Chapter Text
Sam Winchester had a very bad track record when it came to people he had romantic attraction to. For Heaven’s sake, his first kiss turned out to be with a monster! He should have known right then and there that it wasn’t going to end well and just become a monk. But he was a romantic at heart and just kept fighting what the universe seems to be trying to tell him: that he was poison and that everyone Sam Winchester loved died because of him. It wasn’t until that faithful night in that godforsaken hotel that he finally got it.
Sam Winchester, unlike what most people would think, was in fact bisexual. His first real relationship was with Brady, something he tried desperately not to think about considering the man was a demon.
So, he had no trouble at all flirting back with the cute blond janitor at Crawford Hall. The way that man’s whiskey gold eyes sparkled and that mischievous smirk playing across his lips made Sam’s heart stutter with something that wasn’t fear for the first time since Jess had died. He certainly felt a pull toward the man and it took everything in him not to ask the guy out when he showed them out of the building. But then his brother made some crude comment about how they couldn’t keep their eyes off each other and Sam didn’t want to deal with Dean’s endless teasing and awkward comments if he knew his preferences.
Then he found out the janitor was the thing they were hunting. He was sad, but it wasn’t like he had fallen in love with the guy. Even though he couldn’t get those eyes, and that wink the Trickster had sent him a split second before Dean had stabbed him, out of his head. They always lurked at the edge of his mind. A flash of gold eyes in his dreams or some witness’s laugh suddenly sending him back to that office and that brash humor and smirking lips. He tried to shove it all away and managed for a while, too caught up with his powers and then Dean’s demon deal.
But then Mystery Spot happened. He didn’t understand, at the time, why the Trickster was doing it. And it hurt. God, did it hurt, not just because he had to watch his brother die over and over again but because it literally pained him to think that the Trickster was doing it. He couldn’t understand why.
He got an inkling of the answer while he pleaded with the god to just send him back. There was mischief in the Trickster’s eyes but also a kind of sorrow and a deep rage as he spoke of it only ending in pain and blood, like he somehow knew. He was almost desperate for Sam to understand. But all Sam could think about was his brother. He needed his brother back. Then, as Sam gave one more broken plea, the mask slipped, just for a split second, and he saw a great sadness and something else run across the man’s face right before the Trickster gave in. It was only later, when Sam would lie awake and run the encounter through his head again and again, that he realized it was pain.
He tried to push the Trickster out of his mind but his subconscious wouldn’t allow it. Most times he dreamed of those Tuesdays and the dark months after that Wednesday. Waking up with a racing heart and wild eyes as he searched for Dean, having to know he was safe and sometimes not seeing him. Then there were the rare occasions when he dreamed of slamming the Trickster against a wall and taking his anger out on him with bruising kisses and grinding hips. He would wake up hard and aching, his conscious brain fighting his subconscious one, disgust on his face at the thought of feeling like this for a monster. He didn’t know which dreams were worse.
Then Dean died, the dreams got worse but he was too high to even feel anything about them. That year he didn’t remember much, partly because he had blocked it from his mind, partly because the demon blood had played with his memories, and he was glad. The next time he saw the Trickster he was clean and had time to think over their past encounters more carefully.
_________________
He could see now that the Trickster was trying to help, in his own strange way. And even though he still sometimes had nightmares about the Mystery Spot, Sam had forgiven him. Because now Sam understood. Hindsight was a bitch; he knew now what the Trickster was trying to do. And Sam hadn’t listened and gone off the deep end anyway. So, he was willing to try and figure out what the Trickster was trying to teach them this time when he and Dean found themselves in TV land.
When they first encountered the Trickster on Dr. Sexy he couldn’t help but think that the name was an apt description. With his almost too big doctor coat and that smirk, Sam’s heart was pounding in his chest. When those gold eyes landed on him as he asked to talk, he had to use all his self-control to not blush or stutter. There was just something about the Trickster that sent his heart beating in a way it hadn’t in a long time, not even for Ruby.
He knew that the Trickster wasn’t trying to hurt them when he operated on Dean. That bullet should have killed his brother; it was so close to his spine. Then when they played ‘Nutcracker’; a bowling ball to the nuts with that much power should have broken his pelvis, but it didn’t. It hurt yeah, but not as much as it should have.
When Dean told him of his plan in the cop show he was hesitant. He didn’t want to stab the Trickster, and in the back of his mind he knew the Trickster was too smart to let him. The thought of how the Trickster knew Cas, how he talked of the prize fight, it sounded too familiar, not something a Trickster would say. Something told him he wasn’t even a Trickster. Sam’s reasoning for stabbing him was he knew it wouldn’t hurt him.
Then when his suspicions were confirmed, that he wasn’t just an angel but a damn Archangel, well . . . Sam’s heart broke a little. He was already out of reach when he was the Trickster now he was an angel. Something holy, something pure, someone who could never want Sam. He knew now that the flirting was just a tactic. Gabriel was just acting like he cared because they were important for the apocalypse.
As he told his story in the warehouse, Sam heard the pain in his voice. The pain of losing his brothers, watching them turn on each other and knowing there was nothing he could do. Sam started to understand. Gabriel was a lot like him. He wanted out of the life he was handed so he ran away and became something else. Sam saw so much of himself in the man in front of him. And then as Gabriel made the comparison between him and Dean and Michael and Lucifer, he saw the hesitation before he spoke about Lucifer and him. He saw the mask slip back on as he played his own role.
Crawford Hall made sense now, he was trying to help, maybe even trying to stop it all before it happened but they were too stubborn to see it. When Gabriel said, it was always supposed to end with them, he looked at Sam and Sam saw the sadness in his eyes, saw the pain that he couldn’t stop this from happening. Gabriel had tried: Crawford Hall, Mystery Spot. He had been trying to stop all this from happening. And they ignored him, too intent on their own problems to see what he was doing, what he was sacrificing to help them.
Well, Sam saw it now. He was going against God’s orders, against Michael and all the other angels. He was risking so much by just talking to them. It still wasn’t helping. He was tired, as he said ‘he just wanted it to be over.’ And Sam understood. He wished he could do something but with Dean standing right there, blinded by his anger for Gabriel, it wouldn’t help. So, that night he did something he hadn’t done for a long time: he prayed.