HEADCANON #2 – Anna Babysits

"And then Dean got in trouble for pushing Gordon and he had to go sit in timeout but then Gordon stuck his tongue out and he got in trouble too. Then I had to play at recess by myself 'cuz Dean wasn't allowed to go outside while he was in timeout."

Cas continued to chatter, oblivious as to whether or not Anna was actually paying attention. She smiled down at him as they walked but after a while, Castiel's unending blabber began to blur together. Which was just fine to Cas, he didn't really need a partner to have a conversation with; he talked enough for the both of them.

The brother and sister were making their way through the neighborhood to the Winchester's house. Mr. Winchester had called Anna at short notice with another one of his vague, clipped messages that Anna had learned to expect from him. She could count on one hand the number of times he had called ahead of time to schedule her to babysit. The other times she would get a phone call from John saying something like "Got called away, can you watch the boys?"

Under any other circumstances, John Winchester might seem shady, but as it happened, the Winchesters and the Miltons used to be somewhat close. Well, it might be more accurate to say that their mother and Mary Winchester were friends but John was no stranger. When the Milton children's mother died almost six years ago, Mary Winchester had done her best to step in and help them through it.

Anna remembered that time very clearly. She'd only been nine at the time but the death of a parent has a way of forcing clarity on you. She remembered being in class on a Tuesday when she was called to the office. All the things she'd done that day raced through her mind as she tried to figure out what she'd done wrong. Instead, she was told there'd been a car accident leaving her mother, Lucifer, and Castiel in the hospital. She remembered the world being especially quiet after that.

Mary had tried her hardest to keep the Milton children from collapsing; after all, their father wasn't doing much. Anna liked her and the light she brought back to the household. Back then, John was still a fun and laid-back dad. A few years passed and they started to move on. Sammy was born and then six months later, the world took Mary away as well.

When their mother died, the Milton's father had shut down. The number of words he had spoken to them since the accident were painfully slim. Anna thought the same thing would have happened to John if it hadn't been for Sam. Having the baby there to demand his attention kept John from becoming a complete recluse. But nevertheless, Mary's death changed him. He may not have shut off but he broke down.

He took good enough care of Sam and Dean but he still left Dean to grow up a little too fast. John was away for work a lot of the time, leaving Sam and Dean in the care of Anna or before and after school programs. He put food on the table and kept Sam and Dean protected from physical harm but he didn't quite know how to provide them with that tender touch that Mary could.

Hand in hand, Anna and Castiel walked up the driveway and rang the Winchester's doorbell. After a moment, John answered the door with a somber smile and let Cas and Anna in. Dean came hurtling around the corner to greet them and Anna could see Sam sitting on the floor of the living room.

John was grabbing his keys and jacket, already halfway out the door as he called back to Anna "I should be back before midnight, the usual's fine." She nodded and John left. The rumble of the Impala's engine sounded as he backed out of the driveway.

The 'usual' consisted of keeping them busy until dinner time, ordering take out, keeping them busy until it was delivered, feeding them, then keeping them busy until 8 when she put them to bed, and then keeping herself busy until John returned.

Cas and Dean had already raced off somewhere so Anna kicked off her shoes and trod into the living room. Sam looked up as she came in and giggled, waving his arms. She smiled back and sat down next to him.

"Heya, Sammy."

"Anna!" The toddler crawled into her lap and settled in, turning his attention back to the television and pointing at it with one stubby finger. "Cwifford."

"Yes, I see. Big Red Dog, huh?"

Sam nodded and put his thumb in his mouth, slumping back against Anna's chest. They stayed that way for a while, watching the TV in silence unless Sam felt the need to commentate. Cas and Dean charged into the room, toy pistols strapped to their hips and cowboy hats on.

"Reach for the sky, Sammy!" Dean said, pointing one of his guns at his brother.

"You too, Anna. This is a hold up!" Cas said, moving to stand behind Anna.

Anna wrapped her arms around Sam and fell to the ground, curling up around the boy. "No, please don't hurt us, we're innocent!" Sam giggled and squirmed away from Anna, making his way over to Dean.

"Don't come any closer," he warned. Sam, oblivious, continued his advance. "I mean it, I will use this!" Dean took a step backward but Sam caught up with him and tugged on Dean's jeans, hauling himself to a standing position. Dean yelled and dropped his gun, falling down and taking Sam with him. "Aaah! He's got me!" Sam's gap-toothed grin lit up the room.

In the commotion, Castiel took the opportunity to pounce and attacked Anna, tackling her from behind. She yelped in surprise but then pulled him around, tickling his rib cage. Castiel shrieked and yelled for Dean who untangled Sam from his legs and rushed over to help. The two of them teamed up on Anna and were eventually joined by Sam.

