Wayside School Fan Fiction

Wayside School Fan Fiction
_____W A Y S I D E - S C H O O L - F A N - F I C T I O N_____

Saturday, April 18, 2026

Mr. Master

This story is inspired by D.J.’s view of happiness in the sixteenth chapter of Louis Sachar’s Sideways Stories from Wayside School. Before we dive into the fan‑fiction, let’s take a look at Chapter 16, “D.J.”


CHAPTER 16. D.J. — SUMMARY

D.J. arrives at school wearing a huge grin. When Mrs. Jewls and the rest of the class see his smile, they catch it instantly and begin smiling too. It feels as if the whole classroom (walls, desks, and chairs included) wants to laugh, especially since D.J.’s face never stops looking cheerful. Everyone asks him what he’s so excited about, but D.J. just keeps smiling. Even at recess, when Louis presses him for an explanation, D.J. simply says that you need a reason to be sad. You don’t need a reason to be happy.



D.J. wanted nothing more for his birthday than to invite Mr. Master, the great magician, to perform at his party. He still remembered how excited he’d been at Todd’s birthday — right up until Jason marched onto the stage and ruined the whole show. D.J. had been devastated.

So, his parents decided to call Mr. Master directly.

“Did you say D.J.’s birthday party?” the old magician asked over the phone.

“Yes,” D.J.’s father replied. “I’m his dad.”

“Is D.J the boy who goes to Wayside School? Same class as Todd?”

“That’s right. Do you know Todd?”

“Oh, I know Todd,” Mr. Master muttered. “And Jason. I know them very well.”

“Excellent!” D.J.’s father said.

Mr. Master cleared his throat. “I’ll perform for D.J., but only if no one else attends. Just him and his parents.”

D.J.’s father hesitated. “So, no guests? Well, all right. Should I give you our address?”

“No!” the magician barked. “If I come to your house, we could be interrupted by uninvited guests.”

“Uninvited guests?” D.J.’s father repeated,. “Then where should we meet?”

“In a hot air balloon,” Mr. Master declared. “No one can disturb us up there.”

D.J.’s father laughed. “That actually sounds like fun.”

“Good. Book a ride on a sunny day with wonderful weather. D.J. will see the best magic show of his life.”

When D.J.’s parents explained the plan, he was thrilled. And confused.

“I checked,” his father said. “Only two companies offer balloon rides: Balloonicorn Flights (cheaper but shorter) and Skyberry Balloons (pricier but more fun).”

“Let’s choose Skyberry,” D.J.’s mother urged. “Mr. Master probably expects us to pick the cheaper one.”

“He can’t prepare anything anyway,” D.J. laughed. “How could anyone set up tricks in a balloon basket?”

He was wrong, of course. Mr. Master had secret arrangements with both companies, allowing him to install hidden trapdoors and compartments in one of their balloons. So, when D.J.’s family booked their ride, the magician was already waiting.

They met him at dawn beside a wide green field, where a tall red balloon swayed gently in the morning breeze.

“Good morning, my friend,” Mr. Master said, shaking D.J.’s hand. “Excited?”

“Of course! It’s my birthday. And the best magician in town is performing for me.”

“And you’re riding in a hot air balloon,” Mr. Master added with a wink. “By the way, the ride lasts a couple of hours, and we’re not allowed to bring food or drinks. So, we’d better hydrate first.”

He opened a black leather bag at his feet and pulled out a carton of orange juice and four plastic cups.

“Amazing!” D.J.’s father exclaimed. “How did you know we were thirsty?”

“Part of the job,” the magician chuckled.

They drank quickly. Mr. Master pretended to sip his, then spilled it onto the grass when no one was looking. He tossed the empty carton and cups into a nearby bin, locked his bag with a long metal key, and climbed into the basket with them.

The balloon lifted off smoothly. Mr. Master handed his leather bag to D.J.

“Take care of this while I get us into the sky.”

He pulled ropes, adjusted levers, and soon they were drifting above the city. Then he turned around with a flourish and produced three sun umbrellas.


“These will protect you from the bright sunshine. And help you see my moves better.”

“Where did the umbrellas come from?” D.J.’s mother gasped. The magician wore tight trousers and a short sleeved shirt; there was nowhere to hide umbrellas.

“Magic,” he said simply, placing his hands on a small table in the center of the basket.

