Cyndra Rae (cyndrarae) wrote,
Cyndra Rae

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Fic: Sleeping with the Enemy (Gilmore Girls, Jess/Dean) (10/?)

A/N: Am gone for the weekend to a place with no internet access (yes there are places like that still out there!) but I wanted to post this one before I left. Sorry for the mistakes, not enough time to proofread. There is no SPN or Vampire Diaries this week right? Good weekend to go away I say heh.
Previous Chapters: One | Two | Three | Four | Five | Six | Seven | Eight | Nine

Chapter 10…

Jess couldn’t believe what he’d gotten himself into.

Here he was, in the middle of the night, halfway up the tree that flanked the Forester house, sweating profusely from running all the way from Luke’s and now climbing this tree that was damn near impossible to climb.

“You can do it, Mariano. Come on…” he hissed to himself, and hauled his weight up another branch until he was almost three-fourths of the way there.

Please let that be Dean’s window, Lord, and not his mom’s. Or his sister’s.

Someone up there heard him, because when he finally made it up to the window ledge, he sighed with absolute relief. It was a guy’s bedroom alright, and right next to the window stood a low bed with a tall figure stretched out diagonally across it. Dean lay face down, his shoes and tattered soil-ridden jeans still on, like he’d walked in from work and just dropped like the dead.

Jess sighed, and once again prayed for cosmic assistance as he tried the latch. Once again luck favored him (Jess was a believer now and forever from this night on) and the window slid open soundlessly.

He crept in, knocking a decorative lamp or something to the carpeted floor and the soft thud almost gave him a heart attack. He waited for footsteps running up the stairs, or women screaming, anything.


Jess exhaled in relief, then quietly closed the window behind him. He crouched up beside the bed, next to Dean’s face that lay turned his way.

“Dean…” he whispered, so low he could barely hear himself. But he loved saying it nonetheless, his beloved’s given name, loved the thoughts of adoration it conjured in his mind, how it rolled off his tongue so sexily.

How could Rory have let go of something so precious? Jess shook his head, feeling sorry for the girl and thanking his own stars over and over again. Quietly, he also thanked his partner, Dillon, for convincing him to spend a part of his break with his uncle Luke in Stars Hollow. Of course the fact that he ended up spending all of it here and even took additional time off was all thanks to this amazing man sleeping before him.

Dean’s mouth was slightly open, again, one hand curled up right under his chin as if he were holding a microphone in his dreams. His hair was all over the place, as usual, and Jess couldn’t resist reaching out to stroke it softly. Gently he pushed a few stray locks behind Dean’s ears, so they wouldn’t block his view of the chiseled face anymore. And God those lips! How he possibly be expected to just watch from a distance, when he could reach out and actually touch them, the impossible softness of them? Would it really be so hard to believe if he couldn’t stop himself from kissing them?

Dean woke up then, at the first feeling of pressure against his lips. He stirred and Jess pulled back ever so slightly, not all the way though. Part of him felt guilty for disturbing Dean's much needed sleep, but Jess just missed him so much. Dean hadn't shown up at the diner for two nights straight.

Dean’s eyes slid open at last and a second later, he jumped.

“Wh-Wha…? Where…?”

“Shhh,” Jess put a hand on Dean’s cheek, his thumb coming to rest on top of his reddened lips. “You’re in your own bed. You didn’t sleepwalk, relax. I came to you.”

Dean frowned. “H-How?”

Jess grinned. “Perfectly planted tree right next to your window, that’s how.”

Dean just gawked at him in silence for another few seconds. And then together, as if in perfect synchrony, they both started sniggering. Dean shushed him hurriedly, just in case his family woke up.

“The door!” He hissed, and started to get up.

Jess pushed him down. “I’ll get it.”

