Hey everyone! Here are the tags/warnings for this story that I forgot to add before because I'm a ding bat.

Castiel/Dean Winchester, Gabriel/Sam Winchester, Castiel/Gabriel/Dean Winchester/Sam Winchester, Dean Winchester/Sam Winchester, Castiel/Gabriel (Supernatural), Castiel, Dean Winchester, Sam Winchester, Gabriel (Supernatural), Foursome - M/M/M/M, Anal Sex, Anal Fingering, Blow Jobs, Wingfic, Wing Kink, Wing Oil, Misuse of wing oil, Food Kink, Gabriel does what he wants, Gabriel does who he wants, Wincest - Freeform, Destiel - Freeform, Sabriel - Freeform, So much smut, First Time, Virgin Castiel, Bottom Castiel, Bottom Dean, Top Dean, Top Sam, Top Castiel, Top Gabriel, Switch Dean, Switch Castiel, Bottom Sam, Switch Sam, First Time Bottoming, First Time Topping, First Time Blow Jobs, Plot What Plot/Porn Without Plot, There was a plot somewhere, a little AU, Oh there's where I left the plot, Slight Season 10 spoilers!, Nothing big or too revealing, Mainly a few quotes from the show, future sabriel, Future foursome, Past Torture, Aftermath of Torture, Set around season 9 - 10

"On the Wrong Side of Heaven"

Dean was sitting down in the library pouring over the many books that the Men of Letters had, trying desperately to find anything he could about removing the Mark of Cain. His nightmares had been getting worse and he really didn't want Cass to have to go through with his promise.

"Cass, I need you to promise me something."

"Of course."

"If I do go dark side, you gotta take me out."

"What do you mean?"

"Knife me, smite me, throw me into the freakin' sun. Whatever. And don't let Sam get in the way, because he'll try. I can't go down that road again, man. I can't be that thing again."

Dean's arm burned as he thought about what he made Cass promise him. He didn't know how much longer he would have till the Mark consumed him once again. A flutter of wings went unnoticed by the hunter as said Angel appeared behind him.

"Dean."

"Dammit Cass!" The hunter shouted as he spun around in his chair to see the Angel standing very close to him. "How many times do I have to tell you not to do that?!" Dean asked as he put his head in his hands and leaned back, the back of the chair resting against the table.

"My apologies Dean. I did not mean to startle you but I heard you calling me and you sounded distressed. Is everything alright?"

"Yeah, man. I'm just getting fed up looking through these books and finding nothing." Dean looked defeated; like a man that had no hope left in his being. He rubbed his arm over the Mark and just shook his head. "I'm scared Cass. I don't want to become that thing again and risk hurting you or trying to kill Sammy again. I just can't, man. Not again." It had been a long time since Castiel had seen Dean this depressed. At least this time the hunter wasn't drowning his sorrows with Jack Daniels.

"Dean. Is there anything I can do to help?" The Angel asked, fighting the urge to pull the hunter into an embrace as he had learned in the past was a way humans expressed comfort and caring. But Cass knew Dean had this weird thing about personal space, so he opted to stay put. Dean looked up at Cass, having been fighting his feelings towards the Angel for a long time, and thinking that now may be the time to express those feelings; before the Angel would have to put him down so he didn't go on a killing spree again. Dean looked up at the ceiling, trying to wrap his brain around what he wanted to do. He finally admitted to himself that he loved Castiel, but would his Angel return those feelings? His Angel. Dean liked the sound of that. The hunter looked up at Cass before sighing, his resolve made. "Dean?" Castiel questioned as Dean wrapped his hand around the Angel's wrist.

"Do you trust me, Cass?"

"Of course, Dean," the Angel stated as he looked down at the hunter in confusion. Dean smiled and pulled the Angel towards him, spreading his legs apart and making the Angel straddle his hips. Castiel's face flushed crimson at his new position. "D-Dean? What are you…?" The Angel was cut off by Dean's lips against his own. Castiel gasped and froze at the hunters actions but when Dean's tongue darted out and licked at the seam of the Angel's, Cass let his lips part. The hunter slipped his tongue into Cass's mouth, sliding alongside the Angel's. Cass moaned as Dean's hands gripped at the Angel's hips, pulling him closer. Cass carded his fingers into his hunter's sandy blonde hair, pulling him towards him. The need for air became too great, causing the men to pull apart from each other, panting heavily. "D-Dean…what are…" The Angel groaned as he felt the length of Dean's arousal against his thigh.

