A Better Life!

I apologize for the delay guys. I was having a serious case of writer block. Luckily I got through it and I think the resulting story is a good one. As always, please give me your honest feedback and enjoy the story.

All characters are over the age of 18 and are in a purely fictional world.

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Prologue: Life in a Small Town!

Jesse longed for a different life. His current one at home was mundane and repetitive to the point he often forgot what day it was. He tried anything he could think of to add some variety or excitement to his life but there weren't many options where he lived. Jesse was born, raised, and despite hating the idea, he had a strong feeling he'd eventually die in the small rural town he resided in.

As long as he could remember the drab town he called home was one filled with people who all fit a certain norm. The men did the heavy lifting and tended to the fields while women either stayed home looking after their children or got a quiet office job that helped their husbands. Such was the fate of everyone in the small town, his parents included. They had fallen victim to the town's predetermined roles with his father waking up at 5 in the morning everyday to tend to the crops and his mother waking up a little later than that to prepare meals for the rest of the day. Neither of his parents had gone to college but the family farm still made them a very good income.

His father had leased the farm to an agricultural company. They would man the fields, maintain the crops, and harvest them. Jesse's father just had to sit back and relax as the monthly six figure check rolled in but he wasn't the kind of man to sit idly by doing nothing. So despite not having to work his father still went to the fields everyday to help the workers out. Jesse may not have wanted to follow in his fathers footsteps but he deeply respected him. To the point he sometimes wished he could go out and help his father in the fields but that was something he physically couldn't do.

It wasn't that he was injured or had an underlying health issue but rather he simply lacked the body necessary for manual labor.

If a person was to meet Jesse for the first time not knowing he was a man, they'd have thought he was one of the most beautiful girls they'd ever laid eyes upon. It was an odd mystery not just to Jesse himself but also to his family.

For starters despite being a boy he was the shortest person in town standing at an embarrassing 5'2. He had his mother's red hair, her ocean blue eyes, and his father's freckles but that was about the end of their similarities. Jesse's eyelashes and eyebrows were both full, with his eyebrows always looking perfectly done despite him never touching them. His lips were soft and big, which were the opposite of his mother's thin lips.

His mother had often been called the prettiest woman in town but that was only because Jesse was born a man. His mother looked good enough to win the town's beauty pageant but Jesse had looks that far outshined everyone around him. Jesse figured that had he been born in a major city he would have achieved supermodel status overnight. He was gorgeous but that wasn't where the oddities stopped.

His facial features despite them being far more beautiful than his parents still somewhat resembled them but his body was something else. Jesse had thin arms that were attached to a slender frame that lacked any true muscles aside from the somewhat toned abs he had. He had grown to accept his looks and lack of manly muscles like his father had but it was the rest of himself that he was self conscious about.

Jesse had thick thighs that constantly rubbed against each other. Something that along with his naturally feminine strides made him look even more so like a woman but it was his backside that truly bothered him. Jesse had hip dips which made his appearance from the front give off the illusion that his posterior was lacking when in reality it was anything but that. It baffled not just Jesse and his family but the entire town as to how a young man could have such a wagon.

His butt was big, round, and jiggled like jello with every step he took. None of his pants ever fit him correctly with the top of his butt often poking out the waist of his pants. Not even his underwear was safe with his large buttcheeks constantly eating them turning them into thongs which he'd have to fix on a regular basis. Jesse would sometimes catch his own mother looking at his backside with a jealous look on her face. Being the wife of a farmer most people would imagine her with a nice big butt when in actuality she was lacking in all forms of curves.

However it was his fellow townspeople that made his already boring life an unbearable one. He had never done anything to wrong them yet the mere fact his appearance was the way it was made them ostracize him. From hurtful remarks to outright ignoring him, people treated Jesse horribly and it was the handful of people his age who did it the most. He was bullied constantly growing up for his girlish looks. Guys would pick on him and sometimes even beat him up just because they knew he couldn't fight back. They did so for a while until they got bored and ignored him like the rest of the townspeople but it was the girls who truly broke him. They would make fun of him in ways that were just too cruel to be considered anything but evil. His most painful memory was when Lory, the girl whom Jesse had been in love with since they were kids pulled a "prank" on him with help from a bunch of other girls.

