The Birds, The Bees, and the Brothers Winchester

A/N: I don't post a lot of the Supernatural fics that I write, because I know people are passionate about their Winchester boys. This one, though, I thought came out kind of cute. It's fluffy and really not meant to be angsty or dark in anyway. Hope you enjoy the fluff.


Sam Winchester had never been a cool, calm, and collected kid. Teaching little Sammy how to pull off a con without his his tell-tale blush alerting the mark to his ruse was the hardest lesson his older brother, Dean, was sure he would ever have to teach anyone. Even harder than teaching Sophie Lerner not to use her teeth. But they'd gotten through it somehow, and Sam knew his strengths. At the age of sixteen, he could use his doe eyes to worm his way into even the most skeptical person's confidences.

So why was he staring at the floor of the dingy hotel room with hot pink flames of embarrassment lapping at his neck? There was no one there, nothing to make him squirm. Dean wasn't sure if it was the blushing, or the staring that creeped him out more. "Dude," he finally stated, causing his brother to jump, dart a glance in his direction, and then busily set about collecting his school books from the bed around him. "What is your problem, Sammy?"

"Sam," the younger Winchester muttered under his breath as he hastily shoved his books into his back pack. Dean wouldn't understand. Dean was good at this stuff. He was suave and confident. Hell, he was almost arrogant. Girls loved that. Sure, they loved bumbling Sam, too. In the way that they loved their best friend's little brother, or a rescued puppy. Not in the way that they loved Dean. Sam could never seem to get them eating out of the palm of his hand. Not like he could a client or a suspect. That was different. Lives were at stake when he was working. Outside of that? It was just his personal dignity, and his body chemistry didn't seem to care nearly as much about that as it did 'the good fight.'

Dean watched as his brother dumped the contents of his bag once again and then threw the bag against the floor in frustration. "What's goin' on with you, man?" Dean chuckled, his fingers scratching over the Henley adorning his chest. He'd seen Sam withdraw into his own head on plenty of occasions, but he'd never seen the kid this tweaked. Something was definitely going on with his little brother, and in Dean's experience, only one subject could turn Sam into such a scatter-brained puddle. "Who is she?" he asked firmly, his gaze fixed on the lanky form atop the other bed.

Shaking his bangs out of his face, Sam wordlessly denied that Dean was right. What was his brother going to be able to do about it anyway? He couldn't fix the problem. Certainly not before eight o'clock, when Sam's life would be ruined for good. Why couldn't this be an in-and-out job? Why couldn't John have just taken them with him? Most of the time, Sam longed for the stability of a school that he could become a part of. Usually, he loved the idea of being dropped off at some seedy motel for three or four months, allowed to learn something from someone other than Encyclopedia Britannica. But this time? This time, he would have been okay with a last-minute phone call and an escape in the dead of night.

It wasn't that Dean was incredibly intuitive, but he had spent sixteen years knowing the young man across the room. Sixteen years spent watching Sammy learn and grow and develop. Dad wouldn't know that something was wrong, but Dean did. Because Dean was there. Always there. "Sammy," he tried again, standing from the bed and cutting the power to the television. "Sam," he added with a sigh when his brother finally turned wide, terrifying eyes to him. "What the hell, man?"

What was the point in trying to hide anything from Dean? For as long as Sam could remember, Dean had protected him like a father, taken care of him like a mother, and hung out with him like a best friend. Even when girls in whatever town they were in fought for Dean's attention, the older Winchester always made time for his little bro. If there was anyone in the world who knew Sam's mood just by looking at him, it was Dean. "Look, I'm supposed to go to this party tonight," he finally managed to mumble, though Dean had trouble hearing while Sam's gangly hands covered his face. "And there's supposed to be this girl there," he added even quieter than before.

"Amber?" Dean asked, shaking his head when Sam seemed surprised. "Dude, not only do you talk about her all the damn time, but you mumble some pretty naughty things about her in your sleep," he winked and nodded, but Sam didn't find the teasing remotely funny. Instead, he tossed a pillow, which Dean caught easily and held in his lap. "Look, Sam, you like her. She seems cool," he went on, remembering the one time he'd picked Sam up from school and been introduced to the shy, 'most likely to become a hot librarian,' object of his brother's affection. "You guys go to this party together, maybe you can spend seven minutes in heaven with her. What's the problem?" As far as Dean could tell, his brother should be bouncing off the walls, not trying to disappear into the ugly-ass paisley bedspread.

