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Ash admitted it: he liked wearing dresses. It took him seven years, but he finally admitted that he liked them. The problem with that, and the reason he loathed to actually enjoy it, was that he could not see himself comfortably wearing a dress and battling as well as he did in jeans or shorts.
The first time he wore a dress was for battling, though. He wasn’t allowed in the Celadon Gym, so he dawned the disguise and created Ashley. Granted, even as he thought back on it at seventeen years old, he still hated that day, and that wasn’t the first time he actually wanted to enjoy being in a dress.
No, it wasn’t until he was in Unova that he actually enjoyed being in a dress. He didn’t admit it, of course not. He couldn’t. But the flowy fabric and pretty wig, the light make-up and just daintiness of it all was far more pleasant than he could ever remember it being. So, when he was presented the opportunity once again in Alola, he didn’t protest as much as he could have. The nurse’s outfit was very comfortable, and he wouldn’t admit it in front of Kiawe or Sophocles, but he really liked how he looked in the dress… He didn’t admit it to himself until much later, after having gotten over his embarrassment and was looking through the photos by himself.
So, even though he could admit it to himself now, Ash still didn’t know if he could ever admit that he did like wearing dresses aloud and to his friends. Instead, he kept it to himself as he headed home for a short spring break from the Pokemon School. It burned in his mind, thinking about how he did like dresses, and he liked wearing them, and he liked looking feminine. It still didn’t sound right to Ash; he was a battler! He battled, usually intensely, and that was far from feminine. If he wore a dress with the way he battled, it’d be in tatters before the end, he was sure of it! Then again…he had worn a dress and battled before…and nothing happened to it.
Ash shook his head and stared out the window of the plane, ignoring Pikachu when he called to him.
At home, Ash hid himself away in his bedroom. His mom was content to babysit his pokemon and play with Pikachu, so he was able to pull out his laptop and start looking things up without worry.
There were tons of dresses he found online that were just so pretty. Orange ones, yellow, pink, green, blue ones… One that caught his eye and made him hover over ‘Add to Cart’, was a cute powder blue dress that was supposed to fall right at the knees. It had half-length sleeves and a sweet, rounded collar, a barely gathered waist, and the design had simple white hearts. The dress was very cute, and Ash…Ash desperately wanted it.
With the option to actually have a dress on be his decision, he actually found himself looking forward to putting it on. The hard part was…buying the dress.
Correction, Ash decided, the hard part was putting it on, even the safety and comfort of his own room. His mom had gone out for the day with Mr. Mime, which meant that Ash and Pikachu had the house to themselves. His dress had just come in that morning, and now Ash stood in front of his mirror with the garment in his hands, willing himself to put it on.
“Pikapi?”
Ash shook his head, groaning and throwing his head back. “This is way more difficult than I thought it would be, Pikachu…” He turned away from the mirror and tossed the dress on his bed, sighing and yanking his shirt off; he slipped off his shorts as well, and took the fabric of the dress in a shaky hand, tossing it over his head and yanking it down like a shirt. “…Well?” he started at Pikachu, “How do I look?” The question was more to break his own nerves, not for a response.
Pikachu nudged his hip toward the mirror, and Ash squeaked as he moved to face his reflection.
…He didn’t look half bad. In fact, Ash felt…really pretty. He saw himself smiling in the mirror, and he blushed brightly. Oh, Arceus, he was actually smiling, he was happy about wearing a dress! Soon the smiling turned into giggles, and then Ash did a quick twirl in the mirror. This was so nice when it was his choice! He felt…happy, confident, pretty –
Ding-dong! Ding-dong!
And now that happy feeling was replaced with pure fear. The bell rang again, and Ash cursed, headed down the stairs quickly and hiding himself behind the door as he opened it. “Hello – Gary! Wh-what are you…what are you doing here?”
“I was coming by to drop something off from Gramps; when did you get home?” Gary asked, eyebrows knitted together and head tilted in confusion.
