Hello people! This is part of a series of one shots I am doing about the Winchester home life. It is about their off time with Jack and will have fluff, angst, hurt/comfort, family, and more oneshots. It's just a big collection of little stories of Jack and his Dads having moments that we may not get to see on the show. Hope you like it! -Lola

It was a rare day at the Winchester's Men of Letters Bunker, because there was no case. Sam had put his foot down and said they needed to take a break. They had a kid now and he was not going to let Jack become as obsessed with hunting or really get dunked head first into the life like he had.

Sam was sitting at one of the bunker tables with a book in front of him. He was taking a break from actually going places but that didn't mean he was going to stop reading lore. Sam couldn't turn the hamster that was in his brain off, it just kept going around the wheel full of constant thoughts and predictions about the future. He wanted to know what was going to happen to Jack if he or Dean took an unfortunate end. Would Cas be equipped to handle him by himself? What if Cas died? He just couldn't stop the anxiety from running through him.

"Sam," a flat voice called out. Sam looked up to see the young Nephilim in front of him.

Sam rubbed his face as he closed the book on angels he had been pouring over. "What's up Jack?" Sam asked, he looked down at the boy's hands and saw what looked like a board game in the young boy's hands. "What's that?"

"It's a game." Jack said a small smile coming onto his face as he came into the room. "I found it in one of the rooms. It's called 'Monopoly'." Jack read out holding out the game for Sam to take from him. "Can we play it?"

Sam took the game, he remembered playing this when he and Dean were kids. Dean would always cheat just so when they made bets he could have Sam's candy bar. It always annoyed the crap out of Sam and Monopoly wasn't very fun with two people. Luckily, they didn't just have two people.

"Sure," Sam said giving a small smile to Jack as he put the board on the table. "Dean! Cas!" Sam called out to his brother and his friend. "Come in here."

Dean came in first with a beer in his hand, the other green eyed brother looked at the game board and his eyes lit up in recognition. "Monopoly," he chuckled with a smirk. "We used to play this all the time when we were kids."

Sam snorted at him. "Play is one word for it. More like I played, and you cheated." Sam said as he began to unpack the game board and caught Jack trying to hide a smile from next to him.

Dean grinned as he sat down from across his brother. "I played to win Sammy. Not my fault you couldn't figure it out." Dean began to reach over for the play money. "I'll be the banker."

Sam rolled his eyes as he quickly grabbed the money and kept it out of his brother's reach. "No way. Last time you were banker you just kept pulling money every time you got low on cash." Sam said as he put the money over by him. "I'll be the banker."

"What's going on?" a voice called from behind him. Sam turned and saw Castiel in all of his trench coat glory.

"We're going to play a game." Jack called with an excited grin. He was so happy he was getting to spend time with his Dads and that no one was about to die for once. "It's called Monopoly."

Cas came in with a frown as he looked down at the board with a curious expression on his face. "How do we play the game?" He asked as he sat down next to a too smug faced Dean.

Sam looked over at his brother with narrowed eyes. "Empty your pockets Dean." Sam said knowing his brother all too well.

Dean rolled his eyes as he did as he was told, probably only because Jack was here, and they were doing the game for the kid. "You're such a prude, Sam." Dean said as he handed the money back to his younger brother who put it in the bank and moved the banking area WAY out of Dean's reach.

Sam explained the rules of Monopoly to the group in careful detail before handing out money. He let each person pick out their little character they would move around the board. Naturally, Dean picked the car, Jack picked the dog, Cas picked the wheel barrow, and Sam picked the thimble.

"Seriously Sam, the thimble?" Dean snorted in his brother's direction. "How gay are you?"

Sam rolled his eyes at his brother as he ignored his comment before looking over at Jack. "Okay Jack, since you're the youngest you get to go first." He said handing him the dice.

Sam couldn't help but smile at Jack's grin as he threw the dice onto the board. Sam was happy he could make Jack happy, God knows the kid deserved some enjoyment every once and a while. The dice landed on eight, so Jack moved his piece eight times. It landed on some sort of railroad.

"Now what do I do?" Jack asked with a frown at the board.

"You can either buy the railroad or not buy it." Dean informed him as he looked over at his son. "Just between you and me, I wouldn't buy it. It's not worth it in the long run." Dean said giving Jack a wink before sitting back and taking another swig of his beer.

Sam rolled his eyes, he really thought the railroads were important. "Railroads can be useful later in the game when all the places have been bought. It's up to you though." Sam said as he watched Jack nod with a frown.

Jack looked over at Castiel, the one who gave some of the best advice, and frowned. "What do you think I should do?"

Cas tilted his head as he looked down at the board with a thoughtful expression on his face. "I think you should buy the railroad." He said in his deep voice as Dean took another swig of his beer.

