Wincest Headcanon Daily
@wincestdailyhc.bsky.social
I write headcanons about the Winchester brothers, usually theyre fucking, but not always.
Gifs arent mine, all headcanons are free to use, just tag me.
❤💙 18+
Gifs arent mine, all headcanons are free to use, just tag me.
❤💙 18+
(implied noncon) "How the hell did he find me?" Sam asks, pushing his hair back. He glared at Cas. "You said this was soul binding, that he couldn't..." Sam shivered. Dean had always been a little obsessed with him, but after he got back from Hell, something was different. Wrong.
December 2, 2025 at 4:44 AM
(implied noncon) "How the hell did he find me?" Sam asks, pushing his hair back. He glared at Cas. "You said this was soul binding, that he couldn't..." Sam shivered. Dean had always been a little obsessed with him, but after he got back from Hell, something was different. Wrong.
#Wincestmas #1 (cw: m!preg) "You wanna what?" Dean asked.
"I wanna get a Christmas tree." Sam repeated. "The baby will be here by then, and I want him to have a tree."
Dean smiled. "By you want a tree, you really mean you want me to go to the store and buy a tree and set it up"
"I wanna get a Christmas tree." Sam repeated. "The baby will be here by then, and I want him to have a tree."
Dean smiled. "By you want a tree, you really mean you want me to go to the store and buy a tree and set it up"
December 1, 2025 at 6:05 PM
#Wincestmas #1 (cw: m!preg) "You wanna what?" Dean asked.
"I wanna get a Christmas tree." Sam repeated. "The baby will be here by then, and I want him to have a tree."
Dean smiled. "By you want a tree, you really mean you want me to go to the store and buy a tree and set it up"
"I wanna get a Christmas tree." Sam repeated. "The baby will be here by then, and I want him to have a tree."
Dean smiled. "By you want a tree, you really mean you want me to go to the store and buy a tree and set it up"
Excuse me, everyone! Dean would like to show you something. Created by the always amazing @kamidiox.bsky.social
October 30, 2025 at 1:53 AM
Excuse me, everyone! Dean would like to show you something. Created by the always amazing @kamidiox.bsky.social
"You fucking cheater!" Dean shouted throwing his duffle bag at Sam. "Outside help isnt allowed in prank wars!"
Sam smirked. "Where does it say that? Can I see it in writing?"
"Sam, I'm fucking sparkling!" He pointed to the floor. "There's a trail of goddamn glitter everywhere I
Sam smirked. "Where does it say that? Can I see it in writing?"
"Sam, I'm fucking sparkling!" He pointed to the floor. "There's a trail of goddamn glitter everywhere I
October 13, 2025 at 8:48 AM
"You fucking cheater!" Dean shouted throwing his duffle bag at Sam. "Outside help isnt allowed in prank wars!"
Sam smirked. "Where does it say that? Can I see it in writing?"
"Sam, I'm fucking sparkling!" He pointed to the floor. "There's a trail of goddamn glitter everywhere I
Sam smirked. "Where does it say that? Can I see it in writing?"
"Sam, I'm fucking sparkling!" He pointed to the floor. "There's a trail of goddamn glitter everywhere I
Wrote a little thing. Sam can't be too evil if he cooks Dean dinner, right?
archiveofourown.org/works/70888446
archiveofourown.org/works/70888446
Dinner Time - WincestDailyHC - Supernatural (TV 2005) [Archive of Our Own]
An Archive of Our Own, a project of the Organization for Transformative Works
archiveofourown.org
September 15, 2025 at 8:50 PM
Wrote a little thing. Sam can't be too evil if he cooks Dean dinner, right?
archiveofourown.org/works/70888446
archiveofourown.org/works/70888446
"Surely (He)aven waits for you"
Created by the amazing @kamidiox.bsky.social
I cant begin to describe how beautiful she did on this.
The way Sam and Dean come back into color when theyre reunited, when their souls are together, melts my heart.
#HappyBarniversary #Supernatural #Wincest
Created by the amazing @kamidiox.bsky.social
I cant begin to describe how beautiful she did on this.
The way Sam and Dean come back into color when theyre reunited, when their souls are together, melts my heart.
#HappyBarniversary #Supernatural #Wincest
July 19, 2025 at 1:30 PM
"Surely (He)aven waits for you"
Created by the amazing @kamidiox.bsky.social
I cant begin to describe how beautiful she did on this.
The way Sam and Dean come back into color when theyre reunited, when their souls are together, melts my heart.
#HappyBarniversary #Supernatural #Wincest
Created by the amazing @kamidiox.bsky.social
I cant begin to describe how beautiful she did on this.