"C-Cass…you know I'm no good with words…and I don't know when this thing might take control of me again…and before it does, and my best friend has to put me down…I wanted to tell him how I felt." Dean's throat suddenly felt dry and his words got caught in his throat. He swallowed around his nervous lump and looked into those beautiful baby blue eyes of his Angel. "I love you Cass. I should've manned up a long time ago and just told you instead of waiting till now to tell you this. And if you'll have me, I wish to make you mine. Will you let me, Castiel?" Dean's eyes searched the Angel's with hope that Cass shared his feelings. After a long silence, Dean cast his eyes down.

'Of course he wouldn't feel the same. What was I thinking?'

"Yes."

"What?" Dean looked back up into his Angel's eyes.

"Yes, Dean. I too have had feelings towards you, but did not pursue them for the same reason you yourself had not done so. For fear that I would be rejected. I am glad that you have chosen me Dean. I would be glad to become yours. I wanted to be connected to you by more than just our profound bond. I want to mark you as mine, so that every creature that walks this earth will know to whom you belong to." Dean's eyes lit up as he smiled brightly at Castiel.

"I would like that Cass." The hunter reached his hand up to wrap behind Castiel's neck and pulled the Angel into another deep kiss. Cass groaned as he felt his pants becoming more constricting. He reached his hand down to push at the pressure he felt but was stopped by Dean grabbing his wrist.

"D-Dean…I don't understand…what's…"

"Shh, it's okay, Angel. I've got you." The hunter says softly as he leaned forward to nip at the Angel's neck.

"Dean…I don't know what to do." Castiel groaned as he ground his hips against Dean's, moaning at the contact and not understanding why he was feeling so primal. "Dean…please." The Angel panted.

"Get up and come with me Cass." Dean whispered against Cass's neck. The Angel nodded and got up. Dean stood and took the Angel's hand in his and led him down the hallway to his room. He pulled the Angel inside and closed the door, pinning Cass to it and attacking his lips with a more demanding kiss. Cass groaned into the assault and wrapped his arms around Dean's back, pulling the hunter closer to him. Dean slipped his hands under Cass's trench coat, pushing it from the Angel's shoulders and letting it fall to the floor. Dean then moved to the neck tie that hung loosely around his Angel's neck, pulling the knot free and discarding it alongside the coat. Castiel broke the kiss and leaned his head back against the door. Dean admired his Angel's flushed face, his pupils were lust blown, and leaving a very thin rim of blue and his mouth was opened slightly. The hunter smiled and took the opportunity to mark the Angel's throat with kisses, sucks, and bites, leaving red bruises that would take a while to go away. Dean smiled at his handy work as he started unbuttoning Cass's shirt, licking and sucking at the skin hidden behind the offending clothing. Castiel's breath hitched when Dean took on of his nipples into his mouth, sucking and teething at the sensitive nub.

"D-Dean…w-what are…"

"Shh. Remember, I got you Cass. I'm not going to hurt you." The hunter said reassuringly against his Angel's chest.

"I trust you Dean." Came the Angel's reply and the hunter continued removing Cass's shirt. The Angel slid his hands down to the hem of Dean's shirt and pulled at it till Dean lifted his arms up so that Cass could remove it, dropping it to be forgotten on the ground. Dean hooked his fingers through Cass's belt loops and pulled the Angel away from the door, guiding him over to the bed in the center of the room. Cass looked at the twin size bed and snapped his fingers, the bed became a queen size bed and Dean smiled at his Angel.

"Good thinking." Dean smirked as he pushed Cass to lie down on the bed, toeing off his shoes and socks before pulling Cass's off and climbing onto the bed, straddling his Angel's waist. The hunter leaned down and captured Cass's lips again, dominating him. The Angel bucked his hips against Dean's, their arousal's rubbing together in much need friction, causing them both to groan.

"I think we need to lose more clothing Dean." The hunter chuckled at the Angel's eagerness and how deep his voice had gotten. Dean undid Cass's belt and pulled it free from the loops of his pants. Dean then shimmied down the bed a little and opened the Angel's pants, freeing his throbbing cock. Dean arched an eyebrow at how big Cass was, wondering if he could fit him in his mouth or not. The hunter licked at the tip a little, testing the waters so to speak since this is his first time giving a guy a blow job. It tasted salty and Dean was a little unsure at first, but the sound he pulled from the Angel was worth it. The hunter took the tip into his mouth and swirled his tongue over the slit. The moan that came from Castiel could put most of the pornos he had watched to shame. It encouraged Dean to continue by taking more of the Angel into his mouth, hollowing his cheeks and sucking softly, pulling more delicious sounds from Cass. "D-Dean…what are you doing? Feels amazing…" Cass panted softly, looking down at his hunter, watching his cock disappear past those perfect pink lips. Those deep forest green eyes looking back up at the Angel as he took Cass deeper into his mouth. The heat driving Cass wild. "Dean…I feel funny…" The hunter pulled off the Angel with a satisfying pop.

