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You’re So Pretty (When You Cry)
Dean sauntered into the bunker, Castiel right behind him. They descended the stairs, Dean glancing around for Sam, making sure the coast was clear. The two of them had just gotten back from doing some personal shopping, and much to everyone’s dismay, Sam recognized the plain, black bags. The time Dean caught Sam and Eileen strolling home with one was burned into his corneas against his will.
“Here,” Dean handed the bag to Castiel, “just hide this in your coat and take it to my room. I’ll see you in a few hours. I gotta help Sam with some research for a case.”
Castiel easily stashed the bag, giving Dean a quick kiss on the cheek before starting towards his room. “I’ll be waiting.”
Hours ticked by, and though Dean had been doing research like he was supposed to, it was a struggle to stay focused. He had much more interesting plans waiting for him.
“Alright, I’m gonna call it,” he announced, closing his book and setting it aside.
Sam shot Dean a look, then reaching across the desk and grabbing his noise cancelling headphones. “Goodnight.”
“Night, Sammy.” Dean took off like a bullet, head straight for his room.
He pushed the door open, going over to the bed where Castiel had left the bag. Grabbing it, he peered around the corner before taking off to Castiel’s room.
“Hey,” he greeted as he stepped inside, shutting the door behind him.
“Hello, Dean,” said Castiel as he reached for the remote, pausing the show he was watching and turning off the TV.
Dean set the bag on Castiel’s bedside table, then climbing into bed next to the angel. He laid on top of Castiel, pressing a gentle kiss to the angel’s lips. Castiel’s hands found Dean’s waist, holding the hunter in place. They lazily kissed each other, their movements slow and soft. There was no urgency, not when they had the rest of the night to themselves.
Castiel changed the pace first, parting his lips just enough to gently bite down on Dean’s bottom lip and pull. Dean groaned quietly, rolling off of the angel and guiding Castiel to move with him, swapping their positions. Castiel didn’t hesitate to follow along, settling on top of Dean and trailing kisses across the hunter’s jaw and neck. Dean hummed contently, tilting his head back for more and groaning when he felt the heat of the angel’s tongue press against his skin.
“You’re gonna make me forget about what we bought,” mumbled Dean, rolling his hips to tease the angel.
Castiel groaned against the hunter’s neck, then reluctantly moving away. “We wouldn’t want that.” He rolled off of Dean, his eyes trailing down to Dean’s ass the hunter reached across the bed to grab the bag.
Dean flipped the bag upside down, letting everything fall out. They’d purchased a cock ring, a vibrating anal plug, a pair of handcuffs, a red, satin blindfold, and deep throat numbing spray. The saleswoman had told them to have fun, giggling when Castiel’s entire face turned bright red.
“Think we went a little overboard?” asked Dean, mostly teasing. Most of it Castiel had chosen, his curiosity only growing the more the two of them experimented.
Castiel shot Dean a playful glare, then reaching up to wrap his hand around the hunter’s throat to yank him closer. “Considering how insatiable you are, I don’t think so.” He felt Dean swallow against his palm, his lips turning up into a faint smirk. “What do you want to try?”
Dean’s breathing shuddered, arousal pooling low in his core. “You pick.”
“Hm.” Castiel let go of the hunter’s neck, turning his attention to the pile of new toys. He looked them all over, recalling what they were and what they did, deciding what he was most curious about. He picked up the plug and the cock ring, bringing his gaze back to Dean. “These together.”
Dean’s eyes went wide, his heart slamming against his ribs. That combination was brutal, and he knew damn well he was going to be the one to wear them. “Are you trying to kill me?”
Castiel chuckled, moving forward to kiss Dean’s cheek. “You can say no, Dean. It’s all within your consent.”
“I’m not saying no.” Dean felt his face flush, the angel’s concern for him making him feel even more shy. “You open them.” He looked away, focusing on putting the other items back in the bag for now. When he turned back, both toys were out of their packaging and sitting on the bed, waiting. Right, angel mojo.
“Come here.” Castiel put his hand on Dean’s chest, leaning in and pressing their lips together.
