@yamujiburo this is very much your fault that I had to make this at 4am, but here we are.
The hoot-hoot clock on the wall ticked away the early morning hours as Jessie sat up reading on the couch. It was one of those restless nights where her brain kept reminding her of her various screw-ups. Once, she would have channeled that energy into devising some new caper with James and Meowth, but now they were upstanding citizens- the boys assisting Sam with his research, and Jessie…
Well, here she was, reclined on a couch she helped pick out, living in the house she shared with her wife and her stepson. How much of a screw-up could she really be? Take that, brain.
She only caught herself smiling when it was startled from her face by an unexpected voice.
"Da- Jessie," Ash started from the hallway. "...do you have a minute?"
He called her Dad most of the time because she pretended to be annoyed by it and it was hilarious. To hear him use her name… maybe she had screwed up and the kiddo was about rain down thunderous judgement. Between Delia's cooking and her relative lack of activity- criminal or otherwise- she wasn't sure she was spry enough to go blasting off again.
…But looking at Ash framed in the doorway, she could tell that wasn't the case. He looked small - he was small- only a few years out from the grandest of his adventures when he was ten years old. But he always seemed larger than life, so full of spark and spunk and an eagerness… stuff she'd thought she'd lost long ago. In hindsight, she'd been jealous. But now he looked uncertain. Maybe even afraid.
"What's up, twerp?" She said it warmly- it'd became a term of endearment between them now, though she'd never say it in front of Delia. She folded her book closed and sat up, patting the seat on the couch beside her in invitation. Ash hesitated, looking for a moment like he wanted to flee, but then crossed the room and sat down next to her. "Ash… what's wrong?"
He was quiet for a long moment. Fidgeting with something in his fingers. One of his older badges, worn but well-maintained. A small, bright, multicolored flower turned over between his digits again and again as he gathered his words.
"Do you remember… Celadon City Gym?" He asked finally.
She thought for a moment. Gyms weren't usually her scene, though she'd definitely been to a few, and with Ash… ah. The fire. "Gosh we really bunged that one up. I'm glad no one got hurt." She leaned forward and grasp his arm in sudden realization, "Ash you could've been killed, I'm… I'm sorry."
He smiled and shook his head. "No, not that part. Though I'm glad you aren't blowing stuff up any more." His brief sunny smile slipped back into melancholy. "No I mean, before that. When you helped me get in. With the disguise."
"Oh! That!" Jessie said, relieved, "definitely rushed but some of our better work, if I do say so myself. What about it?"
"I just… nevermind, it's stupid." He moved to stand, but Jessie held him back by his arm.
"Whatever it is, it's not stupid," she said firmly. "Tell me." She relaxed her grip and smiled up at him what she hoped was reassuringly "Please? It'll be okay."
He hesitated again, searching her face for… something, before sitting back down. He ran his hand through his hair and sighed.
"Being Ashley… was fun," he said. "I thought it was just the excitement of sneaking in, and it was that, too but… I don't know, it was… easy?" He shook his head. "I think… I wanted to talk to you… and maybe James? I know he… uh… dresses up a lot. Or did." Ash flushed red as Jessie let him talk. She could tell he'd been thinking pretty hard about this- she was touched that he felt he could come to her, with this or indeed at all. She wasn't really sure where she stood with him most of the time, but now… she couldn't help but smile.
"James and I would be happy to talk about anything you wanted, Ash," she said. "I know it probably hasn't been easy- Pallet is kind of a backwater- and you're kind of a high-profile kid… Anyway, we're both here for you, I can wrangle the boys tomorrow and we can send Meowth off to run some errands, if that's what you want."
"Okay," he said. He seemed relieved already, if a bit still uncertain. "Do you think… do you think you could keep this a secret from Mom for now? I don't want to disappoint her."
Jessie gave him a sharp look. "Kiddo, your mother could never be disappointed in you. She almost broke up with me when I said that Riley kid had maybe filled out a bit better than you at the last Indigo awards ceremony." Ash chuckled and she smiled again. "But. I won't tell her if that's what you want. We can talk to her together, when you're ready, if that's what you want."
He nodded and she ruffled his hair. "Alright, get your butt in bed. It's… ouch, almost 4am."
He stood and walked toward the hall, toward his room. He paused in the doorway, filling it more than he had before, somehow.
"Thanks, Dad," he said, and smiled.
"Goodnight… Ashley." She winked. A bit of a nudge, perhaps, but his smile widened as he disappeared down the hall.
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