A/N: This fic is written as part of a comment!fic meme over at LJ. Unbeta-ed as usual.

Prompt is at the end of the fic.

Disclaimer: They belong to me. Yup. In my dreams.

*SnSnSnSnSn*

Castiel picked up a boot and stared at the brothers.

"So I use this footwear to indicate my position?"

Both brothers nodded. Dean picked up the car while Sam chose the dog. Dean sniggered at Sam's choice, Sam glared back and Dean held his hands in front of him in a placating gesture. It wasn't worth riling Sam up so early in the game anyway. He would save it for later.

The trench-coated angel was still examining his silver picking, turning it one way and then the other. He had a frown on his face, the same frown he had when Dean told him that they were going to be stuck in the motel room for the time being while Castiel regained his strength from their blast from the past.

"I understand that you need a pair of these for them to be useful. Is the other half lost?"

Sam ignored the question, intent of the tiny piece of paper with the even tinier print, while his hands were busy dividing up the money for all three of them. It had been a while since he had handled such large amounts, and he was being careful with the amount.

Dean cracked a smile. "Maybe the other half fell into a drain, just like Sam's shoe."

At that, Sam looked up from his accounting and presented Dean with his second glare in five minutes, before focusing back on the money in front of him. Dean just grinned back at him, and Castiel looked on with the patented confused expression.

Dean turned back to Castiel. "Enough with the thinking Cas. You are supposed to be resting and chilling, not wasting your energy on over-thinking."

"I am not sure that thinking needs energy. And this bed, although uncomfortable, is considered as a place of rest, I believe."

Dean's mouth widened into a wicked smirk and he answered the angel. "Not just for resting, Cas. There are other…physical pursuits."

Before Castiel could ask what those physical pursuits were and how could you perform them on a piece of furniture designed for sleep, Sam announced that he was done distributing the cash, and handed each of them their share. Then he slid out the board from the box and laid it open in the middle of the bed.

Dean kissed the wad of cash in his hands and placed it in front of him, and then rubbed his hands in glee.

"Prepared to be bankrupted, dudes. Let the games begin!"

*SnSnSnSnSn*

The fun started after everyone had gone a round.

"Crap." Sam wanted Connecticut Avenue, but Dean got there first, and the younger Winchester reluctantly handed over the title deed to his older brother.

Since this was the first purchase of the game, Castiel looked understandably baffled. "Does this mean that he's the owner of that avenue now? Will the residents in that area be paying to him?"

"Damn straight they should. I own the land now!"

"Dean!" Sam threw his hands in exasperation. He then spun to the other player of the game, trying to explain what was happening.

"No, Cas, it's just in this game he has purchased the area, but the real Connecticut Avenue still belongs to whoever it belongs to now. Do you remember what I have explained before?"

Castiel nodded, seemingly satisfied with the explanation, and when he finished his turn, he stated that he wanted to buy the property his boot had landed on. Dean was actively opposed to the idea.

"No! Oriental Avenue's no good. You should wait until you get to the railroads!"

"But I don't like travelling by train. Nisroc and Nathaniel tried to kill me once on a moving train in India." Castiel was looking painfully earnest, and Sam rolled his eyes.

"He just doesn't want you to block his chances of taking the whole color section." He indicated the blue strips above the names of the places. "If he buys the whole set, then he could start developing them. If you want to block him, then you should buy it."

"Is there a reason that I should block him?"

"No, there isn't." Dean cut in. "Trust me, Cas, you don't want to be in my way. I would return the favor twice as hard."

Castiel looked at Sam, who shrugged his shoulders, leaving the decision to the angel.

The latter turned back to Dean, and then back to Sam, and smiled serenely at him. "I am not afraid of Dean. I would like to buy the property please."

Sam returned the smile while Dean narrowed his eyes.

*SnSnSnSnSn*

"Cas!" Now it was Sam's turn to yell at the third member of their team.

Dean just snickered, watching Castiel handing out the money for Pennsylvania Avenue, effectively preventing Sam from collecting the green set.

He knew that Castiel would catch on to the game quickly.

*SnSnSnSnSn*

"You are caught stealing. You are going directly to jail. Do not pass go, do not collect two hundred dollars." Sam read from the card that he had picked up from the centre of the board.

Dean had a little jolt at hearing familiar words spoken by his younger brother, but it was brief and failed to cloud his currently contented mood. Being the helpful brother that he was, he took Sam's silver dog and moved its position to the Jail corner. Sam just scowled.

"Did you steal this game? You would go to jail just because this card told you to?"

"No, Sammy borrowed this game from the front counter, and, yes, if this card tells us to go to jail, then we are going to jail. In real life, however, we try to avoid prison whenever possible."

"You could bust me out, you know. You have two free passes out of jail." Sam employed the puppy-dog eyes. Dean however, remained unmoved.

"Little brother, I would bust you from behind bars in a second, but not for this. You should cool your heels and learn the errors of your ways." Dean mocks solemnly. Sam scowled harder and Castiel just looked on with a blank expression.

*SnSnSnSnSn*

"This property is mine. You will have to pay me five hundred dollars for landing on my land."

Castiel was still sporting the blank look on his face, but Sam could swear that he saw the angel's eyes dancing with amusement. He looked at his ever-thinning stack of fake cash and unwillingly took out the amount needed. He would have to come up with another strategy to strengthen his cash flow.

Beside him, Dean lolled his head on the pillow and just shrugged his own shoulders.

*SnSnSnSnSn*

"I cannot believe I lost to a newbie." Sam declared four hours later, having forked out the last of his property and money to Castiel.

"I can't believe I lost to an angel." Dean made it sound so much worse than losing to a first-timer. He glared at the angel. "Did you use up some angelic mojo or something?"

"I did not employ any unfair moves during our play."

"I demand a rematch." The older Winchester was clearly not satisfied at losing to a supernatural being.

Sam just shook his head and started gathering the pieces to be stuffed back into the box. Castiel stood up slowly and faced the brothers.

"I'm not opposed to a rematch, and I accept your challenge, but not today. Three days from now, at the next rest stop that you will be staying in."

Dean looked like he wanted to object, but changed his mind at the last minute. "Fine."

"Alright. I'm going to continue my search for my Father now." With that pronouncement and the sound of swishing of wings, he disappeared from the room.

Dean twisted his head to look at his younger brother. "Bring the set with us. I'm going to beat that winged freak if it's the last thing I do."

Sam just nodded, expecting the outcome. The next few days were going to be fun.

*SnSnSnSnSn*

Prompt: Sam, Dean, Castiel - Monopoly

A/N 2: I hope I got the editions right, since I'm not from U.S and had to rely on Google to show me the editions. I wanted to use the World edition, but they don't use paper money! Sheesh. Takes the fun out.

Thanks for reading!