1 Live, die... repeat?

*Warning* I will be posting in this story in big chunks of maybe 5-10 chapters. Meaning there could be massive time periods of silence with no updates*Warning*

"GRENADE!!" Is the last thing I said before I was blown up. I died fighting in WW3 in a trench at 19 years old, not the death that I expected but what could ya do? I saw nothing it was pitch black and there was a ringing in my ear but slowly the ringing faded and my vision started to return. I felt a pulling sensation and agent to grab onto something but when I tried I realized that I had no body and was just a spirit without a construct. Soon I arrived in a infinite white plain with no structure or differences in the land. I began to move around but noticed that a palace began to rise from the ground around me, as if I was in a video game and the world was still generating.

I felt a strange sensation and looked down as I watched the platinum looking mist that made my soul began to take form of a body, mesmerized I watched as each bone was formed followed by nerves before being covered by skin.

"Hello son." A masculine soothing voice said, startled I turned around and saw a slightly overweight elderly man who appeared to be 5'10, he had pale skin and a grey mustache, wearing a buttoned up old fashioned three piece suit and bowler cap.

"Uhh hello?... do I know you?" I said in response to him as I awkwardly rubbed the back of my head

"Well you certainly know OF me, Odin, Ra, God, the beginning and the end, so on and so forth." He said with a slight chuckle. I was dumbfounded by this statement and was trying to comprehend what he said. He snapped his fingers as a small table rise from the ground.

"Tea?" He asked as he sat at the table

"Yes please..." He nodded and poured me a cup

"So, am I dead?" I asked while still flabbergasted at the whole experience.

"Oh yes quite dead. I believe that you have a one way ticket to Arlington." He said while he sipped on his cup.

"I feel like I should be shocked, sad or even angry, but I don't... why, why can't I remember any form of personal details?" I asked while I tried the tea, shocked at how perfect it was.

"Because I promised there to be no heartache after death and I always deliver." He said without elaborating any further I shrugged and sipped my tea.

"Well anyways you have three options for sacrificing your self in combat. Reincarnation, Heaven or Asgard... the choice is yours my boy." He said before he took a bite from his crumpet.

"Uhh I suppose I'll choose Reincarnation.." I said with a shrug

"Very well then, choose your world, choose rather you'll be a cannon character or your own character and decide on your three wishes. Take all the time you need." He said before continuing with his evening snack

'Okay, I would love to be in Marvel or Naruto, but that could be a death wish, Pokemon is relatively safe as long as you have a Pokémon of your own...

but should I be my own character... or should I stick with Brock or ash to confirm my place in cannon... but thinking closely I could probably just ask him to put me in Kanto the same age as Ash, he seems understanding... okay I'll be born in Pokemon as my own character... now for my wishes... I for sure want to have a powerful aura ability, next I want to be lucky seeing as this is pokemon, I could always wish for stupid powerful abilities but that would get boring fast... for my final wish I want to be born incredibly intelligent!'

"Okay I know what I want, I want to be born a week before Ash in the Kanto region as the son of a pokemon breeder.

For my first wish I want to have a system that can boost Draconic, Ghost and Dark type pokemon making them stronger and smarter, I want to be incredibly lucky for my second wish, and I want to be incredibly intelligent for my last wish."

"Okay then, Good luck." He said as my vision faded next I realized I was being born

-1 traumatizing event later-

ITS A BOY!!" The doctor who was holding me started to wipe me off and as he was I looked over and could see my mother, she had red hair with green eyes, her hair was matted to her head thanks to her sweat. She was obviously exhausted and was holding the hand of, who I assumed to be my he father had blonde hair blue eyes and was massive he appeared to be extremely muscular and had a scar on his left cheek making look badass however not at the moment seeing that he was nursing his hand back to health and had tears in the corners of his eyes. The sight made me laugh a bit which in turn made my mother smile.

The doctor handed me to my mother after he finished wiping most of the blood off of me. My mother held me while my dad leaned over her shoulder and kissed her on her forehead, she however didn't acknowledge the kiss as all of her attention was on me for the first time in any of my lives I saw someone look at my with absolute love in their eyes. I couldn't hear what was being said but for some reason I heard two words loud and clear...

