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Where's Your Pretty Wings?

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Castiel opened the door quietly in case Sam and Dean were still asleep, a tray of coffee and a bag of pastries in hand. He would cuddle with them at night, but since he didn’t sleep, he liked to slip out of bed early in the morning and get his favorite humans breakfast. He’d been studying their behavior when purchasing food, mastering the technique, just so he would be able to do this.

He shouldn’t have worried about waking them. Sam and Dean were both up and dressed. Sam was sprawled on the bed typing on his laptop, and Dean was rubbing a towel over hair that was still damp from a shower. They both looked up at Castiel when he entered.

Castiel raised the food. “Breakfast,” he offered. He walked over to the table and set it down.

Sam closed his laptop and put it away, folding his strong arms behind his head. Dean was starting to grin when Sam asked casually, “Where’s your pretty wings, angel?”

Castiel stiffened, freezing for a moment. The phrase was a code, a question. He glanced up at the Winchesters and saw them both grinning at him with more than a little hunger. Anything other than the specific reply for “yes,” and they would back off. Castiel swallowed.

“...I don’t show them to sinners.”

Dean bit his lip and stalked over to Castiel. Castiel backed up until he was pinned against the wall, Dean leaning over him.

“And do you know what sinners do to angels?” the hunter asked softly.

Castiel swallowed. His heart was pounding, and it was staggering how hard he was already, without even being touched. “Wh-what are you talking about?”

Castiel shuddered when Dean’s fingers trailed hungrily over his chest. He pressed back against the wall, panic starting to grow in his voice. “...What are you doing?”

“Gonna get myself a taste of Heaven,” Dean whispered, leaning in to lick at Castiel’s ear. Castiel flinched, trying to shove him away, careful to use only the strength of his vessel.

“Stop, that’s not—Th-this is sinful, I won’t do it!”

“Don’t worry,” Dean purred, sliding his hands between Castiel’s legs and making his struggles falter. “We’ll make you love it.”

Dean grabbed Castiel’s tie and used it like a leash to drag him away from the wall. He guided Castiel over to the bed, still looking him up and down hungrily. “Looks like we caught us an angel, Sammy.” He bit his lip and tilted Castiel’s chin up gently. “What should we do with him, hm?”

Sam tsked, still sprawled on the bed. “He’s wearing far too many clothes.”

Castiel’s heart was racing. He choked when Dean grabbed his trenchcoat and shoved it off his shoulders, letting it drop to the floor.


“You think the rest of him’s as pretty as his face?” Dean mused, undoing Castiel’s tie and grabbing the collar of his shirt. Castiel yelped when Dean literally ripped it open, buttons flying across the room. His clothes rarely survived these little games, but it was a simple matter to fix them, and so worth it.

“I bet he is.” Sam bit his lip, shifting to get comfortable on the bed. “Come on, let’s see the best part.”

Castiel squirmed in Dean’s hold as his shirt was torn off his arms. “Wh-what are you talking about? Please, stop!”

Dean made a low, threatening noise that had Castiel’s heart skipping. “He’s struggling too much.”

There was a jingling noise from the bed. Castiel couldn’t turn around, but he knew it was the handcuffs. Thick leather straps connected by a short chain, branded with just the right Enochian sigils to keep him from struggling. He’d helped Sam and Dean make them just for this game.

“Looking for these?” came Sam’s voice from behind him.

Dean grinned and held up his hand, catching the cuffs when Sam tossed them. “Now you be a good little angel,” he whispered to Castiel, grabbing his hands and wrenching them behind his back. “And we’ll be gentle with you. We’ll make you love it, I promise.”

Castiel tried to yank his hands away, whimpering when Dean attached the cuffs. His whole body shivered as he tried to struggle—really struggle, throw his angel force behind it—and couldn’t move.

