HEY GUYS, I AM STARTING SOMETHING NEW, A DIFFERENT KIND OF STORY HERE, I WILL CONTINUE THE OTHER ONE, I PROMISE!

QUICK NOTE -

ASH IS 22

JESSIE IS 28

I KNOW SHE IS SUPPOSED TO BE ABOUT 10 YEARS OLDER THAN HIM, BUT WHO SAYS I NEED TO FOLLOW THE RULES?

Chapter 1: A New Beginning in the Eterna Forest

In the chilly region of Sinnoh, a trainer quickly made his way through the Eterna Forest on his morning jog. This trainer for many years now had traveled across the many regions of the Pokémon world, with this being his third trip to Sinnoh. That trainer was Ash Ketchum.

The brisk breeze created a cooler, yet not unbearable climate.

The forest was enveloped in a constant shade, as a thin fog enveloped the canopy of trees.

This forest was said to be harboring dark secrets, while many spoke of the Old Chateau in the deepest parts of the forest, others would say it felt as if the forest itself was one, malevolent entity.

Ash began to feel uneasy; something feels…

Wrong.

This is not an uncommon feeling in this forest, but something else is at play here, and Ash could feel it.

Ash paused in his tracks, and with his head on a swivel, he began to survey the area, only to find…

Nothing.

"Get ahold of yourself Ash," The raven-haired trainer said to himself, "You're just psyching yourself out."

The young adult removed his red and white cap with a Poké Ball crest in the center and ran his hands through his damp, spiky hair. With that brief pause, Ash began to make his way back up the path, but little did he know, his life was about to change forever.

CRASHHHHHHHHHHHHHHHHH

Ash's vision fades, and the last thing he sees is a feminine figure standing over him.

ASH'S POV:

Ringing.

All I hear is ringing.

I can barely see the room around me, for my vision is blurred.

Where am I? How did I get here?

I quickly realized that I could not get up, I am restrained. I looked up to see my wrists tied down to a bedpost, and my legs tied down as well. My shirt and jacket are also gone, in a pile next to this bed. I must be in the Old Chateau, the haunted house of legend. I do not understand, how did I get end up here? The last thing I remember was jogging down the path, and then it went black. Was I attacked?

Fuck…

This is exactly I always travel in a group.

Wait a minute, I think someone is coming. Yes, footsteps. Who did this? What do they want? Nothing you could have told me would have prepared me for what I saw next.

"Hello, twerp."

Jessie?! What the hell does she want from me? Yeah, Team Rocket has been a pain in my ass for years on end now, but this is different.

"Jessie, what the hell is this? I don't have Pikachu, as a matter of fact, I don't have any Pokémon with me at all, so I am no use to you."

THIRD PERSON POV:

A cold, sinister grin formed on Jessie's face.

"Oh, twerp, I've come for something else this time."

The 28-year-old Team Rocket agent was absolute eye candy, even Ash would admit this. It was bewildering to many people how such a beautiful young woman found herself working for a criminal organization such as Team Rocket, but there was a story behind it, one that needs to be saved for another time.

A perplexed Ash could only wonder what the villainous, magenta-haired woman wanted.

"What can I possibly have that you want? Don't tell me you are this desperate for money, those bums at Team Rocket have to be paying you enough, right?"

Jessie realized just how well Ash was handling the situation, but as far as his last statement goes, he was dead wrong.

"Well, twerp, I've come to realize that there is no way my crew and I will best you, years after years of failed attempts have led us up to this moment. One way or another, I will be a successful agent, and one way or another, you will be involved."

Ash simply cannot believe what is happening, nor can he anticipate what will happen next, all he knows is that he refuses to help Jessie in any way.

Ash furrowed his brow and let Jessie know how he felt, "In your dreams Jessie, nothing you can do will make me want to help you in your evil quest, you'll have to go through me if you want to keep abusing Pokémon for your own, selfish goals."

Jessie could not help but laugh at that last remark,

"What do you mean "Go through you", silly twerp, I have you bound up, I could just leave you here to starve forever and go after your friends, get your Pikachu, and climb my way up the Team Rocket ladder!"

Ash realized the reality of the situation but refused to give in.

"Then you'll have to leave me here, my friends can fend for themselves, and Pikachu will fight you tooth and nail for doing this to me!"

Jessie took a step forward to the bedside, right next to Ash, and bent down closer to his face.

"Well, luckily for everyone involved, I have other plans for you, and it all starts now."

The magenta-haired agent began to slowly remove her white Team Rocket jacket, never breaking eye contact with the raven-haired trainer.

"Tell me, twerp, with all of these cute girls you've traveled with through all these different regions, has that little twerp penis ever been handled by another woman?"

Ash was stunned at what was happening. Jessie was undressing and asking him about his sex life. What the hell kind of a day was this? Ignoring the question, Ash began to struggle, trying to force his way out of his bindings.

"Jessie, this is wrong, even for you, and you know it!" Ash exclaimed with a ferocity she had rarely heard from him, but unfortunately for the 20-year-old from Pallet Town, these words fell upon deaf ears, as Jessie had already stripped down to her underwear.

Anyone in Ash's situation would be less than cooperative and accepting, but Jessie could just tell that Ash was a virgin, and it gave Jessie a great deal of pleasure to be the one to take his innocence, especially like this.

