A/n: I own nothing, all known characters belong to the CW, I only play in this world. This is for the writing contest in the Facebook group, "It's Funnier In Enochian." Many thanks to my Sammy: SarahWinchesterFics for giving me help on this.

Summary: It's Halloween and the guys are bored, so much to Dean's chagrin, they decided to dress up and head to a Halloween party with Cas in tow.

"Dude, come on, it will be fun and we have nothing better to do."

"Sammy, come on. We are grown ass men who fight the supernatural every day. I can't believe that you are suggesting that we get dressed up and go to a costume party for Halloween."

"I am confused," Cas said from the chair in the corner, "why do people get dressed up on this day every year just to go to a dance and get free candy?"

Dean snorted, he loved Cas like another brother but his confusion on the way humans did things sometimes got on his nerves. Cas never took things at face value, he always wanted to know the whys of something. Sam just rolled his eyes and decided that it was up to him to explain to Cas the origins of dressing up on Halloween,

"The traditions of Halloween are a hybrid of Pagan, Celtic, Catholic and ancient Roman. Traditionally, Halloween was a celebration before winter hit which came from Celtics and Gaelic people believed that it was important to honor their dead. When the Romans invaded what is now France, a lot of the traditions got mixed up with Samhain and it was the Irish who started the tradition of trick-or-treating."

"But, what does that have to do with dressing up?" Cas asked.

"Well, it again comes from Samhain, people would dress up and go from house to house and recite verses or songs in exchange for food. And, it just evolved from there."

"So, you are saying that we get dressed up in costumes and go to a party just to dance?" Cas asked to make sure he understood.

"Yeah, "Sam replied.

"Very well," Cas answered.

"Well, if you two are going then I guess I'll come too. Let's head to that costume shop that I saw when we drove in." Dean responded.

So, Sam, Dean and Cas got into the Impala and drove to the costume shop. The place was busy with people trying to find last minute costumes. The guys didn't know what kind of costumes they wanted, so they just started to look. It was hard to look for anything with everyone pushing and shoving but it was Dean who had found the costume for Cas. Dean grabbed it from the rack and then went to look for him.

"Hey Cas," Dean said when he came across the angel looking at female sexy angel costumes. Dean had to laugh at the look on Cas's face.

"Dean, what is this?" Cas asked turning to look at his friend.

"It's a sexy angel costume."

"Doesn't look like any angel I've seen before."

"Yeah well humans don't normally get to see angels, so they just make it up. Anyways, I found the perfect costume for you." Dean held up the costume for Cas to see.

"What is it?" Cas asked taking in the purple fur lined costume that had zebra print around the collar, sleeves and on the pants as well.

"It's a pimp costume," Dean replied.

"What's a pimp?"

"I'll tell you later. Just go try it on."

Cas looked at the costume again and then took it and went in the direction of the changing rooms. Dean went to search for the hat that went with it; it was also purple that had a zebra band around it. Once Dean had that in hand and a pimp cane, he went to look for his costume. Dean rounded a corner and came across Sam who had two costumes in his hand.

"Hey Sammy, what's up?" Dean asked his little brother.

"I'm trying to figure out which to go with, Preacher or Robin Hood."

"Well, we've already been preachers, so go with Robin Hood."

"Yeah?"

"Yeah, why not."

"Ok, Robin Hood it is. What about you?"

"I'm still looking but I did find Cas's costume." he laughed.

"Dean, what did you do?"

"Made him a pimp."

"Dean!" Sam exclaimed.

"What? He's going to get so many chicks and it will be a great laugh."

Sam just shook his head and then went to the changing rooms to see if the costume fit him. Dean went back to the accessories part of the story and looked for a bow and arrow for Sam. With Cas's accessories and Sam's in hand, he went back to looking for his costume. It was harder than he thought to look for a costume. He used to love Halloween when he was a kid; that was until he found out that monsters were real and then Halloween like every other holiday went out the window as he took up care of Sammy. Dean passed a lot of hot chicks in the aisles that were checking him out and inviting him to different parties.

