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Dean loved his brother, he really did. If he could choose between his life and Sammy's, there would be no contest. He'd sold his soul for the guy, and tried to die for him more than once, even though it never seemed to stick.
But sometimes how easy things were for his brother just made Dean hate him.
He wasn't talking about school. He had long since gotten over the fact that Sammy could easily ace classes that Dean struggled to pass. He didn't care anymore that Sam had gotten his bachelor's at Stanford while he had fought for a GED.
It was just that… Sam made normal, things Dean struggled with every day, look so easy.
Sam was secure enough to eat like a girl and grow his hair and avoid the macho bullshit without having everyone in a 50 mile radius questioning his sexuality, and as many jokes as Dean made about Sam being gay, he never once thought it was true. Sam had a couple of long term girlfriends and by all appearances loved the shit out of them, and Dean was happy for him, he really was, but he couldn't not feel jealous.
Sam never thought that maybe it might be nice to have hard muscle against his body, not soft curves.
Sam never wanted to wear the wrong underwear, or felt like his leather and plaid wardrobe just didn't fit.
Sam never felt like his body was wrong for him, never wondered what it was like to have soft curves of his own. When Dean made that comment about wanting to be a hot cheerleader back a couple years and Sam gave him that disgusted look, something curled up inside him and he fell silent, because Sam couldn't get it, couldn't know that maybe his macho big brother was just a little serious, not ever.
Sam never had to hide who and what he was, because he was exactly what people, what Dad expected him to be.
Sam was the good son, no matter how hard Dean tried and how hard Sammy didn't.
'Look after Sammy,' Dad said, over and over and in varying states of sobriety, but not once had he ever said 'Look after Dean.' And as much as he put the macho act on, sometimes he wanted to be looked after.
It was one night after a really long hunt that this came to a head. Dean was just back from purgatory, he hadn't slept through the night in what felt like years, and they'd been up for more than 36 hours straight and Dean had enough, but instead of lying down on the bed, he sat down on the floor next to it, leaning his back against the sheets, too tired to even get out of his clothes but still too awake to sleep.
Sam sat down on the other queen, stifling a yawn. "Dean, get in bed and try to sleep, at least. I'm worried about you–"
That was it. "Worried about me? You didn't try to find me, I gave everything for you, Sammy! You found a girl and you didn't even think twice about me. Dammit, I am so happy for you and you know that, but I feel like I'm always gonna be the one pushed under the rug when it comes to everyone else's lives."
"I'm sorry Dean–" Sam started, but Dean interrupted him.
"It was always, 'Take care of Sammy' until I started to think I wasn't important anymore, and really I'm not, but it was so nice when Cas acted like I was, and Benny did too, and he's the only one anymore but you–" he choked back the sob that threatened at the back of his throat, but carried on. "And sometimes I don't want to sleep with girls, Sammy, did you know that? Sometimes I want to wear the clothes that make me feel nice, but they're not the ones that I'm supposed to wear…" A sob escaped his throat, and he had to pause and take a deep breath. Sam had no idea what that meant, but just sat on the bed watching his brother in silence, letting him vent. He could feel how much Dean needed this, and honestly, it was nice to see his 'no chick-flick moments' brother finally dealing with his emotions in a somewhat healthy way.
Dean continued on, almost oblivious of Sam's presence. Years of things he had held back were coming out, and there wasn't anything Dean could do to keep them in anymore. It felt like a primal scream, both liberating and painful and he knew he would regret it later but he just couldn't stop. "And yeah, sometimes going to bars is nice, and sex with girls is nice, but it isn't all I want to do. Did you or Dad or anyone ever think to ask me that? And you know I haven't had a decent, honest to god hug since mom died, and I know I'm not supposed to want that but… I'm just… I'm just not the right person, Sam. I'm not what I'm supposed to be."
He hid his head in his arms, unable to look at his brother, suddenly ashamed of everything he had put out in the open, expecting to hear the motel room door open and shut any moment, Sam leaving again. Instead, he felt a warm weight settle around his shoulders and found himself being pulled into Sam's side. Against his will he felt his body turn and his head fall to Sam's shoulder. He let out a breath he hadn't known he had been holding and the knot in his chest that he had been carrying around for who knows how long seemed to untie, just a little bit.
Sam rested his back against the bed as he pulled his brother closer, feeling him shaking so hard it was like he could fall apart any second. They'd talk about this in the morning, or tomorrow afternoon while they drove in the Impala, or maybe that evening when and if they stopped at a motel, whenever they both could form a coherent thought. But for then, he only said the thing he knew Dean needed to hear: "You're just fine, Dean. You're just fine."