Cyndra Rae (cyndrarae) wrote,
Cyndra Rae

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Fic: Sleeping with the Enemy (Gilmore Girls, Jess/Dean) (11/16)

A/N: This chapter is dedicated to all (okay, most) men and their foolish pride. I'd ask them to grow up, but they don't actually know what that means ;) 
Previous Chapters: One | Two | Three | Four | Five | Six | Seven | Eight | Nine | Ten

Chapter 11…

They settled into a routine.

Jess would meet Dean for lunch, and leave him to his three hundred thousand jobs the rest of the day. He would hit the bookstore instead and read for free until the owner started to frown, or help Luke at the diner till it closed and then he’d wait for Dean to show up, sleepwalking at night. If he didn’t, and he didn’t three out of the next five nights, Jess would trek out around midnight, climb up the tree and into Dean’s bedroom instead.

Most nights they would make out for awhile and then go to sleep, nothing more. Dean would always be too incredibly exhausted for anything more than that anyway. God knows he tried, but Jess couldn’t bring himself to torture the poor kid when he’d really rather just curl up around Jess and sleep. Besides, Jess guessed, Dean still wasn’t completely ready to go all the way, not even when Jess offered to bottom first. So he waited patiently, trying to ignore the little niggling at the back of his head reminding him that his days were running out fast, and he’d have to leave soon.

Most mornings, Jess would be his creepy obsessed self and prop his head up on one elbow to watch Dean sleep. He couldn’t believe how much this guy had come to mean to him in a span of just three weeks. He wondered if the process of breaking a thirteen-year old's solemn pledge, in other words, the process of him embracing his sexuality, had really started back when he’d first met Dean. Maybe that’s why there’d always been this heavy-breathing, chest-thumping, overly macho friction between the two, besides the obvious reason aka the Gilmore girl. Jess shook his head, reminiscing the way they used to be. Clearly, Dean had started to work a charm on Jess way back then. Too bad Jess took so very long to realize it.

One of those mornings when Jess was sneaking back into the diner from Dean’s, Luke caught him. He was sitting downstairs with a mug of coffee and a newspaper, ever so casually, like he always got up at five o’ freaking clock every morning.

“Didn’t know this sleepwalking thing was contagious.”

Jess scratched his head, unable to think of a good way to explain this. Instead he just smiled sheepishly, but Luke did not look amused.

“I’m guessing Marge does not know about you spending the night under her roof, does she?”


“Then maybe you shouldn’t be doing this, Jess.”

Jess sighed helplessly. “Come on, Luke. Night’s the only time I get to see him. The guy has three jobs and no time for me all day!”

“All the more reason to let him sleep, Jess. Or do you want him to start sleepwalking again?”

Jess relented reluctantly. “No, of course not.”

“Look, Jess, you know I’m not against the two of you being together. I just don’t think it is right for you guys to be… you know… doing it under Marge’s very nose because she’s not going to be very happy when she finds out about it. And trust me, if you move with the same degree of stealth in her house as you do sneaking in here, she will.”

Jess just rolled his eyes in response. Luke exhaled in equal irritation and stood up understanding that no matter what he said or believed, Jess was only going to do whatever he pleased. He hesitated for just a second before changing his pressure tactics, starting off on the safe sex lecture that Jess really did not want to hear.

“Look I know you’re an adult…”

“Then treat me like one, Jesus!!”

Of course, Luke was persistent, like he could be when he’d made his mind to get onto his nephew’s nerves. Jess groaned and cursed and stalked back to his bedroom and slammed the door shut behind him.

Luke just shouted out the rest of his lecture through the door.


That night, a little after eleven, the door bell rang. Jess came bounding down the stairs where Luke already was, still cleaning up after a really hectic day. The older man looked at him quizzically before going to get the door.


“Uh, hi Luke…”

“You’re… not… sleepwalking.”

Dean flashed him a quick shot of his brilliant thousand watt smile. “No sir, am not.”

Luke paused, and no one spoke for a whole five seconds. Jess just watched, waiting at the last step of the stairs.

“Then, what are you doing here, Forester?”

The smile vanished. Only to be replaced by fumbling nervousness. “Ah, well, uh, I figured… i-if I don’t sleepwalk tonight and if you don’t want Jess to come over then… uh…”

“You figured I would just let you sleep over? Seriously?”

Dean threw Luke his classic lost puppy dog eyes that no one in the world could possibly resist. Jess had never been prouder of his boy. He tried to bite back his smirk as he watched his uncle made absolutely no effort to contain his exasperation, or mask the fact that he’d already caved. Luke followed it up with a lot of huffing and puffing about everything and nothing consequential. What could he say anyway? They were both consenting adults, and Luke was nowhere near homophobic.

“Yeah, alright.” He grunted at last and went back to his cleaning, not looking up as Dean thanked him quickly then hurried up to where Jess stood grinning like a loon. Luke pretended he did not see Jess holding out his hand and he pretended to not see Dean taking it either, as together they bounded up the stairs to their bedroom.

Once the door was locked, it didn’t take long for them to lose their clothes and fall into bed with a soft thud. They knew they could be as loud as they wanted in here, but kept it down with due consideration to the man downstairs who’d been nothing but outrageously kind and forgiving to the both of them.

