Dean knew long before he told him. Sam had always been different from other gurls. How he liked to wear Dean's hand-me-downs and play with "boy stuff" instead of the Barbies Dean stole for him. He'd always been a "tomboy". The way he'd insisted they call him Sam instead of Samantha. The way he always wanted his hair cut short like Dean's. Dean just laughed when Sam introduced himself as Dean's brother. Thinking back, he could've sworn Sam had looked sad whenever someone called him "she" or "her".

John hadn't minded, it was easier for him to have two boys. Easier to buy the same stuff for both of them. He'd raised them exactly the same. Sam was just as good with a shotgun as Dean. When someone said, "Nice boys you got there," he didn't bother correcting them. Sam went in the same bathroom as them because it was convenient and they could look out for him in there.

Puberty was an awkward time for little Sammy. Dean was 16 and he was busy sleeping with every girl he laid eyes on. But he noticed the cuts on Sam's wrist and thighs. He had thought once Sammy hit puberty he would be more feminine. He had thought it was just a phase. But Sam still wore his old clothes. Dean walked in on him in the bathroom one day binding his chest with ace bandage. Sam said he didn't want to talk about it and Dean didn't push him. He didn't know how to talk about it with Sam. What ever "it" was. He knew Sam was hurting. And there was nothing he could do because Sam was shutting him out. And dad wasn't there. So he did extensive research online. He'd found out about something called "transgender" and "female to male". It sounded a lot like his Sammy. But he waited for Sam to come to him.

It happened that summer. They were camping in Montana in midst of a large population of moose. As always, Dean and Sam shared a tent and ended up in the same sleeping bag at some point during the night.

"Dean?"

"Yeah, Sammy?"

"I-I need to tell you something." He sounded nervous.

Dean turned to face him. "You know you can tell me anything, right?"

Sam nodded, taking a deep breath. He couldn't meet Dean's eyes. "I've always felt wrong in my body. I've always felt like I was a boy, you know? I-I think I'm trans."

Dean grinned. "I knew it!"

Sam stared at him. "What?"

"Come on Sammy, I know you better than anyone. And I can use the Google machine."

Sam smiled. He didn't know what to say. He was surprised Dean was so cool about it. "So do you-do you think you could maybe call me "he" now? I mean you don't have to if you-I know it's weird-"

"Sam." Dean grabbed his face. "Of course."

"Thanks, Dean." Sam buried his face in Dean's chest. Dean's cock twitched as Sam's lips brushed his nipple.

"Does dad know?"

"No."

"Do you want me to tell him?"

Sam looked up at him and slowly nodded.

"It's gonna be okay, lil' brother." Sam smiled. Dean wrapped his arms around his slender frame and they fell asleep.

"Dad? Can I talk to you about something?"

John was sitting at the kitchen table nursing a can of beer. They'd finally caught a break. No cases, no new leads on the yellow-eyed demon and more importantly, Sam was liking school here and had made a friend.

"It's about Sam," Dean said slowly, unsure how to broach the subject. But he had promised his sister. Brother. Brother.

"What about her?" John asked gruffly, not taking his eyes off the paper he was reading.

"Dad, she-she wants to be a boy."

"She's always wanted to be a boy. My fault probably. She never had a female role model."

"No I mean she-he is a boy. She told me she feels like she's in the wrong body. Asked me if I could call her "him" and "he" now… Have you heard of transgender people?"

John frowned, but nodded slowly. "Why isn't she telling me this?"

Dean sighed. "She's scared, dad."

John grunted, his frown deepening. "She's only 13."

"So?"

"So she's only thirteen. She's just a kid who can't possibly know what she wants ! She'll grow out of it." He threw the can across the room into the trash.

"Dad, please. This isn't a phase. Come on, think about it, it makes sense."

"Think about what? This is ridiculous. If she has something to tell me, she can tell me herself."

Dean shook his head. "Well of course you wouldn't notice the signs, you were never there," he snapped, immediately regretting it.

John looked up at him coldly. "I was protecting this family," he said icily, standing and slamming the door closed behind him as he left. Dean stood in the kitchen, dumbfounded.

"Dean?" Sam's anxious face was poking out the bedroom door.

"What are you doing, you're supposed to be asleep?" He tucked his baby bro back into their shared bed. "Did you hear everything?" Sam nodded, biting his lip.

"It's gonna be okay, Sammy, he just needs some time."

Luckily Sam was tall, thin and muscular, allowing him to pass well. He could hide what little curves he had in slightly baggy clothes and layers. When they started at new schools Dean made sure to enroll him as Sam, male. It only took Dean a few weeks and he had the whole male pronoun thing down. But the words "take care of your sister" would still be branded in his memory forever.

