My Little Brother's Babysitter - Jonathan Byers/reader

Chapter One: The Best Babysitter Ever

It was almost lunchtime at the Wheeler household and a familiar tune of knocks rang throughout the house. Mike ran throughout the house shoving past his mother and sister so that he could be the one to answer the door. Today was the first session of the Dungeons and Dragons campaign that he had been crafting for weeks. He was confident that this was his best one yet.

"You're here!" The Wheeler boy exclaimed after he swung open the door to reveal four familiar faces. His mother laughed at his antics but stopped when she saw the boys' babysitter.

"Oh (y/n) I didn't know you were sitting. Nancy can watch over the boys while they play their game." She laughed, expecting the teen to take off with that sentence. Nancy was already grimacing in the corner at the thought of having to cancel with Barb over a dumb kid's game.

"Actually," (y/n) started. "Mike invited me. I wanted to join in on the game and I'll watch the boys. No charge." She smiled. (Y/n) was well-liked by the parents of Hawkins, so her small babysitting business did well and gave the teen something to do after school. Despite her popularity amongst her clients and their children, people her age were much harder to please.

Mrs. Wheeler thought for a moment, mainly why a high schooler would want to play a game with a bunch of middle school boys. "Oh alright, but at least let me leave you with some pizza money for later. I feel bad leaving you with these four all by yourself." She playfully remarked as she fished some cash out of her wallet and handed it off to the volunteer sitter, who took it gratefully. "You know the drill by now. Call me if you need anything and make yourself at home."

She laughed, "Don't you worry Mrs. Wheeler. Handling these boys is my second nature by now." with that, the Wheeler women left for their own time out. "Now," their (h/c) supervisor looked back at the quartet with a grin "it's game time." All the boys cheered and raced down to the basement almost falling over one another. They couldn't figure out which was cooler: the new campaign or playing with a high school girl.
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"Alright, boys! Pizza break." The table was quickly cleaned off as a steaming pepperoni and sausage pizza was placed in front of them. Digging in (y/n) asked, "So you boys got dates for the winter dance?" A teasing look graced her features when she saw the disgusted and embarrassed looks of the kids in front of her.

A chorus of "ews" and "no ways" came from them. However, Lucas countered her pry with one of his own, "Well do you have a date for the high school winter dance?" Now she was embarrassed and they could all tell by the rosy hue that bloomed on her cheeks. Their babysitter quickly shut down the thought of her having a date and returned to her pizza.

"Is there a special guy you haven't told us about?" Dustin wiggled his brows while emphasizing "special guy." The rosy pink turned to cherry red at the question. "Oh my gosh, you do!" Dustin exclaimed after noticing her expression. "You have to tell us who!"

She looked between the four boys about to decide her fate. They had the eyes of pure curiosity. Of course, that curiosity was directed at the poor excuse of her love life. She focused on Will a little longer wondering if he'd hate her for liking his brother, but better tell them like this than have something come up in front of the man himself.

Fiddling with the straw stuck in her Coke can she started "Well.. you know him.." dragging out her words to mess with their anticipation. "He's about my age-"

"Tell us already!" Mike interrupted. He was interested, but he also had two sisters so this wasn't his favorite topic.

"It's Jonathan."

Their jaws went slack. Will seemed most in shock, but it quickly turned into joy. The thought of two of his favorite people being a couple made him so happy.

"We have to tell him!"

"No! Not in a million years!"

Will's smile dropped. "Why not?"

"Your brother doesn't like me like that, Will. I don't want to make things weird between us." The confusion was still evident on his face, but Will didn't like to argue. "However, that doesn't mean you can't be my wingman." She said, trying to lighten the mood. "But, you guys cannot tell anyone this, especially Jonathan. Ok?"

They all smiled and agreed, but she held her pinky out. "I mean it." The group messily linked their pinkies together "Deal!"
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After ten or more hours of serious campaigning, Mrs. Wheeler finally shut down the game and bid everyone goodnight. (Y/n) usher Will, Dustin, and Lucas into her car since she was their ride that morning. One by one she dropped off the boys, walked them to their doors, and greeted their parents. Will was the last one to be dropped off.

He saw her face light up when her headlights illuminated his older brother, who was waiting outside for them. They both got out. Will ran and hugged Jonathan while she stood a few steps before him. "I think he had fun today." She was struggling to hide the grin that she had when she was in his presence.

Jonathan let out a light chuckle. "I can see that." Ruffling Will's hair, "Thank you for looking after him today. I hope he didn't cause any trouble."

"He never gives me trouble. I love looking after them. They're my boys." A kind smile graced her features. "You're welcome to join us too. Only if you want." Her smile remained, but grew slightly awkward.

"I might take you up on that. I bet they're a lot to handle four to one." He returned the awkward smile with one of his own.

"You could say that"

"Yeah."

"Yeah."

"..."

"..Well it's getting late. See you tomorrow. Be safe on your way home." He breathed, finally cutting into the awkward tension.

"Thanks, you too! I mean on the tomorrow part- but be safe when you drive! Uh- goodnight." She stumbled over her words as she retreated to her car.

The Byers boys waved her off. As soon as her car left their makeshift driveway Will finally questioned what just happened "Why was that so hard to watch?"

"Was it that bad?" Jonathan asked, looking down at his younger brother.

"Really bad."

He poked Will's head. "Go to bed."

Will just laughed as he walked into the house "You've got it bad!"

He was right. Jonathan had it bad, and he had it bad for you.