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#sam winchester headcanons
5sospenguinqueen · 14 days
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(At Y/N and Dean's wedding)
Sam: To my new sister-in-law!
Sam: Thank you for releasing me. He's your self-destructive deathtrap now.
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were-all-idjits-here · 10 months
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Sam or Dean extremely flustered by badass, couldn’t-care-less-what-you-think-of-me, punk reader in black leather with piercings and tattoos galore
Bonus points for Sam because that’s not really someone you’d expect him to fall for
Also bonus points for Dean cuz that’s also kind of his aesthetic and we usually see him sweeping women with girlier aesthetics off their feet, but not usually a fellow punk
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munsonshire · 29 days
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Sleepless Nights with Sam
Pairing: Sam Winchester x reader (gender neutral) Warnings: none Masterlist
Sam Winchester knows the importance of a good night’s sleep, especially on the eve of a hunt.
So when he learns that you have been plagued with many sleepless nights, the hazel-eyed man quickly leaps into action.
Sam spoons you, pulling the blankets up and over your heads, creating a ‘safe zone’ within the bedroom.
He kisses your cheeks, lips, and neck, all while whispering sweet nothings into your ear.
You talk with him, knowing that he will always give you a shoulder to cry on, make you feel loved, and never judge you or your feelings.…and that in itself, is immensely comforting.
You try to assure Sam that he didn’t need to do any of this, that you would succumb to exhaustion eventually; but he just shakes his head in disagreement.
“It’s okay, to not be okay, [Y/N].” he would tell you, reaching down to twine your fingers together. “…and it’s okay to accept help when you need it. I love you, sweetheart.”
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graceloveswolves · 2 years
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Imagine… the boys realizing your “girls night” was actually a case.
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6lostgirl6 · 3 months
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Sam Winchester Masterlist
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Fics:
Headcanons:
Sam As Your Boyfriend HCs - Coming Soon!
Imagines/Scenarios:
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Sam as a Clingy Drunk Headcanons
Requested by anon
Word Count: ~400
Join the celebration
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it always starts out subtle, a couple of beers in and Sam keeps holding your hand
of course you don't mind, the conversation is interesting, Dean keeps talking with his entire body on the other side of the booth so you start playing with his long fingers
he watches that for a while, content to see you happy
a round of shots later, Sam pulls you in his lap
it's sudden and you don't really expect the movement so you startle which makes him laugh
"did I scare ya, Baby?" "you just surprised me a little" "but this is okay?" "Sure thing"
his hands are on your skin at all times
not inappropriately (yet), just drawing circles underneath your shirt on your lower belly
it makes you shiver whenever his fingers brush a little too tenderly over your sides
Dean is torn between laughing and being grossed out by his brother being affectionate
but that is only as long as he's coherent
when Sam gets shitfaced he is even more hands-on
never to the point to make you uncomfortable but a walk to the toilet becomes a hardship for you once Sam crosses a certain barrier of drunkenness
we're talking legs wrapped around your hips, face tugged into your shoulder and arms around your neck
It's adorable
and good for blackmail
especially on Dean's part who likes to take pictures as long as he isn't drunk off his face too
whenever Sam plays koala, you are again amused and amazed by how small he can fold himself around you
ironically, where certain people grow horny once they're drunk, Sam only gets sweeter with every new drink (not that he isn't before, it's just amplified)
sloppy kisses peppered all over your neck
he likes to mumble random compliments into your skin too
"so pretty. So gorgeous, love you"
Sam accidentally made you cry twice now with it
which of course resulted in panicked shushing and wide eyed stares on his side
slurring words together and still squeezing in endearments and all
"please don't cry m'love, did I say som'thin' wrong? 'm 'n idiot, so sorry"
these nights ended with him wrapped around your body completely, your head tugged into his chest while his fingers were playing with your hair
all the forehead kisses!!
Sam is a clingy, affectionate drunk and you can't change my mind now
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sapphirecherry · 8 months
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my sam headcanons!
likes honey in his coffee
elastics > scrunchies
loves to cook big hearty meals in crockpots and slow cookers (dean won’t let him near open flames or ovens)
allergic to dust
favourite flavour is vanilla (the real stuff not fake)
homemade pesto is his favourite dip
uses spearmint and pine scented body wash
owns (and lives in) an oodie
treats himself to a long bubble bath at the end of every week
rebinds his favourite books with leather covers and gold lettering
no playlists just liked songs
always wins at monopoly
always loses go fish
picks his nails/lips when he’s restless
i’ve got a lot more i just don’t want this to be too long
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fruitmilkshake · 6 days
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Toddler Caregivers! Sam and Dean Winchester stimboard.