“D-don’t do this,” he begged. “Please, this is wrong—”

Dean silenced him with a kiss, deep and hungry, devouring his mouth like it was the sweetest thing. “It’s not our fault, you understand that, right?” he panted as he pulled back, yanking at Castiel’s pants. “A mortal just can’t resist an angel. We need to have you.”

“S-stop, please, you have to stop—”

“Can’t,” Dean groaned, sucking on Castiel’s lips between words, yanking his pants down and grabbing his bare ass. “You’ve gotta know what you’re like, what people see when they look at you. So damn beautiful. The way you look, the way you move, fuck, you even smell pure.”

Castiel heard a low whistle from the bed, and whined as Dean squeezed his bare ass again.

“There’s the part I wanted to see,” came Sam’s drawl from the bed. Castiel heard shuffling, and he craned his head around to see Sam pulling his shirt off. The sight alone made his heart jump into his throat. When Sam grinned and started tugging down his jeans and boxers, revealing a line of dark hair and then the first veiny inch of his cock, still caught in his jeans, Castiel’s knees almost gave out.

He felt Dean chuckling against his neck, felt Dean let go of him for a moment and pull his own shirt off. But he couldn’t take his eyes off the sight of Sam’s thick shaft being revealed inch by inch, finally springing up against his toned stomach as the jeans pulled down. Sam gave it a slow stroke, looking Castiel over, and Castiel bit his lip on a hungry noise.

His attention snapped back to Dean when he heard a zipper being undone. Dean gave him that crooked half-grin he always had, dragging his jeans down. Castiel started to back up and stiffened when Dean grabbed his hair, dragging him close and breathing against his lips.

“You’re not going anywhere, angel,” he panted, brushing his lips over Castiel’s as his jeans dropped to the floor. Castiel felt Dean’s cock bump against his own, rubbing thick and hot against his stomach.

“L-let me go, please,” he begged. “I-it’s a sin to hurt an angel.”

“Oh, we won’t hurt you,” Dean purred, nuzzling his face against Castiel’s neck and kissing it. “Just gonna make you feel really good. Make your wings quiver.”

Dean was kissing Castiel again, herding him back towards the bed. Castiel tried to squirm away, whimpering in fear. It was hard enough to fight against Dean with his hands cuffed, but once Sam was grabbing him too, big hands splaying over his body, they’d be able to move him around however they pleased.

The thought made his hard cock throb against Dean’s stomach.

Castiel gasped and lurched back from Dean’s mouth when Sam grabbed his ass and squeezed. Sam let out a low groan that made Castiel’s breath catch.

“Oh fuck, can’t believe that’s all for us...”

Dean sucked marks onto Castiel’s neck, giving his hard cock a stroke. “Gonna make it so good for you, angel, you’ll be begging for more...”

“S-stop, please...” Castiel could barely find the words. Sam grabbed his hips suddenly and turned him around. Castiel’s cock bumped against Sam’s pectoral muscles, leaving a glistening smear of precome, nestling into the dip between them. Sam was panting up at the angel, holding his hips firmly.

“God, you look so good,” he groaned, running a hand up Castiel’s chest. He sucked a bruise onto Castiel’s stomach, his fingers finding one dark little nipple and twisting gently. Castiel gasped, hands clenching in their cuffs.

“W-wait, don’t... a-ah...”

Dean was kissing down Castiel’s back, murmuring words of praise against his spine. Castiel tried to tug away when he felt Dean grab his ass and spread it.

“Wait—not there—”

Castiel cut off with a groan as Dean’s tongue swiped over his hole. He could feel Dean moaning against him, hear the muffled words, “Fucking perfect...” before Dean buried his face in Castiel’s ass.

Castiel was panting. “S-stop, it’s... it’s sensitive...” The words choked off in moans as Dean licked and sucked.

Sam slid off the bed, kneeling in front of Castiel and giving his cock a stroke. “You look so sweet,” he murmured, giving the head of Castiel’s cock a kiss. “I gotta taste that...”

