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The Boarding School Adventures of Laughing Jack and Isaac

Summary:

What if Isaac had brought Laughing Jack to boarding school with him? What would his life had turned out to be like? Will everything end happily? (Of course it will, I’m in denial :D)

Notes:

And so it begins! What delightful adventures will our friends get up to? Find out below!

(It picks up right in the middle of “The Origin Story of Laughing Jack, so I definitely recommend reading that first! With that being said, enjoy! :D)

(See the end of the work for more notes.)

Chapter 1: First Grade: Moving In

Chapter Text

Neither Jack nor Isaac said a word as he crept down the stairs alone to face whatever horrible fate was coming to him. Jack could hear much yelling from downstairs but couldn’t make out what was being said. After about thirty minutes, a teary eyed Isaac ascended the stairs back up into the room.
“Well?” Jack asked nervously. Isaac just starred at the ground as he spoke, “I… Tried to tell her it was you who hurt the cat… She didn’t believe me… Said you weren’t real…” Jack frowned, knowing this was all his fault.
Isaac used his sleeve to wipe away his tears, “I’m being sent off to a boarding school. I’m leaving tonight…and you can’t come with me.”
Laughing Jack’s face turned to shock, “What?! I-I can’t come? Where will I go?” Isaac said nothing but pointed over at the beautiful colored box from where his friend had originated.
“Back in there? But I won’t be able to get out until…” Jack paused.
Isaac looked up at his only friend with tears streaming down his face, “Jack… I promise I’ll come back for you as soon as I can!” Jack looked at the box, then back at Isaac.
“And I’ll be right here, waiting for you, kiddo.” Jack smiled, as a single tear ran down his cheek.
Isaac stared up at Jack, overcome with grief as the thought hit him: No. No, he couldn’t just leave Laughing Jack, the only true friend he’d ever had to rot in his box back here in London. Only a monster would do that. Just as Jack was about to vanish back into his box, Issac tugged at his colorful sleeve.
“Wait, Jack. Don’t go, please.” The clown turned back to the boy with a soft, melancholy expression.
“Yes, Issac?”
The boy’s face hardened with a sense of determination and resolution.
“I’m…I’m taking you with me.”
“Wh-what?” Jack was stunned, but before he could even protest, Isaac had grabbed the signature colorful box and was stuffing it in with his clothes and everything else he had packed. “Really?”
“I don’t think I’m gonna survive boarding school without you there. I can’t. I…I need you, Jack. You’re all I have.” The boy grew misty eyed once more and hugged Jack tightly, the clown squeaking like a toy as Issac squeezed.
“I…Oh, Isaac…” Jack cooed, stretching his arms around Isaac and pulling him close to his chest. “You mean it? I’m really coming with you?”
“Only if you want to. Although, it might be kind of boring most of the time, and- ack!” Jacked laughed joyously, spinning in rapid circles while holding Issac.
“Yippee! I get to come along with you!” He set Isaac down gently on his bed as he spun. “Oh, I’m just so happy, I could sing!” With that, Jack summoned his trusty accordion and took a deep breath, preparing to burst into song when Isaac cut him off.
“Wait, wait, wait! Jack! Not now!” The clown deflated slightly, but nodded, making the instrument vanish into thin air. “You’re coming with me, but for now, you’re going to have to hide until I get to school, okay?”
“Of course! Anything for you, kiddo! See you at school!” And with one last whimsical laugh, Jack vanished back into his box. Isaac breathed a sigh of relief, knowing that his friend was going to be okay, and finished packing up his things for the carriage waiting outside the house. As it sped away, Isaac stared out the coach window at the sprawl of London, a sight he wouldn’t get to see again for quite some time. The stillness of the night and the rocking of the carriage worked to lull the boy into a gentle, dreamless sleep.

Upon his box being opened, Laughing Jack burst out in a colorful explosion of confetti and streamers the way he always did, now with even more excitement than ever.
“Isaac! Hello! How did the trip go? Are we there yet? I-“ Jack took in his surroundings and found he was now standing in a drab little dorm room.
Towards the left side of the room was a small wireframe bed and mattress that had already been made, topped with a small peacoat that had been left upon it. To the right was a small writing desk with an equally miniature chair to compliment it, along with a fairly large wardrobe cabinet and a fairly small ticking clock. On the back wall was a tall, rounded window with a pair of olive green curtains adorning its end, the afternoon sunlight streaming in through the dusty panes. It was plain, but not unusually sparse for a dorm room. Below him stood Isaac, now donning a refined looking school uniform. Whatever misfortune was visible on his face vanished as the rainbow colored clown appeared.
“Jack!” The boy instantly hugged him, creating the same old squeaker sound from Jack. “I’ve got so much to show you! Here, come look at our view!”
The clown curiously followed Isaac over to the window as he got a look outside at the courtyard below. The grounds below were draped in a blanket of pure green grass unlike anything Jack had ever seen, with various colorful flowers budding along the walking paths, vines reaching up and ensnaring the buildings they grew on, and other kids running around beneath the trees in the sunlight.
“Welcome to the Silas Mendel Boarding School, Jack.”
“My goodness, it’s so wonderful! Where even are we? I don’t remember London ever being this colorful.”
“We’re in Edinburgh, Jack.” Isaac giggled upon seeing Jack’s confused expression. “It’s in Scotland.”
“Sockland?” This caused Isaac to burst out laughing, collapsing on his bet in a fit of sweet little giggles. Jack, while confused, knew that somehow, something he must be doing was funny, so he decided to run with it.
“So, if we’re in Sockland, the king must be the man with the most socks, correct?” This made Isaac wheeze with laughter. The clown continued as his ideas grew, reaching into his pockets.
“Well, if that’s the case, I should have an easy time matching him, shouldn’t I, kiddo?” One by one, in rapid succession, Jack began to pull all sorts of random socks out of his pockets in all different shapes, sizes, and colors. By the time he was finished and bowing, the floor of the dorm was littered with colorful socks, and Isaac could barely breathe from how hard he was laughing.
“Oh, of…of course, Jack!” He panted, finally regaining his breath and sitting up. “Whew! Goodness, you’re funny.” At that moment, the boy took a look at the clock and froze. “Wait, 5:20?! The orientation dinner starts in ten minutes! I have to go!” The boy quickly grabbed his peacoat as Jack quickly dissipated all the socks. Just before he left, Isaac turned back to Jack with a smile. “I’ll be back again tonight, I promise.”
“And I’ll be right here, waiting for you. Have fun at dinner, Isaac!” Jack waved goodbye to his friend as the door swung closed and let out a sigh of relief. He seemed so much happier here. Before he slid back into his box, the clown looked around the room with a hopeful smile. Maybe this whole school thing wasn’t going to be so bad after all. Maybe everything was going to be okay.