Someone at school let Dean in on a little secret he hadn't known about before. They told him about...
The Tooth Fairy.
During the time Dean's teeth had been loose, the family hadn't been quite settled. They'd spent several years hopping from place to place, living out of seedy hotels and by-the-week furnished rentals. When Sam became old enough to start kindergarten John decided it was time (and safe) to put down some shallow roots so that the boys could get some schooling under their belts. It was the first time in a long time they'd have any sort of real home.
Dean started school already far behind and struggling. Academically he barely kept his head above water. Most of his learning came at recess, when the other kids filled him in on a bunch of knowledge his former isolation had not provided him. He had lost his baby teeth, but had been clueless about the Tooth Fairy and the cash-for-teeth deal he/she/it had going, and therefore was unable to collect any money. Dean found this horribly unjust.
John had let him in on the truth about the boogyman, the closet monster, and the thing under the bed, but not Santa Claus, the Easter Bunny, or the Tooth Fairy. When Dean did find out that he had missed out on yet more cash and prizes as rewarded by such entities, he'd been a little bent out of shape about it. When he confronted his father John simply gave him a cool look and said,
"You want me to lie to you?"
The Tooth Fairy, Dean discovered, was simply Mom or Dad being sneaky, but he wasn't going to let that stop him. He might have been unable to collect it himself, but there was still money to be had and he wanted it. With judicious use of bribery and coercion, Dean developed a tooth exchange racket himself in which he got a cut of whatever his co-conspirators collected from the teeth under their pillows. Sometimes the teeth were their own, sometimes they were teeth Dean had gotten in trade, exchanged for little things like toy cars, rubber balls, marbles or dice that he collected from the sewers around the neighborhood. (Only Dean was ballsy enough to actually go down manholes, a skill for which he was well respected. Kids often hired him to go collect a cherished object accidentally lost down the sewer grate.) He in turn handed those bartered teeth over to his crew so that they could claim them as their own and collect more money.
Animal teeth were employed as well, and sometimes Dean managed to procure teeth that looked suspiciously like adult teeth - old, yellowed, adult teeth. Nobody dared ask where he got them.
Coming up with teeth was hard work, and so was keeping track of what kids were still losing baby teeth and which ones had stopped. It wouldn't be wise to have the same set of kids leaving teeth under their pillows for an extended period of time. Dean had discovered that parents who came up with such creative lies as a jolly fat man who rode around in a sled pulled by flying deer, were pretty crafty in other ways. They frequently knew how many teeth their kids were supposed to have, and extras raised suspicions. Dean got really good at record-keeping. In another life he might have grown up to become an accountant instead of a credit card fraud felon.
When Dean turned eleven, his voice started changing and he suddenly developed less of an interest in climbing around in sewers and more of an interest in girls. At eleven he was also thin as a rail and covered in freckles. His squeaky voice, his slight build, and his reputation for running scams, led to the unfortunate nickname of Weasel. (Some seventeen years later he would run into a guy in a bar in Topeka who actually recognized him from those days. The old school chum was unlucky enough to also remember the despised nickname, so Dean broke his nose for him.)
The only way Dean could impress a girl at that age was to take her out and give her gifts. To do this, he had to have money. He amped up the tooth scheme, or tried to anyway. Most of his tooth sources had dried up by then and his money collectors had started becoming greedy about their own profits and unwilling to share. He found one dorky little first grader who was willing to place the teeth under his pillow and give Dean a cut, but Dean still had to come up with the teeth.
It didn't take him long to figure out he had a source right under his very nose. In fact, said source not only lived with him, but shared a bedroom with him, and both front teeth were loose.
The only problem was that said source was also notoriously uncooperative when it came to Dean's schemes.
"If they're really loose I can just get a pair of pliers..."
"Oh, I know. You can lean out the window upstairs and I can tie your teeth to a brick and then drop it..."
"Come on, Sammy! Give 'em to me!"
They were sitting on the front steps of their apartment building watching some high school kids playing roller hockey in the street. Dean leaned back on the steps and wondered if it would be better to spend his money on Susie Crimchiss or a pair of skates. Sam was busy breaking in a brand new box of Crayons with a Transformers activity book. As he colored he poked his tongue out one side of his mouth and, much to Dean's annoyance, occasionally used said tongue to wriggle his loose teeth around.
"You want an apple?" Dean asked. If he could get the teeth to fall out, stealing them afterward would indeed be an option he'd happily employ.
"I can run down to the IGA and get some of that taffy you like."
"I can punch you in the mouth," Dean growled under his breath.
Sam didn't miss a beat. He didn't even look up, nor did he color outside the lines. "DAD!" he yelled. "Dean said he was gonna punch me in the mouth!"
From upstairs, through the open window of their apartment, John bellowed back.
"Dean! Knock it off!"
