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Sam didn’t know about Dean's situation until he was 14. In hindsight it was kind of embarrassing but Dean was his brother and how was he supposed to know dudes normally had dicks? It was an average day up until health class. Sam dimly remembered Dean smirking and giggling as he forged the slip two days back but didn’t think much of it, he’d been living with Dean for Christ sake he knew all about that. Heck he'd seen Dean doing That! Ewww! He had figured the whole experience would be pretty lame. He was supposed to sit there and giggle with the other kids as Mrs. Pelagic named off body parts, showed some diagrams then told them not to do it or their dicks would fall off. But no. Here he was suddenly confused about who was a boy and who wasn't. Now the Teacher said that boys had poles and girls had holes, but Sam wasnt all to sure that Mrs. Pelagic had ever got laid. She was married, but.... He just wasn't sure that she was a reliable source of information. He'd ask Dean when he got home. But for now here he was bright red in ex ed.
Bobby found out when Dean was 19, after a hunt. It had been a long week. Him and that fool boy of Winchester’s had been hunting a wendigo and all he wanted was some damn coffee. So his kind hearted self had let the kid sleep and trudged off to the nearest dinner. The dinner wasn’t anything special: shitty eggs, decent bacon and good enough coffee. Well good enough for seconds anyways plenty of time for Dean to sleep off that throw from the bastard . He himself was aching something fierce from a little smack. He got back to the motel room to hear the shower running and Dean’s bed empty. Thanking the lord he wouldn’t have to wake the hell beast up he went to set breakfast on the table, but when he walked by Dean’s bed it was soaked though in blood.
“Balls!” He exclaimed as he rushed in the bathroom to see just what that idjit thought he was doing.
“Dude I’m in here!” Dean was protesting as he started scanning for injuries. He was one big giant bruise but no cuts and certainly not any to bleed like that. It took Bobby a good minute to realize where that blood was coming from. When he did he backed out and shut the door real quick like.
Witches. He rationalized, witches. He’d heard that it happened to that Ripply fella back in ‘84. Wore off in a few weeks too if he remembered right. Dean would be back to normal shortly and he shouldn’t worry about it. And when he looked back over it was a lot less blood than he’d seen originally. So he shouldn’t worry. In the few minutes it took for Dean to shake the water off and put some clothes on Bobby had just about worked himself into a fit.
“So what’s to say I clean this up and we forget all about this?” Dean tried.
Bobby started to help pull off sheets but before he could stop himself he was asking “So what done it?”
“I’ve just been off my meds for a while,” Dean sighed.
“Meds? Not witches?”
“Not witches. T-shots err testosterone shot they uhh make sure my body does the whole guy thing.”
“Why do you need the shots?” Bobby asked, trying to think of all the weird medical conditions he’d ever heard of.
"'Cuz I'm a guy,” Dean said defensively. He knew exactly how these things normally went.
“I know that ya idjit. But what do the shots do?”
“I wasn’t technically born a guy. They make my voice drop and grow a beard. Stuff like that.”
“Where do you get these things?” Bobby demanded. Dean just looked down at the floor.”You’ve been buying ‘em in an alley haven’t you? Does your Daddy know about it?”
“He said it’s fine as long as I’m using my own money,” Dean defended.
“Your buying drugs with gambling money but it’s fine ‘cause your Daddy told you you could.”
Jody was told by bickering brothers and a barrel of whiskey. The Winchester brothers where spilled haphazzardly over her living room floor bickering idly as they where passing a bottle between them occasionally handing it over to her when they rembered she was there. Despite their drunkeness they reminded her of her boy. She was drug out of fond memerories of Owen by a retort she dosen't think she has heard since middle school.
“Dude suck my dick!”
“You don’t even have one,” Sam argued as he sprawled even further across the living room rug.
“That’s not true. I’ve got five and most of them are bigger than yours.”
It wasn't till two months latter that she realised what Sam was saying. Well put that with a few other things about Dean she had accidentally found out. It made her feel kinda dirty knowing a secret she wasn't suppost to know. She didn't feel comfortable just out right telling Dean and honestly it kinda felt like a breach of privacy to even mention.
Charlie had found out by snooping. Curiosity killed the cat and all that. In her defense all hackers were all snoopers and the Winchesters knew that. Honestly though, she was wondering who kept their medical supplies in the cookie jar? Sam and Dean were out on a late beer run when she happened to find the syringes. Not the full set like the medical room but a pack and a half worth thrown in there amidst a good number of little vials. And Scooby Doo band aids, for Spock's sake! How could she not snoop when there's Scooby band aids? When Sam and Dean got back she didn't say anything. Why would she?
Crowley saw way to bloody much of him during their howling at the moon tour. He wished for the days when parts of Dean were still secret. He didn't know before, from when Dean was in hell he had still been just a crossroads demon. The other demons didn't talk about that kind of thing. Any of the demons worth their salt had been in hell so long they'd forgotten things like that matter. Dean had got that way too. Though he didn't think Dean had been modest by any stretch of the word before. He didn't care. How did it matter to him? He just wished Dean would keep his damn clothes on.