He asked D.J.’s parents about their favorite colors, the first letters of their names, and their favorite fruit juices. It was mango for Mom, cherry for Dad. Then he and used the answers to guess their birthdays with fantastic accuracy.

Then he turned to D.J.

“Your turn.”

“You already know my birthday,” D.J. laughed.

“True,” the magician admitted. “Then let me ask you this: if you could have one wish, any wish at all, what would it be? Think carefully.”

D.J. thought carefully. “I’d wish to be happy.”

“A wise choice,” Mr. Master said. “After all, being happy is the best thing you can wish for. But if you think of it, you don’t even need a wish for happiness.”

“I need a reason to be happy,” D.J. insisted.

“Then please hand me the red tube from my bag,” the magician said, giving D.J. the long metal key. “I’ll hold your umbrella.”

The bag was full of top hats, colorful scarves, white bunny plushies, and card decks. D.J. rummaged through it until he found a wide red plastic tube.

“It’s just a normal tube,” Mr. Master said, peering through it. He set it on the table.

D.J. nodded.

“What about now?” the magician asked, lifting the tube.

A tall glass appeared on the table.

“Wow!” D.J.’s mother gasped.

“Unfortunately, it’s empty,” Mr. Master said. “And what do people think when their glass is empty?”

“They think they’re unlucky,” D.J. replied.

“Exactly.” The magician lowered the tube, hiding the glass. “And what about now?”

He lifted it again. The glass was now full of orange juice.

“What’s your favorite juice, D.J.?”

“Orange.”

The magician threw up his hands. “How did I know?”

D.J.’s father frowned. “But what does this have to do with happiness?”

“Everything,” Mr. Master said. “D.J., how do people feel when their glass is empty?”

“Sad,” the boy answered.

“And when it’s full?”

“Happy.”

“Good. Now drink half.”

“But I drank a cup of juice only five minutes ago,” D.J. protested.

“That was half an hour ago,” Mr. Master said. “Do you want the show to continue?”

D.J. gulped down half the juice.

“And now?” he sighed.

Mr. Master placed the glass on the table.

“What do people think when they see a glass like this?” he asked.

D.J. scratched his head.

“Optimistic people think the glass is half full, while pessimistic ones believe the glass is half empty,” D.J.’s mother explained.

“Yes,” the magician exclaimed. “For some reason, they’re happier when they enjoy a lot of liquid. So, please drink the rest of the juice, D.J.”

“But I’m full!”

“Do you want me to continue?”

Groaning, D.J. finished the juice. His hand trembled as he set the glass down.

“You’re full of juice,” the magician said. “Are you happy?”

“No!” D.J. yelled. “I need a toilet right now and we’re in the sky!”

Mr. Master yanked ropes and pushed levers. The balloon descended rapidly and landed beside a porta cabin toilet at the edge of a park. D.J. sprinted inside.

When he returned, the magician asked, “How do you feel? Happy or sad?”

“Happy,” D.J. sighed with relief.

“That’s your lesson, my boy,” Mr. Master said, packing the umbrellas into his bag. “You need a reason to be sad. You don’t need a reason to be happy.”

 

Ruining All the Fun

This story is inspired by Deedee’s efforts to get a green ball in the fifteenth chapter of Louis Sachar’s Sideways Stories from Wayside School. Before we dive into the fan‑fiction, let’s take a look at Chapter 15, “Deedee.”


CHAPTER 15. DEEDEE — SUMMARY

Deedee always wants to get a green ball from Louis, or at least a red one. But because she has to run down thirty flights of stairs to reach the playground, she always arrives after Louis has already handed out all the good balls. Every recess, Deedee tries a new strategy to get to the schoolyard faster: she takes the stairs ten at a time, she cuts across the grass like a professional runner, and she even asks Mrs. Jewls to let her go to recess early. Nothing works. Eventually, she disguises herself as a dead rat, and because Mrs. Jewls doesn’t allow dead rats in her classroom, Deedee suddenly finds herself outside on the playground, first in line to ask Louis for a green ball.



At recess, Dameon never made the teams. He always ended up on the bench under the chestnut tree, waiting for someone to slip or get tired so he could take their place.

He was watching the clouds drift behind Wayside School like a playful herd of white sheep when he heard quick footsteps pounding across the volleyball court. He turned just in time to see Deedee’s sneakers tearing a line through the grass. She reached the monkey bars, checked her watch, and bent over, panting.

