The Runt of the Litter

what is it they say about the apple and the tree?

Note: Wow, okay, another crappy week, but we made it to the end, didn't we? Thanks for voting and commenting and reading and all that lovely stuff. I've loved talking to you guys this week.

This chapter was requested by Mmiller13 who wanted to see Anna and Dean go under cover as father and daughter. You requested this ages ago. I'm sorry it took so long, but I appreciate your patience. I hope you find it worth the wait.

Also, to everyone still waiting for me to write their request, I promise I will write it. all in good time. ❤️

In this chapter, Anna is fifteen.

what is it they say about the apple and the tree?

"Tell me one more time why we're dressed like this," Anna grumbled while Dean fixed the back of her shirt collar.

"Because," he said, putting his hands on his shoulders and holding her at arm's length so he could take a good look at her. "This school's got standards."

"Hella old-fashioned standards," Anna complained. She looked down at herself in displeasure. This school insisted on plaid skirts, collared shirts, and blazers. She wasn't even allowed to wear her OSIRIS sneakers, because they required dress shoes for their students. It all seemed pointless and mildly insulting to her, being forced to dress up for the sole purpose of conformity and appearances. She'd always been the type to dress for comfort in every circumstance but the most rare. "Why are we even doing this? Can't you just break in or something?"

"We could. But this is easier. We'll get the Headmaster out of his office, Sam will sneak in and download the files onto his harddrive. Bam. We're good to go."

Anna fiddled with a button on her shirt until Dean smacked her hand away with a warning to quit messing with it. "Man, I feel like I'm in a super lame version of Mission Impossible," she whined and reached down to straighten her skirt. It went all the way down to her knees, and she wanted so badly to toss it aside for a pair of jeans or a denim skirt. She had an aesthetic, and this crap did not align with it. She felt like her self-expression was under attack.

"You can't call me 'man' if this is gonna be at all believable," Dean reminded her and turned to the mirror while he tied his tie. "Quit messing with everything. You look fine."

"I don't look fine. I look like I go to Chilton." She stepped beside him at the mirror and gestured to the plaid skirt in particular, then registered the first half of what he'd said. "And about that, what's the point in pretending I'm your kid? Why can't you just be my brother?"

"I'm just trying to make us look as normal as possible. Divorced single father is probably a more familiar story to these wealthy dickbags than devastatingly handsome older brother."

Anna pursed her lips at that. "I'm not calling you Dad."

"Yes, you are." Dean went over to the bed where the clothes hangers to all their rented clothes still lay. He held open her blazer for her, and Anna made a face at it before reluctantly sticking her arms into the sleeves and letting him adjust it. She'd never worn anything quite so fancy before. It made her feel expensive. And not in a good way. "It won't take that long, Rugrat. I promise."

"You gotta stop calling me that," Anna groaned and tossed her head back. "Seriously. I'm not five."

Dean just grinned smugly at her and ruffled her hair. "Come on. Sam's waiting."

Anna groaned and made a vain attempt at fixing her hair. She was having a remarkably good hair day with almost no frizz, and Dean had to go and muss it up. She straightened her skirt and stole one last glance at herself in the mirror. The outfit didn't suit her, but she did look rather... professional. It would definitely help her get in character.