Cyndra Rae (cyndrarae) wrote,
Cyndra Rae

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

A/N: Okay so yeah, finally I got this done. Flying's pretty conducive to my writing, apparently. But it's way longer than I planned it and un-betaed.
Previous Chapters: One | Two | Three | Four | Five | Six | Seven | Eight | Nine | Ten | Eleven | Twelve | Thirteen | Fourteen | Fifteen

Eight months later. Queens, New York.

Dean emerged from the bathroom in a cloud of steam, toweling his hair dry, completely oblivious (or pretending to be) to the effect his six feet and four inches of naked perfection had on his boyfriend.

How the hell did I get so lucky?, Jess Mariano thought to himself, and softly smiled.

Sitting cross-legged on his side of the bed, he’d been going through some official documents on his laptop when he was oh-so-inappropriately distracted. His hungry eyes stayed glued to Dean’s subtly swaying hips. his super-tight backside and corded thigh muscles, from one end of their bedroom to the other.

“Freshen you up?”

Jess blinked. “Huh?”

Dean chuckled and turned towards him, pulling a pair of sweats up to his disproportionately narrow waist. Not that Jess minded the anomaly one bit.

“I’m going to get myself some tea. You want?”

That’s when Jess remembered the empty mug he was still holding in one hand. “Oh, um, no thanks. I’m good.”

His eyes twinkled as they met his lover’s and Dean, getting the hint, ambled his way to the bed first. By pressing a chaste little kiss on the lips and quickly backing away, he left Jess in greater torment than ever before. Jess just sighed and waited for him to get back from the kitchen.

Twenty minutes later, he was pouting hard enough to make his face hurt. Stupid chamomile wouldn’t take this long to brew. He suspected Dean just liked to keep him waiting, just another of his ways to get Jess riled up and damn it, it always worked.

When Dean returned at last, Jess kept his anti-glares on and his nose buried (figuratively speaking) in his new proposal document. The taller man took a seat beside Jess on the bed facing him, sipping his tea. When still Jess wouldn’t look up at him, he leaned in and tried to kiss his boyfriend again. Jess deftly moved away.

“Dude, you’re still drippin’. Watch the laptop, will you?”

Dean grinned coyly. “Playing hard to get, are we?”

Nooo. Trying to get some work done, so please…”

“Put it away, partner. It’s my turn to take care of you tonight.” Dean’s bedroom voice was soft and guttural, and it always managed to slither its way down Jess’ spine, wrangling it from the inside out. “And I intend to honor my end of the deal, whether you like it or not.”

Jess couldn’t help but surrender when Dean left his cup standing on the bedside table, moved the laptop to one side, and sexily crawled up to straddle Jess’ thighs. He lowered his face just as Jess craned upwards and their lips met, reliving the first time they’d ever kissed each other. Jess never could tire of this taste of Dean… the way Dean’s wanton tongue snaked into his mouth, entwined itself with Jess’, sparking a thousand flames in the back of his throat.

The laptop toppled over and off the bed, suddenly startling Jess out of his stupor.

“Let it be…”

“Wait, the proposal for Seattle, let me just save it.”

“Seattle?” Dean frowned, pulling back a little to put some distance between his and Jess’ face. “I thought Dillon was doing that meeting?”

Jess winced softly. He was hoping to break it to his boyfriend the next morning. Guess now would just have to do. “Uh, looks like I will have to. Dillon can’t make it. You know, with the new baby, and Allie needing all the help she can get…”

Dean’s eyelids fluttered as he shifted to sit on his side of the bed and leaned against the headboard. He bit his lip for a second and then cleared his throat. “Uh, alright. Yeah that’s… yeah. You should go.”

Jess smiled. His brave little boyfriend, who by the way wasn’t little by any stretch of the imagination. But after eight months of living together, and getting to know each other through good times and bad - there was very little Dean could hide from Jess inside that hyperactive head of his.

“So h-how long will you be gone?”

“Five days. I fly Monday morning.”

“This Monday?”

Jess nodded, still studying Dean closely just as the other man still avoided direct eye contact. He just kept nodding, incessantly, as if trying to convince himself it was really okay.

“Dean, you’ll be fine.”

“Yeah, of course. Why wouldn’t I be?”

Jess braced himself. But it had to be done, and done now. “But I’ve asked Rory to stay over just in case.”

“WHAT?!?” Dean’s neck practically snapped towards him, utterly shocked and affronted. “What the hell, Jesse?”

“It’s just a precaution, babe.”

