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Dean woke up next to Castiel, snuggled right into his chest and held tightly in a pair of strong arms. He reluctantly slipped out of them, stumbling out of the bed with a wince and into the bathroom. He shut the door and quickly peed, washing his hands in the sink and looking at himself in the mirror.
He was a mess.
There were marks all over his neck and back that he didn’t even remember getting. His eyes were a little bloodshot and his short hair was all over the place. His wrists were a little bruised, and his ass throbbed with a reminder of Castiel’s fucking monster dick; his entire body ached. And he had a contented, if slightly dopey, grin on his face.
He limped out of the bathroom, grimacing at the sting in his ass. He quickly and quietly redressed in his old clothes. Dean wondered if he should leave a note or something for Castiel, but then remembered they had each other’s numbers. If Castiel wanted to talk to him again, he’d contact him. Dean locked the handle of the motel door and stepped out, pulling it shut behind himself. He wiggled the handle and nodded, finding it decently secure.
He shuffled back to his car, unlocking the door and sliding inside. Dean groaned softly as he sat down, shifting uncomfortably. It was fucking worth it. He slammed his door shut and started his car, letting the engine heat up for a moment before shifting gears and pulling out of the nearly empty parking lot.
Castiel didn’t contact him for three and a half weeks. Dean was in the middle of English class when his phone buzzed with a text from ‘Cas,’ his nickname flashing on Dean’s screen followed by an apple emoji. He shuffled down in his seat and opened the message, frowning.
Castiel was asking if he was free tomorrow night. Tomorrow was Thursday, but the day after was a day off for high school students. ‘no’ he wrote quickly, disappointed. ‘i have work tmrw night. friday?’ Castiel’s reply took a few seconds.
‘I see.’
‘I’m busy Friday and this weekend.’
‘You work?’
'yep’
‘gotta get money somehow’
‘Of course.’
‘i can myb switch my shift arnd’
It might take some pleading, but Benny was usually willing to switch shifts with Dean if he ever asked. Something about wanting him to live his life while he’s still young.
‘Where are you right now?’
‘class’
‘I’m sorry. I didn’t realize.’
‘its ok’
‘its boring’
‘i hate english class’
‘I’m an English professor, Dean.’
‘well fuck me’
‘I did.’
‘well fuck u’
‘If you know how to use that little cock of yours, sure’
‘srsly man fuck u’
‘I’m sorry. Did I offend you?’
‘no but fuck u’
‘I don’t understand.’
‘nvm’
‘wrud’
‘Excuse me?’
‘what r u doing’
‘jfc dude get with it’
‘What does that mean?’
‘jesus’
‘fucking’
‘christ’
‘I am not doing much. I am waiting for my next class.’
‘slackin off prof?’
‘Hardly. It appears you’re the one slacking, young man.’
‘I wonder if I should punish you.’
Dean almost choked as he read ‘young man’ and ‘punish’ because fuck. It reminded him of a porno he’d watched a while ago. His cock twitched in his pants, and he squirmed a little bit, uncomfortable.
‘dont’
‘Don’t?’
‘Don’t, what? :)’
‘just... srsly pls not rn’
‘Are you getting hard, young man? How very naughty.’
‘fucking hell man’
‘Are you hard? Is your cock throbbing in your panties?’
‘yeah’
‘Good boy.’
‘awfuck’
Dean bit his bottom lip to refrain from whimpering. He glanced up to check if his teacher was watching him, but he didn’t seem to be.
‘Touch yourself.’
‘And send me a picture.’
Dean squirmed again, biting his lip harder. He looked around him, but no one was paying him any attention. He sat alone in the back of the classroom, with his bag on the chair beside him. He was hidden from the side, and the student in front of him was so close to the front of his desk that he had nothing to worry about. The desks in this classroom were the ones with the holes for books and pencils in them, so they were thicker and could easily block him. Dean swallowed thickly and tentatively cupped himself in his hand. He inhaled sharply, cock pulsing in his grip. Dean quickly pulled up his camera, snapping a photo and sending it to Castiel.