Castiel gasped when Sam’s mouth slid over him, warm and wet and suckling gently. He felt Dean groaning behind him, felt strong hands running over the curves of his legs. He could hear Dean shuffling forward, felt one of the hands leave his legs, and a second later Sam groaned around his cock. Castiel could imagine what Dean was doing, and the mental image of Dean rubbing his big cock against Sam’s was almost enough to make his knees give out.

“Please,” Castel panted, trembling. “P-please, I can’t—”

Sam’s wet mouth was nursing him into a state of throbbing. Castiel let out a needy noise when Dean’s tongue plunged into him, thrusting, working him open.

“Oh God, oh God, I’m going to—”

Sam looked up at Castiel and slid him into his throat. Castiel shouted and twisted against the cuffs as he came in Sam’s mouth, gushing come into it. He could feel Sam swallow it, saw a trickle run down Sam’s chin when he pulled back with a smile.

“You taste just as sweet as you look, angel,” Sam whispered, giving his cock another kiss. Castiel panted down at him, his sensitive cock jerking when Sam stroked it.

Sam stood up, and Castiel gulped when the hunter towered over him. Sam’s hand was on his hip, holding him still, the other still grabbing his cock. Then Dean was standing up too, stepping next to Sam, tilting his brother’s face towards his gently.

“Got a little something there, Sammy...” he murmured before leaning in and licking the come off of Sam’s chin. Sam let out a breath at the touch, ducking his head down to press his lips against Dean’s. Dean groaned and ran his hand down Sam’s stomach, finding his cock and giving it a squeeze. A thin, excited noise escaped Castiel, and Sam and Dean pulled apart with wet lips as if just remembering he was there. They kept their faces close, lips almost brushing as they looked him over from the corners of their eyes, like he was a dessert they couldn’t wait to sample.

Castiel gasped when Dean’s hand found his slick cock and gave it a stroke. “I think our little angel wants more,” he purred.

Castiel shivered, twitching under the touches. Since he’d started having sex in his vessel, he’d always been able to go for multiple orgasms. It was probably an angel thing. But God... after the first one, everything was just so twitchy and sensitive, he was on a hair trigger. Just the light touch of Dean’s hand had him wriggling.

Castiel gave a startled grunt when Sam tilted his chin up and kissed him. His eyes fluttered closed and he moaned, hips jerking forward into Dean’s hand.

Sam pulled back, brushing his thumb over Castiel’s wet lips, taking in his flushed face and hazy eyes.

“I think our angel is starting to enjoy sin,” he whispered.

Castiel swallowed, trying to pull back. “I—I’m not—”

Dean grabbed Castiel’s ass when he tried to retreat, squeezing it possessively and holding him close. Castiel’s protest was cut off as Sam claimed his mouth again. His back arched and he muffled a plea into Sam’s mouth when Dean’s grip on his ass shifted, a finger nudging against his wet hole. Dean let out a low, hungry noise that had Castiel shivering.

“Fuck, I gotta try that...”

Sam pulled back from Castiel’s mouth and sat down on the bed. He kept a firm grip on Castiel’s hair, tugging his head down. “You can have his ass,” Sam panted. “I want those sweet lips.”

Castiel struggled, but with the cuffs holding back his angel power, he couldn’t hope to match Sam’s strength. Sam bent him over easily, pushing Castiel’s face against his thick cock. Castiel tried to turn his face away when Sam offered it to his lips.

“Come on, beautiful,” Sam breathed. “You’ll love it.”

Sam’s cock pressed against his lips, leaking precome onto them. Trembling, Castiel let his mouth open, and Sam’s cock slid in.

“Ahh, god, yeah...” The groan rumbled through Sam’s chest as Castiel sucked him gently. Sam stroked Castiel’s flushed cheek, using his other hand to pull the angel’s head down, sliding further into his mouth. “Knew you’d be good at cocksucking, got such a beautiful mouth... looks amazing with my dick disappearing into it...”