“For what?”

Jess rolled his eyes. “You know what.”

Dean pouted hard as he looked straight into Jess’ eyes. “I don’t need a babysitter, Jesse. I can take care of myself.”

“I know you can. But like I said, it’s just a just-in-case type of thing, alright?”

Dean was still agitated. “But why? I haven’t sleepwalked since I left Stars Hollow, man.”

“Yeah, but I haven’t been apart from you in all this time either,” Jess added quietly.

Dean flinched and looked down at the back of his hands, skin still wrinkled from his long hot shower. “Think maybe you’re giving yourself way more credit than you deserve, Mariano. Co-dependence is a pretty serious allegation, you know that right?”

There was no bite in the words or the tone even though it was clear Dean hoped there‘d be some. Jess rubbed his brow with two fingers, leaned back against the headboard and sighed.

“I hate it when you call me Mariano, you know that.”

Dean just glared at him briefly and looked away, keeping to the very edge of his side of the bed, his legs folded under him.

“There’s something you should know. Something I’ve been keeping from you for… for awhile now.”

Dean turned back to him at that. “What is it?”

Jess couldn’t help but wince guiltily, his courage suddenly shriveling up under the sharp gaze Dean had him fixed with. “The last time you sleepwalked, was not eight months ago.”


“It was one month and six days ago.”


Dean jumped out of bed and stood with his hands fisted by his sides. Jess exhaled nervously and continued. “You have been sleepwalking pretty much once every month since we got back to Queens.”


“I’m sorry I kept this from you but… do you remember how conscious and freaked out you were about sleepwalking when you first got here? Hell you were stressing yourself out so much, it was scaring the hell out of me, Dean.”

Dean got a lost, faraway look in his eyes at that. At least it replaced the betrayal and hurt from about a second ago. Jess could live with that.

“That first couple of nights, you sleepwalked because you were stressing about sleepwalking, itself.”


“Obviously, I couldn’t tell you. It would only have made things worse. After a week went by, you started to believe that you were going to be fine after all, and your stress levels really did go down. And then you really did stop sleepwalking and started sleeping soundly through the night.”


Jess was the one freaking out now. Not because he thought he was in the wrong, hell he would have done anything to help Dean relax, even if it meant fibbing a little. But it was Dean‘s lack of reaction that kept gnawing at him.

“Say something, please.”

Dean took his time processing the facts in silence. After a couple of minutes, he sighed and heavily let his weight drop back onto the bed. He sat hunched, one feet still planted on the floor and the other folded under him.

“I guess I get why you had to keep stuff from me in the beginning.”

Jess started to exhale in relief.

“But you said I’ve been sleepwalking almost once every month. Why did you lie to me about that?”

“Same reason, sweetheart. I didn’t want you worried anymore than you already were.”

Jess sat up on his haunches and slowly inched closer to his boyfriend. “Every time you’re stressing out about something at work, you sleepwalk. And a couple of times, I think you were just missing or worried about your family.”

“Wh-what do I do?”

“Nothing much. If it’s about work, you get out of bed and go to the study and stand in front of your drawing board for awhile, until I come and get you. Or you go and sit in the kitchen with the phone in your hand, like you’re waiting for a call or something.”

“So, I’ve never tried to leave the loft?”

Jess let out a short, grateful, laugh. “Not yet, thank God, no. Imagine how I feel every night it happens - I go from panicked to relieved to fucking ecstatic that you’re still here… and that I haven’t run you off just yet.”

Dean smiled a little hesitantly and lowered his eyes. Jess understood his dejection though. He put a hand on Dean’s shoulder and squeezed gently.

“I’m sorry, baby. I know you must feel like this is a setback. But it’s really not that bad. All we have to do is stick to our routine like we have and take the right precautionary measures, and we‘ll be just fine.”

Dean rolled his eyes. “I’m drinking the stupid chamomile every night and doing the stupid yoga every morning, aren’t I? What good is it if I’m still going back to my zombie act once a month?”

Jess took Dean’s face in both his hands, pulling the boy closer to himself very insistently. “You’re down from twelve times to once a month. It’s working alright. Now if I can just get you to shut that wired brain of yours down once in awhile and stop thinking so damn much…”

Dean snorted, almost without intent, and looked up through the curtain of his auburn bangs half-shielding his face. Jess could already see the forgiveness and the acceptance pooling in those glittering eyes, the anger and self-derision from before abating slowly. It made Jess want to crush his boyfriend to himself and never let go.

“So, are we good?”

