Time Skip / Exposition :
Upon returning to Kanto, Death, Esdeath, Valerie and Leaf did not come alone. Surprisingly, Serena had asked her mother if she could travel with them, and her mother agreed, albeit only after Serena begged a while.
This had surprised Death, but he accepted it. Serena clearly had a crush on him and needed time to sort out what she was going to do about it, and she chose to do so while traveling with him.
He had thought that she might be scared off a bit after meeting all of his wives and learning about different worlds, but she hadn't been. In fact, Serena seemed pretty excited to be back in Kanto. Apparently she had once attended a Summer Camp in Kanto, but hadn't gotten a chance to truly explore it at that time.
Death let Leaf challenge the Gym leader first and then he challenged it as well. Since it was their third gym battle, Surge couldn't use elite-ranked Pokémon, so the battle was finished swiftly without difficulty.
After this, they stayed at the Pokémon Center and left to train for the day while Death was waiting for Ash and the others to catch up or for the St. Anne incident to occur. Still following the timeline of the show, Death hadn't sensed the trio approaching after one week, when it was time for him to visit Kalos again and meet Diantha.
He had kept in touch with Diantha over phone basically every day, but this was his first time returning in person. She had been busy since becoming Champion, though she was never too busy to take his calls, and she damn sure had made time to meet with Death, as he understood that this was very important to her.
They arranged to meet at a nice restaurant in Lumiose City. and of course that meant Paparazzi were following her still. She was a brand new champion and had publicly displayed her Gardevoir using an unknown form change, which she still hadn't publicly explained. She was, as a result of this, not just a trending topic in Kalos, but also around the entire Pokémon world.
Death didn't mind meeting Diantha in public, and even wore a necklace that matched hers as he thought it would just make them ask more questions and would rub it in their faces a bit. Diantha and Death Quietly spoke to each other with the paparazzi kept at a distance, though still snapping pictures of them, while they enjoyed their meal together.
After eating, they both got up, headed to Diantha's car, then hugged each other before Death seemed to turn to leave. This, however, was him using light magic to deceive them. In truth, he had slipped into Diantha's car first, unseen by anyone present, and once she slipped into the car with him, Death placed his hand on her inner thigh.
Even though she couldn't see him, Diantha smiled in his direction "Why did you want to meet in public anyway?" he asked.
"Well, as your boyfriend, I don't want others thinking that they can snatch you away from me, Darling." Death insisted "We don't have to advertise the depth of our relationship or anything, but just thought it seemed wise to let them talk about us a bit so that you can reject others easier. They'll be scratching their heads when they realize that none of their photographs will be usable today."
Diantha chuckled and nodded "Understood, dear. Yeah, I wouldn't dream of accepting anyone else's advances, so thank you for helping to cover for me a bit."
Soon enough, they arrived at Diantha's place, and the driver got out to open the door and let her out. Because of the privacy window, he did not know Death was in the car with her, so Diantha let Death slip out first, still invisible, before following him out of the car. Diantha thanked the driver and headed inside.
Inside the house, once the door was locked behind them, Death cut off his light magic and became visible again and moved up to Diantha, and the two wrapped their arms around each other and started to passionately kiss and Diantha led him towards her bedroom.
While an avatar was spending the day training with Leaf, Valerie, Serena and all of their Pokémon, he spent the whole day with Diantha in bed, letting her truly enjoy being with a man for the first time. Diantha was fairly insatiable, so they went on until she was completely exhausted and fell asleep for the night, cuddling with him.
Death made sure to have breakfast in bed prepared for her when she woke up, and was extremely affectionate so that she'd definitely know that she was loved.
She had to wash up and get back to work and Death had to return to Kanto, but he made sure to leave behind an avatar to pamper Diantha whenever she came home.
After returning to Kanto, another few days passed and Ash, Misty and Brock entered Vermilion City, then it was time fr the St. Anne incident happened. Death brought Serena, Valerie and Leaf with him onto the ship and was ready to deal with and apprehend the Team Rocket members the moment that they revealed themselves.
With forty avatars acting together, apprehending everyone was easy, so the cruise went without incident. The St. Anne didn't end up sinking.
After the Rocket members were gathered together and were tied up, Death's Avatars, who had hidden their faces, teleported all of the criminals to the prison in Lyonesse. The appearance of the Team Rocket members, followed by their apprehension and then disappearance, was surprising, but at least they made it back to Vermilion City without any more incident.