"Tattletale!" With a sigh, Dean went back to watching the hockey game. After a while, he finally just came out and asked the question he'd been avoiding. "Well, what do you want for 'em?"
"Bike," Sam said promptly.
"Ain't worth a bike."
"Salvation Army has 'em for cheap."
Dean grumbled under his breath and did a few mental calculations. Taking out his accomplice's commission and what it would cost to get the teeth away from his brother in the first place would leave Dean himself a very small profit margin.
"How about a skateboard?"
Sam poked the Crayon he was using back in the box, closed his book, and stood up. "Bike," he said, and went inside, leaving Dean to stew alone on the steps.
At this point, it had become less about earning the money and more about thwarting his stubborn baby brother. Dean was bound and determined to get Sam's two front teeth away from him, somehow. He was running out of time too, as school was getting ready to let out for the summer and Dean would soon lose his first grader accomplice to tee-ball camp.
He sat on the steps mulling over various strategies for clandestine tooth extractions until the hockey game broke up and John called him in to eat supper. Much to his chagrin corn on the cob was not on the menu (as if they'd ever had corn on the cob) but instead, they would be dining on Hamburger Helper. Hamburger Helper was not going to help Sam's teeth fall out, especially since it was more helper than hamburger. It was comprised mostly of elbow macaroni too, so Sam couldn't even slurp his teeth out with a long length of noodle.
Dean suspected a conspiracy between Sam and the Winchesters' head chef - their father. Since he didn't dare vent his spleen on John, he flicked the peas he picked out of his dinner at Sam instead. Sam batted them back at him with a spoon until it turned into a game and they both got busted.
To add insult to an already frustrating day, Sam graciously gave Dean his share of dessert because the cold ice cream hurt his mouth. This magnanimous gesture made Dean feel guilty. (Although not enough that he didn't eat both desserts with joyous abandon.) That the loose teeth actually hurt Sam bothered Dean's conscience as well and he made not a single protest when John sent him out to the store for a bottle of children's aspirin.
It was Friday night. John had a gig in Missouri that weekend and wouldn't be around. The last words he had for Dean (aside from the customary "take care of your brother, don't open the door, etc etc") were, "Don't get into trouble."
Since he'd never been told that before, Dean suspected Sam had been filling John's head with all sorts of wild tales regarding Dean's school-yard exploits. Annoyance at this possible betrayal justified the end of his guilt tripping. He vowed that by morning he would have Sam's two front teeth in his possession no matter what and damn the consequences.
It wouldn't be hard, Dean decided, to just steal the wrigglers right out of his brother's head. They were very loose and just a little tug would probably do it. It wouldn't be too hard to get Sam to open his mouth either. All Dean had to do was wait until the little twerp fell asleep. Sam was a notorious for sleeping with his mouth open. He also snored and drooled on his pillow, which Dean thought was beyond gross.
When John wasn't home, bedtime was when they wanted it to be bedtime. Usually they both stayed up watching the late night horror picture show and tonight that was more than fine with Dean. If they went to bed he might fall asleep himself. If they stayed up watching tv on the sofa, it was pretty much a given that Sam was going to conk out first.
Sure enough, right after midnight, Dean looked over at his brother and saw that Sam had collapsed in a limp sprawl over the arm of the sofa, one hand dangling over the edge and his mouth hanging wide open. His head back position gave Dean good access to his mouth and he could always claim he was trying to prevent the loose teeth from falling down Sam's throat and choking him to death.
Pulling a pair of pliers out of his back pocket, Dean inched slowly off the couch so he wouldn't disturb Sam. Quietly he made his way toward his victim, prepared to move swiftly and, if possible, yank both teeth out in one pull. Halfway there he paused to retrieve a small flashlight out of his other pocket. He put it in his mouth. He held the pliers ready as he leaned in and shone the light in Sam's mouth.
Dean frowned around the flashlight. "Whatthuhu...?!?!"
Sam cracked an eye open. His jaws snapped shut. "Go away," he mumbled grouchily. "You're not gettin' 'em."
All Dean's excuses for what he'd been doing went out the window. He took the flashlight out of his mouth. "But...they're gone!" he exclaimed, feeling more than a little gypped. It might have been really interesting to play dentist.
"Fell out," Sam informed him.
Sitting up, Sam rubbed his eyes. "When I brushed 'em." The yawn confirmed it. Sam was now sporting a large, empty gap where his two front teeth had once been. The absence of his teeth made it easier for him to stick his tongue out at his brother, which he did.
Dean was furious. "Where are they?"
"Not tellin'." Sam said. "Get me a bike, and you can have 'em."
"Sammy, come on!" Dean flushed as his voice hit a squeaky note desperately in need of DW-40. "Jimmy Curtis' Mom is a cheapskate. I'm not gonna get that much for 'em!"