The way Sam and Dean come back into color when theyre reunited, when their souls are together, melts my heart.
#HappyBarniversary #Supernatural #Wincest
Look at what I just got from the amazing @kamidiox.bsky.social Who needs a purification ritual when you can have a slinky? #Supernatural
June 29, 2025 at 4:26 AM
Look at what I just got from the amazing @kamidiox.bsky.social Who needs a purification ritual when you can have a slinky? #Supernatural
Dean grabs Sam and pulls him onto his lap, kissing his neck. "Hey, there you are, I missed you."
Sam chuckles, leaning back into his brother. "Just went to the bathroom, you missed my after five minutes?"
"I miss you after five seconds." Dean pouts. "This place sucked till you
Sam chuckles, leaning back into his brother. "Just went to the bathroom, you missed my after five minutes?"
"I miss you after five seconds." Dean pouts. "This place sucked till you
May 11, 2025 at 7:10 AM
Dean grabs Sam and pulls him onto his lap, kissing his neck. "Hey, there you are, I missed you."
Sam chuckles, leaning back into his brother. "Just went to the bathroom, you missed my after five minutes?"
"I miss you after five seconds." Dean pouts. "This place sucked till you
Sam chuckles, leaning back into his brother. "Just went to the bathroom, you missed my after five minutes?"
"I miss you after five seconds." Dean pouts. "This place sucked till you
Fic idea: Sam counted down the days until his son was 6 months old. He made preparations, carved sigils into different corners of the house, and used an entire bag of rock salt around the doors and windows. He didn't expect anyone to actually be stupid enough to come, but still,
May 11, 2025 at 7:09 AM
Fic idea: Sam counted down the days until his son was 6 months old. He made preparations, carved sigils into different corners of the house, and used an entire bag of rock salt around the doors and windows. He didn't expect anyone to actually be stupid enough to come, but still,
Dean kisses the scar on Sam's hand. "You never told me where this one came from."
That was true, Sam hadnt. He didn't like to think about that one, much less talk about it. But now, they were both in heaven, and they would never be apart again. "I had to dig a grave in Illinois."
That was true, Sam hadnt. He didn't like to think about that one, much less talk about it. But now, they were both in heaven, and they would never be apart again. "I had to dig a grave in Illinois."
May 11, 2025 at 7:06 AM
Dean kisses the scar on Sam's hand. "You never told me where this one came from."
That was true, Sam hadnt. He didn't like to think about that one, much less talk about it. But now, they were both in heaven, and they would never be apart again. "I had to dig a grave in Illinois."
That was true, Sam hadnt. He didn't like to think about that one, much less talk about it. But now, they were both in heaven, and they would never be apart again. "I had to dig a grave in Illinois."
Reposted by Wincest Headcanon Daily
#FanfictionFriday
How to not flirt with your brother by @wincestdailyhc.bsky.social
archiveofourown.org/works/646104...
Dean's a demon, Sam doesn't have a soul, and sometimes they pick fights with each other.
You'll enjoy this. It's... sizzling hot.
How to not flirt with your brother by @wincestdailyhc.bsky.social
archiveofourown.org/works/646104...
Dean's a demon, Sam doesn't have a soul, and sometimes they pick fights with each other.
You'll enjoy this. It's... sizzling hot.
April 11, 2025 at 12:57 PM
#FanfictionFriday
How to not flirt with your brother by @wincestdailyhc.bsky.social
archiveofourown.org/works/646104...
Dean's a demon, Sam doesn't have a soul, and sometimes they pick fights with each other.
You'll enjoy this. It's... sizzling hot.
How to not flirt with your brother by @wincestdailyhc.bsky.social
archiveofourown.org/works/646104...
Dean's a demon, Sam doesn't have a soul, and sometimes they pick fights with each other.
You'll enjoy this. It's... sizzling hot.
Dean: Dear, Honey, Sweetheart, Babe, Baby, Love, Cupcake...
Sam: What are you doing?
Dean: Trying to pick out a pet name for you.
Sam: What's wrong with Sammy?
Dean: It's your name.
Sam: But you're the only one who gets to call me that so it's kind of a pet name.
Dean: True
Sam: What are you doing?
Dean: Trying to pick out a pet name for you.
Sam: What's wrong with Sammy?
Dean: It's your name.
Sam: But you're the only one who gets to call me that so it's kind of a pet name.
Dean: True
April 2, 2025 at 6:03 PM
Dean: Dear, Honey, Sweetheart, Babe, Baby, Love, Cupcake...
Sam: What are you doing?
Dean: Trying to pick out a pet name for you.
Sam: What's wrong with Sammy?
Dean: It's your name.
Sam: But you're the only one who gets to call me that so it's kind of a pet name.