“Alright, class-”
Dean jolted, ripping his hand away from his cock and lifting his head with wide eyes. His teacher didn’t even notice him. Dean licked his lips, and shuffled his butt in his seat. His teacher put on a short film, one that would last for the rest of class. So... five minutes, great. People basically ignored it, all of them slipping down to text each other or their other friends in different classes and look at their social media. Dean pulled up his phone again, unlocking it to check his unread messages from Castiel.
‘So good, Dean.’
‘Unbutton your pants for me.’
‘dude i cant’
‘I’m not asking.’
‘holy shit i hate u’
‘That’s alright. ;)’
It was followed by a picture that Dean quickly opened. It was a picture of his cock, it was as thick and long and hard as Dean remembered it being. His mouth started watering, and he licked his lips again as he imagined sucking it down, choking on it. Dean nervously unbuttoned his pants with one hand, pushing his jeans open and reaching inside to tuck his panties behind his cock. It pressed into his balls and god, it felt so good. Dean snapped a quick photo and sent it to Castiel.
The bell rang. Dean sat forward immediately, quickly moving his shirt to cover his crotch. He shot Castiel a quick text. ‘class is over’ He stuffed his phone into his pocket. The students around him quickly left, so he hastily buttoned and zipped his jeans up, standing up to begin collecting his books.
His knees weakened as he felt his panties press tightly into his balls. There was a prominent bulge in his jeans and he could feel his cheeks begin to warm up. Dean shoved his things into his backpack, using it to block his crotch as he darted out of the room and headed for the bathroom. He locked himself in one of the stalls, trying to ignore the kids shuffling by the sinks and urinals. Dean dropped his backpack to the floor, pulling his phone out to look at Castiel’s messages.
His phone started buzzing in his hand before he could read them. Castiel was calling. He quickly answered, holding the phone to his ear. “Hey, princess,” Castiel said immediately, voice rough and deep and so fucking perfect. Dean had missed it. He shivered as it rumbled through the phone and into his ear.
Dean quickly unbuttoned his jeans, shoving them down to mid-thigh along with his panties. He switched his phone to his left hand and wrapped his right hand around his swollen cock. His poorly concealed moan elicited a chuckle from Castiel. Good thing it was loud enough in the bathroom that Dean knew no one could have heard him.
“Are you touching yourself, princess?” Dean whimpered quietly. “Oh, a very naughty boy, aren’t you?”
“Yeah,” he whispered, listening as the warning bell for the next class went off. The students quickly left the bathroom, and Dean stopped breathing for a second as he waited to make sure they were all gone. He dropped to his knees and checked for feet. None. Perfect. “Please. God, I’m gonna come.”
“Not yet,” Castiel replied immediately, moaning softly. Dean could hear the slick sounds of his hand on his cock, the slide was no doubt wet and easy and perfect. “Let go of your cock, little boy.”
“Come on, man,” he groaned, reluctantly obeying.
“Where are you, Dean?”
“Bathroom stall,” he said, glancing at the walls. He was at the end so there were two concrete walls and two dark green ones. “Come one, old man, I need to come. It fuckin’ hurts.”
“Yeah?” Castiel laughed, the sound dark and uncaring. “What if I told you to bring yourself right to edge and stop? Huh? Would you? Would you be a good little boy for me and stop?”
“God, yes,” Dean whined, cock twitching. “Please, don’t. Can-can I touch myself?”
“Sure, princess,” Castiel started. “But you won’t be coming until I see you tomorrow if you do.” Dean clenched his jaw, glaring daggers at the green door of the stall. “Aw, are you mad, princess?”
“I don’t have to fuckin’ listen to you,” Dean said through clenched teeth.
“Of course not. But you want to. Very badly. You want to be a good boy for me, isn’t that right?” Dean refused to answer. “How about this, you touch yourself right now, jerk off your cute little cock until you make a mess, and you come on my cock tomorrow. How’s that sound?”
“Too good to be true,” Dean admitted. Really, it sounded too good. “What’s the catch?”
“Allow me to clarify, you come untouched on my cock tomorrow.”
“Easy,” he said slowly. Not true. He’s tried it but he’s never come untouched before, he needs at least a small touch on his cock, something to push him over the edge.