Dean huffed, the action inadvertently blowing a stray lock of hair out of his face. “If I don’t actually leave the loft, I see no reason for Rory to come stay here while you‘re gone. I can stay on my own too, you know.”

Jess rolled his eyes. “Do you remember the purple bruise on your right shin from three months ago? You were telling me how you couldn’t remember where you got it from?”

Dean squinted at him suspiciously. “Yeah?”

“You knocked it against the coffee table that, for some reason that I can‘t remember, was out of its usual place that night. You walked right into it but still didn’t wake up.”

The pout returned, harder this time.

“And God knows what you’d do when I’m in Seattle. What if you tried to go to Grand Central or something?”

“That’s ridiculous. I would never do that!”

Jess tilted his head to one side and smirked. “Uh-huh. Like I’ve never woken you up at a bus station before.”

Dean flushed slightly but he was smiling. “Yeah, whatever. Why can’t I come with you instead?”

“Because you got that Chase bank project to wrap up, that’s why. Like you could ever bring yourself to leave one of your clients hanging, ever.”

They both knew that, and it was a rhetorical question anyway. This time when Dean pouted, it was impossible for Jess to keep his hands to himself anymore. “Oh, Good Lord! Come here, you.”

Dean snorted and slid over to his boyfriend, bringing his arms around Jess just as Jess snuggled up into his chest. They kissed and made up, Jess quietly asking for forgiveness once again and Dean complying with a further deepening of their passionate lip-lock. Moments later, they found themselves in their usual position - stripped naked and flat on the bed lying on their sides facing each other, limbs entangled into an unrecognizable mess just the way they liked it.



Jess pressed his mouth against Dean’s closest ear and whispered something that made Dean’s face blush the darkest shade of red. He looked up into Jess’ eyes and smiled. “Changed your mind again, I see?”

“I’ll let you pamper me tomorrow, sweetheart,” Jess maneuvered Dean until he was lying flat on his stomach, the sight of his gorgeous ass taking Jess‘ breath away. “Tonight, you’re mine.”

Dean chuckled huskily. “Aren’t I always?”


Jess grabbed the slim hips and pulled them towards himself. Dean happily complied, spreading his legs to make space for Jess and got his hands under his chest to prop himself up by his elbows. The posture pushed his luscious bottom upwards, open and wiggling ever so slightly in open invitation. Jess slid his right index finger down the enticing crack, taking his time to tease the sensitive flesh, exacting revenge for when Dean had made him wait earlier.

“Dude, c’mon…” Dean moaned.

Jess planted a playful smack to the right cheek. “All in good time, sweetheart.”

After what must have felt like a small eternity, Jess asked Dean to pass him the jar of slick from their bedside table. Dean fumbled for it and threw it back over his shoulder, almost like a projectile aimed at Jess’ head.

“Dude!” Jess exclaimed, catching it just in time with his free left hand.

“Get on with it, asshole! Before I change my mind.”

Jess sniggered at what he knew was an empty threat. Dean wasn’t going anywhere, he had his gorgeous lover by the balls, literally.

Dean whimpered his loudest when Jess grabbed them, rolling and squeezing it to his heart’s content. At last, he took mercy and opened the jar of water-based lubricant. He dipped three fingers into it, coating them generously. No need to take it too slow, Dean was loose enough post their Hi-honey-I’m-home quickie couple hours ago. The tall figure writhed and rubbed his face in his pillow, pleading soundlessly for Jess to put something inside him. So Jess did.

Plugging the gaping hole with all three fingers at once, Jess lowered his face and licked over the soft pink handprint he’d just left on one butt cheek. For the next few minutes, he held still and let Dean rock back and forth, fucking himself on the triad of digits inside him. Dean reached out with one hand to fist himself as Jess continued to fondle his balls for him as well.

“I’m dying here, Jesse. Please… come on…”

Jess squeezed harder, making Dean mewl, and then he started to move his fingers, twisting and curling until he found what he was looking for and went to town on it. He let Dean’s sounds and curses and pleas for mercy guide him, slowing down or speeding up in his bid to milk the prostate for all it was worth.

“Ah, Jess, I’m gonna…”

That was his cue. Jess suddenly stopped, pulling his fingers out. And just as Dean started to crane his neck to grunt out his annoyance, Jess bent down and closed his mouth around the hungry orifice. All of Dean’s protests melted into another string of wordless moans and he buried his face back into his pillow, backside arching up into Jess’ face with shameless abandon. Jess proceeded to jab his tongue in and out, reaming his lover’s ass, kissing it in that ferocious and most decadent French variety ever.

