Kanto - Pewter City

The next day our favorite trio woke up groggy from celebrating the night before. They had spent the money Jessie had received from winning the battle on having a party. Jessie checked how much was left from the money and saw there were still two hundred pokedollars left. She woke the other two up and told them to get ready because they would be going shopping.

James yawned, "Shopping for what, Jess? We already get our supplies from the base."

Jessie, "Those are the basics, I meant get something for ourselves and our Pokemon."

James turned to Meowth who shrugged, "It's hr m'ney. If she wants ta spnt it, let er."

Jessie, "That and we can tag along with them too. Reduce the chance of being rejected, you know?"

James, "Well if you put it that way. Let me clean up! I feel gross."

Meowth yawned, "You two go! I'll stay 'ere and get in contact wit ta base and infrm dem of dis devlpment."

Jessie, "Thanks Meowth, you are the best!"

Meowth preened, "Course I am!"

The two left after an hour towards the market where they saw Ash with Misty and Brock's younger sister shopping for items. James decided to approach them after Ash noticed their presence and wave at them.

James, "Ah! Young Ash. How have you been?"

Ash smiled, "Great, how are you guys? How was your battle?"

Jessie, "Look, I won."

Ash saw the badge case she was carrying, "Wao! Congratulations Jessilina! Hey Misty, come here, I want to introduce you to some friends I made."

Misty, "They are the ones you told me about, the siblings."

Ash nodded, "Yep! This is Jameson and this is Jessilina!"

Misty smiled, "Nice to meet you."

Cindy snickered, "You are the lady, big brother was telling us about!"

Jessilina blushed making Ash raise an eyebrow, 'Huh? If they are not criminals, I guess Brock really would flirt with Jessie!'

Ash, "By the way, we talked it over."

Misty, "And we don't mind having more people to travel with."

Jessilina, "Wonderful! Now what are you kids getting? We can shop together!"

Misty smiled, "Sure, I was getting more bread!"

Ash, "Vegetables and fruits, already got the meat."

James, "I'll help you pick the them, you are already carrying a lot of bags!"

Ash, "I would like to have extra hands."

Jessilina put her arm around Misty's, "I know a good bakery. It has really good ratings among bread lovers. Let's go there!"

Misty, "Great, fresh bread is best bread!"

Jessilina, "I know right?"

They split into two groups, the boys going one way and the girls the other way. The girls entered a bakery at the end of market street and Cindy commented Brock usually ordered bread from this cafe. Misty figured it must make really delicious bread if that was the case, the three of them even decided to try out their famous Chesto berry muffins. Misty brought a whole tray of it since her Pokemon seemed to enjoy it a lot. The boys on the other hand were shopping for vegetables and then moved on to fruits. Lucario and Pikachu put their noses together good use and picked out the best produce making the vendors watch in amusement. One vendor lady even commented on how sweet it was of Ash to allow the Pokemon to choose the food. Ash just laughed and said they had a better idea than him when it came to raw ingredients.

James sat with Ash at a food booth enjoying the lunch, "So, do you do this all the time?"

Ash who was making sure every Pokemon got their food, "Do what?"

James, "Let your Pokemon decide what ingredient to get?"

Ash nodded, "Yeah! Lucario kinda memorized what they like to eat, so I leave it to him. Also it helps he has a good nose to sniff out the best produce."

James sighed wistfully, "I wonder, if my Arcanine would have been the same."

Ash, "Is your Arcanine your first Pokemon?"

James smiled, "Yes, he was a gift from my late grandma, bless her soul."

Ash, "Sorry, I didn't mean to bring up a sad memory."

James waved it off, "It's fine, besides it's good to remember them from time to time. Anyway I had Arcanine as an egg, who hatched into a Growlithe. We grew up together, as far as I can remember truthfully speaking. He's just three years younger than me."

Ash's eyes widened, "Oh! That long, that's amazing."

James smiled brightly, "I know right? He's my strongest Pokemon and the reason why I trust him to protect my parents."

Ash, "Your parents sound like interesting people."

James, "They are a little air headed and have a strange habit of ignorance to the strangest things happening. It makes me worry they will be kidnapped and sold by someone malicious."

Ash frowned, "Like your ex, you mean?"

James nodded, "What about your family, Ash?"

Ash grinned, "My family is my mom, cousin, aunt, the Oaks, they are literally family at this point and Pokemon."

James smiled, "Wait... What about your Dad?"

Ash gave a sad smile, "He passed away before I was born."

James was shocked, 'Boss!!!! WTF? You just can't pretend you are dead!', "I'm sorry, Ash!"

Ash shook his head, "It's fine! As much as I don't want to admit it, it is hard to miss someone you never met. Although from what mom said, he was an amazing man."

James sighed, 'Meowth was not kidding about boss's complicated family.', "Well look at the time, I believe you were planning on meeting the others at the TCC, right?"

Ash got up finishing his food and placing the money, "Yeah! Let's go!"

Jessie was also having a similar conversation with Misty and just leaving the cafe they had lunch in. Misty was telling her about her sisters and how much they loved each other and at the same time drove each other up the wall. Jessie was laughing at some of the stories, Misty shared about their shenanigans and the Pokemon. Jessie told her James had been more of a family for her than anyone else in the world, Misty wanted to ask about their parents but figured they had probably passed away like hers. They met the boys at the TCC and got to work preparing food for the road with Cindy helping them. They first released their Pokemon and made their food for them, it surprised the older man and woman a bit but they had to agree it was not such a bad idea. After the Pokemon food was done, Ash showed James how to make simple and easy, yet delicious sandwiches for lunch and easy yet nutritious burgers for dinner. Breakfast consisted of berry pancakes and milkshakes made from berries and milktank milk.

James, "This is actually good and it's my first time making food."

