Summary: Despite the rising of Samhain, Dean still loves Halloween. He talks Sam and Cas into celebrating with him, and may or may not regret the results.

Rated: T

"I fail to see how this holiday could possibly appeal to you," Cas muttered, standing eerily still. Sam, on the other hand, was pacing back and forth in front of the Impala. Dean rolled his eyes, grabbed onto both men's coats, and dragged them toward the store.

"It's Halloween! Y'know, candy, happy children, half-naked chicks everywhere! What's not to like?"

"Well, Samhain-" Sam started, only to be cut off my Dean.

"Well, Samhain," Dean mocked, eyes crossed and tongue sticking out. Sam pushed him lightly on the shoulder and sighed.

"Look, Dean, I'm just trying to say that after what happened, why would you want to still celebrate?"

Dean stopped on the pavement right in front of the large Halloween store, looked around, and pointed forward. Sam followed his finger to a group of store employees dressed as a french maid, sleazy robin hood, and an angel.

"That is...not what angels look like." Cas watched the girl in confusion.

"Alright boys, let's get this party started!"

Sam parted ways with the men as soon as they entered the store, off to look at the decorations. Dean eyed each shelve carefully, looking for the perfect costume. They had no real intention but to dress up, eat loads of candy, and get a bit drunk, but Dean was going to make the most of it. He figured he could get away with just about anything since he had the holiday as an excuse.

Ten minutes later, while looking at the Freddie costumes, Cas tapped Dean on the shoulder.

"I found my costume," he stated. He had a bag under his arm, having already bought it.

"Great, lemme see!" Dean reached out, only to have the bag pulled away.

"It's a surprise." Cas reached behind Dean and pulled a random costume off the shelves. "You should wear this one."

"What?" Dean arched an eyebrow at the tacky pizza delivery costume. "Why the hell would I want to be this?"

"Reasons." With that, Cas wandered out of the store. Dean shrugged and stuffed the costume under his arm. Cas usually had a good reason for his actions, so Dean figured he'd just roll with it and see what happens.

By the time they got back to their hotel room it was already dark out. They decided to treat themselves to a better hotel this time around, so they had plenty of room to be comfortable and have fun. Since Cas didn't sleep, they had only asked for a room with two beds (Dean purposefully ignored the strange look the lady at the desk had given him). Dean quickly stripped and put on his delivery boy costume, tore open a bag of milky ways, and sat patiently on his bed.

Sam had decided to go western, complete with a cowboy hat and buttless chaps.

"Shut up, Dean," he spat out when Dean doubled over in laughter. "I didn't know."

"Sure you didn't," Dean gasped as he wiped tears away.

The bathroom door opened and both men turned to stare at Cas. Sam choked on his beer and Dean felt the color drain from his face, as his blood was rushing somewhere very different.

It was a skirt. Cas was wearing a goddamn skirt. It was a typical schoolgirl outfit, though a bit more modest than most. If Dean had to be honest, it much more fit the description of "naughty catholic school girl" than anything else. The black and white plaid shirt didn't even cover halfway down his thighs; the top covered most of his front except for two inches of stomach, where toned muscles revealed themselves. Jimmy's body was smaller than expected, though no one could say it lacked shape and appeal.

The heels weren't helping, either.

Dean cleared his throat and looked over at Sam, noting that his brother was now shaking with uncontrollable laughter.

"Was this your idea, Dean?" Sam said between gasps for breath.

"What? My ide- No! The hell gave you that idea?"

"Um, hello! Pizza man, babysitter! That has you written all over it."

Understanding dawned on Dean as he peeked over at Cas again. The angel had one hand on the frame of the door, the over resting on his hip. His hip was sticking out and one leg was planted behind him, the toe of the heel against the floor. All in all, Cas had the sexy pose down.

"Um, Cas...Why did you insist I wear this?"

Cas' lips twitched and he pushed off the door frame, sauntering over to Dean before sliding into his lap. Dean's hands automatically wrapped themselves around Cas' waist, despite his mind screaming at him to let go. He was momentarily distracted by Cas' firm ass pressing against him.

"In the movie, the pizza man was the more experienced person. And you're more experienced than me, so-"

"In what area?" Dean grunted. Cas didn't answer, only stared at him and dragged one hand slowly up Dean's spine, causing him to shiver and blink rapidly.

"Um, I'm gonna...go get more beer! Yes, beer! Be back never!"

Sam hadn't even closed the door all the way before Dean wrapped Cas' legs around his waist and flipped them over, pinning Cas against the mattress.

I haven't spellchecked yet, so I apologize if there are any mistakes. Pretty please review, and if you have any requests let me know! I'm someottersmarryhedgehogs on tumblr if you're interested in a (semi) good destiel blog! REVIEW PLEASE!

NOTE: If this idea has been done to death, I apologize. I'm a bit new to the show/fandom so I'm not too familiar with what's popular in SPN fanfiction. I just write what makes me happy.