Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/ works/859793. Rating: Explicit Archive Warning: Underage Category: M/M Fandom: Supernatural Relationship: Castiel/Dean_Winchester Character: Bobby_Singer, Dean_Winchester, Castiel, Sam_Winchester, John_Winchester, Mary_Winchester Additional Tags: Underage_Sex, Alternate_Universe_-_Human, Neighbors, brat!dean, Shota, shota!dean, Older_Man/Younger_Man, Teacher_Castiel, Rimming, Blow_Jobs, Face_Slapping, Jailbait, Punishment, Dubious_Consent, Anal_Fingering, Anal_Sex, role_play, Come_Swallowing Stats: Published: 2013-06-27 Words: 4893 ****** I've Sinned (But I'd Do It Again) ****** by IceFemme Summary Dean Winchester is a little brat. He's pranked Castiel more times than the man can count and he moved onto Mr. Novak's street just less than two months ago. When he finally gets caught and stuck doing chores around the older man's house, he begins teasing Castiel and testing his patience (and libido) like no one has ever done before. There's just one solution: teach the little twink a lesson. Notes severe underage, guys. Castiel is 30, Dean is 16~17. he acts young so i'm going to call it shota. spark of this idea came from a pic on tumblr (broken link) and of course the wonderful PastelCastiel on tumblr! “Dean, yah li’l shit! Pay some respect to Mr. Novak!” Dean audibly growled, glaring at his uncle who was watching him for the afternoon. “Good morning, Cas,” he spoke resentfully. The older neighbor cocked a brow at the little boy. Dean was maybe fifteen, a little squirt with long brown eyelashes that framed his bright spitfire green eyes. His hair was a wild mess of golden brown and chocolaty tresses. He was possibly the cutest thing Castiel Novak had ever seen. “Good morning, Dean. Robert,” he said, standing up from his garden and wiping his hands on his pressed khaki pants. “What can I do for you?” Bobby was grumbling something and Castiel was still confused. The older man finally smacked Dean on the back of his neck and the boy took a step forward. “I came here to apologize for putting a rat in your house last night,” he said, looking like he was having a hard time keeping a straight face. Castiel paled and narrowed his eyes. Oh yes. He should’ve known Mary and John’s little brat son Dean had been the one to toss the rodent in through the open window and made the thirty-something-year-old man simultaneously cry and wet his pants in fear. It had not been one of his finer nights cooking spaghetti sauce. “I’m sincerely sorry and I won’t ever pull any pranks on you again, Sir,” Dean added, his head bowed more this time. The Winchesters and Castiel Novak haven’t been neighbors for long. Castiel’s lived on Lazarus Street for who knows how many years, but Dean, his parents, and his little brother Sammy just moved in about a month and a half ago. Mary and John are still working overtime in new jobs trying to pay off the mortgage of their new house so they hadn’t been around that often. Dean was deemed not mature enough to watch his twelve-year-old brother Sam so their uncle Bobby usually had to come down something like every other weekend to watch the kids. “I’ll have you know I wasn’t very impressed with that stunt, Dean,” Castiel said, using his reprimanding Professor of Economics voice he usually uses on his lazy students at the big university a couple cities over. “It chewed through my telephone wires so I’m going to have to get them rewired.” Dean pouted up at Castiel. The sheer adorableness of the boy’s fat lower lip pushing out accompanied by his splash of orange freckles across his cheeks was almost overwhelmingly arousing. Castiel was no pedophile… He was just… Actually you know what; nope, this is pretty pedophile-y right now, man. Just yell at him and get back to your boring garden work that’s less boner inducing,he told himself. The teenager spouted more about how he was so sorry and embarrassed of his ‘juvenile actions’ which sounded pretty scripted until the gruff older man stopped Dean’s babbling all together and announced that they had agreed Dean would help Cas around the house or wherever he was needed so he could pay off the rewiring costs. The Winchester boy sagged but agreed with his uncle that it was ‘only fair’, although he looked like he could drown a kitten with the amount of anger his wide emerald eyes. Castiel realized this was not good. More time spent with jailbait was not a good thing. He tried to shake his head and wave his hands, telling Bobby that it was all right, that he could take care of it on his own but the old guy was stern and a little scary. In the end the raven-haired man nodded. Fuck, bad day bad day bad day! Cartoon Jackie Chan would say. He really needed to stop watching Kids WB. Like seriously, he didn’t even have any nephews or nieces so he had absolutely no reason to even own that channel. But it seemed like what with Bobby’s idea that Dean comes over every day after school for an hour that the show would be on more often.       