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Your eyes flutter open sleepily when you feel something cold press against your wrists, and you’re jolted into alertness when you hear a clink. You try to pull down your arms but soon realize they’re stuck, handcuffed to the bar of the headboard on your bed. The covers have been pulled off of you, leaving you cold and exposed in only the dark pair of boxers and gray t- shirt.
You glance up in confusion and see bright green eyes smiling down at you, a glint shines in them that gives you goosebumps.
"Dean… What are you doing?"
"Just having a little fun Cas…"
You tug again at the cuffs, realizing that you aren’t going anywhere until the hunter releases you. You open your mouth to question what kind of ‘fun’ Dean has in store for you; you hope maybe it’s something that will be fun for you as well, but by the predatory look Dean’s giving you, you highly doubt that.
Dean continues before you can ask, “See… I know you’re ticklish Cas… I just haven’t really mapped out your worst spots yet. I know all of Sammy’s, and I…I’m curious. I think I should figure out yours as well.”
That really makes your stomach drop. Your mouth is dry as you process the words, “W-Wait- what?” You start tugging at the handcuffs again. “No- Dean!” But ever since you fell and became a human to stay with Dean…strength hasn’t exactly been your strongest asset. “Dean… Let me go- Please?”
"Sorry bud- not gonna happen- not yet anyway." Dean grins with a flash of his teeth, shooting a chill down your spine.
You squirm as Dean looms over you, making himself comfortable and straddling your waist. “I’ll just go through all your spots and rate them on a scale of one to ten, alright?” His grin is positively wolfish, “So Cas, where do’ya think we should start?”
You shift your legs nervously, “I believe removing these restraints would be a good place to begin..” You give a half-smile, but Dean only rolls his eyes with a chuckle.
"Nice try- but how about here?" Dean’s hands slowly moves toward your stomach and you begin to tense up, your eyes locked on his fingers. A centimeter before your skin, Dean abruptly halts, catching your eyes again and smiling, "Actually, how about we make it easier and go bottom to top?"
You scrunch up your toes at his words, and he slips off of you, turning and sitting over your shins, facing your now wildly wiggling feet.
"Dean please-" You whine as he slowly drags a finger down your sole. You clench your hands into fists and clamp your mouth shut, hoping that Dean will grow bored if you give off no reaction, but unfortunately your body is rather sensitive.
He rakes his fingers down both of your feet and you squeak before giving a few rather hard tugs on the cuffs.
"Dean- no!" You feel your resolve crumbling when he pries back your toes on one foot and scribbles his nails all across the ball of your foot.
Dean smirks at the grunts and yelps you make while trying to contain your laughter which only escalate and egg him on. He scribbles his nails across your feet until you’re cursing yourself for giggling already. Each time a short laugh bursts out you desperately fight to contain it, but eventually it’s too hard to fight and the laughter is coming out in a much more steady stream, intermingled with lots of “please Dean”s and “stop”s and “no don’t”s.
"Alright your feet seem like a pretty good spot, I’d give’em a 7 maybe. Yeah I think a 7 sounds about right." Dean chuckles mostly to himself and wiggles his fingers between your toes which elicits a particularly girlish squeal from you, but soon enough (or not nearly soon enough) he slows his hands and begins to move them from your feet.
You take this first as a blessing but then realize where his hands mean to go and your struggling begins anew. “Dean please don’t…”
"Cas, I’m not stopping until I’m done." Dean quickly replies, and you shut your mouth, compressing your lips into a tight line in frustration, trying to silently construct some way to convince the hunter to let you go.
But he won’t.
Dean skins his fingers up the sides of your shins, scooting back on your legs and giving you simply a view of his back. You kick uselessly as much as you can, but he’s still sitting on your thighs and restricting the amount of movement available to your legs.
When Dean’s fingers reach your knees it sends a shiver down your spine; he ghosts his nails over your knee caps and then quickly turns to scratch the undersides, which draws a string of cackles and spasms from you. Dean glances back over his shoulder at you and shoots you a wink, which you would try to glare back at but the laughter renders that response quite impossible.
Dean grins as you whimper out, “Dean- Dean PLEASE- This is ahahahahaha childish!”
"I’m childish? You’re the one ticklish as some little kid!" Dean laughs and wiggles his fingers over your thighs, at which you try to buck and throw your head back laughing.
Dean scribbles his fingers all across the tops and insides of your thighs which causes helpless giggles and loud, desperate laughter and then squeezes the lower parts of your thighs just above your knees over and over, at which you yelp and laugh madly. “Dean hahahaHAHAHAHASTOP no no hahaha! Please- no!”
