Pokemon: I Transmigrated Twice

Stephen had just stepped out the door when Umbreon leaped onto the windowsill, watching her trainer's retreating figure. For a moment, she fell into contemplation.

Should I… just stay here?

While her master was out running around for her sake, was she really okay for it to just nap away at home?

At that moment, Umbreon caught sight of a few familiar faces passing by outside.

"Hey, Will! You're finally challenging the Cianwood Gym today, huh?"

"So jealous! We're the same age, but you're already good enough to take on a Gym. If we were as strong as you, we wouldn't have had our favorite Pikachu cookies stolen by that guy..."

Umbreon recognized two of the kids.

They were the same unlucky pair whose snacks had been—well, not stolen, but fairly won by her trainer two weeks ago.

But this time, their group had a new addition.

A human kid who looked about one or two years younger than her master, with a slightly chubby, baby-like face.

Yet what caught Umbreon's attention even more was what these three kids were talking about.

A Gym Leader?

Back when she had stayed with the old woman, she had heard about such things.

It was a title given to humans who commanded exceptionally powerful Pokémon.

So now the question is… the "Elite Four" that cranky old man mentioned last night, and the "Gym Leaders" these kids are talking about—who's stronger?

After a brief moment of thought, Umbreon noticed the trio of kids walking farther and farther away. She pawed at the window latch, nudged it open, and leaped out.

Like a black cat darting along the edges of rooftops, she silently followed the three children.

...

Inside the Cianwood Gym

A middle-aged man with a small mustache, a well-built physique, and abs that gleamed in the sunlight streaming through the windows roared.

"I am Chuck, the Gym Leader of Cianwood Gym! State your name, challenger!"

The boy smirked confidently and introduced himself,

"I am Will, a genius specializing in Psychic-types, currently traveling across Johto!"

Will, who appeared one or two years younger than Stephen, gave a respectful bow to Chuck, though his tone carried little actual respect.

"Will? I've heard about you from Suten. You seem to have some potential," Chuck mused, recalling the name.

The "Suten" he mentioned was the current Gym Leader of Violet City and the father of Falkner, the future Gym Leader of the same city.

"Hmph, I didn't expect my reputation to spread so quickly. That old man at Violet City wasn't much of a challenge. I hope you won't disappoint me, Mr. Chuck."

Will pulled back his collar, revealing three badges pinned inside his jacket, one of which was unmistakably the Zephyr Badge from Violet Gym.

"A talented but arrogant brat, huh…"

Chuck, still sporting his six-pack abs, smiled faintly.

"Then bring it on, kiddo!"

Chuck assumed a karate stance as he tossed out a Pokéball.

Out came… a Timburr, a Pokémon native to the Unova region!

Chuck was holding back. After all, the kid in front of him was only eight or nine years old.

How strong could he be?

Even though his friend Suten had lost to this boy, Chuck wasn't about to rely on over-leveled Pokémon to crush him. That would be too low.

"Hmph! Take care of this, Natu!"

Will tossed out his own Pokéball.

A small, birdlike Pokémon with seemingly unfocused eyes landed on the battlefield.

A Psychic/Flying-type Natu—a perfect counter to Chuck's Fighting-type specialty.

"The Gym Challenge between Gym Leader Chuck and challenger Will begins now… Battle, start!" the referee declared.

The moment the match began, Will launched a swift attack.

In mere moments, Chuck realized that this arrogant kid's strength wasn't limited to his sharp tongue.

The boy's talent was undeniable. With proper guidance from a skilled mentor, he could undoubtedly reach the level of the Elite Four someday.

However, neither the two combatants in the arena nor the sparse audience noticed a shadow lurking in the corner of the stands.

Umbreon crouched on the back of a chair, her blood-red eyes fixed intently on the battle unfolding below.

"Machoke is unable to battle. Jynx wins."

Moments later, the referee raised a flag.

"Since Gym Leader Chuck's two Pokémon are both unable to battle, the winner is challenger Will."

"Well, well. Looks like Suten's going to laugh at me now," Chuck muttered as he recalled his Machoke.

After his Timburr had been defeated, Chuck had gone slightly more serious and sent out his Machoke, a solid mid-tier Pokémon in his lineup.

But it still wasn't enough to beat Will.

"Hm, a bit tougher than Violet Gym, but still nothing special," Will shrugged, spreading his hands.

Admittedly, his attitude at this moment was highly punchable.

But Chuck didn't say much. When you have the strength to back it up, a bit of arrogance is understandable.

He wasn't about to make excuses about using non-main team members or anything like that. Even with his choice of Pokémon, as a Trainer, he had lost to Will. That was the undeniable truth.

"Well then, Psychic kid, this Storm Badge is yours."

Chuck handed over the badge that symbolized victory in the Cianwood Gym Challenge.

He was already looking forward to this year's Indigo League Conference.

If no other prodigies appeared, it seemed unlikely that anyone would stop Willi from claiming the championship.

But what intrigued him even more was what might come after—the Elite Four challenge or even the Champion battle.

Who would be the one to take this kid down a peg?

Would it be the bespectacled young woman Lorelei, whose mature physique belied her age?

Or would it be the cape-wearing Dragon Trainer Lance, who always looked like someone owed him money?

Heh, given those two personalities, neither of them would go easy on Will.

Chuck could hardly wait.

"The next Gym Leader I crush—who will it be? Honestly, this is starting to get boring," Will remarked, still as insufferably smug as ever while accepting the Storm Badge.

Thud!

Suddenly, a dull noise drew the attention of Chuck, Will, and the scattered morning spectators.

A figure crouched low, its knees bent in a battle-ready stance, slowly advancing toward the center of the battlefield.

It was a Pokémon that most of them had never seen before.

"It's that bad guy's bad Pokémon!"

"Darn it! My Psyduck chips!"

Among the crowd, only the two unlucky kids recognized the Umbreon.

But as they glanced around, they couldn't spot the bad guy anywhere.

Could it be… wild?

"Huh? A Pokémon I've never seen before. What do you want?"

Chuck asked.

In this era, before Professor Oak invented the Pokédex, even a Gym Leader's knowledge wasn't as comprehensive as it would be in later years.

Not to mention that types like Dark, Steel, and Fairy hadn't yet been officially recognized by the League.

Umbreon slowly raised her right paw, extending one claw and curling it toward Chuck in a beckoning gesture.

Its intent was unmistakable.