It was 4 months ago, they were in highschool at the time and were getting ready to graduate. Jesse had finally decided to ask her out, so he approached her after school where she told him to meet her in the barn in 15 minutes. Looking back Jesse realized there were plenty of red flags, the most obvious being how Lory was trying to stifle a laugh while looking at him but he was in love with her so they flew right over head. He met her in the barn just as she instructed only for no one to be there. Jesse's heart fell apart at the realization of how Lory truly felt about him but it was what happened next that made him desperate to leave town. Jesse turned around to go home only for Lory and a group of girls to pop out of the barn stalls catching him off guard. Before Jesse could even react Lory tossed a small bucket filled with horse pee at him before pelting him with eggs.

Jesse found himself soaked in urine and covered in egg whites but it was the fact that Lory was the one that put him in his current state that made him cry. The tears that flowed out of his eyes that day and the emotions he let out were unlike anything the girls had ever seen. His deep sobbing quickly killed the laughter of all the girls around him. It was at that moment they all realized they had gone too far and immediately attempted to apologize. They all approached him trying to comfort him, telling him it was just a joke. Jesse swatted away their hands and ran home, breaking down even further in front of his parents. They had known for years that he was the subject of bullying but never to this extent.

His parents drove straight to the school, where a couple of the girl's parents were already there. They tried to defuse the situation, telling his parents that they would discipline their daughters but Jesse's mother wasn't having it. She pushed them aside and went straight to the principal's office. There was yelling and accusations of turning a blind eye to which the principal denied. But it wasn't until Jesse's mother threatened the school with a lawsuit did the principal take things seriously and take action. The resulting punishment was harsh for everyone involved, with all of the girls being expelled only weeks before graduation but for Jesse it was the last straw.

He was done with his hometown.

Jesse decided to get away at any cost. He figured anything would be better than his life in a town where everyone treated him poorly and knew that if his parents truly loved him they'd support his decision to leave. He was desperate to see what the world had to offer, what an alternative life where he was treated fairly would be like. However, Jesse's inexperience with the outside world was something he overlooked.

Something a beautiful hung woman would take full advantage of.

- Chapter 1: Freedom, Only a Flight Away!

Jesse sat in the living room flipping through TV channels hoping to find something he could watch. Such was his daily routine for the past month and a half. He would wake up around 9am, take a shower, brush his teeth, eat breakfast, and spend the rest of the day lounging around watching television. There wasn't anything to do in town and if there was it meant interacting with the townspeople that treated him like was the butt end of a joke. After the evil prank the girls pulled on him, Jesse saw zero reason to leave his home and became a shut in.

His mother was currently out getting groceries and his father was out in the fields fixing a broken water pump with some of the workers. He kept flipping through channels with nothing catching his eye. Jesse was about to give up and go play games on his laptop when a commercial caught his attention.

"Do you need a change of scenery? Are you a person that likes to help others? Hi, my name's Mei Sato. I'm the owner of Helping Hands! We find kind and caring individuals from all over the world and send them to people here in Japan that could use some help. You'll aid in a variety of tasks ranging from financial management, to medical aids, and sometimes personal. In return you'll be awarded with a handsome paycheck. So what are you waiting for? See the world and help a person in need."

Jesse was locked in. This was it. This was what he needed. Not only would he get to leave town and go to a different country but he'd also get a nice paycheck to support himself. He quickly called the number on his phone and was connected with a representative.

"Uh...H-Hi! My name's Jesse. I uh....I saw your commercial and I'm interested in applying."

"Oh, wonderful! I just need your full name, age, and an email so we can set up a zoom meeting."

"Cool. My full name is Jesse Smith and I'm 19 years old! My email is....."

"I'm sorry Jesse, did you say 19?"

"Uh...Yes, ma'am."

"Well at that age you don't have any medical or financial degrees. I'm not sure there's much we can do with you."

"Please, ma'am! Just give me a chance! I'm begging you!"