"Hmm… Your legs are pretty bad… I’d say maybe an 8 here, what do you think?" Dean grins and scribbles his nails all over the insides of your thighs again, and your legs beat out against the bed haplessly and your laughter crescendos out.
Dean spins himself around again, facing you now and giving you his best shit-eating grin. You let out a quiet, unhappy whine and lay your head back on the mattress dejectedly, “Dean…please? You know I hate- hahahahaHAHAHANO STOP-” Your laughter begins anew as Dean drills his fingers unexpectedly into your hip bones. You shift your weight side to side and kick your legs out wildly, “NO DEAN STOPHAHAHAA ahahaha hahaaplease hahaha!”
"Ooh haha I forgot how bad your hips are- maybe an 8- or an 8.5?" Dean smirks at your struggles and switches from tickling your hips harshly to scratching and spidering over them, which leaves you giggling and wiggling around and shaking your head.
"Quit squirming Cas!"
"Dean I cahahahahahan’t! Hahahaha stop! Hahahahaahhaahahahha!"
Dean’s curious fingers walk their way up from your hips to your stomach and skitter over it through your shirt, the material at least offers some sort of buffer from the sensation, but you have a bad feeling that he won’t stay over it too long. Your laughter comes out in giggles and pleas, legs kicking rhythmically and hands tugging at the restraints, the constant sound of your laughter drowning out all other noise in the room, except of course when Dean decides to speak up or taunt you more, which only seems to make the tickling that much worse.
Dean flashes his teeth with a short laugh and catches your eyes; he draws back his hands and wiggles them menacingly at you before diving them under the fabric of your shirt, and your eyes go wide before helpless giggles and bubbling laughter pours out of you, intermixed with squeals and “nonono”s and “pleasepleaseplease”s.
Dean chuckles, “You’re so adorable when tickled Cas… It almost makes me neeeeeveer wanna stop..” He occasionally digs his fingers into the muscle in your stomach and then switches to spider and wiggle his fingers all across your tummy, and you laugh like, well, a little girl as he does.
Dean’s fingers explore underneath your shirt before finally pushing it back up to your chest. He grins and wiggles his fingers just above your tummy over and over, and even though he’s not touching you, you still giggle and squirm at the sight, “De-Dehehehean plehehehease th-that’s just cruelhehehee don’t hahaha!”
"It’s not cruel- I’m not even touching you! What are you laughing about?" Dean brings his fingertips within a half-centimeter of your skin but still doesn’t make contact, yet meanwhile you are still going crazy with laughter. "I’ll give you somethin’ to laugh about.."
You struggle uselessly as Dean pushes up the hem of your shirt and brings his face down to your stomach, resting his chin gently and smiling up at you; you stare back with a panicked look in your eyes, “No-no don’t Dean- please?”
Dean ignores your pleas and places his lips against the taut skin of your tummy. He inhales deeply and then blows a raspberry on your skin; the vibrating sensation causes your muscles to spasm and you to throw your head back in a laughter-filled scream. “DEAN NO NOOOOOOOOOOOOOHAHAHHAHAhahahahahahahahahaHAHAHAHASTOP STOP!”
You kick and struggle as much as you can, but Dean just keeps blowing raspberries onto your tummy in different, sensitive spots, until he eventually pulls his head away with a short chuckle, “you’re too ticklish Cas.”
Before you can come up with some sort of retort, Dean’s fingers are wiggling all across your sides and tummy and lower ribs again, “Shut upahahahahahahahahaDean! HahahahAHAHAHAHA I know I’m ti-ti-hahahahahahahahahahaticklish now stopppp! STOPHAHAHA!”
"Relax, we’re almost done! Just a few more spots! I think your stomach is another solid 8, maybe even a 9!" Dean drums his fingers across your lower ribs and smirks, "Is there anywhere you’re not ticklish?"
You try your best to give him a bitchface, but it turns out as more of some kind of constipated smile. But hey, it’s not your fault you can’t stop laughing! Dean seems to decide you’ve had a long enough break and announces, “Alright, ribs next!”
You let out an exasperated groan which twists into a gasp and laugh when the hunter’s fingers start to dance over your ribs. The way you’re restrained leaves your skin taut over the bones, giving Dean easy access to them as he scribbles his nails over and in between them. He digs in to a few spots which make you jump and let out a yelp before cascading his hands down and playing your ribs like a piano.
Your face is red with exhaustion and embarrassment as you continue to belt out helpless laughter and pleas, and by the time Dean’s done playing with your rib cage he announces a 7 and decides to continue his explorations.
