#guilty!dean

The Mark of Cain takes over Dean and Sam gets the worst blow of it. Sam’s damaged to the point where he’s hospitalized. In this scenario, Cas doesn’t have his grace so he can’t heal Sam.

Dean looks back on how he’s treated Cas over the years, and he’s got a lot of regrets.

Rated Teen, Destiel, 965 words. Guilty Dean, Heavy Angst, Regret, Self-loathing, Canon-Compliant Character Death (And Resurrection), Dean’s Thoughts On Cas Over the Years (and Seasons) Season 4-9

Hey there, my precious anon!! 💕💕 Thank you SO much!! This is the BIGGEST compliment. Seriously, LET ME LOVE YOU. 😭 And of course, babe!! Here ya go. 💕💕 I hope you like it! (I adore YOU! 💋)

Dean knows that he shouldn't be sharing a bed with his sixteen year old brother. Not when the queen sized bed behind him was freshly made and completely empty. Their father would lose his shit if he ever found out.

But Dean also knew that he was weaker than he'd ever like to admit, and that those big misty puppy dog eyes of Sam's were a God damn weapon. One pleading look bringing him to his knees faster than any kick or jab his little brother could ever throw.

"Good night, Dean."

There's something so delicate and pure in the way Sam whispers his name into the darkness. Like a Siren's call, soothing him and driving him mad all at the same time. That sound made Dean ache so deeply, and it made him want. It made him want something from his little brother that he shouldn't ask for...that he couldn't ask for.

"Night, Sammy."

For a brief moment after that, everything is still and Dean thinks maybe, just this once, he will be able to get some sleep. The older boy still holding out hope that he would be safe from his unspeakably twisted thoughts when he finally slipped into unconsciousness.

"Love you."

Sam's voice sounded so small when he spoke next but shit, did it pack a powerful punch. Those two agonizingly sweet words echoing in Dean's ears loud enough to split his head in two; breath catching in his throat when Sam gathered up the courage that Dean could never find to scoot a little closer.

"I-uh, I'll be right back," Dean stutters in reply, his fingers twitching uncontrollably as he drug himself out of bed and stumbled into the bathroom. God, he'd wanted to touch Sam so fucking bad just then. Fuck! Sam had almost touched him.

The very thought of Sam's hands on him made Dean's skin start to prickle and turn bright red as he leaned his head back against the locked door, cursing under his breath.

Jesus, it was almost unbearable, the heat he felt speading across his body. Like someone had taken a lighter to his flesh. Holding the flame there with malice, just to watch him squirm.

"Get it together, Dean. C'mon."

If only it were that easy.

"Oh you sick fuck," Dean growls at himself when his eyes land on a pair of light blue boxers that had been discard on the bathroom floor and long since forgotten.

Sam's boxers.

Shame sits heavy on Dean's chest as he bends over to pick them up, so overwhelming and absolute that he can barely catch his breath this time.

"You're so stupid!" He scolds through gritted teeth as he hits his head back against the door. Trying to knock some God damn sense into himself. But there was none to be had, because this whole situation didn't make any sense. And even if it did, Dean was too far gone for his baby brother to see.

"God damn it, Sammy...you make me so crazy...you-"

A mournful sigh slips past Dean's nervoulsy bitten lips as he wraps Sam's dirty boxers around his fist, squeezing the wrinkled material so desperately that it makes his knuckles turn chalk white.

"Sam."

Dean tries to hold off at first, testing out a couple slow, sensual rolls of hips. The much needed friction sending a shockwave of pleasure shooting down his spine with every crude, deliberate motion.

At this point, Dean was so painfully hard that he was almost on the verge of tears.

God, he'd tried to ignore it though. That sick urge he had to run his fingers through his baby brother's messy hair. He'd lie awake every night for hours listening to the soft hum of Sam's breath, obsession latching on to him like a leech. The insatiable creature feeding freely off Dean's wicked thoughts until he was almost drained; too weak and delirious to stop himself from stealing a kiss from those devastatingly beautiful lips.

And tonight, it was so much worse. He couldn't ignore those undeniable urges. Not when his little brother had been so close, fansty bleeding into reality until Dean swore he could almost feel his nails rake over the long, smooth curve of Sam's back. Swore he could hear his little brother chant his name like a prayer, begging him to take and take until there was nothing left.

It was fucked up and twisted. And it made Dean hate himself more than he could ever put into words. Seriously. How could he trick his brain into thinking that Sam wanted something so filthy and wrong as his touch on that flawless skin?

"Fuck."