Castiel let out a little groan when Sam’s hand started forcing his mouth up and down. His cock was still hard between his legs, swollen with the pleasure of Sam’s thick, juicy cock being pumped in and out of his mouth. Castiel felt a hand slide over his ass and shivered, suddenly feeling exposed.

“Look at you,” Dean purred, “all bent over and helpless... Can’t fucking help it, I just...” The hand squeezed. “God, I need that.”

Castiel squirmed when he felt Dean force his legs apart. He managed to pull his mouth off of Sam’s cock for a moment, gasping.

“N-no, please!”

Dean slid a lube-slick finger into Castiel’s body, making the angel cry out. “Look at that beautiful little hole. You’re gonna take my cock so nicely...”

“P-please, not that!” Castiel begged, tugging against his cuffs. He felt Sam’s cock nudging against his cheek, he could hear the tall hunter panting. He knew Sam was watching Dean over his back.

Dean let out an amused breath, sliding his fingers out of Castiel gently. “Open wide, angel,” he teased, grabbing Castiel’s ass and starting to push his cock in.

Castiel gasped when he felt Dean force inside him. Dean’s hands were firm on his hips, holding him in place as he pushed in. Castiel tensed up, trying to squirm away, begging breathlessly for Dean to stop, whimpering when the hunter only sunk deeper.

“Oh fuck, that feels good. Squeezing my dick like that...”

Castiel cried out when Dean’s hips rolled in a a slow thrust. The wet slide of that cock in and out of his body, stretching his hole and rubbing up inside him, soon had him panting. Dean’s strong hands were grabbing his ass, spreading it, and he could almost imagine how he looked, bent over and impaled on the hunter’s cock...

Sam tilted Castiel’s face up gently, giving him a crooked smile before sliding his cock into Castiel’s open, breathless mouth. Castiel moaned, shivering when Sam’s hand tightened in his hair, dragging him down the shaft. He choked when it pushed into his throat, but let Sam move his mouth up and down as he pleased. Dean thrust hard into him and Castiel gagged. Rationally, he knew that a hand signal would be all it took to make the boys stop, but emotionally, he felt completely helpless, tied up and held down and used from both ends, unable to even cry out. When Dean’s hand closed around his sensitive cock, Castiel’s back arched.

“Little angel likes this,” Dean purred, pumping slowly in and out while he stroked Castiel’s twitching hard-on. “Gonna come for us, sweetheart? Gonna come with cocks filling you up?”

Sam chuckled and Castiel whined. “Naughty angel,” the hunter murmured, stroking Castiel’s dark hair. “Letting a pair of humans take you like this.”

“You had to know we’d do it,” Dean panted, quickening his thrusts. “You must have wanted it, coming here alone, god, the looks you gave us with those beautiful blue eyes...” Dean sounded like he had his teeth clenched. “Fuck, can’t fucking resist you...”

Castiel tried to scream and his cock jumped in Dean’s hand as it shot a milky rope of come across the floor. He whined around Sam’s cock as he came, shuddering in pleasure. Sam was whispering to him, stroking his hair, letting out little grunts of appreciation as Castiel sucked on him.

“So beautiful when you come, you’ve got no idea, god... mmh, you just f-feel so good...” Sam shut his eyes and hissed when he pulled Castiel’s mouth down, pushing into his throat. “God, just need to have you...”

Dean pulled out of Castiel slowly, thumbing his loose hole. “Your ass looks great after taking a cock, angel.” He gave Castiel’s cock a gentle stroke and Castiel bucked, pleasure lancing through him. “Want it to look like that all the time. Wanna have you loosened up on our dicks twenty four seven.”

Castiel managed to pull his mouth off of Sam’s cock, lips and flushed slick from sucking. “N-no, please, just let me go!” he begged.

Sam shook his head. “Let you go? God, we couldn’t. Couldn’t stand to stop touching you.”

