Miles Higher
Pairing: Dean Winchester x reader
Summary: You've convinced Dean to board a plane with you for nine hours. The least you could do is make him more comfortable.
Warnings: 18+ due to language and smut (handjob, oral m, semi-public), fear of flying, new relationship, fluff
Word Count: 2.0k
Posted on Patreon May 21, 2025
A/N: A little follow-up to The Craving but can be read as a stand-alone as well. Time to fly! 🛫
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The airplane engine hums, the constant, low pulse vibrating through the seats and matching Dean’s racing heart. He grips the armrests a little tighter, the white bone shining through his knuckles. His green eyes flick nervously to the window, then to you, and then back to the seat in front of him as if it would make the sensations in his stomach feel less real.
He’s suspended in the air. Willingly.
Flying is fucking unnatural. These heavy machines, built by humans no less, are not meant to soar through the air like goddamn eagles. Everyone knows driving’s the only acceptable way to get around.
Wheels on the ground.
Dean sighs, blowing a raspberry, his gaze drifting back to the window and the clouds floating by. It feels like he’s been locked in this death box for forever. Remember when he had that whole hostile takeover thing with that fucking archangel, and he wanted to lock himself in that coffin and then be thrown into the ocean? Yeah, he’d rather do that.
Forever. And yet, it has only been five minutes since fucking take-off…
“I can’t do this,” he mutters under his breath, the deep voice barely audible over the noise of the plane.
With a raising brow and a hidden smile of amusement, you turn toward him, your fingers already finding his hand. “Hey, look at me,” you say softly, giving his warm, large palm a gentle squeeze. “You’re doing fine. We're almost there, remember?”
The sparkling emerald green eyes are wide and panicked as they stare at you in disbelief, his breathing quickening. “We just took off! It’s a nine-hour flight!” Dean shakes his head with a nervous bubble of laughter. “I don’t know how you talked me into this… Well, I have some idea.”
He subconsciously adjusts his dick in his pants, frowning. This is what he gets for thinking too much with his downstairs brain – death.
You’d made it all sound so hot – joining the mile high club, fucking you raw and relentless in some luxurious honeymoon suite in a five-star resort, which he didn’t even have to pay for with his fraudulent credit card, endless sex on the beach while sipping Mai Tais and Blue Hawaiis, the lei around his neck brushing against your soft skin as he buried himself balls-deep in your warm and wet pussy…
Yeah, you really know how to make a goddamn sales pitch. How could he have said no? If you weren’t such a damn good huntress, you really could’ve had a soaring career in marketing.
“I’m sorry, okay?” you say with a few giggles. “But Dean, come on, you’ve faced worse things than a plane. How can this be scarier than going toe to toe with God and an apocalypse?”
“Oh, I wish I knew,” he admits, barely forcing a shaky chuckle out through his anxiously trembling lips.
Dean has asked himself that question a lot. He knows it’s a bit ridiculous, considering everything he’s gone through, the amounts of times he has died etcetera… But he can’t help it nor explain it, okay? It’s a real fucking fear.
You lean in a little closer, keeping your voice calm and steady. “But you’re doing it, right? You’re here, you’re breathing, and we’re going to have an amazing time in Hawaii. I promise, the whole thing will be worth it.”
He gives you a skeptical glance, still gripping the armrest like his life depends on it. “I don’t know if I can make it, sweetheart.”
You snort a soft laugh, squeezing his hand again. “Luckily, you’re not alone in it. I’m right here with you. We’re going to be okay.”
He closes his eyes for a second, his head tilting back against the headrest, trying to steady himself. The flight attendants move past, their footsteps quick and efficient, and the gentle rocking of the plane is strangely soothing now. You keep your hand on his, the warmth of it grounding him, reminding him he isn’t alone.
Not anymore.
You’ve picked him against all odds. You’ll be with him till the end. So if this plane truly turns out to be his end, he’ll be good.
Happy – what a weird fucking feeling.
“I’m scared," he whispers after a long silence, but he’s not sure if it’s just the fear of flying or something else, too.
“You wanna know a trick?” Your teeth mischievously drag over your bottom lip, your thumb rubbing across the back of his calloused hand. Dean forces himself to look at you with a heavy swallow, green eyes still blown wider than usual. “Close your eyes for a second and imagine the beach–”
“The beach?” Dean’s brow furrows, but he reluctantly closes his eyes nonetheless. “Am I wearing board shorts here?”
“Dean!” You snort in amusement, the butterflies in your belly flying higher than the clouds outside the oval window. You love that goofball next to you with all your heart.
“Alright, alright,” Dean relents, chuckling. “So I’m on the beach…”
“You’re on the beach. You feel the soft sand beneath your bare feet, slipping through your toes…” you continue with a calm and soothing voice as you sneakily grab the blanket and pull it over his legs and almost all the way up to his stomach.
You smirk a little when his brows quirk at the obvious new weight in his lap. Then, you snake a hand underneath the blanket as well, fingers eagerly unbuckling his belt.
“Uh, sweetheart… What are you doing?” Dean pops open one jade eye and arches a brow at your action. He laughs a little nervously, but ultimately, there’s a curious smirk twitching on his lips.