Ash gulped, and he was sure his whole face was burning red. “I, uh, got home three days ago! Spring break, y’know?” He laughed awkwardly, desperate for the researcher to just go back home. Gary had been his crush for years, and at the moment he really, truly, desperately didn’t want his crush to see him. As confident as he felt alone, it was a completely different story in front of anyone else.
“You mean to tell me you’ve been home for three days and you haven’t been by the lab yet?!” Gary sounded genuinely offended, but the smirk on his face said otherwise. “C’mon, Ashy, it’s been a while! Why don’t we play catch up, yeah?”
Panic, panic, panic, panic – “Uh, m-maybe – maybe later, Gary! I, uh, got lots of homework and projects and reading, yeah, reading and-“
He was cut off as Gary rolled his eyes and took a step into the house. “Yeah, yeah, yeah,” Gary drolled, waving him off. “Ash Ketchum, studying! That’ll be the day!” Gary stepped into the house, hand going to his pocket before he turned around to look at his friend, and suddenly his cool demeanor was forced away by the prominent blush on his face. “Uh…”
“Shut up!” Ash yelled, slamming the front door shut. “Don’t say anything; I know it’s weird, gimme a minute!” Before Gary could even say anything else, Ash was up the stairs running toward his bedroom.
“Wait – Ash!” Gary took off after him, tossing the slammed-closed door open and snatching Ash up by the waist.
“Gary, put me down!” Ash barked, thrashing and squirming in his arms. “Let me go!”
“Wait a second, Ash, just…what’s going on? Why the pretty little dress?” Gary asked, setting Ash on his feet and facing the mirror. Ash’s whole face burned bright red with his embarrassment, and he wanted nothing more than to just disappear. Pikachu fled the room to go find Umbreon, knowing the pokemon had to be around if Gary was.
“Just let me go, Gary,” Ash mumbled, pushing on his arms and trying to get free.
“I will,” Gary said, “after you tell me what’s up.”
Ash sighed, slumping in the researcher’s arms as he gave in. “Fine…I’ve – There’s been a few times I’ve had to wear a dress before, and the more and more I thought about it…Forget it! It’s stupid!” He started to put up a fight again, thrashing and pushing as he tried to get free, but Gary just pinned him to his chest.
“You thought…that you actually like wearing dresses?” Gary said, deciding to try and finish the thought for the other boy. Ash stilled in his arms once more and nodded, feeling his face heat up with reckless vigor once again. “And what was your decision, after putting this dress on?” Gary asked.
“…That I do like wearing dresses…” Ash mumbled. He couldn’t believe he’d just said that to Gary. There went all his hopes of him ever returning his feelings.
“Well, that’s a good thing, because you are positively adorable in this dress, Ashy.”
“…Wait, what?”
Gary grinned down at him, finally letting go of his hold on Ash so that he could stand up straight. “I’m not gonna lie or beat around the bush about it, Ash, you look cute… Cuter than normal, even.”
“…Cuter than normal?” Ash repeated. Did Gary Oak just admit to finding him cute? Really?
Gary nodded, grinning wide as he reached out to take Ash’s hand. “Yes, Ashy, believe it or not you’re cute all the time. It’s really not fair, y’know.”
Now, Ash might should have thought it out a little bit more, but he couldn’t hold himself back. He launched himself back into Gary’s arms, tossing his own around Gary’s shoulders to tug him closer as he kissed him. Gary stood shocked for only a second before wrapping his arms around Ash’s middle and holding him close, deepening the kiss.
As they broke away, goofy grins on either of their faces, Ash felt that same surge of confidence he’d had just a little while earlier. He felt happy again, and this time it was because of Gary. How did he get this lucky?
“Hey,” Gary called, rubbing their noses together just to make Ash laugh. “How about a cute little fashion show?”
Ash rolled his eyes and hit Gary’s shoulder. “I should kick you out…but I don’t want to.” He caught the researcher’s lips once more, kissing him sweetly.