Yep lol, I made a sequel to Cross-Dressed Lover! I enjoyed writing it too much and needed to have an excuse for Ash and Clemont to suffer to benefit others. Thanks to MellieCrescent for the idea of a sequel!
It was a good few months after the Lumiose Showcase. Ash and Alain started dating after and were constantly with each other so they could spend time together under the guise of Alain teaching Ash about Mega Evolution. In that time, Alain had secretly found Charizardite X and a Key Stone with Mairin and was waiting for the perfect time to surprise Ash with it.
Serena was back in Hoenn to compete in Pokémon Contests and Clemont was running the gym per usual.
Life was good. Well, except for Alain fondly looking at Ash's picture of him in a dress at least once a day. He took a ton of pictures when they had forced Ash and Clemont to wear all the dresses before Serena took them.
"Can't you dress like that for me again?" he would always ask. Of course Ash would deny him and change the subject.
Today was the day Serena would come visit them as she always did once in a while. She had told them prior that she had something really important to tell them and Ash and Clemont needed to be there. This conversation might sound familiar…
"Serena, are you freaking kidding me?!" shouted Ash, clutching the frilly invitation she gave him. Clemont was shaking his head, color quickly draining from his face.
"No no no no no…I can't do this again," he squeaked, he could still feel the wig in his sleep. Bonnie and Mairin were excited.
"A photoshoot?!" they squealed, eyes brightening. Serena nodded enthusiastically.
"Valerie is making dresses again and she sent me an email and invitations to get 'Ashley' and 'Clemelia' together so the three of us can do a photoshoot in her clothes. She was really impressed with our performances at the stadium. She's gonna make designs based on bonds between humans and Pokémon again, so it would be great if we brought the Pokémon we used in the performance to inspire her, her words." Alain was silently listening, nodding when she finished.
"Obviously, that means I go if Ash goes." Ash did a double take.
"No, why do we need to do this again?! Serena, you can go by yourself and say that you couldn't get us to come!" Serena pouted.
"But that's just sad if it's just me. Imagine how Valerie would feel!" Clemont grit his teeth.
"Imagine how I feel, please!" Bonnie ignored him, eyes sparkling dreamily.
"If we go, imagine all the models we'll meet! Clemont will finally find himself a keeper! We need to go!" Mairin nodded, raising her hand.
"I wanna come too! And are you two getting ready?" she asked when Clemont and Ash began stomping up the stairs.
"Nope. There's nothing to benefit us. No Mega Evolved Pokémon, no cross-dressing," stated Ash as if it were his one reason to do it. Mairin nudged Alain sharply.
"Alain! Do something!" she hissed. He was already moving, running to grab Ash's wrist. The younger male paused, looking back with a scowl. Alain smiled sweetly.
"Guess what I found a few weeks ago." Ash eyed him suspiciously.
"What?" Alain didn't drop his smile.
"Charizardite and a Key Stone." Ash immediately dropped his scowl, replaced with child-like joy.
"So Charizard can Mega Evolve again?" Clemont tried snapping his fingers in front of his face to snap him out of it. Alain flicked his hand out of the way.
"Yeah. If we go, I promise we'll battle after." Clemont tried to growl, but it wasn't threatening.
"Why after? Why do we have to cross-dress for you to battle Alain? Your own boyfriend?" he asked tersely to get Ash's attention. Ash's eyes widened, putting his hands on his hips.
"Yeah, why do I have to dress up to ask you for a battle?" Alain glared at Clemont, then relaxed for Ash.
"If your reason to cross-dress is for Mega Evolved Pokémon, then I'm not wrong." Everyone else was snickering behind him.
"Ash." Oh Arceus, was he simpering? And even pouting? "Please?"
The others had identical begging stares, Bonnie especially. Clemont was shaking his head, grabbing Ash and shaking him back and forth to get a hold of himself. In Ash's head, he could only see him battling Alain. With Mega Evolved Charizard. And let's be honest, Alain went out of his way to get Charizardite. Might as well…return the favor.