Before disembarking from the St. Anne, Serena returned a Handkerchief to Ash and thanked him for apparently giving it to her at camp when they were younger. It surprised Death that she apparently knew Ash, but he didn't think much of it because she promptly returned to following him after returning the Handkerchief.
He did end up buying a certain Magikarp that he found there and gave it to Serena. It had Blue Potential and would likely reach purple or even white potential in the future.
Death figured that if she wanted to talk about what happened between her and Ash, she would tell him, so apparently it wasn't that important. It was just a noteworthy event.
Death then headed to Saffron City with Esdeath, Leaf, Valerie and Serena. He could have just gated them to Saffron, since by now his Avatars had visited every city in Kanto, but there was something fun about just traveling alongside a bunch of beautiful ladies, so he decided not to take and shortcuts. He did visit the other cities that had gyms that were not in the anime, though, and took down most of them in rapid succession. It took two days to reach Saffron City, and of course Death headed straight to Sabrina's gym.
For him, it was easy to beat Sabrina thanks to his Absol, after which, since she was still in crazy mode, Death threw her over his lap and spanked her bottom for being a bad girl.
She snapped out of her madness, and returned to her adult form, seeming absolutely embarrassed, but after a little encouragement she undid the transformations of all the people that she had turned into dolls.
Leaf then took on Sabrina as well, and though she had no dark or ghost type Pokémon, she still managed to win against Sabrina with no psychic mind games going on.
After beating Sabrina, Death left an avatar behind to make sure Sabrina didn't relapse to her old ways, and traveled towards Celadon City with the girls.
Since Death stopped the St. Anne from shipwrecking, he knew that the 'plot' was out of bounds and definitely couldn't be just trusted, hence him getting ahead of Ash and crew and dealing with Sabrina first.
While Death was traveling towards Celadon with Esdeath, Valerie, Leaf and Serena, an Avatar snuck under the Casino in Celadon, and verified that, just like in the games, there was a Team Rocket base there. Using magic to enhance his force powers, the Avatar rapidly put everyone in the base to sleep and systematically sent them to the prison at Lyonesse while looking for information about other Rocket bases. The Lyonesse prison was going to be pretty full after this batch of grunts were brought in, but he was determined to destroy Team Rocket completely.
Death's avatar was sorting through all of the evidence he had acquired and preparing for the next stage of his battle to be rid of Team Rocket when Death, Esdeath, Valerie, Leaf and Serena were entering Celadon and heading towards the Celadon Gym.
------
End Time Skip : POV Death Rose
Approaching the gym, three girls were standing outside of it, two talking to the third..
"Jeez, I'm not here about a stupid gym badge" the lone girl, who seemed a bit tomboyish announced with annoyance "I am the next grass trial captain from Alola. I just want to meet Kanto's grass-type gym leader as a professional courtesy." even if she was a bit tomboyish, the copper-skinned girl was still quite beautiful, with a fantastic bony, even if she wore legless over-alls. Her legs were certainly fantastic as well.
If she wanted to, she could easily dress feminine and look hot as hell. He could guess what happened, though. She probably was asked about perfume and they wouldn't let her in because they didn't like her answer "Sleep" Death said and the two upset teens fell asleep, to the surprise on the green-haired beautiful tomboy.
She turned towards Death "How did you do that?" she asked.
"Trade secret, beautiful." Death chuckled and seemed amused "My name is Death Rose." he introduced himself.
"Oh, my name is Mallow Mao. Nineteen years old. I've come to Kanto from Alola to meet Erica and gain some experience before I take over as the grass-type trial captain" Mallow explained to them "It's a pleasure to meet you, Mr. Rose."
Death nodded back to Mallow "My friend Leaf and I are here to challenge Erica. Shall we head inside?"
"What about them?" Mallow looked at the two sleeping teenage girls.
"They'll be fine. They'll wake up soon, after all." Death insisted and started heading into the gym. he had already left an invisible avatar behind to make sure no one messed with the girls, so he had no second thoughts about leaving them behind.
Leaf, Valerie, Serena and Esdeath followed him inside, trusting in him completely, though Mallow hesitated a few moments while staring at the passed out girls before finally following the others inside.
------
POV Erika Kono
(ooc - Erika has no known canon last name so I made one up for her. No need to look up where I got it from)
Erika was surprised when she say 6 strangers in her gym, one of whom was a male while the others were female. Usually there arrival would have been announced before they reached her "Greetings. How may I assist you? Are you all here for gym battles?"