She did not say anything in response, she just lowered her glove-covered index finger to Ash's chapped lips.

"Believe me, twerp, by the time I'm through with you, you won't be calling this wrong, in fact, you'll be begging for more."

In fact, Jessie was counting on it.

The Team Rocket agent removed her gloves and slowly moved her hands to Ash's waist.

Ash attempted to protest, "Jessie, no-"

He was quickly silenced by Jessie's free hand.

"Shut the fuck up twerp, you have no power right now, if I were you, I'd sit back and enjoy."

Jessie began feeling Ash up, and to her surprise, he already had somewhat of an erection brewing down there. Jessie smirked, realizing that the young man might be more into this than he was leading on.

"Well twerp," Jessie quipped, "it seems as if Ash Jr. here is contradicting your lack of interest, let me take care of him."

Jessie slowly began rubbing the area, and the raven-haired boy let out soft moans, if he wanted to admit it or not, he was beginning to enjoy this.

"Ugh, Jessie, please…", Ash attempted to struggle, but slowly began to give in. Jessie realized this and smiled.

Jessie smirked, one thought going through her mind, "He's mine."

Jessie, realizing she had won, at least for now, needed to pounce. The older woman climbed atop the younger stud trainer and removed her bra, allowing her D cup breasts to hang free in the young man's face. Ash tried to not look, but his will was slowly evaporating, and his instincts were beginning to take over. The erection in his pants continued to grow and harden, becoming ever more obvious to himself and Jessie.

"It seems as if I have won you over twerp, none of those little women you've traveled with have anything close to this body."

Jessie was immensely proud of herself; she was about to change the course of their lives forever. She now decided it was time to give Ash his first real sexual experience. Her hands slowly made their way down to Ash's waist, where she unbuttoned his jeans, unzipped his fly, and slowly removed the trainer's lower body clothing, leaving just underwear.

JESSIE'S POV:

I cannot believe I am about to blow the twerp!

As I removed his jeans, I realized something, this young stud was packing serious heat. I guess he is not much of a twerp after all.

"Holy shit dude, that's some serious heat under there," I exclaimed in utter surprise.

I expected Ash to be big, but not this big.

He didn't respond vocally and just blushed.

"Don't worry young man, I'm about to use what Arceus gave you, and I'll tell you, it looks like he gave you something really good."

Ash rolled his eyes and finally spoke up, "Why don't you just get on with it already, holy shit woman…"

That is a change in attitude, he wants it, good, whatever feeling of guilt I had was no more, he is consenting.

I quickly silenced that tone, "Just remember who is in charge here, twerp."

Enough games, I put my hands on the young stud's waistband and pulled it down.

Wow, it is even bigger than I thought. What I found was eight inches of young hunk cock staring me in the face. My eyes met Ash's, which had a mix of fear and anticipation behind them.

THIRD PERSON POV:

Jessie moved her gaze back down to Ash's fully engorged member. It was an absolute sight to see, a thick shaft topped by a soft, sensitive, and moist glans. The pink tip was still protected by Ash's foreskin, which Jessie slowly rolled back, causing Ash to moan softly, and fully reveal the tip. Jessie began the motion of a handjob, and within seconds, was met by a small amount of precum. In fact, every time she brought Ash's foreskin back over his glans, it seemed as if more precum found its way out.

"Ughh, Jessie please, don't…" Ash muttered,

"Don't what, twerp?" Jessie asked.

"Don't stop," Ash said, finally giving in fully.

An evil grin formed on Jessie's face, "That's right, little twerp, accept it. You're mine now."

Ash gave no vocal response and just rested his head back. Now it was time for Jessie really to get to work. The 28-year-old woman lowered her head to the base of Ash's shaft and licked from the base all the way to the tip, specifically focusing on the frenulum, knowing just how sensitive this spot was. Without any other words, Jessie slowly began to take the throbbing member into her mouth.

A shockwave of pleasure surprised the raven-haired trainer, "Gaaaa, ohh shit."

The young trainer could barely put what he was feeling into words. He had masturbated before but never had felt anything like this. Her technique was perfect, as she sucked, she stimulated the head and its surrounding skin with her tongue. As Jessie continued bobbing up and down on Ash's member, he could feel his muscles begin to tense, he knew what was coming.

"J-J-Jess, I'm gonna c-c-cu—", He could not finish the sentence, as the overwhelming sensation of orgasm began to take over.

Without another word, Ash released a thick blast of cum down the throat of the Team Rocket agent. As Ash's manhood began to soften up, Jessie admired her work. Ash was in the afterglow, his eyes fluttering between half open and shut.

"Well, Ashy boy, there is plenty more where that came from, and if you want more, I suggest you open up to what I have to offer."

Ash just nodded, allowing the overwhelming, post-orgasm sensation to take over his body.

Things from now on will be different,

Very, very different.

WELL, THIS WAS A CHANGE OF PACE… I AM NOT THE BEST AT WORD AND STORY FLOW, SO EXCUSE ME IF THE CHAPTER DRAGS A LITTLE. I AM WORKING ON THAT… THERE WILL BE MORE CHAPTERS IN THIS, AND I AM STILL PROJECTING WHERE IT IS GOING… LET ME KNOW WHAT YOU THINK AND THANKS FOR READING!