Misty looked surprised, "Um, you didn't make food for yourselves before? How did you?"

Jessie gave a sheepish laugh, "Mostly packed food or we ordered stuff."

Ash, "That's... No wonder you are so worryingly thin. I thought it was just your bone structure. You have not been eating properly, have you?"

James gave a nervous laugh, for some reason it felt like he was being scolded by the boss when Ash reprimanded him for being careless, 'Well boss, your kid got your attitude and personality alright.', "It's not that bad!"

Ash grabbed his wrist, "Not that bad! NOT THAT BAD? I can literally only feel your bones here. What were you thinking?"

Misty grabbed Cindy, "Welp, they have done it!"

Cindy whispered, "Is this the mother mode, you were telling me about?"

Misty, "Yep! Come on, he's gonna lecture them for a while."

Cindy giggled, it was a little funny to watch when it was not directed at you, "He looks like a mother!"

Misty, "I know right? It's so surreal sometimes, like one of those movies where someone is reborn as a new person but in wrong body."

Cindy nodded, "That's impossible in real life though!"

Ash took a deep breath, "You are sticking to us alright! And you are eating properly from now on, understood?"

James mumbled, "Yes mom!"

Jessie, "Yes ma'am!"

Ash, "Huh?"

James, "I will!"

Jessie, "No problem!"

Jessie whispered to James, "For a moment I thought I was being scolded by someone older."

James nodded in agreement before joining Ash in making the food, which also included healthy soups and salads. The two older man and woman made a silent promise not to tell Meowth about this, he'll no doubt hold this over their head. They finished up and by the time they left the cooking centre it was late in the evening. Jessie and James left them saying they would see them the next day and their Pokemon were waiting for them, before Cindy could say something.

Cindy sighed, "Well I better get going as well, my grounding is still going on."

Ash smiled, "We'll walk you home."

The three walked towards the gym leader's home and as they got closer, Lucario noticed a similar figure watching the house. The aura Pokemon frowned on seeing him and whispered something to Ash. Ash's eyes widened, he had completely forgotten about him, but then again he didn't see him again after that day at the centre. Cindy however got a little weirded out seeing a stranger near her home and approached him.

Cindy, "Hey, it's you from before."

Flint startled, "Oh hello children! I didn't see you there."

Ash raised his eyebrow, "We can see that, is there a reason why you are here?"

Misty, "Yeah Mr Flint? Why are you peaking on them?"

Flint, "Oh nothing like that. I promise you that much!"

Misty turned to Cindy, "Why don't you go inside? We'll talk to him, you are still under grounding right?"

Cindy nodded, "See ya then."

Ash "Now why are you here?"

Flint winced, "I just keep an eye on them, you see, their worthless father left them to become a Champion but unfortunately he failed to become one and out of shame never returned home."

Misty was surprised, "Really? I thought he was dead."

Flint shook his head, "He is alive, but too ashamed to return."

Misty frowned, "That's stupid, if my father were alive, I would want him to return home, failure or not."

Ash nodded in agreement, "Yeah I would want my Dad back too. I rather they fail and are still alive than dead."

Flint looked up at them at that, "Your fathers... I see, I apologize for bringing up the foolishness of an old man."

Ash shook his head, "You should go inside and meet them instead of beating yourself up over it."

Misty, "What? Oh right Lucario can read auras. If you really are their Dad, go inside and talk to them. They'll be angry? Yes! Furious? Definitely! But they'll be happy to see you alive again."

Flint nodded getting over his surprise, "You are right, I'm being a fool, aren't I?"

The man got up and knocked on the door, Ash and Misty decided to leave and give the family some privacy. Ash hoped things turned out fine for them the way it did in the anime and Brock gets a break from the stress that was very evident in his eyes. Misty chatted with Ash and told him about the stuff she did with the other girls and for all her quirkiness, Jessilina was actually very sweet. Ash smiled and told her about his own day and what he learned about the family, getting a worried look from Misty. She may have just met the two today, but she could tell they were good people who mean well, perhaps a little careless about their health. The next day they met up with Jessilina and Jameson who were standing by the Pewter city gates with Meowth.

Ash, "Good morning."

Misty, "Ready to go?"

Jameson, "Morning you two."

Jessilina, "Ready to hit the road."

Ash, "Yeah, let's go!"

Brock, "Wait!"

Ash turned surprised, "Eh? Brock?"

Brock grinned, "Yeah, got room for one more person."

Misty blinked, "Sure, but what about the gym?"

Brock, "My Dad came back last night. I will be honest, I didn't believe it at first but he's really back. He also agreed to take over the gym and watch over the kids and told me to follow my dreams."

Ash smiled, "I see, welcome to the group Brock! What's your dream?"

Brock, "My dream is to become a high level Pokemon breeder and later on a Doctor. But I need to learn first and check out the different types of institutes available before deciding to get a doctorate."

Jameson whistled, "That's a really hard career you are aiming for."

Jessilina nodded, "You better be ready to work hard actually harder than anyone, I tried going for nursing and boy was it torture?"

Misty, "You studied nursing?"

Jessilina, "Yeah I finished my course but never got into it as I had lost interest by then."

Ash, "That hard?"

Jessilina, "You have no idea. I was so exhausted back then, it was only thanks to my Chansey's support I even finished the course."

Brock, "That's amazing. Not only you are beautiful but also talented and urrrrgh!"

The group laughed as Brock's flirting was cut short, half way by Zubat who came out of her pokeball annoyed. Brock's siblings and father were giggling and smiling behind him at his predicament and wished them safe journeys and good luck with the next gym in Cerulean city. They waved their good byes and left Pewter city with more friends added to their group. Cindy shouted and told Jessilina she was welcome back to their family if she ever wanted to visit getting a blush from the woman.