Oh man, I've been meaning to start this fic for a while now. I personally think I'm going to have a lot of fun with it. James always seems like a fun character to write for.

I guess what initially inspired this is just that I think they should have played a little more on the Jessiebelle subplot (Seriously, they brought her back after 500 some-odd episodes later for a single episode. I'd have thought they'd at least try her for an arc or something).

Anyways, I do not own Pokemon or any related material. Otherwise, this might have been made into a spinoff series.

As a note on timeline, this occurs after Team Rocket has arrived in Isshu/Unova, but before Jessie gets her Kokoro.

Let's get on with the show!

Chapter One: James's Mom and Deed

Jessie, James, and Meowth were walking along a countryside road shortly after having been defeated by the twerps once again.

"Well, that was a total disaster." Jessie sighed heavily. "And I was so sure we had them this time."

"No kidding." Meowth hacked up a small cloud of smoke. He held up one of his paws. "And now I'm not sure dat I have more lives dan I can count on one paw now." He sighed as well. "It's too bad, really. I t'ought dat plan was pretty ingenious. Just dis close." He held two of his fingers just barely apart. "Dis close, and we would have gotten Pikachu fair and square."

Jessie clenched her fists and snarled. "I swear, next time we're going to get those twerps." She pointed at the sky with a glint in her eye. "They'll soon learn not to take Team Rocket lightly!"

"Oh, what's the point?" James trudged a little ahead of the other two. "We're just total failures."

Jessie and Meowth stared at James, to each other, and at James again.

"Like, what's wrong, Jimmy?" Meowth stuck his paws behind his head as he walked. "Jessie's usually de mopey one, when it comes to being a loser."

"Watch your mouth, Furball." Jessie stepped on Meowth, forcing him to the ground. She turned to look at James again. "Still, Meowth does have a point. Maybe it's because you've fallen on your head one too many times, but you usually laugh these things off."

"Oh really?" James began pulling at his hair as he turned to look at the other two. "And just what is there to laugh about? Look around you!" He spun his arms around his head. "We're the first Team Rocket members in a region the gang doesn't know about, and we're still coming face-to-face with the twerps!" He turned back around, covering his face with his hands. "And to top it all off, the boss forced us to leave all of our Pokemon at base!"

"And what am I? Chopped liver?" Meowth escaped from Jessie's shoe and stood boldly.

"Oh, sorry, Meowth." James looked back at the cat Pokemon. "You just act so human all the time that I tend to forget you're a Pokemon at times." He sighed, closing his eyes and dropping his head. "I'm really beginning to think that Cassidy's right, and the boss does just want us gone."

"Now, hold on, James." Jessie stretched a hand forward. "Stop right there!"

"Jessie, I know you don't like Cassidy, but sometimes you have to admit when you're beat." James walked forward, his eyes still closed, shrugging.

"I mean it, James." Jessie took several quick steps forward. "Stop right there!"

"Oh, you stop, Jessie." Surprisingly, James glared back at his redheaded companion. "Just give me one shred of proof that the boss likes us even the least little bit."

"James!" Meowth began jumping up and down, waving his arms. "Jessie really means to stop!"

"I know you like the boss, Meowth, but hone-" James was cut off as he hit his head on a large iron gate. He fell backwards after the impact. He rubbed his head as he sat up. "What was that?" He looked up and flinched.

The large gate had to have stood nearly a dozen feet tall, looming over the team. The gate expanded either way into long stretches of fence to about as far as the eye could see. Behind the fence were fabulous gardens of various flowers, which were followed by a mansion the size of a business skyscraper laid sideways.

"Dis is one fancy place." Meowth hopped beside James and peered through the gate's bars. "It seems kinda familiar, dough."

"You're right Meowth." Jessie held the bars as she looked through the fence. "Why, if I didn't know better, I'd say…" She looked back at the blue-haired man. "James, is this one of your houses?"