xXx Castiel had possibly the biggest house on the block. It was shrouded by all sorts of different types of trees and shrubs that obscured the true size and beauty of the house from the rest of the street. Dean had planned over twenty-five different pranks for the new neighbor that he tried to get Sammy to be his accomplice. The younger boy only shook his head and threatened to scream to their mom what Dean had in mind. “Shut up, Sammy!” Dean cried, thrusting his hands over his little brother’s mouth and straddling his lap. He held on until Sam started shaking and tearing up. “Sorry!” John appeared in the doorway. “Damn it, Dean! Stop hurting your little brother!” Great, Dean thought, here he goes again. He rolled his eyes. “He does nothing but worship you and all you ever do is just take him for granted and use him as your little toy!” he went on and on and eventually Dean stopped listening. “Yeah, okay!” Dean said agitatedly. “I have to go to Mr. Novak’s! I’ll be back in an hour!” he called over Sam’s wailing and John’s annoyed speech. Dean sped out the back door and the side of his house until he was on the main street. Castiel only lived across the street and two doors down. He hurried up the steps to the man’s house and knocked twice. When there was no immediate response, Dean turned the knob, surprised that it was unlocked, and walked in. There was the slight buzz of a TV on but nothing else. When Dean walked into the living room that had the sound coming from the television, he realized Scooby-Doo was on and that was one of his favourite shows. Maybe this helping after school thing wouldn’t be so bad after all… Dean thought to himself, pouncing on the couch and crossing his legs under him. He took off his jacket and dropped it on the floor, getting nice and comfy, glad he was wearing just a tee and his favourite jeans. “Aah—f—fuck!” came a muffled voice. Dean’s cheeks went aflame with nervousness. He had been sitting on the couch for almost ten minutes now and he hadn’t even checked to see if there was anyone else in the house! He tentatively looked down the hallway to see where the cursing voice had come from. Well, duh, it’s got to be Cas since this is his house right? Dean asked himself. He gulped apprehensively. “Ohhhhh fuck yeah, shit yessss—I’m gonna fuck you right there…! Mmhm,” came more of the lewd voice. Dean had heard this kind of talk before… There was that one bleach-my-brain time when the four of his family had went to visit his grandpa’s house and his parents hadn’t closed their door one night. Plus he was an avid fifteen-year- old; he did know what porn was, thank you very much. His face turned a bright pink colour and he retreated to the couch. He gingerly took a seat, staring ahead at Scooby and Shaggy on the screen, but wasn’t really absorbing what was being said. Dean didn’t hear any more of those noises after the show ended. He sat there until Castiel came padding down the hallway in a pair of Chubbies and a white Red Cross tee that you get when you donate blood. He walked into the room, yawning loudly as he bent down to grasp the TV remote on the floor when he noticed the young boy sitting on the couch, his eyes as wide as saucers just staring at the man. “JESUS IN HEAVEN!” Castiel screamed, taking a couple steps back from the boy on the couch who just swallowed the lump in his throat and tried to regulate his breathing once again. “How long have you been here?” Well this was a weird situation. “Door was left unlocked. I just got here,” he lied, relaxing his expression to make it seem like he didn’t just witness one of the most arousing moments of his life. His dick was hard in his jeans but it wasn’t big enough to tent the denim. Judging by how long the average Scooby-Doo episode is, Dean’s been here for a good twenty minutes. The dark haired man took a few deep breaths and then finally turned the TV off. “I’m sorry, Dean, you just scared me. Why didn’t you announce