“We’ll see,” Castiel murmured. Dean wrapped his hand around his cock again, stroking from base to tip and letting out a loud, pleased moan. “As beautiful as you sound, princess, I have to go.”
“Fuck you,” Dean muttered. “You called me.”
“I know,” he sounded guilty. “I’m sorry.”
“Bye,” Dean muttered, hanging up. He pressed his head to the stall door and quickly jerked off, bucking his hips and spreading his legs further apart as he felt his balls tightening. Dean let out a soft cry - muffling the sound by stuffing his fingers in his mouth, as he came all over his hand and the door, come dribbling onto the floor. He blinked a few times, shakily lifting his hand and snapping a photo of the mess to send to Castiel.
He got a reply moments later. ‘Beautiful.’
‘whrs my pic?’
‘Can’t, princess. I have class.’ Dean quickly realized that Castiel hadn’t gotten off. He must have stopped because he was going to be late. Damn. ‘Later. Promise.’ Well, shit.
He kept his promise. Just as Dean was getting ready for bed, Castiel sent him a video of him jerking his cock almost desperately, making a mess all over his neat suit and hand. Dean bit his lip, wondering what he should reply with. He chose Castiel’s own word.
‘beautiful’
Castiel arrived early to the motel on Thursday, booking the same room as last time and shooting Dean a text to tell him. He took his briefcase into the room with himself, pulling documents out of it and spreading them on the small wooden table beside the sink. He figured he could do some grading before Dean got here. He usually lost track of time when he was grading.
He was more than halfway through his grading when Dean showed up, stepping into the room with a tentative gaze. Castiel finished the paper he was working on and set his pen down, leaning back in his chair to gaze at Dean. Dean stared right back at him, shuffling his feet nervously and looking all kinds of adorable with his lip biting and flushed cheeks.
“Uhm,” he tried, clearing his throat. “Hi.”
“Hello, Dean,” he replied, giving Dean a small smirk. He dropped his gaze to Dean’s clothing, slowly dragging his eyes down the length of him, lingering on the bulge already forming at his crotch. “Come here.” Dean obeyed like the good boy he was, padding over to Castiel and shifting his weight from foot to foot beside him. “Take your shoes off.”
Dean quickly toed them off, pulling his socks off as well. He hesitated for a second then sat astride Castiel’s lap, pressing their crotches together and placing his hands on Castiel’s shoulders. Dean grinned at him, cocky, and raised an eyebrow. “Come on, old man,” he said. “Want you to fuck me.” He leaned closer, brushing his lips against Castiel’s.
“Ask nicely, boy,” he cooed, grinning at Dean’s slight glare. “And I’ll consider it.”
“Please, Cas,” he murmured, shuffling his hips. “Need your cock. Need you to fill me up good. Please.”
“I’m not very convinced,” he replied. Castiel grasped Dean’s hips tightly and pushed his chair back, carefully standing and carrying him over to the bed. He pressed his knee into the edge and dropped forward, bracing himself with his arms and watching Dean bounce a little beneath him. He grinned at the surprised green eyes that looked up at him, and leaned down, biting and sucking on Dean’s bottom lip. “Try harder.”
“Please, sir,” Dean tried when Castiel pulled back. He swallowed audibly. “Please, I-I just... need you, need your cock. I feel so empty, want you to fill me up. Want you to fuck me until I can’t walk straight. Please, fuck. I dunno. Just- Please, please, please, please-”
“Shh,” Castiel hummed, leaning down to shut Dean up with a kiss. He nudged Dean’s legs further apart and pressed their crotches together, rolling his hips and grinding down on him. Dean choked on a moan, arching his back and bucking up, desperate. “I got you.”
Dean whined as Castiel shifted his position, legs on either side of Dean’s right one. He pressed his right thigh against Dean’s cock, firm and hard. Dean gasped, lifting his gaze to stare Castiel in the eye. “Please,” he mouthed. Castiel could feel his cock throbbing against his thigh, twitching and leaking as he rubbed himself against his leg. He was pressed firmly up against him, hips moving quickly. “Oh... Oh, fuck.” Dean tucked his face into Castiel’s blazer, coming in his pants with a soft, ashamed keen. “Shit, shit, shit- Sorry, uhm-” Dean refused to move his head to look at him.