James began scuttling backwards, his eyes never leaving the estate.

Jessie and Meowth looked at each other. Shaking their heads and shrugging, they sighed and said simultaneously, "It's one of his houses." They caught up with their crawling comrade and picked him up by the arms.

"Now, hold on. Wait a minute!" James began thrashing in their grasps. "I'm not going in there! You can't make me!"

"Oh, come off it, James." Jessie grinned as she pulled him towards the gate. "I'm sure sitting down on one of those fancy couches for a few minutes will get you feeling good about yourself in no time."

"Yeah, Jimmy, my boy." Meowth grinned at the human he was pulling. "Nothing gets you feeling better, dan de comforts of your home sweet home."

"Have you two gone insane?" James began tugging back on his arms, giving the other two a pretty good fight. "You only want me to go in there, so you can have fancy French pastries and caviar."

"Come on, James." Jessie's stomach growled as she pulled harder. "Stop being selfish!"

"No kidding." Meowth began pushing James, but he was still losing ground. "It's not our fault dat you're scared. Take one for de team!"

James began shaking his head furiously as his efforts redoubled. He pulled himself out of Jessie's grasp and bowled right over Meowth.

Jessie huffed, putting her hands on her hips. "Quit being such a baby, James!" She gestured back to the estate. "All we need to do is just walk in, let the butler see you, spend a half hour eating pate and steak tartar, then run out of there like there was no tomorrow before that horrible Jessiebelle shows up." She smiled stiffly and nodded mechanically.

"Yeah. It don't matter if we go in dere, so long as we get out of dere before dat scary fiancée of yours comes." Meowth nodded as he stood up and dusted himself off. "What say, James?"

"No, no, and no!" James crossed his arms in an 'X' and shook his head violently. "I'm not so much as taking one step past that gate."

"Jess?" Meowth cast a sidelong glance at his female companion. "What do you t'ink?"

"Well, I suppose we can't guilt him into it." Jessie took hold of her chin as she looked at the terrified man. "And without any other Pokemon, I guess we can't force him onto the property." She took a deep breath. "And I suppose it isn't safe to go in there without him."

"Dat's a pretty safe bet." Meowth shrugged. "So we're not getting him in dere, huh?"

"Nope." Jessie sighed as she walked past James. "Come on, you two."

"What?" James blinked a couple of times. "You mean, just like that?"

"Yeah." Jessie hid her smirk as she walked along. "We have to catch up with that twerp and his Pikachu."

"That quickly?" James stood upright, his eyes growing wide. "What are you thinking?"

"Yeah, Jess." Meowth tilted his head in confusion. "Are you sure that's a good idea?"

"Hey, we've been chasing them this long, why not keep chasing them?" Jessie walked along. "I mean, if it's that pointless to try to get James in there, then we might as well do something not quite as pointless."

"Are you kidding?" James shook his head again. "I'm sick and tired of following that twerp! He ruined our whole reputation!"

"So what? That just means that we'll become that much more famous when we catch that Pikachu." Jessie folded her arms around herself. "Who cares that we'll do it starving, with tendencies to be ill, poorer than dirt, and likely to die as a joke?"

"Dat's true, Jessie." Meowth smiled behind James. "It's either dat, or we could go back to de boss empty-handed. Sure, Jess, you could probably rely on your mother to bail you out, and if I can beat up dat stupid Persian, I could be sitting in the lap of luxury." He placed a paw on James's shoulder and faked tears. "I'm so sorry dat all dat blame is going to fall on you, Jimmy."

"Huh?" James looked between Jessie and Meowth, letting their words sink in. He jumped and screamed. "What? You guys can't mean that!"

"Well, it's your choice, James." Jessie feigned a sob.

James paused as he thought of Giovanni's wrath, which meant the wrath of a thousand Team Rocket operatives, which meant the wrath of several thousand Pokemon. "M-mommy!" He turned and sped through the gate, making it clatter as it swung open.

