Cyndra Rae (cyndrarae) wrote,
Cyndra Rae

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Fic: Sleeping with the Enemy (Gilmore Girls, Jess/Dean) (9/?)

Previous chapters: One | Two | Three | Four | Five | Six | Seven | Eight |

Chapter 9 …

Jess peeked out from behind a lamp post and waited for his moment – the perfect moment. And he waited, and he waited.

“Damn it, Dean, come on.” He hissed and looked at his wrist watch, then dug his hands back in his pockets, snarling at the plus-sized grocery store manager in the window.

“For fuck’s sake man, let him go already. It’s his lunch break!”

Earlier that day, Jess had woken up in his bed with a big goofy smile on his face. For a moment he’d paused, the smile faltering, fearing it’d all been just a dream. But then he brought his hand up to the side of his neck and felt the two neat lines of teeth marks there, still there, really there.

Jess could honestly say he’d never felt so utterly pleased with himself all his life.

Sleep evaded him after that, even though it was only nine AM and he’d barely slept for four hours. He stayed in bed anyway, indulging himself, fantasizing of all the things he wanted to do to Dean, all the things he wanted Dean to do to him.

When the clock struck eleven and Luke the wake-up caller from hell had banged at his door for the fiftieth time, Jess finally dragged himself out of bed. Took a long, leisurely shower, threw on whatever clothes he could find that were clean, and decided to skip breakfast. It was nearing lunch time anyway, and he knew exactly what he wanted today.

The company of a certain hazel-eyed boy who looked and sounded (and smelled) unbelievably delectable. Especially more so when he came.

Jess leaned against the lamppost and tried to bite back his grin. A couple of passers-by noticed and gave him weird looks that he easily ignored. He let his thoughts wander back to six hours ago, when he had Dean stretched out beneath him. Those endless legs had spread wide open to make space for Jess to settle between them and grind his own erection against Dean’s hardness over and over and over again until they both came in their pants. Well, Dean came in Luke’s pants of course (which they’d immediately rinsed clean amid a lot of muted giggling) and through it all they’d kissed and sucked on each other’s tongue like their very lives depended on it.

What a glorious start to the day it’d been. Jess couldn’t care less that he looked like a loon, lost in his happy memories, licking his lips as if to try and re-capture the heavenly taste of Dean…

Someone tapped his shoulder from behind and Jess turned about, clearly agitated and in the mood to whale at some poor bastard for not letting him daydream in peace. Only to damn near jump out of his skin at the tall shadow masking the afternoon sun.

“Dean!” Jess almost stumbled two steps back as the other boy sniggered. God, he looked so… so… edible.

Okay, so maybe he was hungrier than he thought.

He took in the oversized denim blue jacket over a maroon striped turtleneck sweater that did absolutely no favors to Dean’s pale complexion but complimented the long chestnut hair shining in the sun, and brought out the color of his eyes. Jess squashed the urge to pummel his head against the lamppost. Obviously he’d been watching way too many ‘Queer Eye for the Straight Guy’ reruns.

“Wh-where did you come from?”

Dean bit his lip cheekily, and Jess noticed his gaze falling to Jess’ lips instantly.

“The store happens to have a back door, like most four-walled constructions do, apparently. What are you doing here?”

Jess shrugged and flashed him a hopeful little smile. “Thought I’d, maybe, take you out for –“

He stopped just in time to catch the beginnings of a frown on Dean’s forehead, so sharp, that he immediately backtracked.

I’m not some girl, Mariano.

And Jess would do well to remember it.

“I mean, I-I was hungry. A-and so… I came by to see if you, uh, wanted to grab a quick bite. Or something?”

He tried to sound like he couldn’t care less but failed dismally.

Dean dug his own hands in his jacket pockets and squinted suspiciously. “So, what, we’re doing the whole dating thing now?”

Jess cleared his throat. Guys date guys too, of course they do. Don’t they?

“I f-figured you might like that.”

“Why bother? I am in your bed every night, aren’t I?”

For reasons he couldn’t explain, Jess heard an element of self-derision in that mocking tone of Dean’s voice, and he didn’t like it one bit.

“I just wanna spend more time with you while I’m here, and while you’re awake. Is that too much to ask?”

Dean shrugged, looking away briefly. “Just, never took you for the, uh, gay-dating type.”

“Well, I never took you for the promiscuous boy type either, Forester, unless that’s what you’d prefer...” and Jess started to turn around and walk away.

“Wait.” Dean bit his lip again, his eyes playful but still mildly apprehensive.

“I hope you realize that we can’t… I mean, no one can know.”

About us. Of course, Jess ignored the faint sinking feeling inside his chest and made a face that basically said ‘Duh’.

“This is Star’s Hollow, Forester. No one knows or cares two hoots about us beyond a little factoid that we both once dated a Gilmore. Far as they’re concerned, we’re just two jilted ex-lovers brooding over a common object of obsession, that’s all.”