Quickly he padded over to the bedroom door that was only slightly ajar and clicked it shut. Then he turned to find Dean sitting up in bed, watching him carefully. The room was mostly dark with a dim yellow night light still on by the other side of the bed, enough to allow Jess to see Dean’s face. His eyes were no longer heavy with sleep but were instead bright with excitement, and hope and… a little something else.

Jess practically ran back to the bed, straddling the taller boy’s torso without asking for permission and capturing Dean’s lips with his own. Dean put his arms around Jess, wrapping him up and holding him close as he surrendered to the invasion of his mouth happily. Jess leaned down with his entire body weight until Dean understood and lay back down on the bed with the shorter boy still on top of him. And still they continued to suck at each other‘s tongue like it was the last time they‘d ever be together.

The thick denim of two pairs of jeans wasn’t enough to keep their arousals hidden from each other. Soon Dean started to thrust upwards with just as much force as Jess who was grinding down. Their erections slid against each other in perfect alignment, the two bodies moving together in musical harmony, back and forth, up then down, urging each other deeper and deeper into a pleasure-ridden state of masculine bliss.

Jess had never felt this raging lust for anyone else ever before. It overwhelmed his senses, captivated his body, mind, heart and soul, until every thought and every sensory perception that did not somehow revolve around Dean, ceased to exist. Part of him, a very tiny, miniscule one, wondered if this… rabid, out-of-control obsession with another person qualified him to be clinically insane. The rest of him couldn’t care less even if it did.

It took superhuman strength to wrench himself away from the kiss (and the humping) but he had to, or he was sure he’d die.

“Dean, let me in…”

Dean paused. “What?”

Jess looked into his eyes, licking his lips every now and then. “I wanna be inside you, Dean, I wanna die inside you. Please…”

He bent lower to lick at the long column of Dean’s gulping throat, until he reached the crook of his neck, where he closed his teeth around it and bit down, hard.



“Jesse, no…”

Dean whimpered softly as Jess continued to leave his mark on the boy’s neck, reaching down with a hand to fondle his generous package.

“Jess… stop!!!” Dean suddenly hissed sharply, making Jess pull away and frown, only for Dean to shove him hard until he fell off the bed and to the floor with a loud thud.

“Owww!!!” but he still had the sense of keep his voice down even though Dean seemed to have no such compunction left.

“What the hell, Forester???”

Dean sat up in his bed. “I told you not to treat me like a fucking girl, Mariano!”

“Wha-? I didn’t…”

I wanna die inside you?!?!?! What the fuck kinda crazy chick-feed line is that? And then you tried to give me a fucking hickey?!?!”

“Okay so the line’s a little corny. But what the fuck’s wrong with a hickey?? Everyone gives everyone hickeys! Hell you gave me a hickey!!”

“No I didn’t!”

“Yes you did.”

“Did not.”

Jess threw his hands up in the air, in no mood to do this with Dean again. “Dude, seriously?”

Dean folded his arms and his legs, pushing them underneath himself. “Well I don’t want a hickey, you idiot! What if someone saw it? What if they found out about us?!?!”

Jess huffed and got back up on the bed, sitting on the far edge seeing how Dean had crawled up to the other end as far away from Jess as possible.

“Okay, I’m confused. What are you upset about, exactly, Dean? One thing at a time, please?”



“I don’t know, okay! Just, I think you should go.”

“Go???” Jess panicked. “No, no, no… not until you tell me what’s going on in your head. Come on, Deano, talk to me.”

“Don’t call me Deano.”

“Whatever. Forester.”

Dean glared harder. Jess sighed, putting a hand up in placation, wondering why they always ended up arguing so much, even in what was supposed to be a romantic setting.

“Sorry. Dean.”

Dean pulled a pillow to his chest and hugged it hard. He seemed breathless but he continued to glare at Jess almost petulantly, and Jess, wheezing a little himself, continued to keep his distance.

“What… what did I do wrong?”


“Dean, talk to me, man.”

“I told you, not a girl,” he whispered quietly.