Again, another one of these, sorry, my daddy issues are Getting worst 😔✌️ so yeah, here another one and also a headcanon from @bitchinfawkseh
There's a lot of headcanons of Sam and Dean being the Big brothers/dads of the reader as a child, and i love all of them, but Tumblr doesn't let me put more than 10 pictures, so here's one, I really like it, It's not my only favorite, but it's one of them
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=Credit to the respective creators of this gifs=
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this-is-spn20 · 10 months
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Sam Winchester Headcanons
A/N: Hey Hey Hey! I’m back in the saddle again with another Sam headcanon. I’m so in love with this man please send help.
Warning, this is a little smutty, nothing over the top but some suggestive and smutty descriptions are mentioned. 
Reader is tall, plus sized, and has short hair, as requested by the absolutely stunning @as-lost-as-sams-shoe! Enjoy the fic darlings! Requests are always open! 
Spread Love, 
-Marissa
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You being tall never deterred Sam from his pursuit of you. Nor being a bit chunky either. Really all he saw was your shining personality and the bright sparkle in your eyes. 
You couldn’t say you were confident about your looks your whole life, but you’ve never really been too concerned about your weight. Really you just ate whatever the fuck you wanted, yet you always kept your health in mind. 
Being thick didn’t mean you were unhealthy.
While Sam encourages you to look after your health, he realizes you’re an adult and can make your own choices. He doesn’t try to force his eating habits on you.
While you wouldn’t dream of waking up as early as Sam to work out, you and Sam set up a time in the day when you both walk a path behind the bunker into the woods. Or even just train and work on both of your combat skills.
With you being so tall, you can reach the top shelves all on your own, yet Sam still calls you shorty because even being 6ft, you’re still shorter by a few inches. Also, he loves that even though you’re tall, you’re still smaller than him. 
Yes even with your thicker form, you could never be as big as Sam, and he revels in that fact. 
Sam likes PDA in moderation. Hand holding, him constantly squeezing your thighs, holding you by your waist, and when you lean into him, he lays his head on yours. 
If either of you fell asleep on the other, you wouldn't wake up to crooks in your necks. Both of your heights mean you two could lay on the other’s shoulders/heads for hours without issue.  
When at the bunker, in Sam’s room, he is all over you. He regularly smothers you in kisses. Squeezing every bit of skin he can reach. With his two favorite places being your stomach and boobs. 
Kissing, rubbing, licking, biting every part of your body. Nights have been filled with both of you worshiping the other’s body. The room was filled with so much sexual energy and intimacy that you could drown in it. 
Both of you drunk off each other. Not just touching, but **feeling** each other. You’ve drowned in Sam’s eyes so many times as he ran his hands all over your plush body. Sam swears you’ve both handed over your souls to the other.
Cuddling wouldn’t be as troublesome as one may think. While both of you have long limbs, it’s pretty easy to contort yourself for each other’s comfort. And your plushy arms make for great pillows. So does your stomach. And your boobs. And ass… you know what, you’re just very comfy. 
Being able to walk at the same pace <3
Sam never looks at you weirdly or says snark remarks when you order a lot of food. Honestly, he just hands you his credit card when you’re finished. 
Boy got stacks so you stocking up on your snack cubby is just another Wednesday. (Fuck Tuesday)
Is pleasantly surprised when you show him you can keep up with his eating. Sometimes you and he even have small bets on who can finish their food first. You always lose :(
 Also having drinking games since both of you can hold your liquor. Sam may eat faster than you, but you can drink him under the table. But only by **that** much. 
POV: you’re in your guys’ shared room chillin' out and Sam bursts through the door. He looks at you, takes off his shirt, and climbs on the bed, only to slide in between your thighs and smother himself. “Bad day?” You question, barely tearing your eyes away from the book in your hand. “Mmmhmm.” Sam mumbles and your hand finds it’s way to his hair. 
POV: one day you’re feeling a bit insecure. Sam tries to bring you out of your mood by treating you both to dinner at your favorite restaurant in town. Sam lets you order first and you order a salad. Sam looks at you like you just killed 10 puppies. Sam waves off your protests and tells the waiter to bring your favorite dish. And yes, dessert is included. All while Sam paints a deep blush across your cheeks, whispering compliment after compliment.
