie, diving into a rack.

"Dark blue for Ash!" decided Serena, fishing out a dress. Bonnie immediately chose a light blue one with a skirt shaped in flower petals. It had a thin top, but the skirt was wide like a bell. It covered the shoulders with a white collar but left everything else bare. Clemont was dying as the dress was shoved in his hands and he was thrown into a dressing room. Pikachu was plucked off Ash's shoulder so he could get his. Ash got a cross between a sailor and maid dress with white ribbons and was tossed into the room next to Clemont. The top was white with navy buttons and the bottom was this embarrassingly frilly blue skirt with white accents. Unlike Clemont's, his had sleeves.