One day, a few weeks before Sam's 14th birthday, Dean came home to find Sam curled on the bed crying.

"Sam?" He ran a hand up Sam's back. "What's wrong?" He knelt down beside him, brushing his damp bangs out of his eyes. That's when he saw the box of pads sitting on the nightstand. He gulped. He'd prepared himself to give Sammy "the talk", had informed himself about periods and the female reproductive system, but now he couldn't remember a word of it. "It's okay," was all he could say.

Sam finally relaxed in his arms, falling asleep on his lap. There was a wet patch on his penis, but that was just Sam's tears.

Sam woke an hour later to find his pad leaking. He dashed into the bathroom. He needed new underwear. He couldn't wear pads in boxers. He felt guilty for how much money new underwear and more pads every month would cost them. He knew Dean would steal for him, but, being the righteous and moral person Sammy was, he couldn't let him do that.

"Hey," said Dean as he came out. Sam couldn't look at him. He felt embarrassed and angry and sad. Suddenly he felt overwhelmed. Sitting on the edge of the bed, he put his head in his hands. He was hyperventilating.

"Hey Sam breathe, buddy, it's okay." Dean rubbed his back.

"I c-can't do this I can't-"

"Shh we'll figure it out. Put your head down." Dean pushed Sam's head between his legs and started singing Hey Jude. That always calmed Sam down. He couldn't imagine what Sam was going through. He'd sure freak out if he started bleeding out of his—no he didn't want to think about it. "Let's watch a movie."

That night after Sam was sleeping, Dean went out and bought a year's supply of every kind of sanitary napkin and panty liner he could find, a few bottles of extra strength ibuprofen and some underwear with a nice wide strip to perfectly place an extra large pad. Being the good brother he was, he kept all these things in a special period bag because he'd promised not to tell dad.

Dad found out a few months later when they were on a hunt together and Sammy had to keep asking for toilet stops so he could change his pads.

"How long?"

"Couple months," said Sam. John merely nodded, a hurt look crossing his face, and clapped Sam on the shoulder.

It wasn't until almost a year later, when he'd finally gone to see the second half of one of Sam's soccer games that Dean was always trying to get him to go to, that John realized he truly had two sons. Sure Sam looked like a boy, he always had, and could take out grown men in a fistfight, but she was still his little girl. He still remembered the look on Mary's face when they'd found out they were having a girl. "How about Samantha?" A loud and slightly drunk voice pulled him out of his thoughts.

"Your son was great out there today." He'd seen the guy before; it was the father of one of Sam's friends. He looked over at where Sam stood talking with some of his teammates. "Yeah, he was." Dean looked up in surprise.

After that John started using male pronouns. It was awkward for a while and he slipped up often at first, but Sam knew he was trying. John could tell he was a lot happier. And for a while everything was good. But Sam wanted more. He wanted HRT. He wanted all the things that Dean had, the muscles, the voice, facial hair. He was sick of binding, sick of periods, sick of his voice giving him away every time. He couldn't do relationships because he was too self-conscious. He didn't like being touched. He didn't want to lie to the people he was with. What would they do if they found out? Who would want to be with a freak like him?! The only person who he felt comfortable around was Dean. And that was beginning to be a problem. Sometimes he got so jealous of Dean he couldn't bear to be around him either.

He'd done his research. He would need to see a therapist first, get an assessment done and then go to an endocrinologist. He'd been saving all the money he made at various summer jobs he worked. By the time he turned 17, he had over $1000 saved. The problem was that they never stayed in one place long enough. He knew therapy alone typically took 3-6 months to complete. He had to get out. This wasn't something he wanted, it was something he needed. Dean would probably understand, but he doubted dad would. He'd just gotten good with the pronouns thing and he didn't want to lay another thing on him just yet.

Luckily Sammy was good at school, like really good, on his way to becoming valedictorian. He wanted to go to college. He wanted to be a lawyer.

He didn't tell Dean when he applied. Whenever he brought up the subject Dean would become weird and dismiss it, like it could never happen. He knew Dean was being a selfish shit. He couldn't bear the idea of Sam being away from him. Of not being able to protect him. They'd never been apart for more than a week. They were too codependent. Dean needed to feel like he's in control and he was able to do that with Sam. The only thing that kept him going was Sam. Without Sam he was just a high school dropout and petty theft. His life was over the moment he'd run out of that burning house with Sammy in his arms. Sam felt bad for him. But it didn't have to be that way for Sam. He could have a normal life.

