Pokémon Sword and Shield Gym Leader Family (REQUESTS OPEN)

Milo in skirt

Allister was in his room, he was scribbling on a piece of paper, not really having an idea of what he was drawing, he was just scribbling for fun. 

Milo knocked on the door, Allister stood up and walked over, creaking it open, Milo smiled at him,

"Allister! Piers and I are going to the ranch today, do you want to come with us?"

Allister nodded, he always enjoyed going to the ranch with Milo. Milo started to slowly close the door,

"Ok, go ahead and get ready, we'll head out when we're all ready."

Allister nodded again, went to his closet, and opened it, he threw on a slightly oversized t-shirt, shorts, tennis shoes, and of course his iconic mask. 

He walked downstairs, Piers was scrolling on his phone, Allister looked around,

"Where's Milo?"

"Still gettin' ready..."

"Oh..."

Allister stood by the door, eventually, Milo walked downstairs, he was wearing a light green shirt, his boots, and a... skirt? It wasn't very long, it was short so still practical for working and he was wearing black shorts with the skirt, he smiled,

"Sorry it took me a bit, it took me a little to find my clothes, let's go then!"

The three were walking to the ranch, Piers and Milo were talking, while Allister was thinking. He was thinking about what Milo was wearing... was it really ok for boys to wear dresses? No one really taught him about that. He wanted to ask Milo but- it was a little awkward but he couldn't exactly keep quiet. 

Allister tugged on Milo's shirt, 

"Milo... can I ask you something?"

"Oh! Of course Allister, what is it?"

"Um... Uh... Is it ok for boys to wear skirts?"

Milo chuckled, 

"Of course it is, Allister! I actually have quite a few skirts."

"Why haven't you worn them then?"

"Ah... Well... When Rose was the chairman, he had very... how would you describe it... black and white view, he believed things like well, boys couldn't wear skirts because they're 'girl clothing' but clothes really don't have a gender, if that makes sense."

"So... if I wanted to wear a skirt... you guys wouldn't care?"

Milo smiled, 

"Of course I wouldn't care!"

Piers nodded,

"I wouldn't either. Why the hell would I agree with Rose? He was the one who called me the t-slur, the motherfucker is cisgender, he can't say that word!"

Allister tilted his head,

"What's the t-slur?"

"I'll tell you when you're older."

"Ok!"

The three made it to the ranch, Milo opened the gate and lead them in quickly, making sure no Wooloo roll out, Milo walked over to they hay,

"Allister, could you help me with the hay, and Piers could you herd over some Wooloo? They normally react if you run at them."

Piers ran to the Wooloo and chased them around. Allister lifted up a small pile of hay and threw it onto the ground, Allister looked at Milo, 

"Hey Milo... Why did Piers come with us?"

"Oh funny story actually--"

Piers screamed from a hill,

"I WAS TRYING TO COMFORT A CHILD HAVING A MENTAL BREAKDOWN SO I WAS DRAGGED ALONG BECAUSE I DIDN'T BUY THE DAMN GROCERIES."

"Y-Yeah that's why."

Allister nodded.

Later, when they finished taking care of the Wooloo, Milo smiled at Allister,

"Do you want me to buy you a couple skirts?"

Allister bounced a little and underneath his mask, he was smiling widely,

"Yes! I'd like that!"

Piers flopped onto a hill, Milo chuckled,

"Let's wait for Piers to get up, then we'll go, I'll get some water for him."

"Can I help?"

"Of  course you can."