Folks would have to be downright stupid to believe that, of course, but far as Jess was concerned, they could think whatever the hell they wanted. Right then, he’d have said anything to get Dean to just be with him. That was all he cared about.

Dean let loose a short chuckle and looked down to the tip of his work boots. Then after a brief moment’s consideration, he gestured with a nod of his head in the opposite direction.

“Come on then. I feel like sushi.”

Jess couldn’t help but smirk triumphantly and he made to follow the other boy in the foretold direction when his feet suddenly ground to a halt, his smirk disappearing just as quickly.

“Please tell me you said Sookie.”

Dean laughed and just kept walking.

“Soo-kie right?”


That night, Jess asked Luke to take a break and waited downstairs instead. He waited till two in the morning.

Dean did not show up.

Luke woke up at around that time to find Jess curled up in a sofa chair with a coffee mug and a book in hand. He sighed, rubbing his eyes.

“It’s good that he isn’t here tonight, Jess. He wasn’t supposed to be sleepwalking more than two or three times a week anyway.”

Jess swallowed the little lump of emotion down. “I know.”

He did know that. It was a good thing Dean didn’t show. He was glad about it. He really was. Except… that he was not.

“Don’t know why it’s gotten to be so frequent recently. Maybe he’s really stressed out these days. Or maybe it’s you.”

Jess snorted. “That’d be me, alright. I’m always stressing the hell out of folks around me.”

“That’s not what I meant.”

Jess looked up at his uncle then, who was smiling knowingly. Luke put the coffee on and came around to perch on the edge of the table in front of Jess.

“I ain’t your uncle for nothing, kid. I see the way you look at him. And I also see the way he’s starting to look at you.”

Jess felt his face burn and he looked away.

“I don’t think he’s sleepwalking just because he’s stressed. At least not every night. I think, of late, he’s sleepwalking because he just genuinely wants to be here. Where you are.”

Jess couldn’t help himself. “You really believe that?”

He had no way to know how hopeful, how young he sounded in that moment. Luke smiled, his eyes shining with reassurance as he put a hand on Jess’ pajama clad knee and squeezed it.

“I wouldn’t say it if I didn’t. Having said that, we don’t completely understand why Dean sleepwalks some days and why some days he doesn’t. His doctor said there will be nights his body would be really exhausted, or his mind would be passive enough to be able to sleep through the night. And that is a good thing, Jess. It is what Dean needs.”

Jess nodded, blushing at the realization that his uncle could read him like an open book, had been doing so all this while. Luke’s words had the intended effect, and when he went back to bed, Jess did the same. Figured he’d have to wake up earlier than his usual eleven AM if he wanted to see Dean soon as possible.

That night, Jess dreamed of the tall boy stripping down to nothing and slipping into bed beside him. Dean hadn’t been willing to part with his clothes last morning, and Jess couldn’t stop obsessing with the brief but tantalizing glimpses of flesh he’d caught the night before.

In his dream, Jess saw himself pull the naked form of his lover into his arms and just… hold him to himself. He watched his own dream-hands skim over every single inch of Dean’s pale skin, splattered with moles in the most adorable places, feeling intimately the parts that were tanned and yet others painfully sun-burnt from his laborious afternoons spent landscaping. He heard dream-Dean hiss ever so softly every time Jess’ fingers ghosted over the more tender spots, watched him close his eyes and sigh eagerly every time Jess found an erogenous spot to caress.

Jess woke up hard and aching sorely, with a longing in his heart and body so profound, it brought fucking tears to his eyes. He brushed them away angrily, cursing Forester for having this uncanny control over him.

And all this time, his face remained split wide open into a stupidly cheerful grin.


Once again, Jess showed up at the grocer’s at exactly five minutes to noon. By the time he made it to his usual spot, Dean had already spotted him coming from the distance, as he stood restocking the exotic fruits aisle by the window. He’d smiled ever so softly but kept his eyes averted and Jess just leaned against the cast iron pillar again and watched.

How could someone look so hot in that ugly green apron? Conversely speaking, how could anyone human make that ugly green apron look hot?

When Dean came out fifteen minutes later for his lunch break, he walked up to Jess directly, wincing slightly against the sunlight.

“Hey,” Jess said.

“Hey yourself.”

“How about a hot dog today?”

Dean laughed. “Sure,” and Jess thanked the stars his boy was not a sushi freak every day of the week. Once every now and then, he could deal with.

After a quick bite during which they ended up talking of everything and nothing at all, they went walking round the corner before it’d be time for Dean to return to work.

“So, sleep okay last night?”

Dean smirked. “I was wondering how long you’d be able to keep it in.”

Jess winced sheepishly. “I missed you.”

Dean didn’t look up or respond, watching the ground intently. But Jess saw his Adam’s apple bob once.

“I don’t know exactly. The pattern is… there is no pattern, I think.”

“Yeah, no, it’s cool. I just… I hope you’re not taking the drugs again.”

“God, no. My mom would kill me,” and that’s when Dean looked up at Jess, his eyes twinkling. “If you don’t first.”