He lost track of how long he let himself indulge in this other taste of Dean, sometime during which, one of his hands made it down to his own boner. And Jess jacked himself off in perfect synchrony with the tongue-fucking of Dean‘s ass.

Sooner than he’d have liked it, Dean’s long frame started to rattle and shudder in a very familiar way.

“God!! I can’t… Oh God I can’t…”

“Then don’t, baby, let go, I got ya…”

Jess closed his left hand over Dean’s still fisted around his rock-hard erection already wet with precum. One tug was all it took, and Dean came with a loud scream that echoed for quite some time through their small but comfortable-sized Queens home.

Jess smirked (victoriously) watching the rest of Dean’s body flop bonelessly to the bed while he continued to hold the slim hips and ass up in the air. He pressed soft feathery kisses into the hot, sweaty skin, licking up and down the hairless crack almost mindlessly. He could feel the strong post-orgasm quivers rack Dean’s spine, could practically hear Dean’s heart racing away, until Dean eventually (grudgingly) descended from his heightened state of sexual euphoria.

“With me, babe?”

Dean just groaned, his eyes drooping already.

“My turn?” Jess asked, mock-timidly, to which Dean snorted and craned his neck to look back at him.

His mouth was open, panting, his lips twisted up into a sated little smile. “Do you even have to ask?”

Jess smiled and stroked his boyfriend’s flanks. No, he didn’t need to. Jess knew (or rather used to know) men who didn’t like being fucked after they’d already climaxed. But Dean wasn’t one of them, luckily. He just turned over, his movements languorous yet graceful, and spread his legs around Jess’s crouching form once again. Jess didn’t waste any time, quickly slicked himself up and sank back into the inviting depths of his lover with a long-drawn sigh.

“Come here,” Dean ordered, and Jess lowered his upper body into the waiting arms with pleasure. Dean wrapped him up tight, bringing both his arms and legs around the dark-haired man and closed his eyes.

Jess took his time, once again, making passionate, heartfelt love to Dean. He planted his palms flat on both sides of Dean’s head for leverage, starting at a leisurely pace and slowly picking up strength and speed with every thrust.

“I love you, you know that right?” He whispered, for what had to be the nine hundred millionth time in the past eight months. Three words that just automatically fell out of his lips every time he so much as thought of Dean. He couldn’t help it, really.

Dean opened his almond eyes, just barely, and flashed his beautiful toothy grin. “I know.”

And that’s all he said, letting his head fall back, his eyes closed and his mouth wide open as Jess continued to pound into him with relish.


Monday came all too soon for Jess. He’d been acting nonchalant about the Seattle trip all weekend for Dean’s benefit. But fact was, he was really losing it inside. What if Dean couldn’t handle the stress of being apart for so long? What if Rory turned out to be one of those people who slept like the dead? What if Dean got himself stuck in their freight elevator, the one they took to get up and down their loft? God, what if he got out on the streets in the heart of downtown Queens, New York?

“Relax Jesse,” Dean smirked as he bent down to kiss Jess goodbye. “I’ll be fine, I promise.”

Funny thing was, Dean did look more relaxed about it than Jess expected him to be. Since the night when Jess revealed the truth about Dean’s sleepwalking, the man had gone from denial and momentary anger, straight to a serene acceptance that no one thought he was capable of. Guess they really did underestimate his bag-boy sometimes.

“I know, you‘ll be fine alright. Rory is coming this evening. You have her number, don’t you?”


“Good. Don’t forget to drink your chamomile before bed.”

Dean rolled his eyes. “Have a good trip, Jess.”

“And remember to lock the doors and get Rory to hide the keys from you, okay?”

“Bon Voyage, Jess.”

“And don’t work too late ‘cause you know when you get too tired you--” Jess was interrupted mid-tirade by Dean planting a big, noisy kiss on the lips.

After which he grinned all too brightly for Jess‘ liking. “Go away, Jess.”

Jess sighed and picked up his bags, then kissed Dean again, gentler and lingering this time, before getting into his cab waiting to take him to the airport. He watched as Dean stood on the sidewalk and waved him goodbye, wondering what storm was brewing behind those outwardly calm hazel eyes.


The meetings were going well. Which was quite a surprise actually, considering Jess was constantly distracted by thoughts of his boyfriend back home.

He called again as soon as his last meeting of the day ended.

“Dude, seriously? We talked fifteen minutes ago!”

