A/N This story is actually the prequel to The Poem, and I owe thanks to my 15-year-old daughter, who has been helping me get some of the dialogue right. I also want to thank Mali Bear's Buddy for her story, The Bet, which gave me the idea of using a bet as part of my plot. The tone of the two stories are very different. Hers is a bit of Jo/Dean romance, but it's an awesome piece of writing, and you should all go and read it, if you haven't already!

Note: This chapter has been revised. John will be in the story, but a bit later on. I hope you like it! Please review and let me know.

Winchester Fun

The Bet

By CFEditor

Chapter One: Just One Number

The best part of a hunt was always the aftermath. The slow unwinding, coming down from the high of having put another nightmare back where it belonged. Dean didn't try to analyze it. He just knew that today had been a hard hunt, the adrenaline pumping. If you called this hunt hair-raising, his hair would have been lifting 500 pounds.

And there had been a few too many close calls. A spirit with a hatchet that came just centimeters from Sam's head... a lighter that caught only at the last moment... John finding the spirit's favorite fishing rod, which for some reason, was tethering the ghost to this world. Damn rednecks and their fishing.

Dean took a long pull on a cold beer. He leaned against the wall, surveying the bar. Sam was at the bar, getting his beer. He and Sam had snuck out for a night of fun - well, not really snuck out. He sighed, remembering the argument that had broken out between Dad and Sam after the hunt. It all started when Dad announced that he had to go out and meet a contact of his about a lead on their next case. It was better that the boys stay at the motel.

Sam erupted. "That's it," he slammed his fist into the table. "No more, Dad," he shouted. "We can't go straight into another hunt!"

"You'll do whatever I tell you to, Sam," thundered John.

"Well next time, you take hatchet man and I'll burn the bones!" Sam threw down his shotgun on the bed of the motel room. "I'm sick and tired of it."

Sam had stormed out, and as usual, Dean went running out to, in Dad's words, "watch after your brother."

Well, Dean decided, he and Sam definitely needed some R&R. So, with a little persuasion (and some blackmail), Dean had dragged Sam down to the local pub - O'Shaunassy's Watering Hole.

O'Shaunassy's was your typical college town bar, with its share of grizzled characters, juniors pretending to be bar-savvy, and the occasional in-over-your-head freshman sneaking in. Sam already looked better. He was talking to a blond waitress by the bar. She was looking at him and laughing. He took his beer and came back over to Dean.

"Hey remember," Dean said, "Only one for you."

"Thanks, Mom." Sam stuck his tongue out at Dean. "I'll have you know, I've been killing things since I was 9. I think I can handle my liquor."

"So what were you two talking about?" Dean asked, gesturing at the waitress..

"The ratio of alcohol in the average bar patron's system," Sam responded with utter seriousness.

"Oh dude, you are such a geek! Couldn't you come up with a better line than that?"

Sam snorted. "Like the lines you come up with? Really? Let's see.. how about 'Do you work for UPS? I could have sworn I saw you checking out my package.' "

Dean snorted. "I never used that line."

"Sure you did. Just yesterday, when we stopped to get gas... Or how about, 'If I told you that you had a beautiful body, would you hold it against me?' "

"Some girls go for that... But hey, if you're talking about drinks, why not just buy her a drink?" asked Dean.

Sam looked at his brother incredulously. "Come on, Dean, I'm not looking for anything serious with her..."

"Hey, it's just a drink. Y'know, you're so damn serious. Lighten up!" Dean looked at his younger brother and shook his head. He'd been brooding a lot lately, and he and Dad were fighting about college almost every day now, but he just didn't know how to go out and have fun.

Well if anyone could get his baby brother to have fun, it would have to be Dean Winchester.

He looked at Sam, a mischievous glint in his eye. "You've forgotten how to have fun, Sam. I bet you couldn't get a girl's number, even if you tried."

Sam glared at his brother. "That is so not true. I have gotten plenty of girl's numbers."

"Oh yeah? Name one!"

"Well..." He thought for a moment. "There's Amy Saperstein."

"Yeah, in like third grade. She was on the class list, dude. She tried to hold hands with you and you ran away, yelling cooties!" Dean laughed.

"Well, how about Nina Henley?"

"That was real romantic. She was your lab partner in seventh grade."

"Come on, Dean... Then how about Matilda Joshikins?"

"Yeah, she forced you to go to the prom with her. I heard you stood by the punch bowl the whole time." He took a swig of his beer. "What a way to treat a girl."

Sam blushed.

"No, Sam, I mean a real number. A real date."

"Fine, Dean! I'll get some girl's number. How about her?" He pointed to a pretty redhead playing pool.

"Let's make it a bet," said Dean. "You get any girl's number tonight and I'll do whatever you tell me to for a day."

"Fine... But what about if you win? Not that that's going to happen..."

"Same thing. You do what I say for a day. Anything," Dean said with a smirk. After all, what were the odds that he'd actually succeed? And even if he did, how bad could it be? This was Sam we were talking about... Square Sam, his baby brother.