“That’s alright,” Castiel said, a little surprised by how quick he came. “You’ll just come again for me, won’t you, princess?”
Dean nodded almost shyly. He smirked and slid off the bed, reaching up to begin undoing his tie. Dean watched him with parted lips, his beautiful green eyes wide and full of want. Castiel pulled his tie from around his neck, dangling the thicker end between Dean’s legs. He made sure Dean was watching as he pooled it on his wet crotch. Dean looked back up at him, nervous and hopeful, so he winked.
“Get naked,” he ordered, setting back towards the table. He carefully put his papers back in his briefcase and pulled out a bottle of lube and condoms from it. He turned around to find Dean’s clothes thrown on the floor carelessly, and him shuffling on the spot wearing- Wow. He was wearing a pair of white stockings with a lace trim at the top, with a matching lace garter belt and panties. He looked pretty, and so very hot. “Shit,” Castiel whispered to himself.
“D-Do you like it?” Dean asked, nervous. He looked terrified, like Castiel would throw him out. “It’s... more than the panties... I- I dunno-”
“You look... beautiful, Dean,” he said, walking back over to him. He dropped the items in his hands onto the bed and grabbed Dean’s hips, pulling him in close and wrapping his left arm around Dean’s back, his other hand sliding up Dean’s arm, over his shoulder and neck and cupping his jaw. He leaned closer and kissed him deeply, pressing his tongue into Dean’s mouth and savoring the sweet taste that greeted him. Dean gripped at his blazer with his left hand, his right arm reaching up to wrap around his shoulders.
“Come on, old man,” Dean murmured after a few minutes. “I stretched myself for you. Just- Please don’t tease me.”
Castiel hummed. “On the bed,” he said, grabbing the tie from where Dean placed it on the bed. Dean lay back on the sheets, shuffling so his head was on the pillow and he was comfortable. Castiel crawled on the bed after him, palming him through his wet panties, dipping his hand inside and squeezing his cock as he felt it harden in his hand. Dean moaned loudly, arching his back, bucking his lips, eyes fluttering almost shut.
Castiel tugged his panties down to mid-thigh and began to wrap the thinner end of his tie around Dean’s cock and balls. Dean opened his mouth to ask, then quickly shut it, biting his bottom lip and looking at him with a nervous excitement that made Castiel’s cock twitch. “Turn over,” he said, letting go of the tie. Dean obeyed, shuffling onto his stomach. “Up on your knees, princess.” Dean lifted himself up, spreading his legs wide and wiggling his ass. Castiel tugged on the tie, listening to Dean gasp, and pulled on it tightly, tucking it between Dean’s ass cheeks.
“Oh shit,” Dean bristled. Castiel pressed his hips down so he was flat on the bed again and gently took his wrists one by one, pulling them to the small of his back. He tied the thicker end of the tie around them, securing them tightly and making sure Dean’s cock and balls were pulled back between his thighs. He hummed softly and unzipped his slacks, undoing the button on his boxers and pulling his cock and balls out. He stroked himself a couple times, then grabbed a condom, ripping it open and rolling it onto his cock. Castiel squirted some lube onto his fingers, making sure the condom was nice and slick.
He tugged the tie from between Dean’s cheeks and easily slid two fingers into him, feeling his ass flutter around him quickly. Dean moaned, the sound muffled by the pillow in his face, and rolled his hips. Castiel smiled and added another finger, watching as Dean shuffled up onto his knees again. He whimpered as the tie pulled tighter around his cock, squirming. Castiel crooked his fingers and pressed the tips to where he remembered Dean’s prostate being. Dean’s thighs trembled and he sobbed quietly, clenching so hard around him Castiel couldn’t help but moan.
“Please-” Dean gasped. “Wanna feel you for a- a while. Three is good. Promise-” It’s not true. It had been a bit of a struggle with four fingers, but... “God, please, old man. Fuck me so good I can’t walk. You promised- Please.” ‘Old man’ was almost becoming endearing; almost. Castiel pulled his fingers from within Dean and added more lube to his cock, and Dean’s hole. He carefully lined himself up and pressed in, groaning as his asshole resisted for a moment before giving in and swallowing the head of his cock. “Y-yeah, yeah, yeah,” Dean’s voice was laced with a small amount of pain but no shortage of pleasure. Castiel slid in slowly, practically panting by the time he pressed his hips to Dean’s plump ass cheeks.
