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You looked up immediately, gently putting down your pen and closing your notebook.

Dean stood in the doorway, leaning casually against the frame, watching you with a small smirk.

His eyes dropped to the notebook in your hands “You’re drawing again”

You smiled sheepishly “It’s more sketching than… actual drawing”

“Still” Dean pushed off the doorway and walked into the library “Haven’t seen you doing it in a while”

You chuckled “Yeah, well… monsters aren’t exactly inspiring subjects”

Dean laughed “Fair”

“But, uh, you know…” You say, tapping the notebook “There are other sources of inspiration around”

Dean immediately looked interested “Oh, really? Like what?”

You chuckled and shrugged innocently.

He smirked and pointed at your notebook “Can I see?”

Your answer came immediately.

“No”

Dean looked offended “Oh, c’mon. It can’t be that bad”

“It’s not bad”

“Then show me”

You hugged the notebook closer to you “Nope”

“Just one page”

“No”

“One sketch”

“Nope”

Dean groaned dramatically.

You laughed nervously “They’re not even finished yet. They’re just… ideas”

A complete lie.

Dean looked unconvinced. But eventually he raised both hands “Fine. Keep your secrets”

He looks away, acting totally disappointed as he takes a step back.

Dean then started talking about something else entirely. You relaxed. The conversation flowed naturally between you.

You slowly lowered your guard.

Big mistake.

Because when you were distracted—

The notebook suddenly vanished from your hands.

“Dean!”

His grin was immediate. He stepped back triumphantly.

You immediately stood to your feet “Oh my God, give it back!”

“Nope”

“Dean”

“It’s mine now”

”It’s literally not!”

“Oh, come on. Just a quick look”

“Dean”

Too late. He was already opening it.

Your stomach immediately dropped.

”It’s just stupid stuff” You said nervously.

He ignored you entirely, studying the sketches.

“Damn” He said “Sweetheart, these are really good”

He started flipping through the pages. There were random sketches, doodles, small landscapes.

Dean actually looked impressed.

Then he turned another page, and his face immediately lit up.

Baby.

The page had detailed sketches of the Impala. Different angles. Close-ups. The steering wheel.

Dean looked absurdly pleased “Now this…” He grinned, nodding approvingly “This is art”

You chuckled despite your embarrassment. Of course that was his favorite page.

“Look at her” He looked genuinely delighted “She’s beautiful”

But then he kept flipping.

You swallowed nervously.

Dean didn’t seem to notice your growing panic, he kept flipping through the pages.

And then… he reached the newest ones.

You wished the floor would open up and swallow you whole.

His smile slowly faded. He stopped turning pages.

Silence.

You knew exactly what he was looking at.

Your sketches of him.

Dean’s profile. Dean’s eyes. Dean’s smile.

Dean.

Dean.

Dean.

And more Dean.

You wanted to die. Immediately.

Dean didn’t say anything, which was somehow worse.

You couldn’t even look at him.

His usual smugness was gone. The teasing grin was gone. His ears were turning slightly pink.

He looked at another page. Then another. Every single one made him somehow more flustered, which honestly would’ve been funny if you weren’t dying from embarrassment.

You risked a glance at him.

He was still staring at the pages.

“Okay, so…” You laughed nervously “Before you say anything, I can explain”

Nothing. He kept staring.

You cleared your throat.

“It’s not weird” You said “I mean, okay, maybe it’s a little weird. But I wasn’t sitting around obsessively drawing you” You try to explain yourself “I just… well, you sit still sometimes, and you’re always around. So, naturally—“

You stopped.

Because he finally looked up.

“Hey” He gently interrupted.

But then you started rambling again.

“I just noticed stuff, okay?” You said nervously “The way you look when you’re focused on something. Or when you’re fixing Baby. And your eyes are kinda—”

“Hey” He repeated, softer this time “You don’t gotta explain”

Your heart did something stupid.

“Oh”

Dean looked down at the notebook again. Then back at you.

“These are… great” He said softly “You, uh… you really see me like that?” He tapped the page.

Your cheeks warmed “Yeah”

Dean looked down. A small, almost shy smile on his lips before looking back up at you. Then he let out a soft laugh, rubbing the back of his neck.

