Kind of an AU. I wrote it a long time ago. I'm just only getting to typing it now. Can you tell that I just don't have any time to do stuff anymore?
"Jess, this is my big brother, Dean."
It was a simple introduction, really. Dean had showed up spontaneously and Sam had, after reprimanding him for not calling first, dragged him back to the apartment. Sam had apologized numerous times for leaving the way he did and Dean had just brushed it all away with a laugh. Sam caught the affectionate look that was tossed at him and grinned back. Dean had teased him and ruffled his hair and called him rude names in a voice bursting with pride. Sam hadn't realized just how much he had missed his older brother, and Dean hadn't realized just how good it felt to be with his younger brother again.
Then Sam had introduced him to Jess, and they had joined forces to tease Sam mercilessly and Sam had never been happier. Sure, he was embarrassed, but Dean had agreed to stick around for a little while, and Jess was thrilled to finally meet Sam's hero. Dean had even impressed her with his cooking skills – he was the only Winchester who was able to cook without catching anything on fire, so all cooking responsibilities were on him and he had actually learned to love it and used it to relax.
Three months later, Dean was still living with them and had claimed what used to be their guest room. He had snagged two jobs, one as a mechanic at a nearby garage and one as a bartender at a bar just off campus. Dad had called a few times, but Dean had just ignored it, albeit with a wince and his teeth gritted. Sam had looked at him funny, but he just shook his head and said that Sam was more important. Later that week, Dean told Sam that he was leaving hunting behind; unless it was nearby, Dean wouldn't go after it. He still looked for hunts, that was too far ingrained in his head to get rid of, but he sent them off to Bobby along with the jobs Dad sent.
Tonight, Sam was working on a project at the library, and he had promised to be home before midnight. Jess and Dean, who had remarkably similar movie preferences, had settled on watching a Rambo marathon. Dean was in an old pair of jeans and his favorite Led Zeppelin t-shirt, and Jess was wearing a pair of sweatpants and a tank top. Jess had curled up against her new big brother's side as they sat eating popcorn and licorice. Dean had an arm around her shoulders and she was resting her head against his shoulder. He let out a sigh and leaned his head against the back of the couch, closing his eyes.
"Tired?" she asked.
"A little," he said without moving. While he usually forbid anyone taking care of him, he found that he didn't mind too much when Jess tried. He let her take care of him and actually liked how she hovered just enough. She gave him space, but was right there when he needed someone to help him into bed, which had actually happened before when he forgot to eat and sleep for a couple days.
"You going soft on me?" she teased.
"Jess, I want you to do something for me."
"Sure, what is it?" she asked, all joking gone at his quiet, serious tone.
"Sammy, he doesn't have a whole lotta guts," he started. "So you're gonna need to make the first move."
"What?" Dean just reached into his pocket and pulled out a little bag. He handed it to her silently, and she opened it up and three rings slid onto her palm. Three gold rings, one with a diamond, one without.
"Dean," she breathed.
"I only bought the big ring, the smaller ones were my mom's," he said softly. "Dad couldn't even look at them after she died. I know Sam wants to marry you, but it might take a few more years before he asks, so I'm giving you the rings so that you can ask him."
"I…I don't know what to say except…thank you." She leaned up and kissed his cheek. He smiled and squeezed her shoulder.
When Sam got home – at 11:58, so he hadn't broken his promise – he found Jess sitting on the couch with Dean completely slumped against her. It seemed like his older brother's hundred-twenty-six hour work week (a sixty-three hour week for each job, just both happening in the same week) had worn out Dean even more than he'd claimed. Sam chuckled at the sight of Dean sleeping with his head on Jessica's shoulder as she stroked his soft, dark blond hair.
"Leave him alone, he worked for twenty hours today alone," she scolded. "Poor baby is exhausted." She gently stroked the side of his face.
"Sam, does anyone else see this side of him?"
"What side?" Sam asked.
"I don't know, the sweet, just wants to cuddle and watch movies side."
"I think he only lets family see that side of him; and the only family we have is you, a priest, and a tow truck driver," Sam said. "So, no, not really."
"That's what I thought," she said. Sam helped her prop Dean up and then the two of them managed to get him to bed without him waking up even once. After they left the room, Dean was awake enough to hear her pop the question and hear Sam say yes.
It was a simple thing really, but Dean couldn't hide his smile as he drifted back to sleep.
FIN