'Come on, Sammy, it'll be fun.' Dean implored as he bit hungrily into his hamburger.

'Dean, what could possibly be fun about the local beauty pageant?'

Dean smirked knowingly. 'Many things, Sam. Many things.'

It's 1997, Dean Winchester is 18, in a seedy motel in St. Louis, and his 14-year-old brother is annoying the crap out of him. Dean was seriously considering setting fire to Sam's homework or something, anything that would cause a bit of excitement on this incredibly dull morning. John had been out for about a week, Dean had no school or college to go to, and Sam was 'keeping up with his studies.' Dean personally couldn't give a flying pig's ass about his studies, but as long as Sam wasn't getting on Dean's nerves, he was okay. Dean sighed, and pulled over the local newspaper that had been unceremoniously dumped outside the door this morning by a sadly unattractive maid who spoke about as much English as an apple pie. The headline, as it usually was with local newspapers, was hardly big news.

LOCAL BEAUTY PAGEANT TAKES PLACE TODAY AT 2:30

That was where Dean had got the idea. That was when Dean started begging Sammy to accompany him.

'Come on, Sam. You can take your little girlfriend with you.' Sam blushed up to the roots of his hair, which in Dean's opinion was getting too goddamn long.

'She's not my girlfriend, Dean.' Sam mumbled, staring intensely at his textbook. 'She's just a nice person.'

'Nice person, whatever. I saw you talking to her in that diner, you were blushing like crazy.' Sam ignored him, tapping his pen on the table.

'How about a casual hookup?' Dean said, grinning. Sam looked up, eyebrows furrowed.

'I'm 14, Dean! I don't have casual hookups! And even if it was legal, I wouldn't. I'm not a massive jerk like you.' Sam pulled his books off the disgustingly gaudy 80s table and stomped into the tiny single bedroom, slamming the door behind him. Dean sighed. He walked over and knocked lightly on the door.

'Sam, all I'm saying is show up to the pageant and look for me around 2:30, okay? We can go out and bond like brothers to compensate for our dad's negligence, etcetera, etcetera.' There was a low grumble in reply.

'Whatever, Sammy! I'm gonna go do some shopping.'

As soon as Sam heard the door shut, he tucked his school books under his bed and gave his hair a quick ruffle, before grabbing his coat and jogging to Ray's Diner. Sitting on one of the tall red leather stools that had probably been there since the 50s, was Amy. Considering Sam had only met her about 3 days ago, he felt all giggly at the sight of her. He'd just bumped into her while he was browsing the local library, and they'd bonded over a mutual love of, well, books. She smiled as Sam entered the diner, his hair ruined by the wind.

'Hey there.' she said, absentmindedly licking the whipped cream off her spoon. She was sitting in front of an impossibly large pink milkshake.

'Hi,' said Sam, breathlessly. 'It's very windy.' Amy laughed, and Sam grinned. He liked her laugh.

'I hope the weather clears up,' she said, stirring her milkshake. 'If it's like this during the pageant, half the girls will fly off the stage.' Sam chuckled as he studied the menu. Amy studied him, still smiling.

'Oy, lovebirds.' The waitress at Ray's swept some crumbs off the bar with a dishcloth and leant on the bar. 'You orderin', kid?'

'Oh, um, sure.' said Sam, flustered. 'Just a medium chocolate milkshake, please.'

'Comin' right up.' said the waitress, pursing her cherry red lips.

'So are you going to the pageant?' said Amy, taking a break from her milkshake which she had been steadily drinking through a straw as she stared at Sam.

'I think so. I mean, it's complicated. My family moves around like a lot and we could easily suddenly leave town in the next hour-that's why I've been meeting up with you so much. When I saw you in the library I just wanted to spend time with you and I know that I could easily be here for just two days so I wanted to get to know you but now I feel bad because you're really nice and brilliant but I'll probably never see you again once I leave this town so maybe I should have left you alone because I don't want to have to leave you and I don't know if you feel the same but I don't want you to be sad about me leaving and I've never really had a girlfriend and-'

'One chocolate milkshake for the boy who talks too much.' interrupted the waitress, an amused smile playing about her lips. Sam went bright red.

'Hey, Sam.' Amy swivelled round on her stool. 'It's okay. Let's just have some fun while you're here. I promise to never forget you. Ever.' Her fingers clumsily found his, and their hands wrapped around each other as they finished their milkshake. Sam couldn't help but notice the grin on the waitress' lips as she walked past them.