“You made me look pretty good”

You smile, still a little sheepish.

Dean closed the sketchbook carefully, almost protectively, then handed it back to you.

His smile finally returned. Smaller than usual, but still genuine.

“For the record…” He cleared his throat “If you need more material…” He gestured to himself, his grin widening “I can pose for you”

Your entire face went hot.

“Oh my God” You groaned, covering your face.

Dean laughed.

When you looked up again, he was still smiling.

Still a little sheepish. Still a little red around the ears.

Which made the whole thing even worse.

And somehow… a whole lot sweeter.

dean masterlist

You’ve got him right where you want him.

It wasn’t easy. Dean Winchester is a lot of things—charming, reckless, annoyingly heroic—but pliable has never been one of them. Usually, he’s the one pinning you to a motel mattress with that stupid crooked grin, all heat and hands and low, teasing growls. The guy drives like he fucks: fast, a little reckless, and completely in control.

Not tonight.

Tonight, he’s flat on his back on the threadbare floral comforter of some roadside dive off I-70, jeans still on (unfairly good ones, the dark wash that hugs his thighs just right), green eyes flickering between smug and something a lot more unsure. His arms are still crossed behind his head like he’s posing for a Girls of the Midwest calendar, but there’s a flush creeping up his neck that wasn’t there two minutes ago.

You’re knelt between his spread thighs, your hips pressed flush against the zipper of his jeans. You can feel him. Not fully hard yet, but interested. A warm, heavy line of potential pressing against your lower belly through the worn denim.

“You sure about this, sweetheart?” he asks, voice a low drawl. One eyebrow arches. Classic Dean. “’Cause I gotta warn you, chest stuff? Kind of a waste of time on a guy.” He shrugs one broad shoulder against the pillows. “Not sensitive like that. It’s not gonna do anything.”

You just smile. Slow. Sweet. The kind of smile that’s already two steps ahead of him.

“We’ll see..” you murmur, and lean down.

Your palms slide up his ribcage, feeling the lean, corded muscle earned from a thousand salt-and-burns. His skin is warm, scattered with old scars and a light dusting of freckles across his chest that he’d deny to his grave. You don’t go for his nipples yet. You just drag your fingernails lightly down his sides, watching his abs twitch involuntarily.

“Tickles.” he mutters, jaw tight.

“Does it?” You dip your head, pressing a soft, closed-mouth kiss to the center of his sternum. Then another, a little lower. Your thumbs find his nipples—flat, dusky pink against the freckles—and you just rest the pads of your thumbs on them. Light as a breath.

Dean scoffs. “See? Nothin’.”

You press down. Just a little. A slow, deliberate grind of your thumbs in tiny circles.

His hips jerk.

It’s involuntary, that’s the thing. One second he’s lounging like a king granting a favor, the next his pelvis bucks up into yours like a live wire got tapped to his spine. The thick ridge of his cock (now definitely, definitely interested) slides hard against your stomach through both your clothes.

He freezes.

“The hell..?” he breathes, more confused than angry.

You don’t stop. You lean closer, letting your breasts press against his chest as you circle your thumbs harder, wetting the tips with a little spit. The friction changes. Gets slicker. Sharper.

“You were saying?” you coo, right into his ear.

“That’s- that’s not—” He swallows. His throat bobs. “It’s just reflex. Guy’s chests aren’t wired like chicks’. Doesn’t mean anythin’.”

But his hips are moving again. A small, aborted little grind upward, chasing the pressure of your pelvis against his. He can’t help it. You can see the war happening behind his eyes. He's currently turning to hot, confused jelly under your thumbs.

You take mercy on him.

Not really.

You pinch.

Not hard. Just a firm, deliberate twist between thumb and forefinger, rolling the little nubs like you’re tuning a radio. Dean’s lips part to let out a sharp, bitten-off sound out, half groan, half what the fuck. His hands come off the headboard for the first time, grabbing at your hips like he’s trying to either push you away or pull you down onto him harder. Even he doesn’t seem to know which.

“You were saying, Deanie?” you repeat, sweeter this time. Mocking. Gentle.