When out in public any judgmental looks or snide remarks from strangers will be met with Sam’s signature Bitch FaceTM and a loud and curt, “Is there a problem here?”.
POV: You and Sam are on a picnic, after you both finish eating, you start reading out loud knowing it relaxes Sam. Sam makes himself comfortable by laying his head down on your ass. When you asked him what he was doing, he said your ass is the softest pillow he’s ever had. 
Both your and Sam’s workouts serve different purposes. While Sam focuses on muscle and keeping himself agile, yours is purely about building and keeping muscle. You enjoyed being thick so you didn’t want to lose weight. You just wanted to keep your muscle. 
On a hunt, or in a simple fight, you’re a force to be reckoned with. While training with you, Sam was surprised to see how many hits you could take before you went down. He has to give your flowers to you, you gave him a run for his buck. You keep him on his toes which is always a good thing in the hunting life.
Sam LOVES taking you shopping. Always goofing around with you, trying on crazy outfits. Sometimes buying those crazy outfits! Whatever type of style and clothing choice you have, Sam makes sure to enable it in every way he can. Loves when you put on a little show for him. 
Encourages you to buy whatever makes you comfortable, yet also tells you to buy skimpy/slutty clothes. That you can only wear around him of course.
Buys you a ludicrous amount of lingerie. Seriously, eventually, you’d have more lingerie than actual clothes. 
Sam doesn’t have neck or back pains/sores from bending down to kiss you. You reach his lips if you stand on your tip toes. 
When you and Sam are both in the bathroom getting ready for the day, Sam finishes before you, mainly because you’re trying to figure out what style you can put your hair into that day. 
With your short hair, there aren't many styles you can wear. But Sam always stays behind to help with some suggestions.
Most days you just decide on a simple middle or side part and comb your hair to make it look decent. 
Sam is totally supportive if you wear weaves, wigs, ponytails, and other hair extensions. He loves helping you with any hair routines you have. He’ll memorize them and even remind you if your routine had slipped your mind that day. 
If you come back from a hunt gone wrong, he’ll insist on running you a hot bath and wash your body for you. While you dry yourself off in the bathroom, Sam will be in your bedroom lighting a few candles.
Then Sam comes back into the bathroom to help you do your haircare routine. He’ll share in your excitement when you share that your hair grew a few inches! 
Sam knowing how precious your hair is to you, will probably try and research hair growth methods that reduce hair breakage. He’ll let you decide if you want to change your routine. 
Sam loves your legs and thighs as mentioned before. But he loves them even more on his shoulders as he thrusts his cock into your plushy, pink pussy. He’ll look you in your eyes as he caresses, kisses, and bites your legs and thighs. He can feel himself lose control when your walls start to squeeze and flutter around him. 
Sam will eat you out nice and slow, making you relax and lose yourself in him. Sam tends to grab and squeeze your thighs roughly to keep him from creaming his damn pants. 
On the rare occasions, you join Sam on his early morning jogs, he never ridicules you for running out of breath. He’ll push you to keep going, but only if you can tolerate it. If not, Sam has no problem making his jog a nice-paced walk for you. And when you feel you’re ready again, he’ll start jogging with you again. 
Emphasizes the importance of stretching before any workout. He doesn’t want you pulling any muscles or ending up really sore. 
Celebrates with you when you run longer distances or challenge yourself more!
Using each other as personal heaters <3
Sam is more lenient with himself about eating more junk food sometimes. 
Sam has to double his workouts because of your cooking. He complains about this but honestly loves when you cook. 
Honestly, Sam is just an awesome and fun boyfriend. Everyone agrees ya’ll are the best couple. 
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I hope you all enjoyed these headcanons! And thank you again to the lovely @as-lost-as-sams-shoe for requesting this! This was super fun to write! Definitely request again if you'd like! And requests are always open for my blog!
Spread Love,
-Marissa
TAGGING: @imaginestuffs @naturalswifty89 @fooshigoomies @of-a-chaotic-mind @as-lost-as-sams-shoe @starlordsimp1358 @slytherinlyn16 @trickstergoddessblog @desimarie12 @lovelynerdylady @samsgirl93 @candy-coated-misery0731 @crazyaboutotps @anjalika03
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mrs-dr-reid · 1 year
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My Personal Sam Winchester Headcanons
Part 1/?