Dean was keening and whining and trembling beneath him, his hole clenching tightly around him. Castiel squeezed his eyes shut for a moment, trying to wait for Dean to loosen up around him because, shit, if he didn’t, Castiel was going to come. “Come on, princess,” he murmured, voice strained. He leaned over him, letting go of the tie and feeling it press against his cock. He pressed himself to Dean’s back, mindful of his hands, and kissed his neck. “Relax for me, sweetie.”
Dean huffed and whined again. It took him a few seconds but then he slumped flat into the sheets and stopped clenching so tightly. Castiel sighed softly with relief, and rolled his hips. Dean gasped, soft and shaky. Castiel hummed in reply, sucking and biting a mark into Dean’s neck, laving at the sore spot with his tongue. “Remember what I said?”
“W-what?” Dean slurred, sounding so out of it that it made Castiel tense. Dean tilted his head to look back at him, glazed green eyes locking onto his own. “What did ya say?”
Castiel frowned down at him, studying him for a moment and making sure he was alright. “You’re going to come on my cock,” he said slowly. Dean’s eyes cleared for a moment and widened, and he winced, biting his bottom lip.
“Dunno if I can,” he muttered, squirming. “I tried it before and it... didn’t work that well.”
“By yourself? Or with someone else?”
“Myself,” Dean said.
“Trust me, Dean,” Castiel said, chuckling, “I’ll make you come with an untouched cock.”
“Holding you to that, old man,” Dean said, fluttering around him. Dean tensed slowly. “Hey, ah, Cas...”
“Mm?” Castiel rocked his hips, forcing a small puff of air from Dean’s chest.
Dean stayed silent for a moment, then started squirming again. “Can you... er, untie me?” he asked softly, nervous. Castiel froze, then immediately sat up on his knees, slipping out of Dean, earning a noise of protest. He deftly untied his wrists and gently but quickly undid the other end from around his cock and balls.
“Are you alright?” he asked, rubbing Dean’s wrists and easing his arms down to his sides.
“Just... was uncomfortable,” he muttered, embarrassed. “’m’sorry. I’m fine.”
“You have no reason to be sorry, Dean,” Castiel said, tossing his tie onto the floor. He pulled off his blazer and dropped it onto the floor as well, undoing the top two buttons on his dress shirt and removing his cufflinks, slipping them into his pockets, and undoing the small extra button on his cuffs as well and rolling them to his elbows.
“Gonna fuck me anytime soon, old man?” Dean said, glaring back at him. Castiel raised an eyebrow at him, and lightly slapped his left ass cheek. Dean’s breath hitched with surprise, and he turned his face away with a darker blush, tucking it into the pillow below. Castiel shuffled closer and slid into his ass again, tucking his forearms underneath Dean’s chest, dropping a little of his body weight onto Dean. He rolled his hips, pulling out of him about an inch and sliding back in with a wet noise.
Dean inhaled sharply, and melted into the sheets. He spread his trembling thighs wider, giving Castiel more room. Castiel tucked his face into Dean’s neck, breathing in his scent, and pulled out again, a few inches this time, before slamming back inside. Dean choked on a moan, his hands fisting the sheets.
“God, yes,” Dean gasped as Castiel slowly started fucking in and out of him. “Aw, man, you- ngh , you feel so good...” Dean made the sweetest noises, keening and whimpering and gasping and sobbing into the pillow. He kept stuttering on a word, like he wanted to say it but was too scared. Castiel decided he would just pound it out of him. He stopped moving, switching angles, and slammed into him.
Dean let out a loud cry, unprepared for the attack on his prostate. It took a few thrusts, but then Dean was gasping and begging and, “Please, oh god. Fill me up, fill me up so good. Ah! Right there, right there, please- don’t- don’t stop. D-d-daddy, daddy, oh god, please. Daddy, daddy, daddy.” Castiel’s hips stuttered, but he didn’t stop. Was that it? Was that the word he kept fumbling with? Castiel’s stomach clenched tightly, and his cock pulsed inside of Dean.