"Leaf and I are." Death explained to Erika, indicating Leaf when he said her name "Valerie, Serena and Esdeath are here as our companions, and we met Miss Mallow just outside."
"Are you perhaps Miss Erika?" Mallow asked the gym leader "In a few months I am to take over as the grass-type trial captain in the Alola region. I am here to meet this regions grass-type gym leader and seek a few pointers from her."
Erika nodded, and seemed excited when she heard who Mallow was "It's a pleasure to meet you, Miss Mallow. I am indeed Erika Kono, leader of the Celadon City Gym. This grass-type gym leader welcomes Trial Captain Mallow." she formally curtsied "You are welcome to stay at my gym as long as you like."
------
POV Death Rose
Erika was, unsurprisingly, a very beautiful and elegant woman. He guessed that she was in her early to mid 20's, so she was older then his other female companions, but there was a certain grace to her, similar to that possessed by Valerie or Weiss.
She had shoulder-length dark brown hair and brown eyes, and wore a nice Komono, with a pink and blue color scheme.
Erika was still looking at Mallow "Miss Mallow, since it seems that I have two challengers, do you feel up to challenging the young man while I take care of battling Miss Leaf?" Erika suggested.
"Sure. I don't mind if you are alright with it." Mallow agreed.
Erika looked at Death and Leaf "How many gym badges do you have?"
"My name is Death Rose, by the way, it's a pleasure to meet you Miss Erika" Death greeted her "Any presently I have eleven badges from the Kanto region and my friend leaf has four of them."
"You do realize you only need eight badges to challenge the Pokemon League?" Erika asked, baffled when she heard he had eleven badges.
"I know, but I am an overachiever." Death chuckled "After this one, I just have the Fuschia, Cinnabar and Viridian Gyms lefts." He opened his two badge cases and showed her his eleven badges, with one holding seven badges and the other four. He was putting the gym badges he remembered from the show in one badge case and the ones not shown in the show into the other.
"Already beaten two of the three pillars of Kanto? I am impressed." Erika giggled "Well, looks like you have a challenge on your hands Miss Mallow."
"I'll let Leaf battle first." Death suggested, to which Erika nodded in acceptance.
"Follow me. I'll bring you all to the battlefield." Erika invited them.
------
Remaiming gyms :
Celadon / Grass Gym
Fuschia /Poison Gym
Cinnabar / Fire Gym
Viridian / Ground Gym
During this time skip, Death has went around to the various unshown gyms around Kanto and systematically conquered them all, including the strongest Bug-type and dragon-type gyms. Rewards were as follows:
Vermilion / Electric Gym : Spark Master Skill Tree, 5,000,000 Shop Points
Ghost Gym : ,Ranch Enhancement 10,000,000 Shop Points
Flying Gym : Wind Runner Skill Tree, 10,000,000 Shop Points
Normal Gym : Eevee Egg, 10,000,000 Shop Points
Saffron / Psychic Gym : Ralts Egg, 10,000,000 Shop Points
Ice Gym : Ranch Enhancement 10,000,000 Shop Points
Fighting Gym : Lucarionite, 10,000,000 Shop Points
Bug Gym : , Swarmlord Skill Tree, Skill Point x10, 15,000,000 Shop Points
Dragon Gym : Jaw Fossil, Skill Point x10, 15,000,000 Shop Points
------
Traveling with Death : Genesis (Shiny Mew), Rasu (Charizard), Khione (Amaura), Janus (Ditto), Shiny Clefairy, Dratini, Larvitar
Traveling with Leaf : Saur (Venusaur), Nidory (Nidoking), Jiggly (Jigglypuff), Greninja, Clefairy
Traveling with Valerie : Vee (Eevee), Zee (Spritzee), Mimie (Mr. Mime), Snubbull, Clefairy
Traveling with Serena : Fletchinder, Gyarados, Eevee
Traveling with Death's Avatar training near Cerulian City: Leviathan (Gyarados), Seadra, Absol, Ralts, Golbat, Electabuzz
Pokémon Ranch : Queenie (Nidoqueen), Arbok, Weezing, 37 Dratini, 64 Pinsir, 41 Scyther, 127 Pikachu, 84 Eevee, 21 Mime Jr, 183 Porygon, 58 Abra, 306 Ekans, 218 Sandshrew, 23 Vulpix, 7 Jigglypuff, 8 Horsea, 2 Larvitar
Other Pokémon at Lyonesse : 5 Ditto, Riolu, Oricorio [Sensu style], Many confiscated from Team Rocket members.