Dameon stood and walked toward her.

“Is that a stopwatch?” he asked, raising his eyebrows.

Deedee nodded between breaths. “Yup. There are fifty yards from the school entrance to the monkey bars.”

“I didn’t know that,” Dameon chuckled. “I’m terrible at guessing distances.”

Deedee tapped the stopwatch. “I can run it in ten seconds now. If I get it down to eight, I’ll reach Louis before Todd does.”

“Why do you need to beat Todd?”

“To get a red ball. Or at least a green one,” she said. “Todd always ends up with the last green ball.”

“But you don’t have to kill your lungs for it,” Dameon laughed. “You’ll make the teams even if you’re not the one who gets the ball.”

Deedee brushed dust and grass off her ankles and jogged back toward the school steps to try again.

“Hey, Dameon!” someone called.

He turned. Todd was waving from the kickball field.

“Did someone get tired?” Dameon asked.

“Nope,” Todd said. “Come sit on the bench.”

Dameon headed back toward the chestnut tree. “I was telling Deedee she can join our teams,” he said. “Or she can sit with me until there’s a free spot.”

“Deedee’s trying to get the ball herself,” Todd replied. “Leave her alone. You’re ruining her fun.”

Dameon snorted. “Did you see her purple face? She didn’t look like she was having fun.”

The next day, neither Todd nor Deedee bothered to chase Louis for a ball. Instead, they slipped behind the school, where Deedee began running back and forth across the porch.

Suddenly she sprinted toward the edge, jumped off, and tucked her knees to her chest, spotting her landing point like a hawk. Dameon watched in awe as she touched down on the balls of her feet beneath the older chestnut tree near the fence. She bent her knees and held her arms out for balance.

“Oh my gosh!” Dameon shouted, rushing to her. “Deedee, are you okay? What happened?”

“Deedee is fine,” Todd called from the porch. “Relax, dude.”

He crouched and offered his hand so Deedee could climb back up.

Dameon frowned. “Does Louis know what you two are doing? What is going on?”

“Nothing,” Todd said. “I’m teaching her parkour. That was a precision landing.”

“Precision landing,” Dameon repeated. “What does she need that for?”

Deedee grinned. “Look. When the bell rings, everyone rushes down the stairs. Some kids take two or three steps at a time. I need to take ten steps at a time if I want a red ball. Or at least a green one. That’s why I need precision landing.”

Dameon stared at her. “That’s crazy,” he whispered. “Let me get the ball for you. You don’t have to do all this.”

Todd squinted at him. “What’s your deal, Dameon? Do you like Deedee?”

“I don’t like Deedee!” Dameon blurted. His face turned bright red. “I mean, I like her, but not that much.”

“Then leave her alone,” Todd said. “She just wants to get the ball herself.”

The next morning, Dameon tried to forget all about Deedee and her bizarre training. He didn’t make the teams again, but Todd told him to wait on the bench until someone slipped or got tired.

He was watching the clouds drift across the kickball field when he noticed something strange behind the school. The crown of the chestnut tree was shaking violently, even though there wasn’t a breath of wind.

He stood and walked toward it.

Suddenly Deedee burst out of the tree like a launched firework, plunging toward the ground faster than a ball Terrence kicked over the fence. For a moment, Dameon was sure she was going to die.

But she bounced, flipped in the air, and landed on her feet. Two long elastic cords stretched from her waist to the branches above.

He sprinted to her. “Deedee! Are you okay?”

“Better than you are,” she laughed, unclipping the cords. “This is just bungee jumping.”

“I know what bungee jumping is!” he gasped. “But why are you doing it?”

“You know I look like a mousy little girl,” she said. “Tomorrow I’ll pretend to be a dead rat. Mrs. Jewls will throw me out the window. I’ll be the first one to reach Louis. Red ball guaranteed.”

“But you’ll break your neck, won’t you?”

“Not if I use these bungee cords,” she declared. “I’ll carry them in my backpack.”

“Wouldn’t it be easier to just carry a red ball?” Dameon asked.

“Leave her alone, dude,” Todd called from behind. “You’re ruining all the fun.”

Knowledge K

This story is inspired by Kathy’s attitude toward her classmates in the twentieth chapter of Louis Sachar’s Sideways Stories from Wayside Sc...