Jack then looked up at Sam with a smile. "I'll buy the railroad." Jack said handing Sam the money with a beaming expression as Sam gave him the railroad card.

Jack put it on the table beside him with a satisfied grin. This game was fun already, he had decided. Especially since he was getting undivided attention from all three of his parents. "Who's turn is it now?"

"Dean's," Sam said as he handed his older brother the dice.

Dean grinned as he stood up and rolled the dice in his hands. "Come on baby, give me something good." He said as he threw the dice onto the table and got ten moves.

Dean began to count under his breath as he moved the dice ten times around the board and it landed on one of the pink squares. "I'm buying that." Dean informed his brother with a grin as he held out the money to his little brother.

Sam counted the money and nodded, his brother had given him the right amount. "Here Dean," Sam said handing him one of the pink cards.

Dean turned to Jack. "This is why you don't buy the railroads Jack. You've gotta wait for the big fish to come along. The more pink, blue, and orange squares you got, the better off you are. Don't worry about the railroads, electric companies, or brown squares. They're not gonna win you the game." Dean passed on to Jack who nodded at all of this taking in the information.

"Got it. Focus on the big fish, not the small ones." Jack grinned with a pleased smile. He liked the fishing reference. Especially since he and Dean went fishing that one time. He wanted to do that again sometime. He really did like spending time with Dean, because he knew he earned that time. Dean didn't like him at first, not like Sam or Castiel did, so he knew he earned that special relationship.

"Alright, it's my turn." Sam said as he grabbed the dice from the middle of the board.

The youngest Winchester rolled the dice and landed on a perfect twelve. He smirked over at his brother who had a scowl on his face. "Want to make fun of my thimble now?" He jabbed as he moved over to one of orange squares which were not too far away from the blue ones. He bought one of the orange places before looking over at Cas.

Dean made some comment under his breath that made Jack laugh and that Sam chose to ignore. He was too wrapped up in his victory of perfect sixes to care his brother was being his brother.

"Alright Cas," Sam began to instruct his friend. "Roll the dice and move your piece that many times and then you can decide if you want to buy the spot or not."

"I got it Sam." Cas said flatly as the angel grabbed the dice.

The group watched as Cas threw the dice into the middle of the game board. He got nine spaces which he landed on the just visiting jail space. "Can I buy the jail?" Cas asked looking up at Sam.

Dean chuckled at that. "No, you can't Cas. That's one of the places that you can't buy, but you can get stuck in." He told his friend as he took another drink of his beer.

The group went round and round for several hours until finally Dean ran out of money and went onto bed. Then it was Cas and then finally Sam and Jack were left. Sam was surprised on how well Jack did, especially for a Nephilim who was less than three years old and had never play Monopoly before. Sam and Jack decided to call it a draw at about one a.m. when it seemed like there was not going to be an end to the game.

Sam began to sort the money back into its rightful place while Jack began to pack up the stray pieces. "So, what did you think of Monopoly?" Sam asked Jack as he finished up sorting the bank out.

"It was…fun." Jack said looking up at Sam with a smile. "I had a good time." Jack said with a nod of his head.

"Maybe we could make it a regular thing." Sam suggested. He had thought about that while they were playing. It would be good for Jack to do some human stuff and a lot of human families had game nights. "We could do a game night every once in a while."

Jack looked over at Sam. "Really?" He asked the youngest Winchester with a curious expression.

"Yeah, sure." Sam said grinning. "We could play a different game every time or we could repeat games. You could even pick the games if you wanted." Sam said with a shrug. He knew Dean would protest but if it was for Jack then he would suck it up. Dean cared just as much about the kid as Sam and Cas did, he would even give up his usual preference of poker just to play some game like scrabble if it was for Jack.

"I would like that," Jack said as Sam folded up the game board and put the lid on the Monopoly box. "Thanks, Sam."

"No problem, Jack." Sam said, he was happy to do normal stuff with Jack. It was like a vacation from crazy town. "Why don't you go to bed? We're leaving for a case tomorrow morning."

Halfway through Monopoly, Sam had gotten a call from an old friend in Texas. There was something Supernatural going on that needed looking at. Sam would have said no, but this was a friend and friends were important to have in the hunter department. He just wished he could have given Jack more time to be normal, but time was something he didn't have. He just had to make do with what he had.

Jack got up from his seat the same time as Sam did. "Alright Sam." Jack said with a yawn before hugging the older man. Sam stood in surprise. He was not expecting Jack to hug him. "Goodnight."

Sam watched the younger boy go with a mystified shake of his head. How could a boy who had seen so much pain be so…happy? He didn't understand how Jack found happiness. He was just glad one person in their family could be happy. It gave him some hope.