There were times when Sam was sure that explaining anything to Dean was completely pointless. How was his brother truly going to understand what it was like to be nervous and insecure? That wasn't Dean's style. At all. Digging into his backpack, he surrendered the only explanation he could think of. "This was in my locker after school," he grumbled, holding his arm out without meeting his brother's eye. The only thing worse than Dean reading the note was seeing him do it.

Dean allowed his eyes to drift over the bubbly letters on the pink paper and nearly blushed himself. So little Amber wasn't quite so shy after all. "You sure this was for you?" he asked, genuinely confused. This wasn't the kind of girl that Sam was interested in. In fact, the words on the page made her much more Dean's type.

If the note hadn't had his name on it, Sam would have fully believed that it belonged in someone else's locker. That it had been left in his by mistake. But she had gone to great lengths to meticulously draw his first and last name on the outside of the note, even using a sticker of a little puckered pair of red lips to dot the 'i' in 'Winchester.' "Dean, how am I supposed to . . . What do I even . . . Dude," he finally gave up trying to vocalize the fear and apprehension in his head. He didn't even know what one of the things she suggested they do was.

Though he'd suspected that Sammy was still a virgin, Dean had never really asked his little brother about his sex life. Mostly because Dean was usually too busy talkin' about his own, and Sammy never offered any details. "Calm down," he finally said, tossing the note onto the bed at his side. "Do you like this girl, Sammy?"

Nodding, Sam raked his hand through his floppy hair and laid back on the bed, his dark eyes affixed to the ceiling. "I do," he admitted, blinking back the angry tears of frustration that were pricking the backs of his eyes. Great. So now, not only did he look like an awkward virgin, but he was going to cry about it? Dean would never let him live that down.

"Do you wanna," Dean started to ask, and then stopped himself short. God, this was weird. "Sam, do you wanna sleep with Amber?"

Sam just turned his head against the pillow and leveled his brother with a less-than-amused glare. "Dean, I'm sixteen. There aren't a lot of girls out there I don't wanna sleep with," he stated, as though it should be obvious to his brother. As though he were a completely normal sixteen-year-old boy. Clearly, Dean didn't see him that way.

And, in all honesty, Dean didn't see Sam that way. Why would he? He'd spent his entire life making sure the kid had food and clean clothes and enough sleep at night. Even when he didn't feel like doing his own homework, he made sure that Sam's was done. In a lot of ways, he was still eight-year-old Sammy who followed him everywhere and asked him a million questions about science and math and shit Dean had never heard of, let alone could explain. He wondered if this was how parents felt when their kids started to grow up. It was a weird feeling, and Dean wasn't sure what to do with it.

Clearing his throat, he looked at the note and then back to Sam. "So, level with me, then. What's the problem here? Are you just nervous 'cause it's your first time? 'Cause, I gotta tell ya," he grinned and shook his head. "It's probably hers, too." Sam opened his mouth to argue, but Dean just picked the pink paper up and tossed it back to his brother. "Girls who like that shit, who know they like it 'cause they've already done it? They don't talk about it - they just do it. Girls who wanna impress a guy they think wants that shit? They talk about it."

"But she doesn't have to impress me! I already like her," Sam exploded, bolting upright in the bed and throwing his arms out at his sides as he turned to face his brother. "That," he nodded toward the edge of the bed where the offending letter was now teetering precariously, "is not impressive. It's scary."

"Why?" The question came out before Dean could really process it, but it was a good question, nonetheless. Why was Sam so scared of sex? Wasn't it something that guys just got excited about and did? Nobody had to tell him how to maneuver his way through his first experience. It hadn't been great, but it wasn't impossible, either. He didn't need an instruction manual. And Sam was way smarter than him. "Dude, I know Dad already gave you the talk. And you're, like, a wizard at science and biology and shit."

But Sam just held up a hand to cut him off. He didn't help with mechanics. "I know what goes where, Dean," he assured his brother. Finally managing to look at the other man for more than a second, Sam tried to convey what he was thinking. Even if Dean made fun of him for months after the talk, he would listen for the moment. He was good at listening to Sam, even when nobody else did. That thought alone managed to calm the younger boy down just a bit. "But Dad's talk wasn't exactly helpful, ya know?"