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Always kisses the top of your head. Mainly because he’s so tall and it’s the part of you he can kiss the easiest, but he does it all the time for every form of greeting
He’s never without a book. He always has at least three different books in his bag that he can grab out if he’s bored on a car trip or if he’s at the bunker by himself and there’s no case to research for
He gets up at the ass crack of dawn every morning to go for a run. He tried to get you to go with him exactly once, because when you grabbed the switch blade from under your pillow and threatened to chop off all of his hair, he immediately stopped bugging you about it and now he just lets you sleep
He can type unnaturally fast, but only if he borderline abuses every key. No joke, you can be in the kitchen and hear him “CLACK CLACK CLACK”ing away on his laptop in the library. It drives you and Dean bonkers, but if he doesn’t do it, he literally has to hunt and peck like an 80-year-old man and it takes him 11 and a half years to type a paragraph that's on the SHORTER SIDE
All of his flannels are organized by color, starting with red shades on the left and ending with the neutrals on the right (black, brown, white, grey, tan, that shit). He’s tried organizing Dean’s flannels that way, but Dean always puts it right back to his “most worn to least worn” system
He likes PDA, but in the gentler sense. Like, he’ll put a hand on your back as he walks past and says a quick “hi”, he’ll rest his chin on the top of your head or on your shoulder while you’re cooking just to be near you, and he’ll grab your hand or put a hand on your knee or thigh while you’re both researching just because he can
He says “I like you” way more than “I love you”, because he knows you know he loves you, but he just wants to reaffirm how much he likes you. Say you make lunch and you bring him some while he’s busy researching. He’ll smile, kiss your cheek, and say, “I like you so much, Babe. Thank you”. You call him a dweeb, but you still say you like him too and go back to what you were doing
When he’s sick, he refuses to let you take care of him because he doesn’t want you to get sick too. The second he feels the teensiest bit under the weather, he kicks you out of your shared room and barricades himself inside so he can’t get anyone else sick. He takes care of himself pretty well, but eventually you pick the lock and mother hen him into submission
You somehow get him addicted to home design shows by making him watch them with you all the time, and now he’ll watch them completely of his own volition. Once you came home from the store to find him watching an episode of House Hunters, and you heard him say, “The hell do you mean you don’t think House #3 is for you, Tiffany?! It checks every godforsaken box you have, and it SOMEHOW is within your shoestring of a budget! Go for it!!!”. Dean still hasn’t let him live it down
He sings to himself a lot, but mostly very specific bits of songs that get stuck in his head and they’re the only parts he can remember off the top of his head. One time he was cooking and you distinctly heard him mumbling the lyrics to “America” from West Side Story, but it was just the first chorus over and over again because he couldn’t remember the rest of the words
When he’s sleeping by himself, he lays on his back and essentially takes up the whole bed because he also starfishes (while snoring like a hibernating bear, but I digress). When he’s sleeping with you, he’s the big spoon, and he holds you as close to his chest as he possibly can by your waist while you essentially melt into him
He either treats his hair like it's the only thing he has going for him or like it's just there and he's overall neutral about it. Like, one week he'll do an eight step haircare routine and sleep in a satin bonnet to keep it from getting frizzy and the works every single night, then the next he acts like he doesn't even know what a hairbrush is
After becoming friends with Eileen (and after his accidental faux-pas), you and him make it your mission to become at least 75% fluent in sign language, and Dean begrudgingly learns a few key phrases so he can get by in simple conversation because whether or not he'll admit it out loud (since he's mr. "no chick flick moments"), he likes Eileen and loves seeing her smile just as much as you guys do
He's the king of New Year's Resolutions. He makes a list of a bunch of really small changes, like "I'll work together with Dean and Y/N and make a chore chart" or "I'll go out and get eco-friendly lightbulbs for the bunker and turn the unused lights off more often", and he sticks with them the whole year. You're always surprised that he can always come up with at least 6 things to change every year
He loves dogs. He knows about 80% of all the dog breeds out there and can identify them mostly on the first try just by glancing at them. It pisses you and Dean off to no end
He’s terrible at strategy games like Connect 4 and Battleship, and nobody has any idea why. He just sucks ass at strategy games. He’s annoyingly good at Operation though, because he has the steadiest hands on earth
His favorite way to kiss you is to pull you closer by your belt loops, then slide one hand up to your neck and one to your waist (and by that I mean partially on your waist but mostly cupping your ass). Mostly because you always melt into him when he does it and it spikes his ego a little bit
He always remembers the littlest details about you. Like you’ll mention offhandedly once that you prefer paperback books to hardcover ones, and then after that every book he gets you for Christmas and your birthday is paperback. Or you’ll casually say in a conversation that platypuses are your favorite animal, and then one day a platypus plushie randomly appears on your bed. And it makes you love him just the teensiest bit more every time he does something like that for you
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5sospenguinqueen · 1 month
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Y/N: You bought a taco?