"Nice work, Jess." Meowth began running onto the estate. "I'm not even dat evil."

"Well, let's face it." Jessie laughed as she ran along. "James isn't the only one who's tired of chasing Pikachu."

James skidded to a halt before he hit the mansion's doors. "Hold on a minute!" He turned and held up a scolding finger as he turned to Jessie and Meowth. "Now, we all know what's going to happen here, right?"

Jessie and Meowth froze in their tracks, before they collided with James.

"Yeah." James rubbed the back of his head. "We know what's going to happen. First, I'm going to walk into this mansion." He knocked on the door, letting it open under his fist. He took one step inside and paused. "Now, the local butler will greet me immediately."

Suddenly, a man in a dark suit ran into the foyer, bowing as soon as he met James. His longer than normal mustache bounced as he looked up at the blue-haired man. "Master James, a pleasure to see you return."

"Hello, Alphonse." James sighed as he looked back at his two teammates. "Then, said butler is going to immediately call my parents and Jessiebelle in order to call them here."

"I'm afraid that's not necessary, Master James." Alphonse bowed again, closing his eyes sternly. "Your mother and Mistress Jessiebelle are already here."

"See, what did I tell y- What?" James turned and stared at the butler. "Wh-what did you j-just say, A-Alphonse?"

"Come with me, Master James." Alphonse took a firm hold of James's hand. "Your mother has been expecting you and is waiting for you in the southern drawing room." He ran away, carrying James along.

Jessie and Meowth looked at each other, before running after James and Alphonse.

It was hardly any time at all, before James found himself in a gussied up room, with the door slamming behind him. He looked up to see a violet-haired woman sitting elegantly on a well-padded chair beside a table with an elegant tea set on it.

"My, my, James." The woman said from behind her fan. "It certainly has been a long while since we've last met."

"M-m-mother." James flinched backwards to his feet. He laughed nervously. "Um, yeah… It's a funny story really."

James's mother didn't say anything. Instead, she simply picked up her flute, which had been sitting on the table alongside the tea set and began to play it slowly.

The young man watched the woman play for several minutes, hanging onto each note, waiting for the conversation to start. As the song continued to play, he couldn't help but notice that there were several empty notes. It finally hit him. "Where's father?" He looked around suspiciously.

"Dead." The single word hung heavily in the air as the flute has barely parted from the woman's lips. After a moment of silence, she smiled softly and said, "And no. This is not a prank." She went on playing.

"Dead?" James racked his brain for a moment. "But there were no newspapers! No funeral announcements! Not a single soul I've met seemed to know!"

"It was a quiet funeral." James's mother decided to put her flute down and placed her hands in her lap. She didn't look at James, though. "After all, what kind of man would he have seemed, had everyone known he'd died of nothing more than a lil' ol' heart attack?"

The answer was sound, but James stood there a moment. "You didn't expect me to come back, even if you did announce it, did you?"

"Not in the least." James's mother looked up and at James, smiling softly. "You never were the sentimental type."

James stared hard at his mother's face, looking for some trace of deception, some wrinkle of a liar. What he saw was several violet hairs turning silver and two thins lines running down the woman's face where tears had been. "Mom."

"Oh, listen to me! Prattling on like some ol' biddy!" James's mother clapped her hands twice. "Oh, Jessiebelle."

A curtain further in the room pulled back to reveal James's infamous fiancée. She laughed loudly as her introduction was made, standing up and running up beside the seated older woman. "Why hello, James, darling."

The blue-haired man flinched as he met the dreaded woman's eyes. His throat suddenly went dry. "M-m-mother, y-you can't be serious. I mean, nobody follows a funeral with a wedding. It's almost mockery to stack the two occasions on top of each other!"

"Well, if that's your excuse, it's pretty weak." James's mother narrowed her eyes slightly, but not with anger or cruelty. "Your father's funeral was more than a month ago." She picked up her own fan again. "However," she snapped the fan open, "there will be a wedding."