He slowly pushed Dean down, settling on top of the hunter and trailing kisses downward. Dean let out a pleased groan, watching the angel work his way down until he reached the hunter’s cock. He lifted his hips, letting Castiel pull his sweats and boxers off. His cock was already half hard, resting against his stomach. Castiel licked a slow stripe up from the base to the tip, earning a low groan from the hunter. Dean’s hips jerked up on their own accord, chasing the wet heat. Castiel slowly took Dean into his mouth, lazily lapping at the tip, his eyes lulling shut when precum splashed on his tongue. He pulled off before Dean was too far along to wear the ring, moving back up to bite Dean’s neck, sucking a bruise onto the skin.
“Fuck,” Dean let out a soft moan, rolling his hips to grind against the angel. “You can’t keep teasing me.”
“I could,” murmured Castiel against Dean’s neck. “Is that not what these toys are for? To tease and overwhelm you?”
Dean sucked in a nervous breath, his hands wandering to grab at Castiel’s shoulders, anchoring himself. “Yeah, I guess. Fuck, you’re going to ruin me again.”
“Only if you want me to.” Castiel pressed a soft, reassuring kiss to the hunter’s cheek. “I know it was a lot last time. I don’t want to push you.”
Dean’s face flushed at the memory. Castiel had pushed him far last time, to the breaking point, but it had been exactly what he wanted. Now, he needed to decide if that was what he wanted again.
“I want to be pushed,” he said quietly, a wave of shyness washing over him. “It was a lot, but it was good.”
Castiel was quiet for a moment, considering. “I want to make sure that I don’t push you too far, even by mistake. I read online about safe words. If we use one, I’d be willing to try it.”
“Okay,” Dean gave the angel a quick peck, wanting more touches, “any ideas?” He moved to kiss and nibble on Castiel’s neck, smiling when he heard the angel sigh.
“How about ‘red’? It will mean ‘stop’.”
“Hm,” Dean gave Castiel’s neck a firmer bite, liking the idea, “okay, but that means you don’t stop unless I say it, or unless you need to stop, right?”
Castiel cupped Dean’s cheek, guiding the hunter in for another kiss on the lips. “Right.”
Dean’s lips curved into a devilish smirk as he reached down, palming Castiel through his pants. “Go ahead.”
A sound just short of a growl rumbled in Castiel’s throat. They both quickly rid themselves of the rest of their clothes, tossing everything to the side. The angel sat up, grabbing the lube out of the bedside drawer. Squeezing some into his palm, he coated the cock ring, then sliding it down Dean’s length. He brought it all the way to the base before beginning to stroke the hunter’s cock, bringing him to full hardness.
“Oh,” groaned Dean, feeling the squeeze from the ring. “Fuck that’s,” he let out a shaky breath, shifting his hips and getting used to the feeling, “that’s intense, but good.”
“You feel okay?” asked Castiel softly.
Dean nodded. “Yeah. Keep going.”
Castiel did as told, slicking his fingers with lube and pressing one finger to Dean’s entrance, slowly pushing in. Dean sucked in a breath, bracing for when the angel would hit that spot inside him. Castiel took his time, continuing to tease, deliberately avoiding the spot.
“Cas,” breathed Dean, moving his hips attempting to make the angel touch where he wanted it. “Please.”
“You’re so impatient.” Castiel pushed in a second finger, hooking them and pressing firm against the hunter’s spot. A much louder moan fell from Dean’s lips, immediately followed by a hiss of pain. His cock fought against the ring, causing an intense pressure. “Are you okay?”
“Mhm.” The faintest whimper escaped Dean. The pleasure was cut short and more overwhelming at the same time, making him already feel dizzy. “I’ll use my safe word if I need to. I promise.”
Castiel curled his fingers again, earning another shout from the hunter, Dean’s hips jerking harshly, his hands balling into fists at his sides. The angel withdrew his fingers and picked up the plug, slowly pushing it inside until the base was flush against Dean. He pressed the button on the base, the toy coming to life and making Dean nearly scream.
“Shit!” hissed Dean, clamping his hand over his mouth, gasping breaths and moans pouring out against his palm. The sensations were blinding, white hot pleasure mixed with aching pressure at the base of his cock. He whimpered against his hand, desperate for the ring to come off. There was no way he was going to be able to come with it on, at least no time soon, keeping him on the edge. “Fuck! Fuck, Cas! Cas, it’s too much!”
“You’re doing well,” soothed Castiel, his own arousal spiking watching the hunter fall apart. He wrapped his hand around his cock, stroking himself slowly. “Good boy.”
