Sam never saw himself as the type of man who lived to flirt. It was an area where he felt as out of place as in a crowded bar with loud music and flashing lights—very different from Dean, who seemed to have been born with a natural talent for flirting with any woman who crossed his path. His brother rarely spent a night alone, as if it were as routine as cleaning weapons.

But Sam… Sam always preferred to keep his distance from casual relationships, partly because he never wanted that kind of life, and partly because the memory of Jessica still haunted him like a silent shadow. After her death, it seemed wrong, almost impossible, to allow himself any kind of involvement that wasn't focused on saving lives or fulfilling his duty. He threw himself into cases because he needed to—to keep the world a little safer and to keep his own mind too occupied to remember what he had lost.

It was then that, in the middle of a bizarre case even by Winchester standards, Dean mentioned that he would call a "contact" for help. Sam expected anything: an old hunter, a strange specialist, someone with specific information.

But he didn't expect Dean to have a friend.

Much less one who had never slept with him. That, in itself, made the situation totally suspicious.

When you entered the motel room, Sam immediately noticed something different about you. A striking presence. A curious balance between elegance and danger. You had that kind of calm demeanor that makes it clear you know exactly what you're capable of—and what others are too. You were sweet and perceptive at the same time, as if your personality had been perfectly molded to intrigue and intimidate, something that made the back of his neck tingle.

And one look was enough for Sam to be sure that you could defeat both brothers without breaking a sweat, if you wanted to. There was something sharp hidden behind that gentle smile, a strength that didn't need to be announced to be felt.

But the situation was about to get even better.

The really fun part—at least for Sam—was watching how you naturally dodged Dean's persistent advances. It wasn't hostility, it was more… habit. As if you were so used to his advances that they were nothing more than background noise. Like someone who'd seen that spectacle dozens of times and wasn't impressed anymore. Dean, of course, persisted—part pride, part stubbornness, part dubious charm. Watching his ego slowly crumble was almost amusing.

But what really surprised Sam was the fact that you turned all your attention to him.

And more than that: flirting with him… openly, casually, almost shamelessly.

In front of Dean.

Sam will never forget the moment he heard you say, with complete calm:

"Wow, Dean… why didn't you introduce us sooner? Your brother is simply irresistible. And tall. And those eyes?"

The laugh you let out immediately afterward left Sam's face flushed for hours. Dean just grumbled, offended, while Sam wanted to crawl out of bed and disappear under the mattress.

Today, Dean had left early for some appointment he conveniently didn't explain—probably something involving trouble, a bar, or both—leaving you two alone in the cramped motel room.

Sam had the strange feeling of being prey left next to a predator.

But, to his own shame, he didn't find it exactly bad.

He'd gone out to get something to eat and returned in a few minutes carrying a bag with instant noodles, soda, and some cookies. Almost a feast.

"Any news yet?" he asked, closing the door with his foot, leaving the bags on the small table in the center of the room.