"That's right, James, darling." Jessiebelle had suddenly appeared by the blue-haired man, causing him to flinch and grimace as she leaned against his arm. "Y'all and I are gonna have such a wonderful kind of wedding."

"What?" James began running around the room, having his fiancée chase after him. "But I don't want to get married!"

James's mother sat silently, sipping her tea. Soon, though, she pointed her fan at the rabid fiancée. "Jessiebelle, we have a new agreement, need I remind you?"

"New agreement?" James stopped, causing Jessiebelle to crash into him, and the two fell to the floor. James was able to untie himself, and he looked up at his mother. "What new agreement?"

"Oh, did ya'll really need to mention that." Jessiebelle stood up and brushed off her gown. "It's really nothing that important."

"It is to me. As it may be to James." James's mother turned to her son. She laid down her tea cup. "And you two can come in as well. This will very likely involve you as well."

Jessie and Meowth screamed, when they realized they had been noticed peeking through the door. Though they tried to retreat, they found themselves pushed inside by Alphonse. They smiled and waved meekly, when they found themselves trapped.

"Very good." James's mother snapped her fan shut and stowed it in her sleeve. In exchange, she pulled out a small scroll and unfurled it. "This is the new agreement."

James walked over and looked at the paper for a moment. "And what's this new agreement about?"

"It's a contract. A contract to take place between you and me." James's mother turned the scroll to herself and smiled as she looked it over. "Starting from the time you sign this contract, you must stay on this estate for thirty days. During that time, you will be living here with several females to associate with."

"Um, Meowth?" Jessie turned to the Pokemon and smiled curiously.

"Hey, I'm a Pokemon translator, not a lawyer." Meowth huffed as he crossed his forearms. "However, if I'm not mistaken, dat piece of paper says dat James has to live in dis house with a bunch of goils for about a month."

James's mother nodded as she continued. "Now, under no circumstances will you be allowed to leave this estate, sonny boy, though your female associates will be allowed to do whatever they want." She began furling up the scroll. "If you can meet these conditions, your initial engagement with Jessiebelle will be null and void, and you may choose whom you wish to marry out of your female associates."

"What?" Jessie turned a suspicious gaze towards Jessiebelle. "It's odd that you would agree to something like that, given what I've seen of you."

"No kidding." Meowth crossed his arms. "Somet'ing smells fishy here."

"James, pay attention to me," the mother coaxed, "this next part is important. Should you either break the rules of this contract or refuse to sign the contract at all, then Jessiebelle will have access to our grand fortune to fund her hunt for you and drag you here to be forcefully wed."

"What? How can that be?" James pointed at the contract. "How can you have a clause that applies to if I don't sign?"

"Because I've already signed it." James's mother turned the paper around and pointed at her signature. "And Jessiebelle has signed as my witness."

The red-haired proper lady flipped her hair and laughed triumphantly. "It's not like you won't pick me, anyways, James, darling."

"I see." James swallowed. "So I don't really get a choice in the matter."

"Just be glad I didn't allow Jessiebelle her manhunt from the start." James's mother smiled softly. "Come now. You can't blame your mother for wanting grandchildren. It is your duty to continue the family line after all."

James groaned. "You've got to be kidding me."

"Are you questioning your mother, young man?" James's mother stopped, before she let her anger get the best of her. "I'm letting you have a choice. You can even let your current lady-friend sign as your witness."

Jessie looked at Meowth and pointed to herself. "She's talking about me, right?"

"Yes, she's talking about you, Jessie." James sighed as he looked the paper over. "Where's the pen?"

"James, you can't be serious!" Jessie placed her hands on her hips. "Remember the plan? Come in, sit down, eat, run?"

"Yeah, Jimmy!" Meowth's eyes grew wide. "I t'ought you was afraid of goils."