Dean: True
Sam: What are you doing?
Dean: Trying to pick out a pet name for you.
Sam: What's wrong with Sammy?
Dean: It's your name.
Sam: But you're the only one who gets to call me that so it's kind of a pet name.
Dean: True
Theres a pillow on Sam's bed, made from Dean's jacket. Sam knows every stain, every rip, and hole in the fabric, knows them the same way he knew every freckle, scar, and curve of Dean's body. On worser days, he sprays the pillow with cologne, and he can pretend Deans still there.
April 2, 2025 at 8:56 AM
Theres a pillow on Sam's bed, made from Dean's jacket. Sam knows every stain, every rip, and hole in the fabric, knows them the same way he knew every freckle, scar, and curve of Dean's body. On worser days, he sprays the pillow with cologne, and he can pretend Deans still there.
The first night at Stanford, Sam got drunk. He held his phone, looking at Dean's contact, and he wanted to call, wanted to say he's sorry he hurt his brother, and he couldnt work up the courage. Instead, he called Bobby. Bobby listened to him tell the whole story, how he and dad
March 25, 2025 at 3:55 PM
The first night at Stanford, Sam got drunk. He held his phone, looking at Dean's contact, and he wanted to call, wanted to say he's sorry he hurt his brother, and he couldnt work up the courage. Instead, he called Bobby. Bobby listened to him tell the whole story, how he and dad
It isn't really Sam's thing, but for Dean, he'll indulge. He expects to feel fresh cut strawberries, the only fruit Dean deems worth eating, and whipped cream to be put on his bare chest, and instead feels something hard and small. Sam yanks off the blindfold, looking
March 24, 2025 at 3:25 PM
It isn't really Sam's thing, but for Dean, he'll indulge. He expects to feel fresh cut strawberries, the only fruit Dean deems worth eating, and whipped cream to be put on his bare chest, and instead feels something hard and small. Sam yanks off the blindfold, looking
Okay, but, a demon just wanting to live upstairs drama free, working at some crappy diner, and in walks the Winchester bros and poor stunt demon's just trying to come up with logical non demonic explanations for why the place smells like rotten eggs, the lights flicker, etc,
March 24, 2025 at 2:40 PM
Okay, but, a demon just wanting to live upstairs drama free, working at some crappy diner, and in walks the Winchester bros and poor stunt demon's just trying to come up with logical non demonic explanations for why the place smells like rotten eggs, the lights flicker, etc,
"How long are you going to keep letting him do this?" Cas asks, Dean, grabbing his arm to keep him upright.
"I asked him to do this." Dean mumbled. "Heal me, or I'm just gonna give myself a transfusion, and do it anyways."
Cas sighed. "I cannot be a part of~"
Dean cut his friend
"I asked him to do this." Dean mumbled. "Heal me, or I'm just gonna give myself a transfusion, and do it anyways."
Cas sighed. "I cannot be a part of~"
Dean cut his friend
March 18, 2025 at 3:21 PM
"How long are you going to keep letting him do this?" Cas asks, Dean, grabbing his arm to keep him upright.
"I asked him to do this." Dean mumbled. "Heal me, or I'm just gonna give myself a transfusion, and do it anyways."
Cas sighed. "I cannot be a part of~"
Dean cut his friend
"I asked him to do this." Dean mumbled. "Heal me, or I'm just gonna give myself a transfusion, and do it anyways."
Cas sighed. "I cannot be a part of~"
Dean cut his friend
Dean sat on the grass and watched as Sam gathers wood, for his pyre. He pet Miracle, and gave a soft, sad, smile. "Good dog. You keep an eye on Sam for me, okay? He gets lost sometimes, and forgets to eat. Just give him some extra love from the both of us, and he'll be okay."
March 18, 2025 at 1:22 PM
Dean sat on the grass and watched as Sam gathers wood, for his pyre. He pet Miracle, and gave a soft, sad, smile. "Good dog. You keep an eye on Sam for me, okay? He gets lost sometimes, and forgets to eat. Just give him some extra love from the both of us, and he'll be okay."
As far as spells went, Dean figured it could be worse. Besides, between Sams shaggy hair and those big misty eyes he used to get anything he wanted, he kinda looked like a dog anyways. "Look dude, I know it sucks, but we'll find a way to fix it, always do." He promised, adjusting
March 15, 2025 at 8:47 PM
As far as spells went, Dean figured it could be worse. Besides, between Sams shaggy hair and those big misty eyes he used to get anything he wanted, he kinda looked like a dog anyways. "Look dude, I know it sucks, but we'll find a way to fix it, always do." He promised, adjusting
Dean knows Sam's dying. He can sense it. Has been for awhile. And he can't wait. He crosses his arm and leans against the doorway, he smiles. "You take your time, Sammy. We go when you're ready." Sam looks in the corner, and Dean knows Sam can see him, even if no one else can.