His fingers creep up over your chest and find your neck and collar bone, at which you wince and try to scrunch up your shoulders, giggling out “no don’t” over and over. You drum your feet lightly against the bed and try to bring your head down to offer some protection, but then he just raises an eyebrow at you and laughs, “ah ah ah Cas- hold still! You’re tampering with my evaluation here!” He brings a hand up and pushes your head back against the bed, further restricting your movements and leaving a lot more vulnerable and ticklish skin open.
Your eyes go wide and pleading as he reaches back down and scratches his nails against your neck and over your collar bone; Dean watches you twitch and laugh with a bemused grin. He traces nameless patterns across your skin and then leans down and nuzzles the side of your neck, deliberately trying to tickle and scratch his short stubble against your skin.
You squirm and giggle with your eyes shut, face flushed and legs kicking out wildy whenever he gets to a bad spot.
"Dean-Dehehehehean pleaaaaase hahahahahaHAHAHA LET ME GO hahahaahahhahenough hahaha no no hehestop pLEHEHEASEHEHE!" You resign yourself to the ticklish sensation and barely struggle anymore, simply laughing and hoping it will be over soon.
"Hmm… Neck, I’d say maybe a 7 or an 8 there… You’re kinda ridiculously ticklish." Dean mumbles against your neck, then pulls his head and arm back to look into your exhausted and pleading blue eyes.
Eyes that go wider than saucers when you realize just where Dean intends to go next.
"So…we’ve got one more spot to try-"
"Dean- Please-please don’t! You know- you know I can’t stand it when you tickle under my arms, please! Please- you don’t have to test this!" You cut him off, uselessly hoping to convince the hunter to start on what was most likely your worst spot.
Definitely your worst spot, you realize, when Dean brings his fingers slowly over to your armpits and begins to ever so lightly wiggle them; he ignores your pleas and continues on his original plan.
Your eyes bug out at the contact and you feel your breath hitching in your throat. It’s barely a few seconds before Dean decides to have even more fun and digs his fingers into the hollows under your arms.
You go berserk.
Your eyes pop open and then screw shut, your head slams back against the mattress and your legs kick frantically, struggles turning desperate to break free.
"DEAN NO PLEASEHEHEHEHEHEHE AHAHAHAHAHAHA NO NO NO HAHAHAHAHAHAHANOT THERE HAHAHAHASTOP hahahahahaHAHAHA I CAN’T hahahaha haha hahahahaHAHAHA I CAN’T STAHAHAND IT NOOOHAHAHAHAA!"
Your tired body spasms as though connected to a live-wire, and your ability to form coherent pleas swiftly fades, leaving you cackling and squirming desperately underneath the hunter.
Dean’s fingers scribble over the hollows and scritch-scratch over the sensitive area. He plops his fingers back down by the bottom of your shirt and snakes them up underneath to wiggle into your overly-ticklish armpits.
The laughter pouring from your mouth slowly turns silent, and Dean eventually takes pity on the cackling mess you are, red-faced with a few mirthful tears leaking out. He drills his thumbs into your armpits one last, quick time before pulling back.
"Okay- I think that deserves a 10…" Dean laughs, wiping a last tear from your cheek. Your face still burns red, from embarrassment, from being so overly sensitive, from laughing so desperately, from everything.
"Will-will you let me go now?" You whimper weakly.
"Nah, I think I’ll try and figure out the best ways to tickle your worst spots, you know, make it tickle even more, make it a little more torturous…" Dean cracks another grin and your eyes fill with fear as you uselessly begin pulling at the cuffs again.
"Relax! I was only kidding! You’re free to go….for now." Dean smiles genuinely and you let out a sigh of relief, "I think you’ve had enough for one day." He picks up a small key from the nightstand and unlocks the handcuffs, rubbing your wrists lightly to soothe the red marks from all of the struggling.
Your arms wrap down around your sides protectively and you long for a nap, all of your energy spent laughing. Dean snuggles up behind you and curls an arm over you, pulling you in close to his body.
"You really do have a cute laugh Cas." Dean mumbles, and you finally feel safe enough to relax into his touch, which no longer evokes panicked laughter from you. "You really should laugh more, then I wouldn’t have to tickle you crazy all the time, you’re always too serious!"
"There are other ways to make me laugh, Dean." You grumble.
"Yes, but this way is much more fun!" Dean laughs and gives your stomach a poke. You squeak and try to squirm in protest, but Dean’s strong arms wrap around you and keep you close. You fall asleep in the hunter’s arms and find some well-earned rest.