The chicks also gave him suggestions of what he should be, like vampire, superhero, pirate, grim reaper but nothing interested him; plus some of the suggestions were things that he's either already been or recently battled. So, he kept looking and looking, finally he came to the costume that he wanted. Dean settled on being a gangster. He pulled the black and white pin stripe suit off the rack and went to try it on. It fit great on him and looked really good; he knew that he had a black shirt at home that he could pair with the suit. Dean took off the suit, put his clothes back on and went to look for Sam and Cas as well as pay for the costumes; he wasn't going to worry about getting a gun or a fedora from the accessories section because he had that stuff at home as well.

It wasn't hard to find Sam and Cas, they were off to the side talking, Cas looked outraged at whatever Sam was telling him and Dean had an idea that perhaps Sam told him what a pimp was. He wasn't going to let Cas put the costume back; it was going to be far to fun to see how he reacted to the women who flung themselves at him. He walked closer to them and said, "Cas before you even say anything, you are buying that costume and I don't want to hear you complaining about it. It's going to be fun; part of Halloween is about being fun."

"I do not understand why you think a pimp; which Sam explained to me what exactly that is, is fun."

"Dude come on, stop over thinking it and analyzing it and just go with it." Dean replied.

Cas didn't look too happy but he didn't say anything else which Dean was happy about. The guys went to stand in the long line to pay for the costumes. The girls were practically throwing themselves over Sam, Dean and Cas; Dean loved it of course, Cas was uncomfortable and Sam was interested in a few of the girls. Finally the guys got up to the counter, paid for the costumes and then hopped in Baby and headed back to the motel they were staying at.

Sam flipped on the TV and was able to find a horror movie on, he sat back against the bed and laughed at how fake the movie looked, after awhile Cas joined him while Dean sat at the table downing some whiskey and eating pie while thinking that it was nice to not have a case to work on.

Finally night began to fall but the party wasn't going to start for another hour, so the guys decided to head out to get something to eat. The restaurant that they went to, was done up to look like a haunted house and while Sam and Dean tried to suppress their laughter because they knew that everything in there was real, Cas found it strangely interesting.

'You know, it's kind of interesting to see people worship these monsters." Cas said while they were sitting in a booth waiting for their food.

"Well, you have to remember that not everyone knows these monsters are real." Dean said.

"Yeah, they love these things because of Hollywood and the monsters being Romanized as well as people loving them from books." Sam supplied.

Cas nodded and asked, "Do you think these people would still worship the monsters if they knew them to be real?"

"Probably," Sam and Dean said with shrugs.

Just then, their food arrived and the guys dug in, the food was really good and of course once they were done, Dean had to order a slice of pie; after all, as he said many times, he loved him some pie. Once they were done and they settled the bill, they headed back to the motel and changed into their costumes. The guys thought they looked pretty good and headed out to baby so that they could head to one of the parties that Dean was invited to.

The first party was pretty lame and they only stayed for an hour, the second party was alright but they didn't stay there long either. It wasn't till the fourth party that they went to did the really start to have fun. The music was great, the drinks were flowing and to Dean, it seemed as if all the babes were at this party. Sam and Dean both found girls to dance with almost instantly, Sam hooked up with a gorgeous raven haired girl named Sarah who was dressed as Maid Marian who even had black contacts, and her dress was a deep blood red medieval style. The dress had a hood, was floor length and had sleeves that almost covered her hands. The corset tied up in front and there was a black fleur de lis pattern all over the red velvet.

The girl Dean hook up with gorgeous redhead girl named Elizabeth who was dressed as female gangster, she was wearing a black dress that stopped mid thigh, and she wore a long black & white pin stripe jacket which was partly zipped. Elizabeth was also wearing fuck me black leather over the knee boots and a black fedora. Dean was in lust as soon as he saw her and he was almost positive that she was in lust also.

Cas had his choice in ladies, they were all fawning over him, Sam and Dean could tell that Cas was slightly uncomfortable but it ended up being a blond dressed as a Playboy bunny that got him out on the dance floor. The guys spent the night dancing, drinking, flirting and at one point Cas lost sight of Sam and Dean, but he was actually having too much fun dancing to worry about where they had gone; plus he knew that if it was a monster that took either of them, they were well prepared to take care of themselves. They were hunters after all, born and breed in the ways and tricks of the monsters that they've dealt with, so they knew what they were doing.

A/n: Hoped everyone liked this and Happy Halloween, there will be a second part; I just need to work on it a bit more because I am not feeling it yet. This is my first Supernatural fic, so go easy on me if you hate it.