Authors Note: This doesn't really have a main pairing. I'm putting Gabe/Sam only because of how Gabriel feels, but this does not end with them together. No happy ending, don't think it's really a sad ending either.

Warnings: Angst.

*** Special notice: I am in the process of deleting my other account and migrating the fics to this one. Please note that the prompts for this series were pictures.

Hot Chocolate and Marshmallows

Over one hundred times.

While he didn't know the exact number, Sam knew it had to be over a hundred times he had lived through Dean dying. While he wanted to be angry, all he could feel was resigned that the inevitable would happen at some point during the day, and Dean would die. Again. How many more times he had to live through the day, he didn't know… but no matter how he tried to protect Dean; it wasn't enough. And then he would wake up to that damn Asia song, again. If it wasn't the cars or guns, it was something as simple as Dean having a shower which would kill him. Over a hundred times and Dean hadn't died the same way twice. In his resigned state Sam had to admit whoever was doing this, they were creative. If it didn't rip a hole in his very being every time he had to watch Dean die, Sam would admit some of the ways Dean died were admittedly humorous.

But it did rip in two.

Every. Damn. Time.

Sitting at a booth in a diner he had memorized the menu for, Sam waited for the waitress to serve his coffee. Sam had told Dean he would bring him back something, while he knew it meant Dean would probably die a bit faster, after the last one Sam needed to not see it today. Groaning while running a hand through his hair, Sam was startled when instead of his coffee, two saucers of hot chocolate were placed in front of him. It smelt delicious, small marshmallows floating on top. Looking at the cup in front of him, Sam could easily tell it was real hot chocolate, not the pre-packaged stuff he had occasionally when indulging in his sweet tooth.

A body slid into the seat across from him, and now that he had something else to focus on, Sam looked up at the man who had brought him the sugary beverage. Eyes wide, Sam stared at the man across from him, instantly taking inventory of what weapons he had. The likelihood was he didn't have anything that could hurt the being before him, but that didn't stop Sam from reaching into the back of his jeans and gripping the handle of the knife he kept there.

"Don't worry Bucko, you're not going to need that," said the god before him, taking one of the cups of hot chocolate and bringing it to his lips. "I have no intention of harming you; if I wanted you dead I've had plenty of time to do so, a hundred and three days to be exact."

The thought made Sam freeze, looking up at the trickster he had thought they killed a year ago. "You're dead." It wasn't elegant; however, the man quirked his lip, both hands wrapped around the warm ceramic mug.

"Hellooo~ Trickster, it's kind of in the title isn't it? The guy your brother was so stabby with? Just another illusion like the girls. I even left you a hint I wasn't dead! Didn't see the bed vanish, did you? Nah, you guys aren't the first hunters to come my way, and you sure as hell won't be the last. I simply provide an illusion during the big boss fight and everyone moves on happy."

"Is that what this is?" asked Sam, letting go of the knife. "Is this simply another illusion?" Not wanting to anger the god when he didn't have anything that would kill him, Sam wrapped a large hand around the still-hot chocolate. Sam didn't take a drink, but the warmth against his palm kept him grounded.

"Nah," began the Trickster, a thin line of chocolate on his upper lip from where he had been drinking his hot chocolate. "Not like you have anything that would work, I mean you may feel naked without a gun or knife… but I very much doubt you keep a stake with my victims' blood on you twenty-four seven."

Taking another sip of his beverage, the Trickster nodded his head towards Sam's cup. "You should have some, I'm not here to hurt you Sam and the hot chocolate is superb." As if to prove his point, the Trickster drank the last of his own before pouting and snapping his fingers, his cup refilling and Sam's going back to temperature.

"I'm not in the habit of coffee dates with monsters, especially ones who keep killing my brother." Not bothering to be mindful of the people around him, Sam raised his voice at the end, glaring at the man across from him.

The Trickster didn't seem phased by the tone, instead, he shrugged his shoulders. "You need to learn to move on. Figure if you experience it enough, you might be able to desensitize yourself to the fact that your brother is a doomed man." The Trickster must have seen the surprise on Sam's expression as he continued, his typical smirk changing to a soft look Sam hated. "Listen Sasquatch, because I'm only going to explain this nicely once, then I'm going back to this trick. You. Can't. Save. Dean. I know, its horrible and everything in your co-dependant mind is screaming at you that if you research enough, if you dig enough, something will show up to save the day."

The Trickster paused then, golden locking eyes with Sam, his voice firm. "It won't work. There's nothing, and I mean nothing, that can interfere with Free Will. Your brother sold his soul out of his own free will, and there is nobody in existence who can overwrite that. I'm sorry Kid, I am. If it were up to me I would destroy Dean's contract, but nobody can, not even the demon who holds it. You kill them, it goes to the next in line, and so forth and so forth." The Trickster leaned back in the booth, his cup of hot chocolate in his hands.

"This little pocket of time may be my own creation, but the message is very real. So, what's it going to be Samsquatch?"

At the question, Sam shook his head. "I can't… he's my brother." Sam understood what the being was doing, what he was saying, and in its own warped way, Sam could see the Trickster was trying to help. Sam didn't know why, and he had a feeling he wasn't ready to know the answer to that question, but he was trying to help. Looking at the man as he let go a long sigh, Sam could see the disappointment in the expression of the other.

"Yeah, I know Kiddo… that's the thing, isn't it? It's always your family that gets you into these kinds of messes. Well if you aren't going to take my advice I guess I'm going to have to try for a while longer. Who knows? Maybe you'll get a clue in a few more rotations."

"No, wait…" began Sam, but with a snap of his fingers, the Trickster watched as Sam vanished. A quick brush of his power and Sam wouldn't remember their conversation, it was for the best. If the Trickster knew one thing, it was that this wasn't going to end well. Looking at the spot across from him where the large man had been sitting only moments before, he sighed. It always came down to love didn't it? Sam loved his brother too much to let him go, and as much as he hated to admit it, the Trickster loved the bright soul too much to simply sit back and watch the world burn.

Draining the last of his beverage, the Trickster reset time before taking his seat at the counter. He would give Sam a few more days to attempt to get over Dean's death before he would take more drastic measures. When Sam entered the diner followed by his brother, the Trickster watched absently while eating his pancakes. Only half paying attention, he nearly gave himself away as he watched the waitress serve Dean his coffee; in her hand was a ceramic mug of hot chocolate, marshmallows floating on top which she placed in front of the taller hunter.

Turning away as to not draw attention to himself, the Trickster smiled. Maybe at least a part of their little impromptu date stuck with the hunter. He just hoped it was enough, this stopped being fun ages ago.