Jess winced against his cell phone, painfully aware that it was still only Monday. He was walking back from the prospect’s office to his hotel ten minutes away.

“Sorry. Thought you might wanna know how my meeting went,” he said, pretending to be hurt by Dean’s tone of exasperation.

Dean capitulated. “Oh right, I’m sorry. How was it?”

And now Jess felt guilty for making Dean feel guilty for nothing. For the next few minutes they talked business, Jess elaborating needless details just so they could be on the phone a little bit longer. When he finally ran out of things to say, he’d also reached his hotel where he kept hanging out at the foyer, fearing he might lose the connection in the elevator.

“So anyway, how was your day?”

An amused huff came from the other end. “Didn’t get much done.”

“Why‘s that?”

“Because you kept calling every hour, that’s why, sweetheart.”

There was no bite in the words, but Jess sulked anyway. “Well, excuse me for missing my boyfriend, my partner, the one and only love of my life.”

Dean laughed. “Now look who’s having co-dependency issues?”

“Whatever, did Rory call? What time is she coming home?”

“She’s already there. Now if you let me go, I could wrap up some paperwork and head home myself?”

Jess squinted. “You don’t miss me at all, do you?”

Dean laughed again. “Nada. Not one bit. Gotta run, babe. Talk to you after dinner, okay?”

Jess wasn’t ready to let go just yet, but conscious of how ridiculous that was, he wisely held his tongue. Reluctantly he signed off with his usual ‘I love you’ (to which Dean responded with his usual ‘I know‘) and they hung up.

Jess immediately dialed Rory instead.


Jess couldn’t sleep much that first night. He paced back and forth in his hotel room, tried watching TV (a social practice he absolutely detested), wished the hotel gym wasn’t out of bounds this time of the night and worked some more on his proposal. He spent quite some time cursing Dillon for making him come to this business trip, even though he knew it was a decision made in mutual agreement. He almost wished this prospective client would just tell him off tomorrow so he could cut the trip short and return home . Hell he even went out for a walk in the middle of the night, making sure he had his cell phone with him all the time. He hadn’t unpacked at all, and had an open air ticket on him all the time, making sure he was ready to leave at any fucking moment, whenever that call came.

It never did. Not on Monday.

And then not on Tuesday either. Or even Wednesday.

“So you’re really okay?” Jess inquired into the phone on Thursday evening for like the hundredth time.

He was walking back to his hotel again and utilizing the time to check up on Dean, as he’d done every hour of every single day this week.

The laughter on the other end both comforted and annoyed him, just a bit. “Yes, I’m fine, Jesse! Really, Rory doesn’t have to do anything at all. I’m sticking to my routine and I haven’t stayed late at work once in three days. See? I can take care of myself, you know.”

Jess pouted, not even sure why anymore. There was silence for a couple seconds.



“I do miss you.”

At that, Jess swallowed softly.

“And I do love you, so very much.”



Jess found himself torn between laughing like a lunatic and bawling like a baby. Resolving to do neither, he bit down hard on his quivering lower lip. “Yeah, I know babe, I know you do.”

The voice chuckled. “Then will you stop acting like a whiny little bitch and just be happy for me already? Jeez, you really do have some heavy duty co-dependence issues, man. We gotta get us into couples’ therapy when you’re back.”

Jess felt a soft giggle tickling at the back of his throat, struggling to escape. God, he really was being such an idiot. He’d been so sure Dean wouldn’t be able to handle being apart from him this long. And he’d been so consumed by worry about it that he totally overlooked his own desperate need to be with Dean all the fucking time.

“I’m sorry I’ve been such a jackass, sweetheart. You know I’m really, really happy you’re not sleepwalking, don’t you?”

“I know. You’re just having a tough time being so far away from home.”

Jess smiled at the softly murmured words. Home. Yes, that’s exactly what Dean was to him now.

“But hey, it‘s only a matter of two more days, right?”

Jess sighed happily, as he came to a halt at a red light, waiting to cross the road. “That’s right. This time tomorrow I’ll be on a flight home. Man I can’t--”

Jess paused, his train of thought interrupted by a face suddenly materializing from the crowd and coming to stop bang in his line of sight.

“Jess.” It wasn’t a question. The tall auburn-haired young man looked right at him with wide, pleasantly surprised eyes. “Jess Mariano.”

That voice, that face… Jess hadn’t seen this man in… wow, over seven months.



Next Part (16B)
Tags: fic: gg: sleeping with the enemy, misc fic

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