"Okay! Send me your email and we'll have a zoom meeting but I want you to know that there's still a good chance you might not be what we're looking for."

"Understood! Thank you, again."

Jesse rushed up the stairs to his room. He quickly opened his laptop and sent the representative his email where she confirmed their meeting. It was set to start in 10 minutes. He quickly put on a buttoned shirt and washed his face before sitting down at his desk. He felt himself quickly becoming nervous but was able to suppress it just in time as he was called on zoom. He took a deep breath and answered the call. There was a brief moment of pure silence as the call loaded but when it finally connected he was met with the voice of the lady on the phone.

"Hi! Jesse Smith, right?"

"Uh...Yes, ma'am."

Jesse was now able to put a face to the voice he heard earlier and it was quite a shock. The voice he heard was none other than that of Mei Sato, the owner of the company. Just as her name suggested she was asian and very beautiful. Nothing was said for a moment as they both studied each other until Jesse finally broke free from Mei's beautiful trance and spoke first.

"Uh...Thank you again for seeing me, Ms.Sato!"

"Oooh, it's not a problem and please, call me Mei. I must say Jesse, you're a very beautiful girl. I'm not exaggerating when I say you're the prettiest girl I've ever seen."

"Oh! Uh...Thank you, Ms.Sato. I mean, Mei! B-But I'm actually a boy."

Jesse could see the confusion on Mei's face as she tried to wrap her head around what he just said. It was something Jesse was already quite used to and had found the best way to prove he was a man was to show his ID. He took his wallet out and held it open in front of the camera to show Mei his ID. He didn't have a driver's license yet but his parents made it a point to get him an official state ID. Jesse could see Mei's eyes bounce back and forth between the gender portion of his ID and his face. She kept doing so for a couple more seconds before finally proceeding with the call.

"My apologies, Jesse."

"It's....It's alright! It happens a lot actually!"

"I'm not surprised. Even though you're a man you look gorgeous, more so than any woman I've ever seen. You should take pride in your looks, especially your lips. They're nice and big. I know a couple special women who'd love to have them wrapped around their....Uh...N-Nevermind, let's get back on track. Do you have any degrees?"

"Uh...N-No."

"Do you have any skill sets?"

"N-No, ma'am."

The call continued in that manner for another 20 minutes. It consisted of Mei asking Jesse questions to see what skills he possessed and Jesse answering "No" with an increasingly defeated tone. By the end of things Jesse all but realized he wasn't going to get the position and that he'd be stuck in the hell hole that was the town he lived in for the foreseeable future.

"Well Jessie, I'm sorry to say this but I don't think we can use you. You just don't have the qualifications for us to match you with someone."

"I....I understand. Thank you for the....the.....Brrrrrr....."

"Are you alright?"

"Yeah, the air conditioning is on right now and it's making the room kind of cold."

"Don't freeze because of me. You can turn it off."

Jesse thanked her and scooted his chair back from the desk before standing up. He turned around and walked to the AC giving Mei a clear view of Jesse's plump backside. She leaned forward and bit her lip as she watched the big juicy looking booty in front of her jiggle as Jesse reached up to turn off the AC. She could already imagine the things she wanted to do to the butt in front of her but remembered she was the owner of a major company. The last thing she needed was a scandal of her preying on a boy who was half her age but a lightbulb went off in her head.

She may not be able to enjoy Jesse but she knew someone who desperately needed someone like him. Jesse was a boy so he would be far more durable than a woman and with the out of this world bonus his ass was he would be the perfect match for someone she knew.

Jesse walks back to his desk ready to hear that he was rejected from the position but was shocked to hear about a different opportunity.

"Jesse, I can't officially take you as part of Helping Hands."

"I figured as much. Thank you for seeing me anyway. I'm sorry I wasted your......"

"But, I do have a different job I can give you. You'll be a part of a side business I run. It's for special women here in Japan who are looking for a long term....helper...that will live with them and...take care of a...big and hard problem...they all have. You'll be...helping...a family member of mine and get paid far more than what you would have if you joined Helping Hands."

