Cherry and Jack in The Boss

chapter 1: Let the Game Begin

"J-Jack..." Cherry whispered in shock to see the YouTuber in his own room, she wasn't sure what was more shocking: the fact that he was right in front of her or that she somehow ended up in his room.

"Oww... My head..." Jack muttered before he soon stood up and saw his computer. "What the... The computer's not responding! Come on... COME ON!" he then looked into the monitor to see his own reflection and another one and spun on his heels.

"Heh... Hello there..." Cherry smiled nervously.

"YOU!" Jack yelled before coming toward her, looking a bit enraged. "Who are you and what the heck are ya doin' in my room?!"

"I-I'm sorry, Jack... I don't know how or why I got here to be honest..." Cherry told him, nervously, but truthfully. "I promise, I'm not here to rob you."

"How do I know that's the truth?" Jack narrowed his baby blue eyes into her chocolate browns.

"Well, uh, don't you think if I robbed you, your stuff would still be here...?" Cherry defended, nervous and in her slight deadpan.

"Huh... Good point..." Jack admitted.

Suddenly the doorbell rang.

"Did ya invite people over?" Jack asked.

"No, I don't even know why I'm here, but I promise, Jack, I would never hurt you." Cherry promised.

"Well... Okay... But I've got my eye on you..." Jack told her seriously which startled Cherry at first, but he soon brought out a plush of his YouTube channel mascot: Sam the Septic Eye and reached out and touched her shoulder with it with a small smirk. "Boop~"

"You're so random..." Cherry rolled her eyes to that, but she had a small smile since she had gained Jack's trust.

"Come on, let's get outta here." Jack told her.

Cherry then followed Jack out the door. Who could be at the door at this hour?

"The bread moved again!" Jack pointed to the black couch which had a piece of bread on it.

"Uh... I'm sure it'll stick around..." Cherry said nervously.

The two soon got to the door and it blasted open.

"Whoa!" Jack yelped.

"What was that...?" Cherry asked before sliding her glasses off and wiped the lenses before seeing three familiar figures, she recognized them all, but it made it even more shocking.

"Hey!" Undyne grinned to the duo.

"Uh..." Jack's eyes widened.

"Hello, Neighbor!" Papyrus grinned as he stood beside Katie in her own pajamas as she seemed to be holding the skeleton's hand. "We noticed you appeared in here and have come to make you feel welcome!"

"Seriously, what is going on here?!" Jack demanded to Cherry.

"I don't know, Jack!" Cherry replied before she caught what she said. "Heh... 'I don't know jack'... Th-That's kinda funny..."

Katie giggled to the unintentional pun.

"Kat, what are you doing here, with Papyrus, in JackSepticEye's house?" Cherry asked before pausing. "Wow, that sounds like a bad fan fiction crossover... Maybe I should write that."

"Write...?" Jack asked her.

"Cherry is a highly acclaimed fan fiction author," Katie smiled proudly before having shifty eyes. "I'm paired with Papyrus in the Undertale story, and she goes with Sans... For some reason..."