Meanwhile, Dean was buying makeup. He wasn't sure how he'd explain it to his dad, but it was Dean's money, and Dean wanted a bit of fun, so for once, Dean decided to not think about what his dad would say, and instead think about what the hell mascara was.

'EH-LAY-DEES ANNNND GEN-TELL-MENNNNNNN, AH-WELCOMMEEEE, TO THEEEE, 21ST ANN-YOOUUU-AAALLLLL SAAAAAINT LOUISSSSS BEE-YOO-TEE PAG-HEEEENT.'

Sam fiddled with the hem of his jacket. Dean had said 2:30, it was 2:30, there was no Dean, and the way the announcer drew out his vowels was making Sam incredibly nervous. Amy was stood next to him, her jacket slung over her arm. The wind had completely settled, and the air was still and dry, the sun beating down on the makeshift stage adorned with wreaths made by the local craft club. Admittedly, pretty much all they did was make wreaths. The winners and runners-up of the pageant won a wreath. The hot dog stand was covered in wreaths. Ray's Diner had an impressive collection of wreaths donated by locals. The wreaths on the stage were made of ribbon, in twee pastel colours that undoubtedly would reflect the similarly twee pastel colours of every dress in the pageant. Sure enough, the announcer screamed a name and a girl in a pink dress stepped onto the stage.

'Oh god, she goes to my school,' said Amy, laughing.

'Is she nice?' asked Sam, half-heatedly. He was distracted by worrying about Dean and worrying about whether or not putting his arm round Amy was a total douche move that only his older brother would pull. He caught Amy saying something like 'total whore' before the girl started to walk up and down the stage, her hand on her hip, a terrifyingly large smile on her face.

'What's she doing?' whispered Sam, edging slightly closer to Amy.

'She's showing off, basically,' she muttered back. 'That's how pageants work.'

'God, this is going to be really boring, isn't it?' Sam muttered, kicking a bit of loose earth at his feet. Amy nodded glumly. The next girl took to the stage, blue dress, larger smile than the first girl, larger hair than the last girl and larger...other things. Sam realised why Dean was so anxious to watch the pageant-if there was anything his older brother loved it was boobs. Sam had learnt this a very long time ago, and decided never to question it.

'They really are very uninteresting people, aren't they?' said Sam, as a girl in a lilac dress wittered on about her hobbies-tapestry, apparently, something Sam thought had died out long ago.

'That's my sister, Sam!' said Amy, her jaw dropping in outrage.

'Oh-I'm sorry...I'm sure tapestry is very-' Sam stopped short when he noticed the mischievous glint in her eye. 'Very funny, Amy.'

She grinned, and Sam decided to act on impulse and linked his pinky finger with hers. She leaned her head on his shoulder, and for the billionth time that day, Sam turned redder than the stools in Ray's Diner.

Dean ran a hand through his hair, checked his eyeliner and made sure his clothes were completely in place. He wasn't going to muck this up-properly stupid practical jokes took preparation.

'You all ready, sweetie?' asked Rosa, the organiser who had been running around backstage with a clipboard pushing girls onto the stage until it was only Dean left. Dean nodded, smiling.

'What's your name again, honey? I need to let the announcer know.'

Dean cleared his throat, and attempted a slightly higher voice. 'Deanna.'

'Lovely,' she said, before repeating it to a guy who ran onstage quickly, presumably to tell the announcer. 'On you go, sweetie.'

'AND LAST, BUUUUT, BY NOOO MEEEAAANS LEEEAASST...DEAAANAA.' A girl timidly stepped onto the stage, wearing a silk green dress with a sweetheart neckline and a slightly puffy skirt that was crinkling under her folded hands. Her hair was neatly combed over her chest, and was impossibly shiny.

'Wow, her dress is gorgeous.' said Amy, for once taking an interest in the proceedings.

'Yeah. She's super hot too.' said Sam. Amy punched him in the shoulder, and he grinned at her. The girl was sashaying up and down the stage, smiling at the judges, her green eyes set off perfectly by the dress. Her red lipstick contrasted beautifully, and Sam was finding it hard to believe she wasn't a model. She was so...interesting looking. Strange, Sam could've sworn he'd seen her somewhere. As she walked off the stage, the announcer walked back on, same fixed smile on his face that had been there since the beginning of the pageant.

'WHILE OUR JUDGES COUNT UP THEIR VOTES, WE HAVE A PERFORMANCE FOR Y'ALL. PLEASE WELCOME THE ST. LOUIS HIGH SCHOOL ORCHESTRA.' A rag-tag collection of musicians around Sam's age trundled out and a frail looking kid stepped up to the microphone, cleared his throat and said 'Um. Carry On My Wayward Son...is what we are going to play. Uh...thanks.' He hurried back to his seat and picked up a clarinet, and the orchestra launched into what could only be described as an...interesting cover of the Kansas classic-Sam was pretty sure if Dean was here, he would run onto the stage and tell the frail kid where to stick his clarinet.