"It's normal, don't fight it." Dean said, his voice a little hoarse as he took the Angel into the heat of his mouth again, taking about half of Cass's length. The hunter sucked and bobbed experimentally, trying to take more of his Angel. Dean groaned when the tip of the Angel's cock hit the back of his throat and the vibrations made Cass buck his hips, forcing Dean to take the rest of the Angel's cock down his throat. The hunter swallowed around the Angel causing him to buck again.

"D-Dean please…" The Angel begged. Dean smiled and continued to suck and lick at Cass's cock, taking him deep into his throat, his nose touching Cass's skin as he sucked him all the way down. Not knowing what else to do, Cass carded his fingers into Dean's hair, gripping it tightly in his hands as he felt a heat pull in his belly and his balls tighten. "Dean…what do I do? Something's happening…ahh DEAN!" The Angel screamed as he came down the hunter's throat, making the lamp in the room flash brightly as his true voice came out. Dean choked a little as he tried to swallow everything the Angel gave him. Tasting his Angel's ecstasy sent chills through the hunter as he cleaned Cass's cock and pulled off of him, licking his lips. Dean's cock twitched at the sight of his blissed out Angel coming down from his first high. It stroked Dean's pride to have made Cass come apart with just his mouth.

"Cass." The hunter's voice was so hoarse and rough that it sent tingles through the Angel. "What do you want me to do, Angel?"

"Want you."

"Want me how? You need to be specific Angel."

"Want you…in me…want you to claim me. Make me yours." The Angel's voice was so wrecked and lust filled that it drove Dean crazy. A growl sounded from deep within the hunter's chest as he leaned up to capture his Angel's lips in a chaste kiss.

"Finish undressing yourself then get onto your hands and knees in the center of the bed." Dean's voice was deep and commanding and it made Cass's body tremble with want. Cass nodded and did as he was told, he shimmied out of his pants and boxers before moving onto his hands and knees, displaying his bare ass to his hunter. The Angel felt so exposed and his face flushed a deep crimson, hanging his head between his arms. "Good boy." The hunter all but purred as he finished removing his clothing, groaning as his cock was finally released from its cloth prison. He walked over to his nightstand and pulled out a bottle of lube he kept on hand just in case and then walked back behind Cass. He climbed onto the bed, kneeling between his Angel's legs, setting the lube down beside him. "So beautiful, my Angel." Dean growled as he gripped Cass's hips. His cock slotted itself along the seam of the Angel's ass so he could feel his hunter's length. Cass groaned and instinctively rocked his ass against the length of Dean's hot cock.

"Dean…want you…" the Angel purred as he continued to slide his ass against Dean, making his hunter groan. Dean gripped Cass's hips tightly, stilling the Angel's movements.

"Patience Cass. I have to prepare you or I will hurt you." Dean insisted as he ran his hand along the Angel's spine. When he reached between Cass's shoulder blades, the Angel moaned loudly and leaned forward, pushing his ass further into Dean. "Cass? You okay?"

"Y-Yeah…just, oh…please…please get inside me…" the Angel begged. Dean smirked and brought his hand back and sat on his haunches as he opened the tube of lube and poured a generous amount on his fingers, coating them well before moving back to his knees again.

"This may feel funny at first but you gotta trust me, okay Cass?" The hunter stated as he trailed a lubed finger along the seam of the Angel's ass. Cass nodded and rested his weight on his elbows. Dean leaned down and kissed the base of Cass's spine as he pulled the Angel's cheeks apart and circled a lubed finger around his twitching hole. Cass whimpered and rocked his hips back towards Dean causing the hunter to chuckle before slipping his index finger past the tight ring of muscle. Cass groaned at the intrusion but moved back, trying to coax Dean in further. The hunter smirked and sunk his finger into the trembling Angel further, getting into the second knuckle. Cass's noises were making was making it very difficult for Dean not to just lube up and pound his Angel's ass into next week but he wanted to draw his Angel's first time out and make it special. "Think you can handle a little more now?"

"Yes…please…" the Angel pleaded with the hunter as a second finger was slide in beside the first, stretching the Angel. Cass whimpered at the slight burn he felt and gripped at the sheets beneath him as a distraction. "M-More…please Dean, need more of you…" Cass begged, fucking himself on Dean's fingers.

"Are you sure? I don't want to hurt you more than can be helped." Dean asked with concern.

"Yes, Dean. Please?" The Angel whined with want. Dean nodded and slide in a third finger, scissoring his fingers and twisting them in Cass's entrance. The hunter's fingers brushed against that spot deep inside his Angel, making him buck forward, a string of Enochian escaping the Angel's lips.