Dean squeezed his eyes close and tried to push the thought of his brother out of his mind. Trembling right hand sneaking past the waistband of his pajama pants as he willed himself to picture anything but a pair of wide trusting eyes and a gorgeous smile that was bright enough to put the sun to shame. But it was no use. Sam's lips were poisoned apple red and Dean was dying for a taste.

"Sammy...oh God."

An excruciating mix of pain and pleasure streaked across Dean's abdomen when he brought Sam's boxers up to his nose, breathing the fabric in deeply. The familiar smell of cheap laundry detergent and sweat filling his lungs and making him ache as he started to jerk himself off. It was fast and rough and so fucking dirty but Dean couldn't bring himself to care. He needed to come before he actually lost his mind.

"Fuck!"

Dean's orgasm hit him like a tidal wave. Guilt and ecstacy crashing over him, twisting and gnawing at his insides until he didn't know which way was up. He fought and clawed to reach the surface but no matter how hard he struggled, he couldn't espace his shame.

"Jesus Christ, Dean," he mutters, hitting the back of his head against the door again in disgust.

"Dean? You okay in there?"

The sound of his brother's voice, a little groggy and far more gentle than Dean ever deserved, made the older boy nearly jump out of his skin.

"Yeah!" Dean can't even hide the fact that he sounds completely wrecked when he answers. God, he was so pathetic. "Yeah, Sam. I'm fine. Go back to sleep."

"But-"

"I said I'm fine!"

Before he could stop himself, Dean used his boxer clad fist to punch the paint chipped door that separated Sam and him in frustration. Almost immediately regretting his decision because he knew by the surprised yelp his little brother let out that violent noise had made Sam flinch. Fuck. As if Dean needed another reason to feel like absolute trash.

"Hey, I'm sorry. Why don't you wanna go back to bed, Sam?"

"...You're gonna make fun of me."

Well, that hurt like Hell.

"I'm not gonna make fun of you, baby. I promise. Just tell me what's wrong."

Dean feels so exhausted. The muscles in his legs starting to spasm and burn as he presses his forehead against the door and silently begs Sam to reply.

"It's hard to fall asleep without you next to me," the younger boy finally confesses after what feels like an eternity of silence. "And I'm cold...I know you hate it or whatever, but can you please just cuddle me until I pass out? Please Dean?"

Fuck, if Sam only knew.

"Just- give me like fifteen minutes, okay Sammy?" Dean pleaded, not even trying to hide the fact that his little brother had him wrapped around his finger.

"Yeah, of course, Dean. No rush."

The older boy didn't realize he had been holding his breath until he heard Sam start move away from the door.

"Shit."

Dean was still sore from the intensity of his orgasm, and he felt absolutely disgusting but that didn't stop his dick from twitching at the thought of holding Sam.

God, if he made it through this night without doing something he knew he was going to regret, it'd be a miracle.

have you considered sam using that knowledge against dean? using it to his advantage? knowing that if he bats his eyelashes and bends over just a little too far he can get anything he wants out of dean? consequently deans anger gets even worse, becoming even more frustrated with himself, and he starts taking it out on other people because they cant find the monsters for him to take his anger out on fast enough. and little sammy getting off on his brothers pain as well as others. (2/2) 🐢

My lovely turtle anon! 🐢 You are speaking right to my sweet little psychopath Sammy lovin' soul. 💕 And self-loathing, trembling with violent rage Dean who loves his baby brother far more than he should? The air I fucking breathe. 🙏

I seriously live for guilt-ridden teenaged Dean, who has a compulsive need to break pretty things out of anger. Like the throwing arm of an all American quarterback who's gaze lingered a little too long on Sam. Or the teeth of that cute waiter that gave Sam a flirty smile and a pat on the shoulder.

And hates himself more and more every day because the one pretty thing in his life he hasn't broken is the one thing he wants to break the most.

"Dean."

His little brother is pressed close to his side. Too close. Too close for Dean to think, or even breathe without his senses being flooded with everything Sam.

It makes his jaw tic.

"Get off me, Samuel," Dean grits out, but he doesn't push his little brother away. He doesn't have the strength, he never has. And Sam knows it.

"Did you see the way that guy was looking at me?" Sam asks, his voice so sticky sweet that it makes Dean's stomach turn. He can feel the younger boy nosing at his jaw, toying with him like a kitten that just cornered it's prey.

It makes his hands shake.

"You know I did."

Sam smiles against Dean's stubbly cheek, little hand slipping between his big brother's legs before he can stop him.

"What are you gonna do about it?"

Dean squeezes his eyes shut and tries with everything he has not to rock himself against Sam's palm. His face is flushed and his chest hurts. A sharp pang of guilt and anger and something else he never wants to admit out loud aching deep in his gut when he feels teeth nipping at his throat.

