What if Sam told Jess all about hunting? What if, in the years they were together, they encountered a ghost or a werewolf or something else? (Not a demon; they don’t know that’s what’s wrong with Brady, they don’t know that there are others, waiting and watching and planning.)
So when Dean comes to Stanford, “Dad’s on a hunting trip,” Sam doesn’t respond with secrecy. He asks “What was he hunting?” and “Where?” and when he leaves with Dean, Jess goes with them. Because she knows, because she’s seen a few things too, because Sam needs her support if he’s gonna get in his brother’s car and sit beside him and feel the guilty longing again.
What if Sam told Jess everything?
What if Jess wasn’t there to be killed, what if she didn’t burn on the ceiling of their home? What if it was someone else - a friend, a family member, a sister - and she’s got a need for revenge now too? So she goes on the road with Sam and Dean. And Dean tries not to be jealous every time he sleeps on the other side of a thin motel wall, hears Sam and Jess in bed together, wraps a thin pillow around his head to try and muffle the sound of them.
What if he can’t take that distance after Bloody Mary attacks Sam, pretends the motel they stop at doesn’t have two rooms available, stays awake to watch Sammy sleep and he didn’t expect Jess to be the big spoon and stay awake too. What if Jess and Dean get talking, and the only thing they really have in common is Sam so that’s what they talk about. And he doesn’t quite know how, but he finds himself talking about how he always feels like a piece of him is missing if Sam isn’t next to him (and it might be a chick flick moment but that’s okay because he’s talking to a smoking hot woman) and Jess gets a thoughtful look on her face before saying “You can hold him, too.”
And… “what?”
“He almost died today. I need to hold him, I bet you do too. You can, if you want to.”
What if Dean climbs into bed with his brother and his brother’s girlfriend, wraps an arm around them both because Jess is tight against Sam’s back, hooks his leg over Sam’s the way they used to when they were kids. And he’s finally able to sleep, with Sam’s head tucked under his chin.
What if Sam never mentions waking up pressed between the two of them, but they start sharing a bed regularly and Dean’s never slept better and Jess is smiling because neither has Sam.
What if Sam had told Jess everything, and she can see that Dean wants the same thing, so she decides to help the man she loves with her whole heart get the brother he loves with his?
And it works out, because somehow they’ve ended up with Sam burying his face in her pussy and Dean holding Sam’s hips while he fucks into him. And when they fall asleep sated, in a tangle of sweaty limbs, something about it feels more right than anything they’ve ever had.
They feel whole.
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