Jess laughed. “I know that, idiot. It’s part of why I like you so much.”


“You’re a virgin, right?”


Jess rolled his eyes. “You know what I mean.”

Dean didn’t respond. Jess bit back a smile.

“Okay, so let me tell you something you already know, genius. Gay sex goes both ways. We can do whatever you want, however you want it. You can be inside me too, you know. I like it both ways. God knows I want to do you more than anything I’ve ever wanted all my life, but I would never force you if you’re not ready. I can wait.”

“Wh-what if I’m never ready?”

Jess shrugged. “Let’s put it this way. Seven years ago was the first time I kissed a boy and I swore to myself then I’d never do it again.”


“I was a kid, give me a break.”

“Go on.”

Jess leaned back and relaxed. “Ten months ago, I was sitting in a Starbucks in Stamford, and I found myself staring at this guy across the room… at his mouth. I-I just, couldn’t stop staring.”


“Took me awhile to let go of my… my fears, I guess, but once I did, it just opened a whole new world of possibilities. I didn’t think I’d start liking guys more than I like girls but I changed. My point is, things change over time, Dean. And… even if they don’t, with you, it doesn’t change the way I feel about you right now.”

Dean looked into Jess’ eyes, as if trying to decide if he believed Jess or not. When he still wouldn’t say anything, Jess forged on.

“You know we don’t have to start with the big stuff. We could always do other things, and that way also find out if you’re likely to, you know, like it.”


“Trust me?”

“Not at all.”

Jess mock-scowled at which Dean chuckled, his petrified expression softening ever so slightly. He shrugged. “Okay, wh-what did you have in mind?”

That had to be good enough. Jess climbed up further on the bed. “Lie down for me.”

Dean narrowed his eyes at him suspiciously.

“Please? Just trust me, okay? If you don’t like it, I will stop. I promise.”

“You stop when I say stop. I shouldn’t have to repeat myself.”

Jess put on his best, most sincerest face. “Cross my heart and hope to die.”

Dean still pouted but put the pillow down. Jess moved closer. “Okay, come on here.”

He tugged at Dean and made him stretch out on the bed face up. He could feel Dean’s body shake a little and he stroked his flanks lovingly, trying to reassure him.

“It’s okay. Close your eyes.”


“It’ll feel better, I promise.”

Dean closed his eyes reluctantly. Jess had a feeling Dean wasn’t a complete novice and he definitely knew what was about to come, which made it slightly easier for him to proceed.

“I’m going to take off your pants.”

Dean trembled, and Jess shushed him quietly.

He took his time with it. There was something so surreal, so incredibly hot about stripping those ugly, shapeless work clothes that hid Dean’s magnificent body. He drew it out for as long as he could, caressing Dean all the way down his flanks, over his jeans and once they were off, over his boxers. Dean bunched up the bed sheet in his fists by his sides, and he bit his lip to keep from making any sounds he’d be embarrassed about later.

“Boxers now,” he waited for Dean to bolt, who didn’t.

Encouraged, Jess put his fingers inside the waistband and gently peeled the fabric down. Dean trembled some more, but at Jess’ insistence, managed to arch his hips up long enough for Jess to be able to push the boxers down. Jess took both his pants and boxers off and dropped them to the floor, then spread Dean’s legs to make space for himself where he sat back on his haunches.

Of course Dean had no way to know, but spread out, open and vulnerable like he was right now, Jess thought he’d never looked so incredible, so... ethereal. The shaft was already at half-mast (which made Jess smile), beautifully long and slender, a healthy pink far as he could guess in the dull glow of the lamp. It was lightly framed by a small bush of downy hair above it. The balls lay heavy and hairless, the skin soft like velvet to the touch and made Dean shiver visibly when Jess casually stroked it.

“So beautiful,” he whispered with reverence, watching Dean’s clothed chest rise and fall shortly.