"Too bad, so sad."
Dean growled. "I'm going to go look. Find 'em myself," he threw the flashlight and pliers down and stalked off toward their bedroom.
"No you won't!" Sam hollered.
"I'll tear the place apart!"
"Okay. Go ahead. You'll never find 'em."
Dean heard him chuckle and knew what he was thinking. If John came home and found everything turned upside down in the apartment, Dean's ass would be grass.
He turned on his heel and headed back into the living room where he tackled Sam over onto the sofa cushions and sat on him. Sam's air went out of his lungs with a little "Ooomph!" under the onslaught. Dean may have been skinny, but he was still twice Sam's size.
"Where are they?" Dean demanded. "What did you do with 'em?"
Sam punched at him, bouncing fists off his chest and his arms, which was actually rather unpleasant. For a little kid Sam could hit really hard.
"Get off! You're squishin' me."
"Give me those teeth!"
Dean finally managed to pin Sam's arms down. He leaned over leered down into his brother's face and said, "I'll hork up a loogie on you."
Sam's face was red with exertion. It took on a horrified expression at the very thought of getting slimed with big brother spit-cooties. "Nooooo!"
Loogie horking noises commenced. Sam shrieked in terror.
"Because why?" Dean sat back, still holding Sam down, but also holding back the sliming. "You know, Sammy, this is a really juicy goober..."
"They're in the car!" Sam said quickly.
Sam used his brother's momentary distraction to wriggle free and roll off the couch before retreating to a distance just out of Dean's reach. "Uh-huh."
"And the car..."
The toothless grin was salt in the wound. "Is in Missouri with Dad."
"Come here and let me pound on you."
Sam's eyes got as big around as dinner plates as Dean lunged at him. In seconds there was a mad free for all down the hallway. Sam dove into their room and slammed the door behind him, just missing his brother's nose. Dean heard the lock click and Sam's muffled voice.
"I want a bike!"
Dean stopped his token door pounding. "You can't even ride a bike!" he yelled.
There was a long pause. The muffled voice sounded rather sheepish.
"Yes I can."
"No you can't." Dean stood back with his arms crossed over his chest. "Have you ever in your life been on a bicycle?"
Long pause number two.
Sam's tone turned hopeful. "You could teach me."
Dean snorted. "Why would I do that? Lookit all the trouble you're causing me. I told Jimmy I'd get him some Tooth Fairy money before he went to camp and you're screwing me all up." He turned away and made a big production of stomping off down the hall. "You're on your own buddy, see if I ever do anything for you again."
He should have expected what happened next. Not, he thought later, that knowing it was coming would have made much difference.
Ten minutes after Dean resumed his movie watching, Sam came creeping back down the hallway. Dean heard his bare feet padding across the carpet and tried to ignore him.
"It's not gonna work, Sam."
Padding footsteps moved away toward the kitchen. There was more sniffling. Sam poured himself a glass of milk and choked out a sob or two.
Dammit. I hate it when he does that.
"I know you're faking!" Dean called. "Forget it, Sammy! I'm not fallin' for it."
Sam sat down with his milk on the opposite end of the sofa.
After a few minutes, Dean stole a look.
He saw the glitter of tears in the flickering light of the television. An arm rose to wipe a runny nose on the back of one pajama sleeve. Sam glanced in his direction and Dean could see his puffy eyes and the milk mustache smeared across his upper lip.
Sam drew in a stuttering breath, and sniffled once more. He said only one word in a tone that was small, and sad, and very, very sharp because it stabbed Dean in the heart and killed him dead.
That's all it took. Dean caved utterly, interrupting before there could be any more.
"Okay, okay, I'll get you a bike! Sheesh!" Rolling his eyes, Dean flopped back into the couch. He shot Sam a glare. "Are you happy? Are you done?
Apparently Sam wasn't done, not just yet. There came more drama in a wobbly, tear-choked voice. Sam was apparently going for the Oscar.
"I duh...don't know huh-how to ruh-hide a buh...ike."
Dean sighed. "I'll teach you to ride it too." He felt his own eyes starting to burn as the sniffling continued. "Just dry up, will ya, you're all snotty and gross."
"'kay," Sam replied softly. He settled back to drink his milk and watch the movie.
"I hate it when you do that," Dean grumbled a half hour later.
"No I don't."
"You do too know." Dean looked down at the wide-eyed, perfectly innocent expression and snorted derisively. "And you look dorky with no teeth."
"You sound dorky," Sam retorted, his feelings obviously hurt. "You sound like Flipper. Squeak, squeak, squeak."
Nothing more was said about the teeth or the bike until Sunday when John arrived home, battered, bruised and smelling of rot. He spent nearly an hour in the shower while the boys snuck down and rummaged through the Chevy's trunk looking for Sam's missing teeth.