Castiel yelped when Sam grabbed him and pulled him onto the bed, moving him around like he weighed nothing. Sam lay down on his back and dragged Castiel on top of him with a groan, holding his hair and kissing him. For half a second, Castiel forgot to roleplay and ground his hips forward against Sam’s, his naked body sprawled over the hunter’s while Sam nipped and sucked at his lips. His legs were spread over Sam’s, the hunter’s thick cock pressed up against his achy, twitching one.

He felt the mattress sink down as Dean climbed onto the bed. A second later there were hands on his ass, squeezing it, pushing him up on his knees.

“Fuckin’ beautiful,” Dean murmured, brushing his wet cock over Castiel’s skin. “Look so good when you’re getting fucked, angel.”

Castiel shuddered, then shouted in alarm when Sam grabbed his hips with a loud groan and pulled Castiel down on his own cock, thrusting up into him.

Dean snarled. “The fuck, Sam?”

“F-fuck, he’s so fucking tight...” Sam groaned into Castiel’s neck as he thrust into the angel. All Castiel could do was lie there, panting, eyes rolling as Sam’s big cock pumped into him.

Dean’s hands grabbed his hips suddenly, pulling him off of Sam’s dick. Castiel didn’t have time to so much as breathe before Dean was plunging into him, sliding easily into his loose hole. Dean grunted and held Castiel’s cuffed hands roughly, shoving his hips forward hard.

“God, God, God, God...” Castiel’s tongue hung out as Dean drilled into him, his face flushed with pleasure.

Sam growled possessively and grabbed Castiel’s ass, pulling him off of Dean’s cock again and back onto his own. Castiel let out a keening cry when Sam thrust up into him hard, the blunt head of his cock pumping deep inside Castiel.

“Knew you’d love this,” Sam panted in Castiel’s ear. “Having that sweet ass filled up.”

Castiel couldn’t even form a response. He felt Dean touching his ass, brushing fingers over his stretched hole, over Sam’s slick shaft pumping into him.

“God...” Dean pushed a finger against the taut skin, and Castiel let out a long, frantic groan when he slipped it in alongside Sam’s cock. “Can’t believe how much you can take, angel. You were just made for this, made to get fucked.”

Castiel whimpered, trying to keep himself loose and relaxed around the girth of Sam’s cock and Dean’s finger. “P-please, stop, it’s t-too much...”

Dean pushed in another finger and Castiel gasped, cock pulsing against Sam’s stomach. He felt Dean’s fingers pull out, felt the hunter pull him off of Sam’s cock.

“G-god, gotta be inside you again,” Dean panted, guiding his cock to Castiel’s loose hole.

Sam growled and bumped his own cock against Dean’s. “Wait your turn.”

“It is my turn,” Dean shot back, teeth bared.

Castiel whined. He could feel both Sam and Dean rubbing against his slick hole, smearing precome all over him, thick cocks bumping against each other. Dean started tugging him back, nudging into him, and Castiel shouted when Sam started to push in alongside.

“A-ah, Sam...” Dean hissed as his brother’s cock pressed against his, both of them pushing into Castiel’s body. He grabbed both cocks in one hand, squeezing them together, and Sam grabbed Castiel’s hips and pulled him down on both shafts.

Castiel shouted into Sam’s neck, his hole aching around the stretch of both Winchesters at once. Sam kept pulling him down until Castiel could feel Dean’s hips pressed against him, his ass pushing down against Sam. He felt stuffed, he swore his stomach was bulging out with the mass of both those huge cocks crammed inside him. Sam throbbed inside him and Castiel whimpered. He felt so damn full he was scared to move an inch, wasn’t sure if any of them would be able to move.

And then Dean thrust and Castiel almost screamed.

Sam buried his face in Castiel’s neck, squeezing his ass hard. “F-fuck!”

Dean leaned over Castiel, rolling his hips forward. He panted each time his cock slid across Sam’s, packed tight inside Castiel’s body. Castiel was practically sobbing. He could feel both Sam and Dean twitching inside him, ready to blow, flood him so much it dripped out—

Sam thrust up into him alongside Dean, and Castiel’s back arched and he cried out, “Yes!”