“Shhh, it’s okay, baby,” you hush him gently, fingers pulling down his zipper. You place a slow and wet kiss on his thundering pulse point, sucking a bit of skin between your teeth. “Close your eyes again. No one can see us, I promise. You just have to be quiet.”
You’ve already scoped out the surrounding area. You and Dean sit in the last row of a half-empty plane, the flight attendants are busy talking up a storm behind a drawn curtain in the front, and the first passenger closest to you sits eight rows away.
“Hm, what?”
Before Dean can fully figure it out, your hand wraps around his cock and frees it just enough from both jeans and boxers to reach properly – tip to base. He’s almost embarrassed to say he’s already semi-hard, but he knew as soon as you whipped out your sultry voice that it was coming.
He’d be coming.
“Holy shit!” Dean hisses through his teeth and presses his whole body into the seat as if he just agreed to a ride in a damn rollercoaster.
“Quiet, baby,” you remind him with a whispered chuckle in his ear. “I’ll make you forget where we are, alright?”
Dean exhales a deep breath, nodding vigorously, his brow drawn into a tight v as he concentrates, eyes still perfectly shut.
“You’re being a very good boy for me,” you tease him, but the cock in your palm is eagerly twitching and swelling quite a bit more.
Despite a years-long friendship, Dean and you are still getting to know each other – sexually. You’ve only been officially together for a little over twelve hours, and you have seen his most private parts a mere two times without being blackout drunk. So it’s safe to say, there’s still a lot of new territory to explore, but you’ve had kind of a feeling about this particular one.
“Oh God…” Dean’s groan rips through his broad chest, gripping the armrests tighter again.
“Alright, where were we… Oh, yeah!” A smirk returns to your pink lips. “The sun is bright in the sky, warming your skin from head–,” your fist glides up his thick and hard length, twisting when you reach the tip of his cock, “–to toes.”
Dean hisses and sinks more into his seat when your hand slides down to his base again, your little ring of pleasure adding more pressure at the end.
“You listen to the soft and calming ocean waves, rocking back and forth... and back and forth… But as the sun burns down on you, you get hotter… and hotter… and hotter,” you draw each word out, your hand pumping him with every seductive syllable like you were auditioning to be the voice of an ASMR video. “So, you decide to cool off with a little swim in the ocean. Get a little… wet.”
“Oh God, no…” Dean almost groans in fear of what’s coming next and swallows the thick lump lodged in his throat. You wouldn’t–… Would you?
Before Dean can answer his own question, your lips seal around his dickhead and suck. And just like that, one of his hands lets go of the armrest and finds its way to the back of your head, fingers carding through your hair and digging into your scalp.
And you fucking giggle around him, winningly too, when his resolve breaks before your Schadenfreude bleeds into a soft moan as he pushes you all the way down his throbbing length till your nose gets buried in that little tuft of hair there. Your vibrations around his cock send a pleasant shiver through him, broad and heavy shoulders slumping as the tension subsides.
“Mmm, so good, sweetheart,” Dean hums, hand on your bobbing head stroking you in gentle bliss. “Love that mouth…”
And as your tongue swirls around his swollen head and massages the thick, throbbing vein stretching on the underside of his cock with each move, you can feel him growing closer by the second.
His hard and heavy dick swells, adds crushing weight, and pulses frantically on your tongue, begging for a release down your warm throat. His breathing quickens again – this time for a different reason.
“F–Fuck…” he hisses lowly under his breath, voice rough and wrecked.
And as you suck him all the way down once more, spit dripping out of the corners of your mouth, the explosion fully hits, Dean shooting thick and hot ropes of cum down your throat with stuttering hips underneath you.
You savor every drop he gives you, finally tasting all of him on your tongue – the savory, the sweetness, the craving.
You let him go with an obscenely wet pop and a wide smirk on your lips as he blinks open his mesmerizingly green eyes again. You tuck his softening member back into his jeans (storing it away for later use) and place a soft kiss on his stubbled cheek.
“Feeling better now?” you check teasingly, but you can tell from the goofy, lopsided smile and his posture that he’s perfectly relaxed.
“Yeah, that was awesome,” he sighs blissfully, grinning, and pulls the blanket over your lap as well, opening his arm for you to snuggle into his embrace.
“Told you I’d make you a member of the mile high club,” you quip as you rest your head on his chest, his steady heartbeats like a beautiful, soothing lullaby.
“Oh, that wasn’t just the mile high club, sweetheart. That was miles higher,” he retorts, making you snort.
He tightens his arm around you a little more before you both fall asleep for the rest of the flight. And when you finally touch down in Hawaii, the plane coming to a gentle stop on the tarmac, you squeeze his hand once more.
“We made it,” you whisper and kiss his lips with a searing softness that encompasses all the love you hold for him in your heart.
Dean’s smile is warm, the cinnamon freckles on his face glistening in the sunlight that spills into the plane from the small window, the gentle crinkles around his eyes proof of his kindness when he meets your gaze.
“Yeah,” he says, pecking your temple like you mean the whole goddamn world to him, “I guess we did.”
And you know he means more than just the flight.
Happy post-series Dean always makes me melt 🥹😭 I still have a little Hawaiian-themed miniseries planned for them. Hopefully, I'll finally get to it this summer 🤞
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