"Okay…" Clemont let go and ran to hug the wall, wailing while the others were cheering. He suddenly had a bright idea. Luckily his friends knew nothing about technology, so maybe he was in the clear!
"C-Clembot needs some maintenance on him! He can't take care of the gym if he's not fixed up, so I might as well stay!" At this, the girls whined, but if maintenance was needed, it was Clemont's job to make sure Clembot was running properly. Like any dutiful robot, Clembot stepped out of the kitchen in his apron.
"You documented that I have approximately two weeks before maintenance is needed. There is no rush. Please go enjoy your day!" Meyer could be heard laughing from the backyard.
"Go, Clemont! You lost again!" Before Clemont could complain, Bonnie latched onto his neck with her arms. Her eyes burned viciously.
"You tried to lie to us?!" Mairin and Serena seized his arms and dragged him up kicking and screaming to get him changed.
Alain glanced at Ash, silently challenging him. Ash knew better than try to wrestle against Alain, having lost many times before. He went to his room to change with Alain following him.
Ash reluctantly stared at himself in the mirror, turning this way and that to look at how the dress was on his body. The dress had long sleeves and was just as short as the sailor maid one. It was more normal than performance. Alain walked in and hummed.
"It looks as nice as the first time you wore it," he complimented. It was the dress he had first chosen for him to wear, after all. Ash frowned.
"Why do you like me wearing these sort of things?" he asked, pausing as Alain wrapped his arms around him from behind.
"Because you look cute," he answered simply. Ash fumed.
"And I don't on every other day?" Alain didn't wait a beat.
"You do, but I like it when you wear things like this too." He grinned and pressed a kiss against his temple. "Thank you for doing this."
Ash grumbled. "No more asking me to dress up after this."
Alain sighed. "At least for a while. Don't forget the stockings."
He voiced it to sound helpful, but Ash couldn't hear the smirk in his voice as he begrudgingly slid them up his legs.
A scream had them both jolting. Ash immediately ran out, not bothering to keep his skirt down. It sounded like Clemont was in trouble.
In his eyes, he was. Bonnie was tugging on him to wear a yellow dress with white polka dots on it. The wig was a mess on his head with Serena trying in vain to set it right. Mairin was laughing while kicking her feet on his computer chair. Ash grimaced.
"Man, we're really torturing Clemont with this, aren't we?" Mairin flounced over and slapped the brunette wig on his head.
"Your turn!" Ash was forced into the chair while Mairin went to work in making him look like Ashley again.
They were heading to Laverre City by train, which was the fastest way to get there in time for Valerie's photoshoot. They were in their seats when Ash felt the need to cool down in the bathroom. It was stuffy and the dress had longer sleeves than he cared for.
He nearly had a heart attack when Clemont grabbed his arm when they were alone in the bathroom. His friend looked desperate.
"Ash, we don't need to go through with this! We can just sneak off the train at the next stop, say we got caught up in the chaos and couldn't catch up to them!" Ash sighed sadly as he fanned himself. He was thinking about all sort of escape routes ever since they got on the train. Pikachu stopped him from jumping out the emergency exit because it was running. He was sure he would've made it.
"I thought about that, but Alain has Charizard. He would've sent him to pick us up." Clemont began to sob, staring at himself in a mirror. He shuddered when he saw how prominent the polka dots are. He looked unsightly in this thing.
The door opened, but they didn't pay attention to lament their disguises. Until that person spoke.
"Why are two girls in the men's restroom?" They froze, quickly realizing their mistake. Before they could come up with an excuse, a chuckle followed.
"It's just me. Nothing to worry about unless someone else comes in." Alain waved at them, letting them sigh in relief. Clemont took off so he wouldn't be caught by the next person heading into the bathroom, Alain moving to the side to let him through. Ash rested his face in his palm, thanking Arceus that it was Alain who walked in and not an unsuspecting passenger.
"I totally didn't think about that! Thanks, Alain." Alain smiled as he walked towards him, taking his hand and pecking it.