“Uh, Cas, buddy,” Dean murmured, his voice shaky. “...That ain’t your line.”

Castiel swallowed, trying to collect himself. “Right. Sorry.”

Sam smirked, squeezing Castiel’s ass as he thrust into it. “Ah, let him ask for more if he wants to. I like hearing it.”

Dean nipped Castiel’s neck, hips bumping against his ass with each thrust. “Wanna beg us for more, angel?”

Castiel whined, squeezing around both hunters. “N-no, please—”

Sam groaned, his massive body shuddering under Castiel. “Oh god, m’not gonna last much longer...”

Castiel squirmed, tightening up again. “N-no, don’t come in me!”

“Can’t help it,” Dean panted against the back of his neck. “F-feels too good, can’t stop...”

Castiel gasped as Dean picked up the pace, slamming into him. “D-don’t, don’t, please, it’s...” He let out a helpless little whine. “It’s w-wrong, I’m not supposed to—”

“Not supposed to let humans come inside you?” Sam panted. He groaned and wrapped his arms around Castiel’s body, hugging him close. “G-god, you’re so tight... no way I’m pulling out...”

“Gotta come,” Dean panted, hands fisting in the sheets. “Can’t fucking stop, gotta—fuck!”

Dean groaned and ground his hips forward as his cock pulsed inside Castiel. Sam was cursing breathlessly, his fingers digging into Castiel’s back hard enough to leave bruises as his brother’s cock throbbed against his. Then Sam let out a shuddering groan and started coming too, filling Castiel while he was still squirming and sobbing, “No, no, no, stop!”

Sam kissed Castiel’s neck and reached under his body, finding his sensitive cock and stroking it. Castiel gasped. Sam was still rocking his hips up, sliding his fat cock lazily through the come in Castiel’s sore ass. Castiel could feel it dripping out of him, hot and messy, and he trembled and shouted and clenched around the Winchesters as Sam stroked him. Dean nuzzled his hair and whispered, “Come for us, angel.”

Castiel came so hard he almost blacked out.

He was panting into Sam’s chest when the stars cleared from his vision, and his ass felt like it was on fire. Dean pulled out first, hissing and shivering, before flopping down on the bed with an exhausted huff.

“Amen,” he panted, holding a hand up. “I’m out.”

Sam gave an exhausted nod, wiping the sweat off his forehead. “Amen. Me too.”

Dean rolled over and unlatched the handcuffs, tossing them to the floor. Castiel let out a satisfied breath as he straightened up and stretched his arms, still straddling Sam, still with the hunter buried inside him.

Sam tensed, hissing. “G-god, Cas, little sensitive here!”

“Oh, sorry.” Castiel pulled himself off, sitting on the bed next to Sam and watching the two brothers try to catch their breath. His cock was still hard, but that would fade in time. “Amen” was the safeword that meant “done for now,” and he would respect that. In any case, it would take days to exhaust him, and his poor humans weren’t up to that. They looked completely wiped out.

Castiel bounced out of bed, reaching his arms above his head and stretching with a happy sigh.

“I feel very good right now,” he announced cheerfully.

Dean gave him a weary thumbs-up. “Kudos.”

Castiel walked to the table where he had set down breakfast, reaching into the brown paper bag and fishing out a scone. He took a bite before picking up the tray of coffee and carrying it to the bed. “Fuel for your human batteries?” he offered.

Sam made a moaning noise and reached a needy hand out. Castiel handed a cup to him, sitting down on the bed and taking another bite of scone as Sam nursed his coffee.

“So,” Castiel said brightly. “What are we doing today?”

“Dying,” Dean groaned, pulling a pillow over his head.

Castiel sighed and continued nibbling his scone, letting the Winchesters catch their breath. His humans needed a lot of taking care of, but they were worth it.