"Sammy? I thought you were on my side!" she protested, as the little boy latched onto her leg. He just shook his head and refused to let go.

The four of them played cops and robbers for a while, chasing each other around the house, occasionally swapping roles until they got hungry. Anna ordered them a pizza and told Dean and Cas to go wash up and put their costumes away to get ready for dinner. Meanwhile, she helped Sam clean up and go to the bathroom, setting him back in the living room to get the table set.

When the doorbell rang, she grabbed the money out from under the flower pot in the hall and paid the pizza man. Cas and Dean swarmed her as she came back into the dining room but she made them sit down before serving them. She set Sam in his high chair and cut a slice of pizza into little squares for him. Once all the kids were eating, she got a few slices for herself and sat down to eat.

"Hey, Cas, I bet I can eat my pizza faster than you," Dean challenged but Anna laid a hand on his arm.

"Uh, no, I don't think so. I'd rather not take a trip to the hospital tonight. And we don't need anyone throwing up either."

Dean already had a bad habit of stuffing as much food as he could into his mouth at once, the last thing he needed was to be doing it faster. The two boys sighed and ate the rest of their pizza normally.

After dinner was cleaned up, Anna left Sam in the highchair and set him up with some paper and crayons while Cas and Dean pulled out their homework for the night. The four of them sat around the table and worked for about an hour.

Anna propped her chin in her hands and watched Dean and Cas work from across the table, waiting until one of them needed her assistance. Dean's face was scrunched up in concentration, staring a hole into his math homework.

Castiel was working diligently but glanced at Dean out of the corner of his eye and saw him struggling. He put his own pencil down and scooted closer to Dean, looking over his shoulder.

"You just have to take away, see?" he explained. He held up eight fingers for Dean to count.

"That's not a take away, that's a minus," Dean protested.

"It's the same thing. Duh," Castiel responded, wiggling his fingers in front of Dean's face. "Now count eight take away five."

Dean huffed but ticked away five of Cas's fingers before scribbling a three onto his homework. Anna smiled but didn't say anything, instead turning her attention to Sam. The two year old had gotten tired of coloring and moved on to pounding the crayons on the highchair tray.

"What are you doing, silly?" Anna cooed, poking his tummy.

"Cowor," he replied, waving the fistful of crayons around.

"No, you're not coloring anymore. Now you're just making a mess." She brushed his long bangs out of his eyes, thinking John should take him for a haircut soon.

When they were done working, Anna suggested they watch a movie to which Dean and Castiel began clamoring and arguing over which one. Eventually, they settled on The Fox and the Hound and gathered on the couch. Anna stuck the DVD in and sat down with Sam on her lap and Dean and Cas on either side of her.

They started out squirming and giggling but as the movie went they seemed to quiet down and before long, Anna looked down to find all three of them asleep. She let the movie finish and then worked on extricating herself from the tangle of sleeping children and went to put Sammy in his crib. She flicked the nightlight on and set his radio to a soft rock station on a low volume. Then came moving Dean which was more difficult but she managed to half carry, half lead him to his bedroom and tucked him in.

Back in the living room, she draped a blanket over Cas and then curled up in the recliner to do her own homework until John returned. She saw the headlights through the window and texted Lucifer to come pick them up. She packed up her homework as she heard the car door shut and then keys jingling in the front door.

John looked a little haggard, but he always looked tired to Anna. Whatever it was that he did–he never actually explained to her what his job was–it must be exhausting. He gave her an apologetic smile and reached for his wallet.

"How were the boys tonight?" He asked as he thumbed through the bills, counting what he owed her.

"They were great, as always. We had pizza and they were all asleep before the end of The Fox and the Hound."

His smile was relieved and a bit happier than it had been before as he handed her the handful of crumpled bills. "I'm glad they're not giving you any trouble. The last thing I need is for them to drive you out."

Anna laughed. "Well, they're not perfect little angels but what kids are. Dean certainly has a mind of his own but that's a good thing I think."

John looked in the direction of Dean's bedroom and smiled. A few minutes later, Lucifer pulled up in the driveway and came in to tote Castiel out to the car.

"Goodbye, Mr. Winchester," Anna said, waving as she slipped out the front door after her brothers. John gave a small wave back before going to the fridge and cracking open a beer bottle and settling in on the couch.

Headcanon request by Anonymous: "Can I please have an hc about Anna babysitting Dean and Cas and baby Sam?"

The second of the headcanons requested by our lovely readers, request recieved on Tumblr. We greatly enjoy writing these, so please, ask away!

We don't own any of these characters, merely manipulate them for our entertainment. I own a copy of The Fox and the Hound, but do not own the rights.

This Headcanon was written by The Captain.