"What's to be done?" James held his hand out to accept the pen from his mother. "If I sign this, you two can have all the steak tartar and caviar you want until your stomachs burst. If I don't sign it, we'll be spending the rest of our lives being chased instead of chasing." He began scrawling his name on the dotted line, despite the paper not resting on a hard finished, he held it out to his female companion. "Jessie, if you would so please?"

Huffing, Jessie took the paper. "You know this is probably going to be a disaster, right?"

"We've lived through worse." James chuckled hollowly, before swallowing. "I hope."

Once Jessie signed the contract as a witness, Jessiebelle snatched it from her and laughed triumphantly. "Better keep track of your calender, James dear, because the countdown has begun."

"Jessiebelle! If you would be so kind." James's mother held her hand out.

The younger lady looked steadily at the contract for a moment, before depositing it into the estate owner's hand.

"I thank you kindly, Jessiebelle." The violet-haired woman picked up a small bell from the table. "Alphonse!"

The butler quickly appeared in the room. He nodded towards his mistress.

"James, the official thirty days will start tomorrow, but you still will not be allowed to leave the estate today." James's mother smiled. "Think of it as your reprieve. Alphonse, show James and his lady-friend where they'll be staying." Her gaze shifted to Meowth. "And take that to the Pokemon preserve."

"Hey, lady, I ain't a da-" Meowth was cut off as Alphonse picked him up by the scruff of the neck. He chuckled nervously. "Den again, I always wondered what it was like to live on a preserve."

Alphonse herded James and the two younger women out of the drawing room. After they had all left, another curtain pulled back to reveal another butler. "Mistress, are you sure this is a good plan."

"Sebastion." James's mother chuckled lowly in reply. "I don't think you quite understand."

"Understand what?" Sebastion stared at the woman intently.

"You aren't the only one who has missed James." The tiniest beads of water tinted her eyes. "I can't even recall how many years it's been. Ten? Fifteen?"

"Actually, it's been sixteen and a half, Mistress," Sebastion corrected.

The lady gave the butler a harsh look for lengthening the time. "Anyways, as I was saying, James never was the perfect gentlemen. He probably never will be cut out for society." She shook her head slowly. "But a mother misses her son. For years, I've been jumping, when I heard padding footsteps, hoping to see his smiling face as he found a new bottlecap to show me. For years, I've been listening to the hollow echoes of only memories of watching him play with Pokemon. Years of empty seats on his birthday. Years of uneaten ice cream sandwiches on Children's Day. Just so many years passing by me."

Sebastion raised an eyebrow. "Forgive me, but you seem much more sentimental than I remember."

"That's what a husband's death will do. I ain't getting any younger." The tiniest liquid streaks streamed across her chin. "My husband was just short of fifty years, which isn't very old. I would like to let his soul rest in peace by righting our estate once and for all. I want to hear childrens' laughter again, and padding footsteps, too." She smiled only slightly. "But most of all, I want to see what I should have sought for originally as a mother. I want to see my son happy."

"But what if Master James should choose his traveling companion to be his bride?" Sebastion placed a concerned hand on his cheek. "What should become of the estate, then?"

"Don't you worry about that." James's mother's small smirk grew into a grin as she turned to look at the butler. "If I know anything about mutts like her, there's no way she'll succeed in this contest." She chuckled. "After all, Sebastion, you make it sound like Jessiebelle is my only bet in this gamble."

"Mistress?" Sebastion watched the older woman curiously as she laughed.

...

Along foggy roads somewhere, an old carriage creaked along being pulled by two Rapidashes. The driver looked ordinary, but the two people inside were of interest. A Haunter floated around the carriage as it progressed.

"Father." The young woman in the carriage had her eyes hidden in the shadows, but her talking mouth could be seen in the pale moonlight. "Tell me, where are we going again?"

"We'll be taking a ship across the sea." The older man had a smile glued to his scruffy face. His eyes were hidden, too, but his smile showed both pride and mischief. "I have an old friend who'd like you to meet her son."