Between the V of his spread legs lay the secret temptation that called to Jess like water to a man stranded in a desert dying of thirst. It took all of his determination and mental strength to not plunge in right there and then.

“You’re perfect, Dean. So absolutely God-like perfect…”

Dean moaned softly, but kept his eyes shut tight. Jess pulled a tube of lubricant out of his jacket pocket (Nothing wrong with always being prepared, is there?) and squirted some out on two fingers of his right hand.

“Here we go,” Jess murmured softly. “You have to relax for me, okay?”

He waited for an answer, and didn’t start until Dean had curtly nodded. Dean gasped at the feeling of the first finger, dipped in the cold slick, prodding at his entrance. In his shock he spread his legs further open even as his internal muscles clamped up.

“Shh, relax baby, it’s just me…”

Jess quietly celebrated the fact that Dean was too distracted to protest the almost reflexive little endearment. He was patient and persistent, waiting for Dean to calm down before pushing in again. After a few more stops and starts, Jess’ second knuckle was in. When he started to wriggle inside, Dean gasped louder.

“Ahh! Oh God…”

“How does that feel?”

Dean spoke in minced words, as if to hold back other sounds he didn‘t want to make. “Like… like… I don’t know. Full, I guess.”

“Wait till we get to the good part.”

And Jess started to push his second finger in. Dean twisted his face to one side and stuffed a fist into his mouth. Jess smirked and with his free hand grabbed Dean’s already rapidly rising erection by the base. Dean moaned deep in his throat.

“Shhh, keep it down, or your mom will come checking on you.”

Dean whimpered miserably at that and tried to gag himself, which only made Jess laugh. By this time both his fingers were all the way in, deliberately curling upwards. He started to twist around to find the sweet spot that could make Dean scream the roof of his house down. And when he found it, Dean nearly did.

Dean pulled his pillow from under his head and put it over his face instead, hiding the bright hot blush rising to his cheeks along with muffling his moans with it. Jess chuckled and continued to tickle and scratch at the little nubbin of pleasure inside Dean, making him writhe harder against him. He also kept fisting the shaft until it started to leak precum, and then he continued until at last Dean let go, releasing his pleasure right into Jess Mariano’s waiting hands.

His own erection strained against the restraint of his jeans and Jess moaned, but he decided to wait. This was Dean’s night. He needed to make sure Dean was taken care of first.

“With me, dude?” He asked a minute later, when Dean’s chest wasn’t heaving as hard anymore and his moans had petered away and his erection now lay completely satiated, still cradled gently in Jess’ left hand.

Dean eventually emerged from behind his pillow, suddenly conscious of his nakedness and lifted his legs to get around Jess and push them back together again, forcing Jess to shift to one side on the bed. Getting with the program, Jess pulled up the blankets and without waiting to be asked, he covered Dean up till his waist with them. Dean quickly grabbed hold of the fabric, wringing his fingers into the frayed edge like he did few days ago at the diner. He looked up into Jess‘ face then, with eyes hesitant and blown wide open, still breathing hard and audibly so.

“Guess its safe to assume you’re gonna like it then, huh?”

Dean bit his lip, looking away until Jess held his face by the chin and made him meet his eyes. “Dean… talk to me, man.”

“I…I, can we just.. not tonight?”

Jess smiled. “Whatever you say.” And he bent lower, making his intent crystal clear. Dean understood and craned up slightly, indicating his consent.

They kissed. Again and again and again, before curling up around one another and settling in for the night. Dean rested his chin on top of Jess’ head and Jess entwined his legs with Dean’s longer ones tightly. They stayed like that, quiet, resting, listening to the other‘s heart beating.

“Um, Dean?”

“Yeah, Jesse.”

Obviously, Dean had chosen his own endearment for Jess, the sheer nonchalance of it making his spine quiver. “Think you’re up to… maybe returning the favor?”

Dean pulled away, looked into Jess’ eyes and smirked.

“Thought you’d never ask.”


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

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