A/N: Pre-series obviously, Sam is fifteen, Dean is no Steen, John is work it out yourself.
Just a little oneshot I wanted to write to keep thinks going, enjoy!
Dean was sitting in front of the TV, beer in hand, when his dad said he is leaving for a hunt.
"Son, I'll need you to stay here, look after Sammy."
"Sam's fifteen dad, he can handle himself." The Winchester replied but didn't push, if he wasn't allowed to join this hunt then it was probably for a legitimate reason.
"I need to go Dean, I'll be in touch." It didn't matter that his dad had only got back late last night and was leaving less than 24 hours later. Nor did it matter than John and Sam hadn't exchanged a single sentence in that time.
"Listen, I need to ask you a favour." John looked a little hesitant as he paused, not meeting his son's eyes, which made Dean wonder what this favour was. He knew that whatever it was though, he would do it, his Dad had a good reason for asking everything he did.
"Sure..." Dean said to end the silence which had promptly filled the room.
"Sam, he's getting to that age... I think he's experimenting... Like teenagers do... Its time to give him the talk, could you give it to him?" John was uncharacteristically uncomfortable, nearly as much as Dean was. It was weird, for his dad to be asking something so... Normal. Yet still awkward. Really awkward.
"Yes sir." Dean replied. John left soon afterwards. Well, at least he would get the opportunity to embarrass the hell out of Sammy, that punk probably hadn't even had his first kiss yet, too busywith books and nerdy stuff. Still, Dean was hardly one to talk, he wasn't exactly experienced himself.
Girls had thrown themselves at Dean - who wouldn't he was amazing - on more than one occasion, but John was always there, the master cock-blocker. Dean had been close a few times, real close, just never quite there. Dean sighed as he thought that over, it was kind of pathetic really.
Dean was dragged away from his thoughts when the door opened, instinctively Dean grabbed his gun with had been sitting on the arm of the couch, to his right, before he realised it was just Sam getting back from school.
"Hey Dean." His brother said as he closed the door then proceeded to toss his backpack onto the bed, the contents rustling about a little as it landed.
"Hiya Sammy, beer?" Dean offered, making Sam immediately narrow his eyes slightly in suspicion; Dean never offered Sam alcohol. Unfortunately.
"Sure Dean." The younger Winchester replied cautiously before walking over to the unsavoury yellow couch and sitting beside where Dean had previously been sat.
Dean estimated it would only take a couple beers and a slug of whiskey to get Sam drunk enough to have this conversation with him, his little brother had probably never drunk anything stronger than WKD before
"Here you go." The nineteen year old held out a beer, with the cap already removed, which Sam took gratefully.
The conversation was kept light through the first beer. By the time Sam had finished his second Dean had pulled the whiskey.
Sam was hardly stupid, he knew Dean was trying to get him drunk, god knows why, he was normally so protective over his alcohol. Sam had also guessed that his older brother thought he was the definition of a lightweight - should that offend him? Maybe. - that wasn't the case, but that didn't really matter.
"Why don't you try this? Probably won't be able to hold it mind you, this is a mans drink." Dean held out a glass which was filled about a third of the way up with some cheap whiskey. Okay, so whiskey wasn't something Sam had regularly, he didn't like the way it burned down the throat or the absolutely disgusting taste which made it no different to most other spirits and liquors. But this was a challenge now; even if it wasn't a challenge it was now.
Sam took a small sip; the first time he drank the ghastly stuff he had made the mistake of taking a mouth full and boy was that a bad decision, he almost cringed thinking back to that disastrous day.
"So, uh, Sam. There's something I've got to talk to you about." Dean said rubbing the back of his neck nervously. The fifteen year old gestured for his brother to continue, he might as well find out what he'd done wrong.
"You're getting to that age... I mean teenage boys... Like yourself..." Lord, he getting as bad as his father was before he left. Get it together Dean!
Dean Winchester had no problem talking about sex, but talking about sex all that birds and bees crap just made it damn uncomfortable. So Dean did what he normally did and just switched off his brain to mouth filter.
"Dad wants me to give you the talk." now Dean was expecting some sort of reaction: awkwardness, face as red as a beetroot, choking on his whiskey - which he was handling surprisingly well - but laughter? A deep throaty laugh was not what Dean expected at all. (How did he even pull off a laugh like that?)
"What's funny?" Dean asked. Maybe his brother was too drunk for this.
"Oh, you're serious?" Sam asked between laughs.
"Yeah." Dean replied, a little put out.
"You're a little late don't you think?" Sam finally started getting his composure back. His brother widened his eyes a little.
"Late? You mean you've already..? With who?!" Sam had to pause a moment in though. Oh god, Dean was dying, his dorky younger brother had beat him to it! That was just plain embarrassing!
"Yeah. I'm fifteen Dean, hardly a little kid. D'you want the list?" A list? He'd had enough sex for there to be a list!?
"Yes." Dean was going to go and beat up every guy that had laid a finger on Sammy, because fifteen kinda was still a kid in Dean's eyes.
"Okay... So a year back there was Stacey, she was cute. After that was Katie? Kassy? I can't remember her name. Then came Brett, but I was only with him once.-" Dean couldn't believe it, not only had is brother fucked but he'd ticked both boxes? Dean was in a sort of state of disbelief. Three people, Sam had already had sex with three people! "-After that was Ally in Texas, then her friend Jenny. Dylan in Mississippi, and the bartender with her boyfriend a couple towns back." Sam concluded. So now his brother was having threesomes with adults? That was it, Deans life was officially over, he had failed at being a man, and no, he wasn't being at all overdramatic! Sam wasn't even legal yet and he had eight more knots tied on his bedpost. Actually, eight was quite a lot...
"Hate to be the one to break it to ya Sammy but you're kind of a slut." Sam shrugged his shoulders.
"Dean, you're hardly one to talk, how old were you you're first time huh? I bet you've been through way more girls than I have." Sam joked as Dean tried not to blush. Apparently he didn't try hard enough. "Wait... You have done it haven't you?" Sam asked but Dean's silence was an answer in itself. "No way! You're a virgin?!" Sam's mouth was agape and he was staring at Dean as if he'd just been told angels and unicorns were real.
"But... With the way you talk... And... But you're always out..." Sam muttered to himself, utterly confused.
"Its not like I haven't tried Sam, I've made out with more than my fair share don't get me wrong but Dad..." Dean tried to redeem himself but he could see resolve building up in his brother's eyes and that was never a good sign.
All of a sudden Sam was standing and had dragged Dean up too. He looked down - damn Sam and his growth spurts - at Dean, turned without a word and started shoving Dean towards the door.
"Sam? Sammy! What in hells name are you doing?" Dean half shouted startled by his brothers sudden actions.
"You need to get laid. Dad's not so you have no excuse, now go!" Sam said before unceremoniously pushing his brother out of their small motel room and slamming the door immediately afterwards. "And don't come back until you have!" Sam added hastily as an afterthought. He then locked the door and turned back to face the room - with walls that were far to yellow for his liking. If Dean going out just so happened to mean that Sam had to drink all the remaining booze himself then Sam would bravely shoulder that burden.
Such is the story of how Dean Winchester got his first lay.