"Jackson, Jackson Holland..." my mother said as she held me close

(Time skip 5 years)

3 years after I was born I learned all about my parents since I had nothing better to do, my father Shayne was a Gym leader in sinnoh but sold the gym when we moved he ended up becoming a Pokémon breeder here in Kanto, he breeds and sells Pokémon to many people which is what provides money for us. His main pokemon team is a Nidoking, Aggron, Rhypiror, sceptile, Garchomp, and a Luxray. My mother, Jade was a trainer as a kid but after marring my dad she stopped adventuring and had me, her team consisted of Staraptor, Zebstrike, Empoleon, Haxorus, malamar, and a Ambipom. My father was once considered to be a elite 4 member however he unfortunately lost against Drake's Salamence. He moved out of Hoenn when he was asked to help Professor Rowan, my grandfather. During the 2 years of helping Rowan he and my mother married each other and decided to travel. They visited every major Pokemon region and caught many rare and powerful pokemon, they were also successful in causing a Raichu to mega evolve, which was thought to be otherwise impossible. After 4 years of traveling my mother became pregnant with me

and moved to Galar region where I spent my first three years of life.

We eventually moved to Kanto in a small cottage in the woods that had about a acre fenced in and inside the fence was about 10 baby pokemon who hatched in this last spring. My father bred Machops, Nidorans, Arons, Treecos, Fletchings, poochyenas, inkeys, rhyhorns, shinx, bagons, Grooky's and Gibles. All of which are really popular because most of them are either rare or a breed you can't find in Kanto. I spent most of my first month in Kanto helping the baby pokemon get comfortable with their new home while my parents did all of the moving, ahh the perks of being a toddler is that you can just have another people do all the boring stuff. I have gotten used to taking care of pokemon because I would spend most if not all of my free time playing with them and nursing them if they got hurt somehow.

(Jackson's Pov)

"Jackson sweetie come here please." I hear my mother call. I look at the house to see her on the front porch with all of her things ready.

"Okay mom I'm coming!" I yell back as I pick up the poochyena I was playing with and put him back in his pin with his friends. I run over to my mom and stand in front of her and do a little soldier salute.

"Honey we're going to go see the professor to get this little Treeco looked at ok. Do you want to come." She asks me in a sweet voice while holding up a poke ball that contained a shiny Treeco.

"Yes ma'am I wanna come! Mommy can I bring dada's NidoKing?" I ask earnestly

"You'll have to ask your father." She says with a small giggle

"Okay!" I yell before I run towards the back yard where my dad is on the phone most likely speaking to a client about adoption.

"DADDY!! Can I bring your Nidoking?" I ask while running to him. He looks at me and tells his client that he'll be right back and puts the phone on mute.

"I'm sorry what did you say, sport?" He asks

"Can I bring your NidoKing with me to the Professors?" I asked him, he thinks about it for a second before shrugging his shoulders and pulling the ball out of his jacket and summoning his Nidoking.

"Yeah sure." He said to me before he turned to the Nidoking

"Watch him okay?" He asks his pokemon, the nidoking nods his head. My dad retrieved the nidoking and handed me the ball. I grab it and run back to the car and buckle in. About 2 minutes pass before we pull up at professor oaks lab. I ended up staying outside with the nidoking I play with him for about 5 minutes before I hear a squeaky voice yell.

"WOW! IS THAT A NIDOKING?!" I turn to look at where the voice came from to see a young ash and Gary with stars in their eyes. I smile and reply

"Yup! This is my dads Nidoking and he's the strongest in the whole world!" I stated while puffing my chest. Nidoking just grins at that comment

"He looks like he could crush a entire house!" Ash says excitedly which only made Nidoking's ego grow more.

"No way! I bet gramps has a stronger one!" Gary said which deflated the Nidoking's growing ego.

"No he doesn't!" I yell definitely

"Yes he dose." Gary said

"No he doesn't"

"Yes he dose."