"Father, I know I've recently become more sociable as of late, but are you sure this is a good plan?" The daughter flipped her dark green hair as the carriage pressed onwards. "I'm not nervous or anything, but I've never left Saffron before."

"Don't worry about it." The father, reached a hand across the carriage and placed it reassuringly on her shoulder. He gave her an affectionate shake. "I'm sure you two will get along famously."

"I hope so." The girl silently watched the Haunter floating around the carriage without a care in the world.

...

Somewhere else, an auburn-haired young woman was skipping around outside of a large building, playing and training with her Pokemon. She laughed as they raced around the lawn, and she soon joined with them.

A limousine pulled up on the road and parked near the trainer and her Pokemon. A butler stepped out of the vehicle and cleared his throat loudly, until he received the young woman's attention.

The auburn-haired girl raced across the lawn towards the older gentlemen, her Pokemon following close behind. "Hey, Mister, can I do something for you?"

The butler nodded. "It has been noted that you have been seen taking positive interactions with Master James, dear lady."

"Master James?" The girl blinekd a couple times as the man handed her an envelope. Curious, she took it and opened it. After reading the letter, she realized that it was an invitation. She purused it again, before slapping herself in the side of the head. "Oh, that James!"

"Precisely." The butler nodded. "If young lady would like to attend, then I would be more than happy to escort her to catch a ship to take her to the estate."

"Okay, just give me some time to pack. I wasn't really expecting to hit the road." The young woman turned and ran towards the large building. She cupped her hand around her mouth to call to her Pokemon. "Hey, Turtwig! Cacnea! Come on! We're going for a trip, and I think you'll be especially surprised, Cacnea!"

...

In a forest that was far away again, two ninjas were jumping through the canopy.

"Come along," the much older ninja called back. He wore his hair quite spiked, and he had a stern expression on his face. "How do you expect to make it in time at that speed."

"My apologies, father." The much younger ninja was obviously one tree shorter with her bounds than her respected father, so her jumps had to be quicker. Her scarf fluttered behind her as she rushed along. "Remind me where we are headed again."

The older ninja smirked as he sped along. "An old aquaintance of mine has asked that I bring you to her estate."

"For special training?" The younger ninja returned the smirk as she thought of becoming as strong as her father.

"Not exactly." The older ninja's smirk creased his face. "Rather, a test."

"A test?" Her brow furrowed. "Is it some sort of legendary ninjutsu to be passed down, or some other rite of passage."

"I suppose you could say that." The father looked back. "You are to meet her son."

The younger ninja froze in midair for a second, but she was lucky by the skin of her teeth to save herself from falling to her doom. She shook her head as she resumed her bounding. "Father, you don't mean matrimony, do you?"

The older ninja nodded firmly. "And I would like you to present yourself properly. Even if he does not choose you as his bride, you must keep your familiy's honor and respect with this family."

The younger ninja nodded with understanding as she continued to follow her father.

...

Okay, end of first chapter, and just to answer the first question/thought that will likely enter everyone's mind, NO! This is not a feel good James/Jessie pairing where James will choose Jessie no matter the trials. He might, but that is not a guarantee worth anything.

Anyways, as you can see, Jessiebelle has more competition than just Jessie. Can you guess who they are?

Also, I'd like to add 2 to 4 more women to live with James for the month, but I'd like to hear from the readers. Who would you like to see? The only real restrictions are: no "twerp" girls (Misty, May, Dawn, etc), no Jenny or Joy, must be female, and has to make relative sense to pair with James (For example, no Agatha or just saying Cynthia would be nice).

Any suggestions will be appreciated in a review. Just give the character's name and reason why you think she'd fit in, and we'll see who makes it in the house. Look anywhere! Old anime! New anime! Gym leaders, one shot characters, recurring characters, etc! I want to hear what the fans have to say.

Enjoy the story and have a fantastic day!