Babying James - Chapter Three Added

[TheLittleWriter]

Hey guys, I’m working on role reversal stories. I have created a Patreon where this story is updated weekly, but I will be posting more chapters in here as time goes on. What other scenarios you’d like to see? Let me know so that I can add them to my list. At the moment I’m working on other stories about role reversals and more! 
My Patreon is https://www.patreon.com/LittlerWriter?fan_landing=true
If you join, I will be adding new stories weekly and you can even tell me if you want me to continue with Evelyn’s regression, From Fatherhood to Babyhood or, if you prefer, something new! 

 

Babying James 

 

James had always been insecure about his height. It didn't help that at nineteen, he was still in the last year of high school or looked more like a middle school boy than a man. Being held back one year didn't really help, and even if he was the oldest in his classroom, he was the one everyone bullied. His only consolation in life was his best friend Kyle, who was a year younger than him but in the same classroom. 

Kyle was everything James wasn't. He was tall and handsome, with dark hair and dark eyes. Captain of the Football team, the swimming team, and basically just better at everything. His grades were also perfect. It just seemed to James that Kyle had everything figured out.

 

Chapter One

 

James' mother, Emma, was a good-looking woman, especially for someone in her forties. She worked for a pharmaceutical company, which meant she had to travel a lot when releasing a new drug on the market. She had two kids, James and Charles. Although James was the oldest, he tended to be a sort of momma's boy, which meant that Charles, at only fourteen, would boss him around when they were alone. To the point where Emma would find James crying after spending an entire day by themselves. Now, she needed to travel for over two months, and there was no way she could leave James in charge of the house. 

She went to the living room, where she found James and Charles playing video games while Kyle, James' best friend, read a book. He seemed so much more mature than both her kids, even if he was younger than James. 

"Hello, Miss Clement," said Kyle, his voice manlier than James and most men her age, "You look great." 

"Thanks, Kyle," she said, blushing; that's when it hit her. Why not leave Kyle in charge? He already spent most of his time in their home, and he was responsible enough to keep everyone safe, "Could I talk to you for a minute? In private?"

Kyle nodded and stood up, a towering man. She couldn't believe he was only eighteen. 

"Is there any problem?" Asked Kyle as they reached the kitchen. 

"No, nothing. I mean, it is not really a serious problem". 

"It's okay, you can tell me," he said reassuringly.

She didn't know why, but his words did make her feel more at peace with her decision. So, she explained what she wanted and offered Kyle money to take care of her kids while she went out to work. 

"Babysit?" Asked Kyle. 

"I know James is already a man, I mean…."

"He is special," said Kyle, "But I meant more about Charles. He can take care of himself." 

"I know, but James, on the other hand."

"So, I'm taking care of James to prevent Charles from walking all over him." 

"That's it," said Emma, "I know it is a big imposition, and you already have your plate full. I mean school, and all your sports, and homework..."

"I'll do it." 

"Really? I'm so glad you said yes." 

"As I said, James is special. And, I think he does need someone to look after him if you are gone for too long." 

"If you are going to do this, there are a couple of things you need to know," she said, "Now, it only happens once a week or not even, but Jamie will sometimes wet the bed. He has these nightmares, and I think he just cannot tell that it's happening until he wakes up. I know it's a lot, but just reminding him to pee before going to sleep would be helpful." 

Kyle nodded. 

"And, he can come from school crying sometimes. It means someone has been mean to him, and I usually hug him until he feels better."

There was a short pause. 

"It's okay. I'll deal with it," said Kyle. 

"So you'll do it?" Asked Emma. 

"I will" 

The two of them went to the living room, where they found James and Charles fighting over the controllers. Though it wasn't much of a fight and more James begging Charles to let him go or he'll tell his mother; and Charles. Well, he was laughing as he pushed his older brother to the ground. 

Emma knew that she couldn't take James with her, but she wanted to. Her son needed her protection, though Kyle would do a good job. He always did a good job in everything. 

 

Chapter Two 

 

"I'm in charge of the house?" Asked James, smiling and excited at the prospect of his mother going away for so long. 

"Yeah," said Emma, lying to her son wasn't something she enjoyed, but she couldn't tell him that his best friend was in charge of babysitting him, "I also talked to Kyle. He will be staying here to keep you guys company."

"Sick," said James, his heart beating faster than usual. He would spend more time with Kyle than ever, which made him smile, though he wasn't sure why. 

"I just want you to be nice to Charles, okay?"

"Okay, mom," said Jame. 

"Now, give me a kiss and go do your homework. I don't want any surprises like last year." 

James blushed. He was ashamed of failing his last year of school, but because of it, he met Kyle, who was the silver lining of his life. Though, everyone else beside him would tease James because of his size, lack of masculine features, and the fact that he tended to cry when bullied. A nineteen-year-old baby, that's what they called him, and part of him felt like it was true. 

He left his mother's room and went to do his homework, though he soon grew frustrated at it. It was his second time going through the same homework and exams, and he was still not good at it. He began tearing, which was a mistake 'cause that's when his brother came into his room. 

"Are you crying?" 

"No," said James, though it was more than evident that he was.

"What is wrong with you? You are supposed to be my big brother, not the baby of the house." 

Charles left the room, disgusted at his older brother. 

