1 - 20 of 133 Works in Insecure Sam Winchester
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All Mick wanted was for Sam to notice him. All Castiel wanted was for Dean to care. The plan was simple: fake a relationship, spark some jealousy, move on.
What they didn’t expect was how well it worked – and how much it would hurt when it did.
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Chapter 3 is focused on Destiel, Chapter 4 on Sam/Mick. -
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Sam and Dean are on a hunt for a malicious dryad—a type of forest creature. They knew how it killed, and how to kill it, but not how it lured its victims. Sam finds himself injured and exposed, forced to confront his deepest feelings he never meant to share.
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The initial wave of contentment that overcame him as he stepped inside the club is instantly replaced by a twisting in his gut as his eyes land on the stage at the back of Sanctuary. A stage that is currently occupied by Gabriel and another one of his clients, presumably.
Sam tries to clamp down on the flare of jealousy the sight of his dom with another sub sparks in his chest. Gabriel will inevitably scene with others, even if he doesn't discuss other clients with Sam. Sam knows this, has always known this, but there's a difference between acknowledging that fact and being confronted with it.
Series
- Part 4 of Sticks and Stones, Chains and Whips
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sammy, you’re the pretty boy (the perfect, itty-bitty boy) by Anonymous
Fandoms: Supernatural (TV 2005)
29 Mar 2025
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Sam barely fits in Dean’s lap.
Series
- Part 7 of little sam
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Sam and Dean move into the dorms and go shopping for swimsuits for Sam's first college party.
Only problem is they're broke, all the shops are expensive and 𝘸𝘩𝘺 𝘵𝘩𝘦 𝘧𝘶𝘤𝘬 𝘥𝘪𝘥 𝘵𝘩𝘦𝘺 𝘥𝘦𝘤𝘪𝘥𝘦 𝘵𝘰 𝘤𝘩𝘢𝘴𝘦 𝘢 𝘷𝘢𝘮𝘱𝘪𝘳𝘦 𝘵𝘩𝘳𝘰𝘶𝘨𝘩 𝘢 𝘧𝘰𝘳𝘦𝘴𝘵 𝘰𝘯 𝘦𝘮𝘱𝘵𝘺 𝘴𝘵𝘰𝘮𝘢𝘤𝘩𝘴 𝘪𝘯 𝘵𝘩𝘦 𝘮𝘪𝘥𝘥𝘭𝘦 𝘰𝘧 𝘧𝘶𝘤𝘬𝘪𝘯𝘨 𝘯𝘰𝘸𝘩𝘦𝘳𝘦. Dean just wanted to get some pie, man, why did they have to be so helpfulOr:
Sam and Dean's experiences during the week before and after the first day of Stanford, from the day they moved into the dorms, until the welcome party, and the first impressions they left on those around them along the way
Series
- Part 3 of Monsters and education, a tricky balance
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What Else Could He Ask For? by writing_gives_me_serotonin
Fandoms: Supernatural (TV 2005)
26 Oct 2024
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Sam hated how much clowns terrified him. Their strange, painted grins that often contradicted their actual expressions, their white faces that were cracking and peeling off most of the time, their stupid little red noses-
All of it unsettled something deep inside Sam, and he knew why it unsettled him, but no matter how much he tried to justify his fear, he couldn't help the wave of shame he felt every time a painted jokester passed by him and he jumped almost a foot into the air.
Alternatively: Did someone say deep-seated sexual trauma?
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“I made him run away, Dean. Jack is gone, he left.”
Series
- Part 9 of Make this bunker a home
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Sam woke up hungry.
They had discovered Famine in the city where they had initially thought there was only an out of the rails Cupid.
Instead, they had been confronted by one of Lucifer’s Knights himself.
And Sam had once again been confronted with the hunger for demon blood that he could never truly leave behind.