It was the spring of his senior year when he got his acceptance letter to Stanford. He had a full ride. It was his ticket out of here. He was still trying to decide what to do and how to tell Dean and dad, when Dean found the letter.

"When were you gonna tell me?" He yelled, sounding angry and hurt.

"I don't know if I'm gonna go yet."

"Come on Sam, it says here you got a full ride! You were gonna leave me, weren't you?"

"Dean, listen. I just applied okay, thought I'd give it a shot. I didn't know I was gonna get in. I didn't want to tell you in case I didn't." It wasn't a complete lie.

"But you want to go?"

"Yes. More than anything."

"You're gonna leave us."

"Dean I-I can't do this anymore. This life, hunting, constantly moving around, it's just not for me. And now I have a way out…I've always wanted to go to college," he added, gauging Dean's reaction. He was more hurt now than angry.

"Well good luck telling dad that," Dean said finally, heading out the door without another word. Sam sighed and cried a little.

Dean came home sometime after 3am, staggering drunkenly through the door, not bothering or forgetting to take his clothes off before falling heavily onto the bed.

When John found out he punched Sam in the nose. It was only afterwards he realized what a scholarship to Stanford actually meant. It meant Sam was a fucking genius. For all the moving around, all the school he'd missed he'd still managed to get into one of the best universities in the world. John was proud. He cursed himself for spending the boys' college funds on ammo.

The day they dropped Sam off at Stanford was the hardest day of Dean's life. That was when his drinking problem escalated. Sam had promised to call and Dean had promised to visit, but it wasn't long until their calls went from daily to once a week to once every couple of months.

It wasn't until a year and a half later that Dean finally visited his brother. He'd just finished a case near Reno and with nothing better to do, made the 3-hour drive to Stanford. He stood in front of Sam's building, nervously biting the inside of his cheek. Maybe this wasn't a good idea. The last time he'd heard from Sam had been over 6 months ago. Maybe he didn't want to see him. He didn't know how long he'd been standing there when he heard a voice. "Dean?"

Dean turned and his mouth fell open. Before him stood his brother. But he looked different. His shoulders were wider, he was more muscular than Dean, and his face was-Dean couldn't quite lay his finger on it-just more masculine looking, with sideburns and light stubble coming in around his chin and jaw.

"Sam?"

"Yeah it's me." Whoa his voice was deep too.

"What-what did you-" He couldn't stop staring at his brother. He was so…HOT.

"Hormones. Been on testosterone nearly 8 months."

Dean could only nod and close his hanging mouth, but not before some spit leaked out. His cock was straining against his tight jeans.

"Um wanna come inside? You look like you're gonna pass out."

Sam led him to his room. "This is Jessica, my room mate."

"Room mate, huh?" Dean winked at him and shook her hand.

"You know it is possible just to be friends with girls."

Dean snorted. "Not if they're as hot as her."

Sam's room was clean and organized. Dean paced around looking at all the awards hanging on the wall. "Damn." He picked up a framed picture of the two of them from the desk.

"Why are you here, Dean?"

"What, do I need an excuse to visit my little brother?"

"Well it's the first time you've come in a year and a half…"

"Yeah."

"How's dad?"

"Fine. On a case with Bobby in Colorado."

"You're looking good."

Dean snorted. "Yeah so are you, I mean wow. If you weren't my brother-" He waved his hand up and down Sam's body.

"If I wasn't your brother, what?" Said Sam seductively, closing the distance between him and Dean. Sam smelled different. Muskier. Manlier. God it was so arousing and it was all Dean could do not to come in his pants right then and there.

"God Sammy, you're killing me," he whispered, leaning down slightly to press his lips to his brother's. Sam grinned, his eyes flaming with lust. Dean grabbed his shirt and pulled him close so that he could feel his raging erection pressing into his stomach.

Sam tore off both of Dean's outer layers of flannel and ripped his t-shirt off his body with his razor sharp teeth. He took a moment to stare at the amulet hanging around Dean's neck. He pushed Dean forcefully backwards onto the bed and straddled his hips, sucking and biting a trail of hickeys down his brother's pale freckled flesh all the way from his neck to his hipbone.

"God Sam," Dean breathed, flipping them over. Sam's hand stopped him when he wanted to pull his shirt off. Right. He'd actually forgotten. Sam had never liked him seeing, let alone touching his chest.