Their mission, was a failure.
"I'm not lying!" Sam wailed. He clearly saw his bike getting flushed down the tubes for lack of Tooth Fairy money. "I hid them in a box of shot gun shells!"
"Well they're not there now!" Dean shot back. "Dad probably dumped them somewhere in Missouri!" He flounced down on the sofa. "You shoulda just given them to me in the first place."
Sam's lower lip trembled. This time Dean didn't doubt his sincerity.
Big, fat tears dampened Sam's eyelashes. One broke loose and rolled down his cheek.
"Sammy, don't..." Dean poked him. "Stoppit! Here comes, Dad."
There was an unspoken rule between the two of them not to cry in front of their father. For one, John tended to be rather unsympathetic when it came to tears. His mission was not to raise a couple of cry babies, but a pair of tough little soldiers who bucked up and moved on through the pain. For two, Dean happened to know the truth of the matter. Tears, particularly Sam's, upset John more than he would ever let on, especially to the boys themselves. Dean only knew because he'd accidentally overheard a late night drunken phone call his father had made to some unknown person in which he had confessed to questioning his parenting ability.
"What if I was wrong? What if a foster home wouldn't be better, safer..."
From that point onward Dean took great pains not to let John see either of them shed a single tear.
John sat down in his chair. He was wearing clean clothes and was rubbing his hair with a towel. Washing off the dirt and grime of the Hunt always improved his mood. He looked at the boys askance, quietly observing them where they sat together on the sofa, before lowering the towel and giving them his full attention. "You know," he said, putting the towel aside and reaching into the back pocket of his jeans. "The weirdest thing happened while I was out."
Dean raised an eyebrow. In the Winchester household "weird" was relative. "What's that, Dad?"
"Well, I opened a box of shot gun shells, and look what I found inside." He held out his hand, and there, pinched between his first two fingers, were two five dollar bills. "Not only that but..."
John gave the money a little shake, and a pale, glittery dust fell down from the bills like snow.
Sam's eyes were huge and bright with awe. "The Tooth Fairy..." he breathed. "The for real one!"
"Don't be stupid. There's no such thing." Dean looked to John for confirmation, and saw, much to his surprise, a very non-committal look on his father's face. "Is there?"
John shrugged, and handed the money to Sam.
Sam stared at it a minute, and then gave one five to his brother. "Here," he said. "We can share it."
Dean looked at the bill, which still sparkled slightly with pixie dust or whatever it was, and thought of the million and one things he could do with it. However, after a moment's silent reflection he sighed deeply and handed the handed the money back. "No," he said quietly. "They were your teeth. You keep it."
"Are you sure?" Sam lowered his voice to a whisper so their father wouldn't hear. "What about Jimmy?"
"Jimmy's a wuss," Dean whispered back. "I'll worry 'bout him. You keep your money, Sammy."
"Maybe we can get a bike and go to the movies then, huh?" Sam said brightly.
This Dean didn't mind. "Sure." He put his hands in his pockets and shrugged. "There's some good stuff showing at the Buck-a-Flick."
After dinner, and when the money was safely tucked away until they had time to go on a quest for Sam's bike, Dean cornered their father in the kitchen. He made sure Sam was out of earshot when he asked, "There's no such thing as the Tooth Fairy, is there?"
John looked at him, and sighed. "No, Dean, there's no such thing as the Tooth Fairy."
"Then why did you do it? Why did you lie to Sam?"
A vague look appeared in John's eyes. His voice grew rough with emotion. "I don't know," he murmured. "I guess, because it's..."
"Normal?" Dean finished. He went on, speaking softly. "Yeah. Sometimes knowing about the pretend good stuff is better than knowing about the real bad stuff."
Gazing up at his father, Dean saw a peculiar look in John's eyes he sometimes saw in his own when he studied himself in the mirror. It was a scared (in later years he would say "haunted") look, like they knew something horrible was lurking just behind them, waiting for its opportunity to pounce. They didn't know where, when, or how the attack would come, just that one day, it would.
As much as Dean tried to pretend that look wasn't there, it was there and it would never, ever go away. It was there because he knew something did wait for them outside in the dark. It was real. It had already taken his mother.
He bit his lip, focusing on the pain rather than the lump in his throat that threatened to make him cry. "Sammy doesn't have to be like us, does he, Dad?"
"No," John replied quietly. "He doesn't." His expression was gentle, reflective. He smiled a little. "Maybe we should try to keep it that way then, huh?"
Dean nodded. "Yessir," he said. "I think that would be a good idea."
After a moment or two of emotional wrangling, something occurred to Dean that made him cock his head sideways, lift his brow, and regard his father with a somewhat sly expression. His tears were sidelined with an epiphany.
"So, uh, Dad. What did you do with those teeth?"