Series
- Part 11 of Cultober 2024
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lying with you (on a tuesday morning) by SomethingChanged244
Fandoms: Shoot From The Hip - Fandom, SFTH - Fandom, British Comedy RPF, Shoot From The Hip RPF
06 Oct 2024
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“Come back to mine,” AJ said, watching the sheer surprise that fleetingly crossed Sam’s face, eyes widening before he schooled his expression into a small smile.
“Okay.”
AJ had never ordered an Uber so quickly in his life.
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Sam’s been afraid of clowns for most of his life, and Dean has wondered and asked why? But he asks the wrong way, the wrong question. And finally with the right one, Dean finds out.
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It’s one thing to have a crush on an angel, it’s another to have that angel know you have a crush on them. That you’re, god forbid, lusting after them.
Sam Winchester’s life absolutely sucks. And the world won’t let him forget it. -
What The Heat Does To An Archangel by orphan_account
Fandoms: Supernatural (TV 2005), Supernatural (TV 2005) RPF
25 May 2024
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“Why are you here?”
Gabriel faux a pout, whining his words, “What? Can someone not visit his dearest boyfriend? Especially if he is literally a whole snack out here.”
“Not your boyfriend”, Sam bit back, physically cringing at the Angel’s remark.
Gabe sighs, he stopped leaning onto the Impala as Sam slammed the trunk shut and walked up to Gabriel slowly.
“Is that what you got from my sentence? I just basically called you hot and that you look mad fuckable”, he snickers as he watched Sam lose color on his face, but it followed with his ears and cheeks slightly flushing.
or
Gabriel for sure thinks Sam looks really hot while working on the impala, dripping in sweat under the usual weather of Texas.
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Sam wanted do relax, forget his past and just let his mind get hazy, but his internal turmoils really got in the middle of his relationship, so Mark was sure to calm him down better than any drug ever could.
It was easy to know why he was so addicted to that man.
(SamarkWeek day 6!
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Sam can’t sleep and they’re out of coffee so he makes do with hot cocoa, then to his surprise he meets a certain angel Dean’s been talking about.
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They had never talked about being exclusive. Sam had just assumed that Dean kissing him and the fact that they lived together and barely had any other friends and neither of them had had so much as a one night stand in the months—years?—before they got together and that they died for each other on the regular meant that when they started fucking it was, well, exclusive.
But maybe he was wrong.
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My Limbs All Froze by guttermud for @So_Clever_I_Dont_Know_April
Fandoms: Supernatural (TV 2005)
16 Jan 2024
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“How can you defend him after what he’s done?!”
Her voice sounds so much like Dad’s and her anger feels so much like Dean’s.
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On November 2nd, 1983, the Winchester home was enveloped in flame, and parents John and Mary were found dead in the morning. Their sons, Sam and Dean, were nowhere to be found. While the town of Lawrence, Kansas, eventually forgot about the family, Sam and Dean were being held by Heaven and Hell to fulfill their great destinies in God's Plan. Dean held by Heaven with Castiel as his trainer and Sam held by Hell with Crowley as his caregiver. When the two brothers meet ahead of schedule, no one could've predicted what happened next.
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Creating life is a hard process. When new life is being formed, first does not come sentience. Not for humanity, anyway. Even after birth, it takes time for a child to know it exists. Of course, this is not the same process for a being who already existed, and then was scattered across the universe. That process is much harder, because sentience arrives before anything else.
In which Gabriel is brought back to life, and is unconveniently tied to the youngest Winchester, Sam.
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Sam had never planned to come out.
He had never expected it to feel quite like this.
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It's obvious to anyone that John never took care of Sam. Dean was always Sam's mom, his dad. And Dean knew his number one priority: Protect Sammy.
But then Sam went to Stanford. Sam grew up. Sam didn't need his big brother anymore.
Dean's fine. He's perfectly fine. So what if he didn't get to comfort his baby brother anymore? Sam didn't need Dean . . . Sam was an adult.
Or, 15 times Dean hugged Sam.