"You're welcome, mademoiselle." Ash winced. Man, agreeing to this was one of the dumbest decisions he'd ever made. And that was saying a lot. The train suddenly jolted at a sharper turn, making them move with it and stumble for balance. Alain held his arms out to stay on his feet, pinning Ash against a sink while Ash grasped his shoulders. The two were familiar with being close to one another, so there wasn't a blush shared between them. The bathroom door opened again, a train passenger immediately bristling when he saw the two pushed up against a sink.
"What are you two doing?" he asked stiffly. Ash froze.
"I-I-" Afraid he might blow his cover, he ran for it with Alain laughing behind him. Ash went to brood in his seat with Clemont, both wanting this day to end.
"Welcome back to Laverre City!" greeted Valerie outside her gym, looking elegant in her kimono. She hugged Serena and smiled at Ash and Clemont politely.
"It's an honor to meet you both," she greeted, grasping their hands delicately. They dropped to a curtsy just like Serena trained them, Clemont's muscles shaky as he was unfamiliar with the action. Ash luckily remembered from his curtsy to Alain. Valerie turned to Alain and Mairin.
"And you two must be…?" Mairin nodded to her.
"I'm Mairin! This is Alain." Alain wasn't looking at Valerie, which didn't go unnoticed by her. Instead, he was smiling at Ash trying to curtsy. Valerie's eyes widened, a new idea coming to mind.
"Are you two lovers?" she asked, gesturing between the two of them, wanting to be sure before saying her idea out loud. 'Ashley' turned red, glancing at Alain who was confident.
"Yes," he answered. Satisfied, Valerie held her arms out welcomingly.
"Then I've decided to change my photoshoot. I want to make a wedding dress to symbolize the bonds of romantic love!" Ash's thoughts screeched to a halt. He could barely handle dressing like a girl and suddenly he was going to be wearing a wedding dress? The girls were shining with joy, Serena gasping at the idea of her in a wedding dress or a bridesmaid one.
"That's such a great idea!"
'For you!' Ash and Clemont thought fiercely. Valerie tapped her chin in thought.
"Actually, I like the idea of having wedding dresses using Pokémon as inspiration. Our new theme is romance!" she announced to her attendants. They all cheered, hurrying to help her draw out her visions as they chirped about their excitement. She smiled at the others, the boys still shell-shocked at the sudden change in development.
"But we can't just have Ashley and Alain as our only couples. Serena, I would still like to have you pose with your Pokémon in bridesmaid attire. As for Clemelia," her eyes shone with enthusiasm, "I shall have someone model with you! An innocent romance between two people. You have the perfect look. I'll have a male model assigned to you immediately."
"A guy?" Bonnie's hopes were dashed. How could she find her brother a keeper if the person he'll be working with is also a guy?
Alain didn't care about the change in plans. In fact, he was really liking it. Ash in a wedding dress. The only time he'd wear it. This was just too good to pass up. He caught Ash when he fell back, his soul desperate to part from his body.
"Why is this happening?" he breathed, Alain chuckling and kissing his forehead fondly. Clemont was looking for any possible exit out of this, but was suddenly approached by a tall male with dark burgundy hair and blue eyes. He smiled at him and reached for his hand.
"Hello. My name's Leo. It's a pleasure to meet a beauty such as you, mademoiselle." He kissed Clemont's hand which was thankfully blocked by a glove. He felt the hair on the back of his neck stand on end. His mind was screaming for him to let go, but luckily Bonnie was running to the rescue while everyone stared in horror at the model's sudden action.
"Let go of my bro-sister!" she corrected quickly, waving a surprised Leo away. "Keepers only!"
Right now, Clemont agreed. He needed to find a way to disappear and fast. But he was quickly taken by Valerie's ladies to get changed with Bonnie in tow. Serena had to follow suit for her dress and Alain took Ash to head to where he was being called.
This was a huge problem. And who knows if they were going to make it to the end of the day? At this rate, Ash and Clemont might go insane!
Lol sorry, Ash, Clemont, but for the good of me, the girls and Alain, cross-dressing is important! But how are things gonna go now? We'll see, hopefully the next chapter's longer!