March 14, 2025 at 1:06 AM
Dean knows Sam's dying. He can sense it. Has been for awhile. And he can't wait. He crosses his arm and leans against the doorway, he smiles. "You take your time, Sammy. We go when you're ready." Sam looks in the corner, and Dean knows Sam can see him, even if no one else can.
Dean and the other hunters he gathered watched as the Boy King brought a whole town to ruin.
"You gonna be able to take him out?" One of them asked. Dean raised his beer to his lips, glancing over his shoulder at the other three men, then nodded. "If anyones gonna do it, it's
"You gonna be able to take him out?" One of them asked. Dean raised his beer to his lips, glancing over his shoulder at the other three men, then nodded. "If anyones gonna do it, it's
March 14, 2025 at 1:05 AM
Dean and the other hunters he gathered watched as the Boy King brought a whole town to ruin.
"You gonna be able to take him out?" One of them asked. Dean raised his beer to his lips, glancing over his shoulder at the other three men, then nodded. "If anyones gonna do it, it's
"You gonna be able to take him out?" One of them asked. Dean raised his beer to his lips, glancing over his shoulder at the other three men, then nodded. "If anyones gonna do it, it's
"Dude, I'm not eating that." Sam said firmly. "Youre still doing that prank war crap, and I don't trust you."
Dean rolled his eyes, grabbed a fork, and stabbed it into the meatloaf, before taking a bite. "See?" Dean asked, swallowing. "I'm above putting stuff in your food for
Dean rolled his eyes, grabbed a fork, and stabbed it into the meatloaf, before taking a bite. "See?" Dean asked, swallowing. "I'm above putting stuff in your food for
March 14, 2025 at 1:05 AM
"Dude, I'm not eating that." Sam said firmly. "Youre still doing that prank war crap, and I don't trust you."
Dean rolled his eyes, grabbed a fork, and stabbed it into the meatloaf, before taking a bite. "See?" Dean asked, swallowing. "I'm above putting stuff in your food for
Dean rolled his eyes, grabbed a fork, and stabbed it into the meatloaf, before taking a bite. "See?" Dean asked, swallowing. "I'm above putting stuff in your food for
Sam sighed contently, leaning against Dean. Dean smiled and kissed Sam's temple. "Whatcha thinking about baby?" He asked. "Besides how much you love me."
"How good you'd look tied up with a cockring and a ball gag." Sam answered.
"You're such a perv, Sam. Everyone thinks it's me
"How good you'd look tied up with a cockring and a ball gag." Sam answered.
"You're such a perv, Sam. Everyone thinks it's me
March 14, 2025 at 1:04 AM
Sam sighed contently, leaning against Dean. Dean smiled and kissed Sam's temple. "Whatcha thinking about baby?" He asked. "Besides how much you love me."
"How good you'd look tied up with a cockring and a ball gag." Sam answered.
"You're such a perv, Sam. Everyone thinks it's me
"How good you'd look tied up with a cockring and a ball gag." Sam answered.
"You're such a perv, Sam. Everyone thinks it's me
Sam had no clue whose idea it was to hire a male stripper for one of his college buddies birthday, but he had to admit, it was pretty funny seeing all the other guys get uncomfortable. Sam had never been shy about liking both men and women, and figured he would get his lap dance
March 14, 2025 at 1:03 AM
Sam had no clue whose idea it was to hire a male stripper for one of his college buddies birthday, but he had to admit, it was pretty funny seeing all the other guys get uncomfortable. Sam had never been shy about liking both men and women, and figured he would get his lap dance
Dean was disappointed with how easily he pinned Sam to the floor. "Easy Tiger." Dean said.
Sam scrunched his face in confusion. "Dean?"
Dean smiled. He knew that Sam may tell him to get lost, to get dead. But at the very least, he would have heard Sam say his name one last time.
Sam scrunched his face in confusion. "Dean?"
Dean smiled. He knew that Sam may tell him to get lost, to get dead. But at the very least, he would have heard Sam say his name one last time.
March 13, 2025 at 9:03 PM
Dean was disappointed with how easily he pinned Sam to the floor. "Easy Tiger." Dean said.
Sam scrunched his face in confusion. "Dean?"
Dean smiled. He knew that Sam may tell him to get lost, to get dead. But at the very least, he would have heard Sam say his name one last time.
Sam scrunched his face in confusion. "Dean?"
Dean smiled. He knew that Sam may tell him to get lost, to get dead. But at the very least, he would have heard Sam say his name one last time.