"Sam I don't care what you got under there, man. You don't have to hide from me." He placed a soft kiss on Sam's temple. Sam was still frowning, but he slowly let go of Dean's wrist, allowing him to pull the shirt over his head. Sam flushed when Dean looked at his chest. He was wearing a binder underneath. Slowly Dean hooked his fingers under the hem, and when Sam showed no signs of stopping him, he pulled it off. The tightness of it had left red lines in Sam's skin. Dean bent down and kissed along those lines, running his hands along the sides of Sam's torso, admiring the perfectly sculpted muscle beneath him. He looked up to see Sam watching him intently.

"Tell me if you need to me to stop okay?" Sam nodded and finally let out a breath he'd been holding, bringing his fingers up to tangle in Dean's short hair.

Sam's breasts were small. Even though they looked out of place on Sam's body, to Dean they looked beautiful because they belonged to Sam, even if he didn't want them. He put his mouth over his nipple and rolled the other between two fingers. Sam growled like a wounded moose and bucked his hips into Dean's.

Dean growled too, but not like a moose, and scraped his nails over Sam's hard muscular stomach flesh to the waistband of his pants. He looked up at Sam to make sure, but Sam's head was thrown back in pleasure so he went ahead and threw his pants down.

When Sam realized he was exposed he gasped. No one had ever seen that part of his anatomy. Not even Jess. And yeah he'd lied to Dean, she was more than a roommate; they were dating. And also taking it very slow.

Sam thought about stopping here. But his pants were already down. Dean had already seen him, so why not.

Dean's heart skipped a beat when he saw Sam's enlarged erect clit sticking out from under his luscious curls. And by enlarged I mean like 3 inches. God he was so turned on. His pants were very uncomfortable and he quickly stripped them off. Good thing he was going commando today. Sam looked apprehensive so Dean asked, "Can I?" and when Sam nodded he closed his mouth around the swollen pink tip. It was enough to make Sam whimper and buck his hips needily. Dean took him all the way in and let him glide back out with a wet POP. He flicked his tongue around in a tornado and had Sam writhing beneath him with release just seconds later. Hot liquid spurted out of Sam's other hole, spraying across Dean's crotch. Woah Sam had just come. He'd never come that fast before. Nothing had ever felt as good as Dean's mouth on his tiny dick.

When he stopped seeing stars, Dean was grinning at him. "My turn," he whispered and grabbed Dean's throbbing cock, pumping it quickly. "God Sam," Dean breathed. Suddenly the heat of Sam's hand was gone. Wide eyes were staring at him.

"Can you-can you fuck me?" Sam was trying to sound confident and sexy but he failed. He was nervous because he was still a virgin. Dean gaped at him. It was all he ever dreamed of doing since he was a teenager. But now Sam looked so vulnerable.

"Fuck yes," he answered and Sam smiled sexily.

"So um which- you know- hole?"

Dean was being completely serious and Sam burst out laughing. He turned onto his stomach and presented Dean with his asshole. He reached into a drawer and hand him a bottle of lube.

"Have you ever done this before?" Dean asked even though he knew the answer.

"No."

"Well I'll break you in good, son," Dean breathed huskily, slipping his dripping finger into Sammy's tight little puckered hole. Sam hissed in pain but demanded "More." Dean loosened his ass with three fingers and eventually his whole hand fisting in and out. Good thing Sam's screams were muffled by the blanket. Jess was still in the room next door. And he didn't much care for a threesome right now. Sammy was his and only his. Sam groaned as Dean's hand was replaced by his penis. He inched his way in slowly till he was buried balls-deep in his brother's majestic ass, stopping to admire the view. He pulled out swiftly and thrust back in, in a smooth glide. Hell yeah, he'd loosened Sam's ass real good. Like a well-oiled machine. Like Baby. No, he did not have sexual fantasies about his car. No.

Sam cried out when Dean hit his sweet spot. He didn't have a prostate but he didn't need one. It felt SO good. Dean raked his nails down his arched back with every thrust and Sam loved the pain. He needed more because he was a masochist. He was also into bondage, but more on that later. Throwing his head back, Dean got the idea and grabbed his hair, pulling it sharply. Sam's eyes watered. His scalp burned and tingled. Dean had his other hand wrapped around Sam's cock, jerking it in rhythm. He was so close but he wanted Dean to come first. Inside of him. He clenched his walls tightly around Dean's shaft and it worked. Sam could feel him pulsing inside him, hot liquid pooling in there, dripping out of him as Dean pulled back. A few more jerks on his tiny dick and he was coming too. "AHHH DEAN!" Trembling, Sam collapsed onto his stomach, his ass sticky with Dean's cum.

Up next: Sam fucks Dean with his strap-on

Up after that: Sam, Dean and Jess have a threesome