“Daddy, huh?” he whispered, panting softly beside Dean’s ear. “Is that why you keep calling me ‘old man,’ princess? You want me to be your daddy?”
“Y-yeah, yeah, please. I-I, please, daddy. I-” Dean whimpered, clenching tightly around him. “Pretty please, daddy,” he said; it was spoken so softly that Castiel almost missed it. Soft, and a little broken and a little ashamed and a little distressed and a little frantic. Castiel stopped moving and pressed a kiss to Dean’s ear and slid his hands out from underneath his chest. He grasped Dean’s trembling hands in his own and hummed quietly.
“Daddy’s right here, princess,” he said finally, sliding out and in of Dean. His body stayed tense underneath Castiel for a few minutes, but then he relaxed, turning his head and looking at him with oddly wide and fearfully innocent eyes. Castiel’s heart clenched in his chest and he suddenly felt like he was being slammed with a truck full of both a horrendous amount of wrong and an immeasurable amount of delight ; the delight overtook the wrong. “... Right here, honey...”
Dean lifted himself up onto his elbows, forcing Castiel to lean back a bit and take back his weight. He turned his head to face Castiel a little more, no doubt straining his neck, and kissed him deeply. Castiel returned the kiss, Dean’s lips willingly parting to give him access to his mouth. Castiel eagerly swallowed up every little breathy noise of pleasure he let out, sucking and biting on his tongue, on his lips, tasting Dean and loving it.
“Daddy, please,” he whispered, eyes still wide, and wet now too. Castiel cursed softly and pulled back, pressing his forehead into Dean’s nape. He shuffled, turning his hips, and started pounding into Dean, hitting his prostate with each thrust. “Wanna come on your cock, daddy, please. Please make me come.”
“Shit, Dean,” Castiel hissed. “You keep talking and I’m going to come before you do.”
Dean moaned and clenched around him. “Please- I- I’m close. I am, I swear, I just- I can’t- It’s-” Castiel took mercy on him. He pulled one of his hands away from Dean and slid it underneath Dean’s right thigh, pressing two of his fingers against Dean’s perineum. “W-w- D-daddy, wait, I-” Dean let out the sweetest scream, body tensing and jerking at the same time as he came messily onto the sheets. Dean clenched tightly around him, and it was one more thrust of his hips, and Castiel was coming, wishing he was filling Dean up rather than the condom.
Dean slumped down underneath him, babbling softly as Castiel rubbed against his prostate and perineum, milking him of every last drop of come. He pulled away when Dean started shaking, and carefully slipped out of his sore, red asshole. Castiel pulled the condom off, wishing he had bothered to undress before, climbed off the bed. He tossed the condom and wrapper into the bathroom garbage, washing his hands and dampening a cloth. He cleaned himself off, tucking his cock back into his pants. Castiel rinsed the cloth, and shuffled out to Dean.
Dean was laying on his back now, arm thrown over his face. Castiel gingerly wiped him off and halfheartedly cleaned the comforter. He tossed the cloth onto the floor, pulled the sheets down, nudging Dean underneath and sliding in beside him. He tugged Dean into his arms, ignoring his flustered face, and pressed a soft kiss to his sweat damp forehead.
Castiel swallowed thickly, throat dry. “Daddy’s little princess deserves better than cheap motel rooms,” he murmured, feeling Dean tense against him.
“Maybe next time,” Dean started hesitantly, voice barely a whisper. “It can be in your bed?”
“Sure thing, princess,” Castiel said, rubbing his hands over Dean’s back. “And maybe some dinner too, huh?” Dean nodded into his chest slowly, gripping tight and relaxing into him. Castiel felt him fall lax in his arms, listening as he started snoring softly. He closed his eyes and squirmed onto his back, feeling Dean snuggle further into him and even slid a little on top of him. Castiel opened his eyes and stared at the ceiling. He sighed softly, and closed his eyes again, hoping Dean would be there when he woke up.