Dean nodded. He did know. He'd been in the bathroom, brushing his teeth, when he heard John's deep bass floating through the thin door that night. Sam had been twelve. His father had cleared his throat about a thousand times during the two or three sentence conversation. And Sam had whined and groaned just as often. But it all boiled down to the John Winchester philosophy. 'I can't stop nature from takin' it's course, Son. Just remember our lives are dangerous and we can't be totin' a screamin' baby around with us. We have work to do. So just . . . be safe.' It took everything in Dean not to laugh outright at the memory.

Instead, he shook his head and looked hard at his little brother. "Sam, what do you wanna know?" he asked, repeatedly telling himself that this didn't have to be awkward. He talked about his own conquests with Sam all the time. Not in detail, but enough to get the point across. He could do this. He had to do this. "What's your biggest concern?"

Oh, it was as agonizing as Sam had imagined. He was scared of everything. How was he supposed to know which concern was the biggest? "Well," he went through the file in his mind until the most logical starting place popped into his brain. "How do you," he stopped and blushed severely as he tried to think of a way in which to phrase his question. "I mean, how do you, ya know," he stopped again and wished like hell that Dean would just instinctively know what he meant. They finished each other's sentences all the time. Why couldn't this be one of those times? "Get started," he finally finished through gritted teeth.

"How do you," Dean stopped short and thought about the question. Sam was supposed to know the basics. He said he knew what went where.

Before his brother could start drawing a diagram, Sam shook his head violently and held up a hand. "I mean, how do you know that a girl even wants it?"

Grinning easily, Dean leaned back on the bed. "Some girls make it obvious," he explained, finally feeling his shoulders relax as relief flooded his chest. This he could talk about. This was a question he could handle. "Some play a little harder to get. Just start slow, okay? If you're sittin' on a couch, or standin' by the wall or whatever, touch her a little bit. Like her arm, hold her hand, maybe play with her hair? Don't think about it, though. If you over think it, you look creepy," he held up a finger and Sam nodded, licking his lips and leaning forward slightly.

As Dean went on to describe the signals that Sam would recognize, the younger hung on the older brother's every word. He had been wrong. This wasn't painful at all. It was just a conversation between brothers. And it wasn't remotely uncomfortable for Dean to tell him that kissing would tell him everything. If her hands were on his arms, or around his neck or waist, but not moving, she was into him, but maybe not ready to move further. If she pressed herself into him or deepened the kisses herself, he could be pretty sure that she was ready for something else. He explained that it was best to go slow, to let her dictate the pace, and feel for things like cringing or hesitating. She might not want to say that she's not ready, but Dean assured Sam that he would know when Amber tired to pull away.

"Okay," Sam finally said when Dean had finished his most thorough explanation. "So what if she's ready, and I'm ready, and we're both, well, ready, or whatever," he started, licking his lips again as he fought to express what he was really trying to ask. "I mean, how do I know that it's time?"

While he thought he understood the question, Dean wanted to make sure. Tilting his head slightly, he raised an eyebrow. "Time for what?" Sam blushed again, though he didn't look away, and Dean just nodded. "Sammy, you know what I always tell you, right? Those eyes of yours? They're your greatest asset." When Sam's brow knitted in confusion, Dean shrugged. "If you're not comfortable asking her out loud, then just look at her. Ask her with those oh-so-expressive eyes of yours. She'll let you know." Growing exponentially more comfortable, and almost finding himself looking forward to the night's party, Sam allowed himself to lean against the wall, casting a sidelong glance at his brother. "Dean?"

Dean rolled over on the bed to pull a beer can from the cooler his father had left behind. "What's wrong now, Sam?" he asked, popping the tab and handing it to his brother. "That's all you get," he winked when Sam took the can and raised it to his lips. "Don't wanna be too drunk," he added with a chuckle.

With a roll of his eyes, Sam waited until Dean sat back down and then asked him, "What's it like?"