Jess bit back a smirk and lowered his eyes just as Dean did. They walked in comfortable silence for a while.

“Do you think you could, maybe, take the rest of the day off today?”

Dean grimaced. “I don’t think so, Jess. I’m sorry.”

Jess gulped down his disappointment and shook his head. “It’s alright, no problem.”

“You know how it is, right?”

Dean sounded worried, even though he probably hoped it wasn’t too obvious. Jess smiled at him, his best reassuring smile that rarely ever got used.

“I do. And I’m sorry, I shouldn’t have asked. I know how important your working these jobs is for your family.”

Dean nodded and looked away.

“Hey, Dean?”


“Do you ever, like, regret quitting college to come back to Stars Hollow?”

Dean thought about it for a minute as they rounded a corner and walked past the grocery. They still had a few minutes of lunch break left.

“Some days, yeah. Some days I fear I’d be stuck working dead-end jobs for scraps for the rest of my life. And that if I’d just held out another two years in school somehow, I might have been able to get a better job – like a ‘white collar’ position somewhere to support my family, you know?”

Jess just bit his lip and nodded.

“But then I remember the mortgage and the thought of my mom and sister losing the house just kills every shred of personal ambitions I ever had. Not like I had much to begin with.”


“My dad didn’t just abandon us, Jess. He betrayed our trust. He made some really bad investment decisions and not only did he lose all our family’s savings and our college funds, mine and Clara’s, he also left behind a huge debt to repay that puts everything we’ve ever owned at risk.”

Dean paused and took a deep breath, as if to compose himself.

“That’s why I came back. I’m going to do everything in my power to protect my family, make sure my mom doesn’t have to suffer any more, and Clara gets to go to whichever college she chooses. I can’t abandon them like he did. It would destroy my mom, this time for sure.”

His heart ached for the bitterness in Dean’s voice. Clearly this guy was having a greater impact on Jess than he’d anticipated. Not only could he empathize, he also found himself actually angry and hurting for Dean. Jess didn’t know how to respond. Funny how he never fell short of words when they were arguing. Kicking himself mentally, he tried.

“White collar jobs are so overrated,” he mumbled almost as if to himself, and tried to turn the conversation to something more objective and less… well, emotional. “If I can help it, I’d rather do my own thing, be my own boss and be answerable to no one but myself, you know.”

Dean scoffed lightly and looked sideways at him. “Yeah, I heard. Construction for corporates?”

Jess grinned. “Yep. So far so good. We’re actually planning to expand pretty soon.”

“You’re a lucky man.”

“Lucky? I worked my ass off to set it all up, man.”

“Of course, I didn’t mean that. But tell me something, do you work as many hours as I do?"

Jess gave it a thought. “Probably not.”

It was Dean’s turn to smirk. “Dude, that sounds lucky enough to me.”

And without waiting to let Jess think of a smart comeback, he picked up pace and started to head back to the store. Jess followed quietly, for once letting Dean get the last word in, although fact was – he really couldn’t think of anything to say right then.

In truth he’d never thought of himself as lucky ever. For as long as he could remember, he’d always been unhappy with everything around him, and angry at pretty much everyone that passed through his life. It had never been this easy – not until he managed to reach closure with his mom and they went their separate ways, and he became old enough to strike out on his own, do his own thing. Which he did, luckily he ran into his buddy, Dillon, and things worked out better than either of them had ever expected.

Luckily, yeah.

Maybe Dean was right. Maybe it was time he stopped bitching and whining about the things he couldn’t have, and start being thankful for the things he did?

Once they reached the front door of the grocery store, the boys stopped and looked at each other for a couple of seconds. Jess found himself drawn to the magnetic eyes again, unwilling to let go so soon. But Dean cleared his throat and gestured with a tilt of his long neck to convey a wordless goodbye. Grudgingly, Jess nodded back, then watched as Dean walked back to wrap up his first job of the day.

As much as he respected Dean’s work ethic and sincerity with which he was supporting his family, Jess didn’t like how much that boy worked. To work hard is not a bad thing, hell it’s an honorable thing, but what good was it if it started to take a physical and mental toll on the individual? Besides, wouldn’t working smart be a better option, if there was one available?

Jess did a quick approximate math in his head to calculate how much Dean might make right now from his three jobs in this little town, versus how much Jess was making right now from just one full-time job in New York City.

It was nowhere near comparable.

Dean was back in his apron by now and glanced up once through the glass window to find Jess still standing where he’d left him. Jess thought he might have detected a little blush in the beautiful face before it turned away, and it brought a smile back to his face.

And it occurred to him then – Jess would give anything to see that face every single day for the rest of his life.

He stood there for another few minutes, then making up his mind, Jess flicked open his cell phone and started to walk to the book store. His partner, Dillon, should be on his own lunch break right now. Good time to catch him before he got busy again.


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Tags: fic: gg: sleeping with the enemy, misc fic

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