The night progressed steadily from cuddling and kissing to handjobs to blowjobs (Dean had developed quite a skillful mouth over the past few days) and back to kissing and cuddling and now they lay spent on the bed. Dean lay on his back, with his hands clasped under his head, and Jess lay with his head pillowed on Dean’s chest, one hand still gripping Dean’s balls, rolling and squeezing them on occasion. At first Dean had laughed and complained that it tickled, but then he’d let Jess play on, seeing how Jess refused to relinquish his hold on the family jewels anyway.

“You know, in a way, this is an experiment my doctor had suggested some time ago. To see what happened if I go to sleep at Luke’s. Do I still get up and sleepwalk? And if yes, where do I go instead?”

"Is that what you told your mom about tonight? That you're conducting an experiment?"

Dean just sniggered and Jess joined in. Feeling drowsy, he nuzzled lower into Dean’s stomach. “Well, you’re not going anywhere. Staying right here, with me.”

Dean chuckled, and Jess felt the body beneath him vibrate with it but he didn’t let it shirk him off. “Getting bit possessive already, are we?”

“Mm-hmm…” was all Jess could manage. He did tighten his hold on Dean’s scrotum as a response though, making the other boy shiver and sigh helplessly.



“Why don’t you insist on… you know?”

Jess opened his eyes. “On what?”

“O-On us, you know, having sex? It’s not like we have all the time in the world.”

Jess looked up at Dean, resting his chin on the flat and ridiculously firm stomach instead. “You think you’re ready?”

Dean thought about it, and timidly shook his head.

“Then we wait. For as long as it takes. You can always do me first, you know. I told you, I’m easy. It’s you who’s insisting on going first.”

“That’s because you want it more. Don’t you remember what you said – that cheesy line from a soft porno flick?”


Dean snorted, then quickly sobered up. “Point is, you asked for something and I want to be able to give it to you first, before asking back for it.”

“And who’s doing the cheesy harlequin lines now?”

Dean just laughed, and Jess pulled himself up to plant a quick peck on Dean’s lips in appreciation. “Baby, I won’t even pretend to understand your fuzzy logic. Just know that I can wait. Okay?”

“But for how long? You’ll be gone soon. In, what, three days to be exact?”

Ah. About that.

Jess bit his lip and slide over to one side of his lover’s frame. He propped himself up on one elbow and looked down into Dean’s face, no longer sleepy. “Dean, I’ve been meaning to talk to you about this for some time now.”

Dean frowned. “What is it?”

Jess tried to bite back his excitement, but he was sure it shone through his eyes. “Come away with me.”


“I spoke to my partner, Dillon, and it’s all been discussed and agreed. You know we own a small construction business in Queens and we’re trying to land some of the landscaping contracts, which you have experience with, so it’s a good fit! It’ll pay you three times what you make working your three jobs here if not more, I can guarantee you that. Well, maybe not in the beginning but that’s fine – we can start you off on a sizable advance until the thing takes off. And we could really use another partner, especially someone as hard working and – “

“Wait, wait… WHAT?”

Jess looked up into Dean’s eyes; he was now struggling to sit up, so Jess let him and followed suit. “What’s wrong? Aren’t you excited?”

“Excited?!?!” Dean looked mad. Why the hell did Dean look mad?

The taller boy suddenly got up and out of bed and started to dress himself. “How could you… how could you think I’d let you treat me like some fucking charity case, Mariano? Don’t you think I get enough of that already?”

“That’s not what I – “

“Or did you think I’d just jump up and down with joy at the prospect of being kept like a fucking whore?”

“I’m offering you a fucking job, genius!”

“And when exactly did you decide to branch out into landscaping?”

“What does that have to do with anything?”

Dean scowled miserably. “Every-fuckin-thing!!”

“Damn it, Dean! Why do you always have to fight me on stuff so hard? Why can’t we for once talk about shit like normal people?”

“That’s rich, coming from you, Jess. You’re the original street fighter of Stars Hollow, remember?”

Jess lost it then. The notoriously short temper he was holding down burst through to the surface because why should Dean get to spew all the venom after all?

“You know what? Forget it. Forget I offered you your only chance to get out of Hells Hollow and actually do something more substantial with your life than stocking groceries.”

“Well, that’s awesomely generous of you, but, no thanks.” Dean suddenly turned away as if… as if to hide his face from Jess. “I gotta go,” he hissed and picked up his jacket and shoes.

And now he was leaving. Jess felt his gut clenching with a fresh bout of despair and helplessness. He was getting really sick and tired of watching Dean walk out on him over and over, and over again.

“Where do you think you’re going? You know you’ll come sleepwalking back to me anyway.”

And that was somehow an even harsher thing to say, but Jess realized it half a moment too late. He recognized that subtle slump in the lean shoulders, and immediately regretted being the one to put it there. Again.


Don’t go. Please stay. I’m sorry…

But his wounded pride would let him say none of that. Dean practically dashed to the door then, opened it and stepped out. Jess heard his footsteps storming down the steps and out the main door.

He couldn’t have stopped Dean from leaving that night. Even if he’d tried.


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

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  • SPN fic: Rarely pure, never simple (see warnings)

    Title: Rarely pure, never simple Summary: Gen. Sam gets hurt on a hunt because he neglects to share something important with his family. Rating:…

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