James knew he was right. An older brother wouldn't be pissing the bed every other night, nor would he cry when things got hard. So, why was he still crying? Was he not the older brother? 

Yes, he was. Decided to change the way people treated him, James stood up and washed his face. He was an older brother, and he was going to start acting like one. The only problem was he didn't know how to. Maybe now that his mom was going away, he could try and be more responsible, and he should start by not wetting the bed anymore. 

Their mother left the following day, and luckily for James, he woke up dry. He was so excited and proud of himself, and his mother made him a special breakfast just before leaving. Yes, things were going to change. He was going to change, and nothing would stop him.

But, as soon as his mother closed the door, things didn't change. 

"Okay, loser, I'll be in my room. Let Kyle in when he gets here," said Charles, as if he was talking with someone below him, and, even if James wanted to impose himself as the older bother, he didn't know how. 

He was alone in the living room until a knock on the door broke the silence. 

Jame opened the door to find Kyle, tall and handsome, holding a big suitcase and his school backpack. He was wearing a classy shirt, some pants that really let people see he was a full man, and his cologne was almost as strong as his body odor. 

"Hello, little one," said Kyle, "Ready to have fun?" 

Little one was the nickname Kyle had given him. He had protested at first but to no success. Now, that and baby were his name whenever Kyle was around. Though, he would avoid calling him that way at school. 

"I'm ready," said James, allowing Kyle in and feeling better knowing that while Kyle was around, Charles wouldn't make fun of him too much. 

[maly]

Curious to see how this plays out.

Maly.

[TheLittleWriter]

 

Hey guys, I’m working on role reversal stories. I have created a Patreon where this story is already finished, but I will be posting more chapters in here. What other scenarios you’d like to see? Let me know so that I can add them to the list. Get access to all Evelyn’s Regression chapters, From Fatherhood to Babyhood, and more, including some Patreon exclusives. My Patreon is https://www.patreon.com/LittlerWriter?fan_landing=true
If you join, I will be adding new stories weekly and you can even tell me if you want me to continue with Evelyn’s regression or you prefer something new! 

 

Chapter Three

 

During their first day alone not much happened. Kyle got them pizza, saying their mother forgot to leave money and she contacted him to take care of that. Though, she did leave the money, but not to James, to Kyle. 

“Let’s play video games all night,” said Charles.

“Yeah, we should” said James. 

“You guys can play a little. But your mother did say you should be in bed by nine” said Kyle. 

“But, but, mom is not even here,” James complained.

“The baby’s right,” said Charles, “We can do whatever we want” 

“Oh, do you?” Said Kyle standing and towering over the two brothers.

None said anything else about it. 

They ate, watched a movie, and at eight thirty, Kyle stopped everything to let them go get ready. But, once Charles was gone, he stopped James from leaving. 

“Hey, little one,” said Kyle, with a comforting voice tone, “You mom told me about your nighttime issues”

James blushed, fifty shades of red. 

“What are you talking about?” He tried to pretend he knew nothing about it. 

“I’m talking about your bed wetting issues. It’s okay, I won’t tell anyone. But, I don’t want to clean any messes, so why don’t you start wearing some protection?” 

“Protection?” 

“Yeah, you know diapers” said Kyle. 

James blushed again.

“No, I’m not a... I’m not a baby”

“I know that. You know that. It will just be to help you keep your bed dry. And, I bet waking up with a wet bed mustn’t feel too good”

It didn’t, and James hated the cold feeling of the soaked sheets against his skin. But, diapers were too much. He had decided to act more like a grown up, and now it felt like that goal was getting further. What would Charles say if he found out? He would tease forever.

“We won’t tell anyone, not even Charles” said Kyle, reassuringly, “What do you say?”

A part of him wanted to say no, but Kyle just seemed so determined that James actually wanted to do it for him. It was his best friend,t and he didn’t want anything to jeopardize that friendship. 

James nodded. 

Kyle stood up, and guided James to his room, as if he was a little kid in need of someone to help him get ready for bed. James wanted to say something, complain that he was the one in charge. But, he didn’t. Kyle opened the door to James’ room, he’s been there before many times, but this time was different. 

He placed James on the bed and grabbed his backpack. 

“You bought diapers already?” Asked James looking at Kyle holding a big adult diaper.

Kyle nodded, “When your mom told me about it, I decided to take matter into my own hands” 

Kyle began undress in James. But, this time he did complaint. 

“If I’m going to..wear diapers, I’ll put them myself” 

“Have you ever put on a diaper?” 

James shook his head.

“But, I’m in charge. I’m the oldest in here. You shouldn’t...I’m not a baby,” said James, tears began running down his cheeks, “Please. I don’t want you to stop being my friend” 

Kyle undid James’ pants and removed his underwear, which had stains of pee all over. James had little to almost no hair in his balls or penis, and Kyle had to admit that even if he had not seen many, James’ parts were extremely small. He grabbed some baby wipes, and began cleaning throughly. Then, he applied baby powder all over James’ parts, paying extra attention to his balls and butthole, which made James blush even more. 

“It’s okay,” said Kyle, “I’ll take care of you”

Then, he placed the diaper on him, locking him for the night. Kyle lift James from the bed as if James weighted nothing, and held him in his arms. James felt so many things at once that his brain zoned off. He felt asleep almost immediately, feeling safer and more comfortable than he has ever felt before.