This resulted in a argument between us that lasted around 2 minute before Nidoking made himself know agian with a loud Roar that cause us all to shut up, internally I sighed since I didn't know how much longer I could argue with a 5 year old, which is already hell but doing it while acting like one yourself is a absolute nightmare. Ash started to giggle which turned to laughter which led to Gary laughing and me joining as well after a while even Nidoking started to laugh. We all played together using the behemoth as a jungle gym and hanging off of his arms and riding on his back. I didn't think he minded hunch he could have punted a car 100 yards so three 60 pound boys couldn't move him if we tried. Once Treeco was done with her check up I invited Gary and Ash over and they were allowed to come after oak called Delia and Naomi Oak they stayed at my house playing with our pokemon after the sun started to set mom drove both of them home and I passed out from all the excitement... from that day on we were best friends, no matter what we did we did it together. And I planned to keep it that way

(Timeskip 10 years)

Today is the day... it's been 15 years since I started my personal heaven. Me Ash and Gary are still friends to this day, yes Gary can be a bit egotistical at times however that's kinda expected when his grandfather is a ex pokemon champion, however he's not as bad since I'm the son of a ex Gym leader I've also beat him on multiple occasions using a game system that simulates a real pokemon battle which is just pokemon fire red. Ash is also somewhat of a idiot, he's a lot better than in cannon but he would still most likely fight a dark type with a physic... but today marks the beginning of our epic journey! I woke up at 5:00 to get the best start of our journey. I finish getting ready and look myself over in the mirror, I have a white undershirt with blue jeans and a black Denzel outwear anarchist jacket. My face looks like Yuhiko from naruto thanks to the orange hair. I pack up separate pairs of clothes and put them in my Silph. Co backpack which can carry 4x what it should be able to, then I go into the kitchen, eat a piece of toast and feed the pokemon. I check my watch to see that's its 6:00 and leave my house and ride my bike to the Professor's house and knock on the door.

"Professor oak! Are you up yet!" I yell. I wait about a minute before he opens the door he's still in his pajamas and clearly was just asleep.

"Jackson why are you here so early?!" He whined to me.

"Well Professor I wanted to get a early start on my adventure!" I say excitedly, oak just sighs and opens the door allowing me in. We walk to a small table that was containing 3 poke balls.

"Well Jackson you may choose one pokemon to become your friend!" Oak states, I nod to him before reaching towards the charmander, once I pick it up I focus my aura ability into the pokeball and feel the charmander, once I could sense him I caused mutation that will alter him into a shiny charmander. I felt the charmander begin to change and as he changed I felt him radiating happiness. I smiled and nodded to Professor oak. He smiles reminiscently at me

"I see you made your decision, so here you are. He said as he handed me a Pokédex as well as 5 pokeballs.

"Well now that your all set run along now, I need to change out of my pjs." He states with a smile. I nod to him and leave the lab. Once outside I pulled out my phone

'Hey Gary you awake yet?'

'Yes I'm awake, can't let you get to far ahead can I?' He responds

'Alright good, ill be waiting for you at the lab, remember don't eat a big breakfast since my moms planning to have a babaque lunch in about a hour' I said before I texted ash

'Ashy-boi you up yet?' No response

'Ash are you awake?' Again nothing, looks like he slept in again so I called him.

Riiiiiing, Riiiiiing, Ri-

"Hello?" A very tired sounding voice picked up the phone

"Hey Ashy, I'm just calling to let you know that I'm not waiting for you to wake up to begin my journey, so if you sleep in you'll end up walking across the Kanto region alone." I tell him

"You sound like a mother Jackson, you know that..." ash responds

"Well this quote unquote mother is the one that's going to be a pokemon champion."

"Oh yeah well not if I have something to say about it!" Ash says now fully awake

"Ight whatever I'll see you at the lab." I answered before hanging up.

I sit down underneath a tree in the front yard of the lab to wait for them. Gary showed up about 45 minutes later and got his starter, he was going to release it however I said to wait until ash has his, after some convincing he begrudgingly agreed to wait, eventually we saw Ash running towards the lab clearly not 100% ready. He hasn't tied his shoes yet, he forgot his jacket, and the silph .co backpack I bought for him last April for his birthday.

"About time." Gary said sarcastically

"I waited for you longer so stop complaining, at least he didn't sleep in." I rebutted to Gary

"Hey guys sorry y'all had to wait for me!" Ash said with a sweat drop

"It's fine just go pick up your pokemon, and after that we need to go to my house." I told him with a smile Ash nodded and went into the lab.

"Why are we going to your house?" Gary asked

"Because all of our parents are there and we need to say goodbye." I tell him Gary shrugs

"Alright guys I have my first pokemon!" Ash said as he ran down the stairs

"We do too, Ash.. How about we all release them together?" I ask they both nod and we throw our pokeballs out at the same time and a light appeared where each ball landed soon the light faded away to reveal a...