“Shut up,” he grits out, but there’s no heat in it. His eyes are half-lidded, pupils blown wide. The flush has spread from his neck to his cheekbones, those stupid pretty freckles standing out like constellations. “It’s- it’s just- you’re right there, okay? Your hips. It's because of your hips. Doesn’t have anything to do with your—your fingers.”

You hum, unconvinced, and lower your mouth.

The first touch of your tongue, flat and hot and wet, against his left nipple makes him seize like you’ve tased him. His whole body locks up, then shudders, and then he’s bucking. Actually grinding up into you in a slow, desperate roll that drags his clothed cock against the soft give of your belly. A wet spot is starting to spread on the front of his jeans. You can feel the heat of him through the denim.

“Jesus-” he whispers, not praying. Just… lost.

You suck the nipple into your mouth. Gently at first, then with more pressure, swirling your tongue over the tight peak while your fingers go back to work on the other side. Twist, pull, roll. Wet sounds fill the tiny motel room. Dean’s making sounds now too: low, wrecked little groans that he’s trying to swallow and failing.

“Still not sensitive?” you murmur against his wet skin, then give a sharp little tug with your teeth.

His hips snap up so hard you have to brace a hand on his stomach to keep from toppling. The muscle under your palm is iron-tight, trembling.

“Shut up-” he manages again, but his voice cracks on the second word. His fingers dig into the meat of your hips, guiding you to grind down against him. He’s so hard now it looks almost painful, the thick line of his cock straining against the button of his jeans. “That’s- that’s just biology, okay? You’re- your mouth is- it’s warm and-”

You laugh softly. The sound vibrates right through his nipple.

Dean makes a noise like a wounded animal.

“Oh, baby..” you coo, pulling back just to look at him. And it’s devastating. He’s a mess. Those green eyes are glassy, his lips parted and pink, chest heaving with every shallow breath. His nipples are wet and peaked, flushed dark pink, standing out like little targets. “You were saying guys’ chests aren’t sensitive?”

He glares at you. It would be threatening if his voice didn’t come out as a breathless whine. “They’re not.”

“Then why are you humping my stomach like a teenager, hmn?”

That lands. His cheeks go scarlet. His hips stutter like he only just realized he’s been grinding against you this whole time, a steady, mindless rhythm that’s left a visible smear of precome on the inside of his jeans. He tries to stop. Really tries. But when you lean back down and flick your tongue over the tip of his right nipple in fast, wet little licks, his pelvis rocks upward again all on its own.

“Fuck.” he breathes, and it sounds like surrender.

You take pity on him. Or maybe you don’t, maybe you just want to see how far this goes. You switch tactics, sucking his left nipple deep into your mouth while your hand slides down to palm him through his jeans where he's pressed against you. He’s leaking. Soaked through. You can feel every twitch and pulse.

“You like that,” you say, not a question. “You really like that. Deny it again. I dare you.”

Dean opens his mouth. Closes it. His hips keep moving, shallow little thrusts into your hand like he can’t help himself. His head falls back against the pillow, exposing the long line of his throat.

“I hate you.” he whispers, but his thighs are trembling on either side of you, and his hands have moved from your hips to tangle in your hair, holding you down against his chest, not pushing you away.

“No you don’t.” you murmur, and bite down gently.

He comes undone.

Not all the way—not the grand finale—but something in him snaps. His whole body goes loose and pliant under you, that stubborn jaw finally unclenching. When you look up, his eyes are hazy, dark, needy in a way Dean Winchester would never, ever admit to.

“Do it again.” he says, so quiet you almost miss it. Then, louder, rougher: “Please... Just—just do that again. The—the thing with your- your mouth.”

You smile against his skin. “The thing I’m doing right now?”

“Yeah.” he breathes. “Yeah, that. Don’t stop.”

And when you take him apart: slowly, thoroughly, licking and sucking and twisting until he’s nothing but a shuddering mess of oversensitive nerve endings and bitten-off curses, he never once tells you that guys’ chests aren’t sensitive again.

His hips, still grinding against you in that helpless, hungry rhythm, tell a much better story.