"REALLY?"

His over the moon response was all Mei needed to see to know how inexperienced the boy was in everyday life. She figured it was a by-product of growing up in such a small and secluded town but it was perfect for her since it meant that he wouldn't question anything.

"Yup! The person you'll be...helping...is my younger sister. I can't go into details but can promise you she'll enjoy your...company...very much. I know she'll like you."

"Cool! We could be friends."

"Oh, no! I mean she'll really like you. She looks like a younger version of me and is actually only a couple years older than you."

"Wow! Your little sister sounds really pretty. E-Especially if she looks like you."

"Oh, stop you flatterer. She's indeed quite the looker but she's only my little sister in age. That girl.....Oh that girl is anything but little. She's the pride and joy of the whole family. She'll be using your...services....practically non stop everyday. I'll email you the documents and once you sign them I'll send over my personal assistant to pick you up."

"Thank you, so much Mei. I promise to do everything I can to help your sister. In fact, I'll do such a good job she probably won't let me leave."

"Oh, I bet things will go exactly like that. I do need one last thing from you before we end our call."

"Anything, Mei!"

"I need to do a quick physical on you. The task you'll be...handling...is uh...quite massive. All her past...helpers...quit the moment they saw how big of a problem she has but I know a winner when I see one."

"Me? A winner?"

"Mhm! My sister has the biggest...problem...I know but I know you'll be the one to help her. I just need you to strip for me to make sure you're physically okay."

Jesse seemed a bit reluctant, which Mei picked up on and addressed with some subtle manipulation and a couple small lies she knew he would never question.

"Don't worry Jesse. I'm a doctor, this is strictly for medical purposes. I can't give you the job unless you complete this physical."

She bit her lip in excitement as Jesse began to slowly undress. Her lies of being a doctor and the purpose behind him stripping going right over his head. Jesse eventually took everything off except his boxers which slightly annoyed Mei.

"Jesse, those need to come off too."

"D-Do they have to?"

"TAKE THEM OFF, NOW!"

Her sudden shift in tone made him realize that it was best not to upset his new boss. He slowly stepped out of his boxers and stood completely naked. Mei drank in the sites of his soft looking thighs and almost laughed at the sight of his pathetically tiny penis but what she really wanted to see was still out of sight.

"Okay everything looks good, Jesse. I need you to turn around for me."

He did so without question and put his bare bottom on display for his boss.

"Goodness, it's...it's amazing. Oh, she's gonna drill your....Uh....N-Nevermind. I just need you to do a few things for me."

Jesse heard what he thought was the sound of a zipper being undone but decided that needless questions would only serve to irritate Mei. With Jesse not facing the screen Mei took the opportunity to quickly fish out her huge 10 inch cock and began stroking herself.

"First I need you to bend over!"

"L-Like this?"

*SHLICK*SHLICK*SHLICK*

"Y-Yes! Now spread your butt."

She was leaking precum like crazy as she watched Jesse's fingers sink into his soft buttcheeks. He slowly spread them apart revealing his small, pink, and undoubtedly tight butthole that Mei could tell hadn't seen any use which was perfect. She quickly grabbed a condom from her desk and put it on before she ruined another computer.

"Y-You're doing great, Jesse! Just a bit more and the job's yours. Next I need you to stand up straight and jump in place."

"Y-Yes, ma'am!"

He stopped spreading his cheeks and did as he was told with a new found eagerness at the idea the job was almost his.

*CLAP*CLAP*CLAP*

His buttcheeks crashing together before rippling apart and jiggling for their sole audience member.

*SHLICK*SHLICK*SHLICK*

'It jiggles so easily but still has great definition and roundness. J-Just a bit more....I'm...Oooh, I'm about to cum.'

Mei's cock was throbbing rapidly. She was never a quick shot but the ass in front of her had her beyond horny. She needed Jesse to do one more thing for her to push her over the edge.

"J-Jesse! O-Ooooh. W-We're almost done. This is the last part. I.....I need you to squat down and bounce on your feet. While moving your hips side to side. Do that and the jobs yours a hundred percent."