"Found it." Dean smiled as he let his fingers graze that spot again, loving the sound of his Angel coming undone. The hunter removed his fingers and Cass whimpered at the loss. Dean reached beside him and picked up the lube, pouring a good portion of it into the palm of his hand before capping it and tossing it to the floor. He lubed up his cock, making sure it was well coated before position the head at Cass's entrance. "You ready my Angel?" Cass looked over his shoulder at Dean and gave a small nod. "Use your words."

"Yes Dean…please…please f-fuck me…" Dean smirked at Cass's usage of words before pushing forward, the tip easing past the ring of muscle. Cass tensed up at the burning he felt and his breath quickened.

"Shh, Angel. You need to relax babe. I've got you. I'm going to go slow so you can adjust okay? Just try to relax for me." The hunter reassured his Angel, who nodded, clutching the sheets, trying to calm himself. When Dean felt the Angel loosen up, he began pulling back and pushing forward again very slowly. He watched Cass very closely for the signs of discomfort to fade before pushing a little further when moving forward, easing his way deeper until he was finally fully sheathed inside of his Angel's heat. It took all of Dean's will power not to start moving but he kept perfectly still, letting Cass adjust to his size.

"Dean move." Cass whimpered slightly and Dean obliged, pulling back until just the tip was left inside before plunging back into the warmth of the Angel's ass.

"Fuck, Cass so fucking tight!" The hunter groaned as he quickened his pace a little, trying different angles until…

"Dean! There!" The Angel cried. Dean smiled and set a punishing assault on Cass's prostate. The Angel's whole body trembled with pleasure, Enochian pouring from his lips. The shelves in Dean's room shook slightly and the lamps dimmed and then brightened again before two large black wings came into existence, arching so high that the tips hit the walls on either side of them before nearly touching the ceiling. Dean halted his movements and stared in awe at the sight before him. "Dean…please don't stop…" the Angel pleaded, clearly not realizing what distracted his hunter. Dean snapped out of his trance and started pivoting his hips again, running his right hand along Cass's spine till he reached the point between the Angel's shoulder blades. He trailed his fingers over to where the right wing connected to Cass's back before running his hand along the shiny, black, downy soft feathers of Cass's wing. "Dean!" The Angel cried again, his back arching in the most beautiful way that made Dean shiver at the sight.

"I'm not hurting you am I, Cass?" The hunter asked as he carded his fingers through the primary flight feathers.

"Ahhah…Dean! N-No…feels good." Cass moaned loudly as he pushed back against Dean, fucking himself on the hunter's cock. Dean smiled and pulled out of Cass, earning a disappointed whimper from the Angel. "Dean? What are you doing?" Dean smiled as he laid on his back beside the Angel and pulled Cass to straddle his hips. "Dean I don't know what to do."

"Don't worry Angel. I'll help you." Dean reassured him and placed his hand on the Angel's hips. Then took his cock in his other hand and held it to Cass's opening. "Okay Cass. Just ease yourself down alright?" The Angel nodded and slowly began to seat himself onto Dean's cock, groaning at the feeling of being filled again. Once he was fully seated on his hunter, Dean placed his other hand that was guiding his cock on the Angel's hip to guide him. "Okay, now slowly rise up, but not all the way, and then move back down." Cass did as he was told and moaned softly as he did it a couple of times till he got the hang of it. "Good…so fucking gorgeous Cass…Keep moving just like that. Yeah, baby. Set a pace that works for you, okay?" Dean panted. Cass nodded and angled himself till he hit that spot that made him cry out, impaling himself over and over again. "Bring your wings closer to me, Cass." The Angel did as instructed and moved his wings closer to his hunter, wrapping them in a veil of feathers. Dean moaned as he carded his fingers through Cass's primary flight feathers again and pulled slightly. Cass arched forward and shouted in Enochian again. The sounds coming from the Angel made Dean pull on the feathers more.

"Ahhah…Dean please…I…so much…going to…again." The Angel stumbled over his words making the hunter chuckle softly.

"Me too! I'm gonna cum too!" Dean panted loudly, his balls tightening and a heat pooling in the pit of his stomach. "Tell me when you feel it coming out." Dean stated as he bucked his hips up to meet the Angel's, hitting his prostate hard.

"Ah! Dean! Now!" The Angel cried out, wings pulling in Dean's grip causing a few feathers to come loose.

"Cass!" Dean groaned loudly as he came deep within his Angel, calming him as his. Cass fell forward on top of his hunter as Dean released his grip on the Angel's feathers. They stayed like this for a few moments before Cass pulled off of Dean and maneuvered his wings so he could lay beside his hunter, laying his head on Dean's shoulder. Sleep suddenly becoming a thing for the Angel. Dean wrapped his arm around his Angel's shoulders, letting sleep take hold of them.


Thank you to my Beta reader QueenBeeComplex for editing this story and finding my mistakes :3