Dean: Yes.
Y/N: From the same truck that hit Sam?!
Dean: (mouth full) Well, me starving isn’t gonna help him.
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were-all-idjits-here · 6 months
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How do you think the Winchester dynamic would change if they had another sibling that was the youngest? I’m particularly curious how you think Sam would treat them and stuff!
Thanks for the ask anon!
I'm the oldest with only one younger sibling, so I don't have much experience with three kids/middle child dynamic. The idea of Sam suffering from that "overlooked middle child" trope breaks my heart for him, but he seems to be the type who doesn't mind avoiding the spotlight, so I'm not sure he'd really mind. I think if they had a youngest sibling who was a different gender than them, he wouldn't suffer from that as much since he'd still be considered the youngest boy. But either way, I don't really think it would affect how Sam treats them.
I think both brothers would be very "no one's allowed to pick on my sibling but me" attitude, and both would be very protective over a younger sibling. There would be a lot of teasing, but also a lot of love, too. I think if their youngest sibling was very fem, they'd be even more protective since a lot of hunters (and the world at large) unfortunately can be a bit sexist and disrespectful, especially of fem hunters.
As far as how the dynamic between the two of them would change, I think Dean would obviously still be protective over Sam as well, but would have less of a "Sammy is baby" mentality and delegate some of the protect the youngest tasks to him. I feel like Dean would be aware of the forgotten middle child trope as well as do his best to make sure he never made Sam feel unimportant or left out, but would slip up from time to time. When that does happen, I think Sam would be more frustrated with Dean than anything else since he's empathetic enough to realize it wasn't the youngest's fault and would work really hard to not take it out on them. But if he ever did, he would do whatever it took to make it up to them while Sam and Dean worked out ways to make sure it didn't become a pattern.
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treacherousrift · 9 months
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Headcanon where Sam Winchester got top surgery as soon as he left for college and Jessica helped him recover
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graceloveswolves · 2 years
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Imagine… coming back from a “girls night” that the boys found out was actually a hunt.
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sweet-heart-jack · 4 months
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Hey friend 😁
Congrats on 300 followers! You definitely deserve it!
Could I have a Sam Winchester headcanon with him dating a short girl, like 5'2?
Thank you girlie! 😘
Hello! Thank youu
Of course you can Sweetheart! Here they are, I hope they're okay<3
Join the celebration here
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Sam dating a short girl
listen, Sam knows that he's a big dude
so when you first started dating, he had the irrational fear of breaking you
roll over you in his sleep while he was having nightmares or something of the like
well, Sam you haven't met a short girl then
we climb wobbly chairs, counters, ladders, a wobbly board over two stools (...) just to get a cup
so dear Sam soon learned that while you were short, you were not the least bit fragile
counter make out sessions become his favourite kitchen activities
it gives you both a comfortable distance without any back pain
(well at least not for you two - Dean frequently complains about the things he walks in on, but hey, it wasn't like he and Cas were any better)
just because your boyfriend is a giant of a man, you don't stop climbing things to get what you want though
much to the chagrin of said boyfriend
"why didn't you just ask me to help you?" "Because it works just fine like this?" "I caught you just in time!"
the fight that followed this exchange was epic
bottom line: Sam arranged himself with you climbing furniture but stays close
his arm is almost always around your shoulder
whenever you wear high heels, Sam makes sure to stay close if the situation allows it
he likes to keep a hand on your back then
because of that one time you fell straight on the nose after taking half a step and he was across the room
you think it's sweet
it drives him crazy to see you wearing his clothes because they're so big on you - the way a simple shirt slips from your shoulder? Or you all sleepy and smiling in the morning when you wore one of his old t-shirts to bed? Sam is dead and gone
Table kisses!!!
Bonus:
Dean likes to pick you up randomly and throw you at Sam when he thinks his brother is in a bad mood
You scowl and complain that you're not a ragdoll but secretly you find it really funny
Also Sam always lights up like a f*king lighthouse when you're suddenly in his lap
Then you proceed to be 'gross' to get rid of Dean
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