"What's it like?" Dean repeated the question and then took a swig of his own beer. "Look, it's gonna feel weird at first, okay? 'Cause I know you, uh, take care of yourself, right?" Sam just shrugged as though it were no big deal, even as his brain screamed for his older brother to stop. He knew Dean did it. And he knew that Dean knew Sam did it. But that didn't mean he wanted to talk about it with his brother. "Yeah, well this is different. Especially if it's her first time, too. Maybe a little uncomfortable at first. But it's gonna get better, I promise. And then it's . . . dude, it's a thousand times better than your own hand."

Sam battled back the urge to roll his eyes again. He expected it would feel better than with his hand - why the hell else would anybody do it with another person? If you could just stay home and make yourself happy all damn day, why worry about going out at all? But that hadn't been what he was asking. "But what's it like?" he asked again, not sure if he was really phrasing it right.

Though he'd never really had an 'emotional' sexual experience, not in a chick flick kind of way, Dean felt like he owed his little brother more than a generic answer to his sincere question. While he liked to refer to sex as nothing more than a total body pleasure experience, even he could admit that there was something deeper than release that brought him back to the table time and again. "Sammy, it's like," he stopped and shook his head. "I don't know, man. It's like nothin' else. Adrenaline and euphoria. It's like a rush, dude. A total rush."

"Yeah, but Dean, you get a rush from hunting," Sam pointed out. It had to be more. There had to be some other reason that everyone who'd already done it wanted it again, and everyone who hadn't couldn't wait. There had to be something that Dean wasn't telling him.

It was true. Dean did get a rush from hunting. But how did he make his brother see that it wasn't remotely the same thing. "Look, this is gonna sound cocky, I guess, but whatever. It is what it is, right?" Taking another swig from his beer, Dean thought back to the last girl he'd been with just a couple weeks back. "Sam, there's this feeling when you're with a girl, and she's moaning and, like, whimpering and shit. And she whispers your name, and you can feel her fingernails in your back. Dude, there's this thing that just . . . I don't know. There's something about knowing that you can make a girl feel that way. It's indescribable, Sammy."

"So it's an ego thing?"

"No," Dean shook his head again and chuckled a little bit. "I mean, yeah," he added when Sam gave him a 'really, Dean, don't bull shit me' look. "It is, it feels good to know you can do that. But it's . . . I don't know. It's, like, the thing that makes you realize, Sammy, that watching her enjoy herself, and knowing that you're bringing her pleasure like that? It makes you feel that much better. Like it makes the experience better. And she's doin' the same thing, ya know?" Licking his lips, he remembered the way that Rebecca Isaacs had looked smiling down on him in the backseat of the Impala. The way she giggled and then groaned simultaneously with him, the give and take of that sweaty, passionate encounter - Dean knew he couldn't describe it the right way. There were no words.

Watching his brother drift away to a place that Sam didn't even want to imagine was starting to bring the temperature of the room back to 'awkward' for him, so he sipped at his beer and then cleared his throat. "So what you're saying is," he started to ask again.

But Dean shook his head and stood from the bed, checking his watch. "What I'm sayin', Sammy," he smiled as he crossed to the dresser and grabbed something from beside the television, "is that I can't describe it to you," he winked and tossed the object to Sam, watching him catch it effortlessly. "You just gotta experience it for yourself, little brother."

Jingling the keys Dean had just thrown his way, Sam stood from the bed. Ten till eight. It would take him a good fifteen minutes to get to the party in the first place, and probably another twenty to talk himself out of the car. "Seriously?" he asked, holding up the keys once again. If Dean was willing to give him the car for the night, sex was a bigger deal than Sam had originally thought.

With a nod, Dean watched his brother shove a wallet into his back pocket. "Just make sure you clean off the seats if you make a mess in the car," he warned, chuckling to himself as Sam groaned and wrestled his coat over his broad shoulders. When his younger brother flipped him off on his way out the door, Dean yelled out a, "Bitch," for good measure.

The sound of Sam's 'Jerk' response was muffled as the door slammed behind him, leaving his older brother to stare out the window at the Impala's low beams swinging into the parking lot.

Dean heaved a sigh and finished the last of his beer with a smile before grabbing another and turning the television back on. Settling on an old Steve McQueen film, Dean decided against prowling for his own party. This night belonged to Sam, anyway. It was the night that little eight-year-old kid across the table stopped asking his brother a shitload of annoying questions, and started to discover some answers for himself. Sammy was about to become a man, and Dean had a feeling that their relationship was never going to be the same again.