'I hope they announce the winner soon,' said Amy, nuzzling closer to Sam. 'I'm bored as hell.'

'Same here.' said Sam, turning to face her. He noticed that she was smiling all the way up to her eyes, and he got butterflies in his tummy.

'AAAAND NOWWW...FOR THE WINNERRR...'

Sam took both of Amy's hands.

'Thank you for making me like St. Louis.' he said softly.

'OF MISS ST LOUIS, NIIINETEEEN NINEETY SEVEEEEN.'

'It was my pleasure.' grinned Amy, taking a step closer to him. Sam was grateful for her height-he'd had a growth spurt recently and he was sure if she'd been smaller he would've had to bend down to even get a good look at her eyes.

'IT'S DEANNAAAA.'

'Huh. I think someone won the pageant.' murmured Sam, his forehead gently bumping Amy's as he leaned in even closer.

'Big whoop.' she said, closing her eyes. Their lips met as Deanna took the microphone and began her speech.

'I'd like to thank y'all for picking me to win this lovely wreath,' she said, her voice almost mocking. 'And also I'd like to thank y'all for appreciating my efforts to look mighty fine today-' and then she pulled off her wig. Everyone in the assembled crowd gasped. Deanna cleared her throat and took to the microphone again, her voice deeper this time.

'Hello there. My name's Dean Winchester. I'd like to thank every shop in St. Louis for providing me with everything I needed to convince you-' he paused to push up his bra, which rustled loudly against the microphone. 'I'd like to thank women everywhere who manage to walk in high heels-seriously ladies, wow. And also my brother, Sammy, who appears to be a little busy.'

Sam hadn't even been listening, and when he broke off his kiss with Amy to see Dean in makeup and a dress, he was more than a little shocked.

'There he is! My brother! In the red hoodie. The one lookin' all embarassed next to the brown haired chick.' Dean winked at Sam, and the whole crowd swivelled to stare at Sam. He waved nervously, and Amy kissed him on the cheek.

''Not your girlfriend my ass.' muttered Dean. He then took an extravagant bow, chucking his wig into the crowd and sprinting off stage. The announcer, for once, had nothing to say, and had begun to make strangled noises into the microphone, when Dean ran back on stage, his chest considerably flatter and the makeup half wiped from his face. 'Before I go-candidate number 2, call me. Thank you, St. Louis!'

Sam stared at the stage, mouth opening and closing.

'Dude, your brother is epic.' He turned to see Amy grinning at him. He was genuinely surprised she still wanted to be anywhere near him. 'Come on Sam, let's go find him.' She took his hand and dragged him to the edge of the stage, where a second later Dean appeared, makeup and dress still on.

'Wait a sec,' said Amy, reaching into her bag, and pulling out a Polaroid camera. Dean pulled Sam to his side, and she quickly snapped one of them together. Dean whooped with laughter when it developed. 'I make a hot chick,' he said, when he'd finished clutching his sides in amusement. 'Here, let me take one of you and Sammy.' Sam took Amy's hand and Dean snapped two pictures. He proudly presented one to Sam and one to Amy.

'You're quite the photographer, Dean,' she said. 'And quite the model.'

'You know it.' said Dean. 'Sammy, I'm off to the motel.' He winked at Sam, and scarpered off. Sam watched him as he began to flirt with Candidate 2.

'You're in a motel?' said Amy, taking Sam's hand.

'Yeah. I told you it wasn't permanent.'

They walked in silence until they reached Ray's Diner.

'One last milkshake?' said Sam.

'One last milkshake.' confirmed Amy.

When John Winchester came home that night, he shook his sons awake and told them to pack. They were moving on. Another town, another job. As they packed their stuff, he found two Polaroids on the table, with captions quickly scribbled on.

One, a picture of Sammy and a girl John didn't know, with the words 'Sam's first girlfriend' underneath. The other, a picture of his eldest son in a dress and makeup, with Sam looking happy and embarrassed all at once, with another handwritten caption.

'Dean Winchester-Miss St. Louis, 1997.'

(A/N: Thank you for reading my silly fic! I hope you enjoyed the weirdness of it all.)

(Disclaimer: I don't own Dean or Sam Winchester, I don't own Supernatural and I've never been to a beauty pageant, or St. Louis. Or Ray's Diner, because it's fictional)