Dean whined, his entire body starting to writhe. His toes curled, his hands twisting in the sheets. All the pleasure continued to build, winding and winding with nowhere to go. “Fuck! Cas, I can’t take it!”
Castiel moved to kiss and bite at Dean’s neck, earning more desperate whines. “You’re okay.” He reached down, pressing his first two fingers to the hunter’s cockhead, moving them in slow circles that made Dean cry out. “You’re so good for me.”
“Too much, too much! Cas!” Dean felt like he couldn’t breathe. The heat in his core was burning much too hot, so deep and intense that it was starting to hurt. It was so damn good, delicious pain tangled with dizzying pleasure that set his whole body on fire. “Fuck, I can’t! I can’t!” He squeezed his eyes shut, his body going rigid.
“Use your word if you need to, Dean, otherwise I’m going to keep pushing you.” Castiel continued massaging Dean’s cockhead, his fingers wet from the steady stream of precum. “I want to see your face stained with tears again.” Dean’s eyes flew open at that statement, clear shock on his face. Castiel cupped his cheek, gently stroking his cheek. “You look fucking beautiful when you cry. I want you to feel so good you can’t help but let it out.”
Dean’s arousal only deepened hearing that, the coil in his belly wound so impossibly tight. “Fuck, I can’t Cas, I can’t.”
Castiel clicked the button on the toy, stopping the vibrations. Dean choked on a relieved gasp, catching his breath. His reprieve was short lived, Castiel immediately pushing his cock inside in the plug’s place. “Fuck, you’re still so tight.” He buried himself to the hilt, wrapping his arm around Dean’s waist to pull the hunter up at a better angle.
“Cas!” Dean was panting like he’d run a marathon, his jaw slack as he tried desperately to draw in air. “It’s too fucking much please!”
Castiel pulled out to slam back inside, relishing in the scream that tore from Dean’s throat. “You’re going to take it.” He started with slow, harsh thrusts, spacing them out to listen to Dean whimper in between each one. “Such a good boy for me. Such a good boy.” He carefully pulled out, moving slowly and watching as Dean’s bottom lip wobbled, waiting for the overwhelming thrust that was sure to come. Staying still, he waited, letting Dean continue to pant and twitch around him.
Dean’s heart hammered in his chest, the anticipation equally thrilling and nervewracking. He felt on the verge of breaking, certain that much more would push him over the edge, all whilst the ring stayed painfully snug around him. Castiel moved suddenly, making Dean suck in a breath, only to not push inside, startling the hunter on purpose. Dean blew out the breath he was holding, calming for just a moment. The angel’s eyes flashed blue, his hips snapping forward with inhuman strength. Dean’s scream caught in his throat, his entire body locked up in shock.
“Be a good boy and break for me,” groaned Castiel, getting lost in his own pleasure as he started thrusting faster.
The coil inside Dean snapped, tears welling and slipping down his face. He let out pathetic little panting whimpers, too far gone for much else to come out. Castiel didn’t let up, keeping his pace as he wrapped his hand around the hunter’s cock and pumping his fist. Dean choked on a sob as he came, thick ropes of come painting his stomach and chest. The flow of his release didn’t stop for much longer than usual, making his vision go white, his entire body convulsing. Castiel yanked the hunter roughly down onto his cock, spilling inside with a guttural moan.
A few quiet moments passed. Castiel carefully set Dean down, pulling out and gently working the ring off now that the hunter’s cock had softened. He moved up, kissing away the tears that were streaked down Dean’s face. Dean wrapped his arms around the angel, holding on tight and accepting the care.
“You did so good,” praised Castiel softly, pouring out some of his power to help soothe Dean. “Do you feel okay?” Dean nodded against the angel’s shoulder, blinking out a few more stubborn tears. Castiel cupped the hunter’s cheek, making their eyes meet. “Dean, talk to me, please.” Dean swallowed, slowly shaking his head. He buried his face in the crook of Castiel’s neck, pressing gentle kisses, trying to convey that everything was okay. “Okay, take your time.”
It was a few minutes before Dean managed to speak, his voice strained. “Hey, Cas.”
Castiel gave the hunter a small smile, kissing him on the cheek. “Hi, are you okay?”
“‘M good. I’m tired.” Dean snuggled closer, letting his eyes fall shut. “Wake me in ten, and I’ll clean up.”
Castiel pulled him impossibly closer. “Whatever you wish.”