"Nothing," he lies, finally maning up long enough to lean away. Those sinful lips of Sammy's leaving his skin tingling and wet with forbidden kisses.

"I see." Sam is pouting now and Dean wants to scream. "So you're just gonna let some creep think all sorts of nasty things about your baby brother?"

"Don't, Sam. I mean it."

"I bet he's got some pretty twisted fantasies, big brother."

Maybe not as twisted as yours a voice inside Dean's mind whispers cruelly.

It makes him see red.

"You should beat them out of him."

Sam's breath is warm against his clammy skin. God, he practically moans the words in Dean's ear. The soft, needy little sound nearly driving him insane. "Or," Sam adds, clearly amused by his big brother's anguish, "you could just take what he wants. I'd let you, Dean. You know I'd let you do anything to me."

"God damn it, Sam," Dean growls before shoving his little brother all the way off of him. Rage burn white hot in his chest as he gets up from the booth, still half hard in his jeans.

"You gonna let me watch? Or are you feeling particularly self-righteous today?"

Sometimes Dean forgets how cruel his baby brother can be. And these little reminders make him want to break Sam in half. They make him want to take all the frustration and resentment that's been eating him alive for as long as he can remember out on that cute little ass.

But the worst part? The thing that drove Dean to drink? That was knowing Sam wanted it too.

Dean was a ticking time bomb of shame and unbridaled rage and Sam knew the timer started counting down the day he turned sixteen. Sam knew Dean needed an outlet for his anger. And he wasn't going to stop until his big brother's slip knuckles finally found the pretty face they were longing for.

He was going to keep pushing him closer and closer to the edge. Until Dean loses that last bit of self control he's been holding onto for dear life. Until he finally puts Sam where he aches to be. On his back beneath Dean, bruises being dug into his writs, with the taste of blood on his tongue.

Of course, Dean knows it's only a matter of time until he takes the bait Sam's been dangling in front of him for years. Because it's clear from the situation at hand that he can make Dean do whatever he wants him to. After all, Sam knew firsthand that using a Winchester's anger as motivation was easy as taking candy from a baby.

"Yeah, whatever."

Dean doesn't bother to look back as he follows the latest victim of his rage outside.

Heaven Help Them - Chapter 13

Gadreel returns from the Empty just as Sam, Dean, Castiel and Jack are trying to solve Heaven’s angel shortage. If they can overcome the past, they might just be able to secure Heaven’s future.

Rated T, Gadreel/Dean, Sastiel, Angst, Hurt/Comfort, Fluff, Guilty Dean, Good Person Gadreel, Emotional Baggage, Baby Angels, Celestial Wavelength Sorta Mpreg, Jack Uses His Nephilim Powers To Help Heaven’s Angel Shortage, Witchcraft, Canon Divergent At 13.22.

Did I mention Lucifer is actually dead and Michael’s actually stuck through the closed portal and Jack gets to keep his grace?

New chapters posted each Tuesday, and this’s looking to be a long fic, so get comfy. ♥

Heaven Help Them - Chapter 7

Gadreel returns from the Empty just as Sam, Dean, Castiel and Jack are trying to solve Heaven’s angel shortage. If they can overcome the past, they might just be able to secure Heaven’s future.

Rated T, Gadreel/Dean, Sastiel, Angst, Hurt/Comfort, Fluff, Guilty Dean, Good Person Gadreel, Emotional Baggage, Baby Angels, Mpreg (Only Not The Squicky Kind?), Baby Angels Are Lil Wavelengths So…Celestial Wavelength Sorta Mpreg, Jack Uses His Nephilim Powers To Help Heaven’s Angel Shortage, Witchcraft, Canon Divergent At 13.22.

Did I mention Lucifer is actually dead and Michael’s actually stuck through the closed portal and Jack gets to keep his grace? ♥

New chapters posted each Tuesday, and this’s looking to be a long fic – 20+ chapters.

Heaven Help Them - Chapter 11

Gadreel returns from the Empty just as Sam, Dean, Castiel and Jack are trying to solve Heaven’s angel shortage. If they can overcome the past, they might just be able to secure Heaven’s future.

Rated T, Gadreel/Dean, Sastiel, Angst, Hurt/Comfort, Fluff, Guilty Dean, Good Person Gadreel, Emotional Baggage, Baby Angels, Celestial Wavelength Sorta Mpreg, Jack Uses His Nephilim Powers To Help Heaven’s Angel Shortage, Witchcraft, Canon Divergent At 13.22.

Did I mention Lucifer is actually dead and Michael’s actually stuck through the closed portal and Jack gets to keep his grace? ♥

New chapters posted each Tuesday, and this’s looking to be a long fic – 20+ chapters.