you were here?” he asked, his face still red as a tomato. Dean shrugged. “Wanted to watch TV here since at my house my dad keeps getting mad at me for playing too rough with Sammy.” And oh if that didn’t make Cas’ spent dick twitch a little. Did Dean like to play rough with his other little friends too? Was he a bully? Did he push them into the mud and straddle their asses and rut— “So are you going to make me a snack or…?” Dean drifted off, annoyed. Castiel shook his head. Was it customary for the host to make a snack for the kid who is supposed to be paying him back? “Yeah… Yeah, what would you like?” Dean demanded a laundry list of food that he would like to have, most of it food that he explained his mom wouldn’t buy for him because it was too unhealthy. In the end they agreed on mashed potatoes and carrots. Dean threw the carrots at Castiel’s cat when he wasn’t looking. Dean checked out the clock on the wall when he was done. “Soo Cas, looks like I’ve been here for around an hour. Let’s pick up where we left off tomorrow? Sound good?” he asked, standing up from his finished plate and pushing his chair in. The boy gave him this edgy look like ‘You say yes and I will walk quietly out the door’. Castiel gulped. He nodded and attempted to smile. “Y—yeah. I’ll see you tomorrow, Dean,” he said, his grin softening into something real. “Great! Bye, Sir!” He was thankful for the table that was concealing his full hard on.       xXx “What happens when you get an erection?” Dean liked playing stupid with Castiel. He loved the embarrassed look the thirty-year-old man got when he was asked these kinds of questions. Dean had never walked in on Cas jerking off since the first time he came over two weeks ago, but sometimes he wished he had. “Cas…?” Castiel cleared his throat. He was grading papers but the boy behind him working on his English homework was quite mouthy. Don’t think about it like that, no not his mouth…! “When all the blood rushes to your penis, you get an erection,” Castiel explained, hoping the boy wouldn’t ask any further questions. He ducked his head down and tried to read his student’s messy handwriting. Dean chuckled. No, God, why would the boy ever let Cas off easy? “No, dummy, I don’t mean how do you get an erection, I mean what do you do with it?” Why did I sign up for this? “Perhaps you should ask your teacher about that, Dean.” “But… You’re a teacher,” Dean said, cocking his head to the side and dropping his pencil. “So you can explain to me what happens—“ “I don’t think it’d be appropriate, Dean,” Castiel replied a little bit more forcefully now. He had gone rigid in doing so, so he straightened out his shoulders and relaxed his back. “Okay…” Dean said, scowling at Castiel’s back, feeling agitated that he couldn’t answer just a single stupid question. The man sighed to himself. What he would give to just have just one minute, just one single fucking minute— “You’ve had sex, though, before—right?” he inquired now. Castiel’s pen cracked with the force he was holding it. He relaxed his fingers and the green pen dropped from his hand. He was thirty for fuck’s sake; of course he’d had sex. Well, no matter how many times, but he’d done it at least once! He debated whether he should expel his information to the boy on the floor. He turned around in his seat and rested his hands on his lap. Dean was sitting on the floor with a miniature table over his lap, his feet spread out on the carpet. He had rolled up his shirt so that it was resting just right above his belly button and his shorts pulled down to mid-thigh, his small cock resting against his lower stomach. There was leaking precum at his tip and almost right as Cas noticed that, Dean lowered his finger and pressed it to his slit, bringing the little dab of wetness to his lips and sucking on the digit. His heart leaped into his throat and his lower regions burned with intense desire. There were no words for what he was seeing, except maybe fucccccckkkk mmeee. “I’m not as big as the other guys in my PE period,” Dean frowned, his voice shy. It was odd because Castiel knew that he had to say something, to put an end to whatever plans Dean had, but he just couldn’t open his mouth wide enough or seem to know how to use his tongue for words. “But I know it’s better down here,” Dean said, smirking extravagantly now as he rolls onto his knees and crosses his arms so he can rest his head on them. Castiel was now presented with Dean’s beautiful pink hole. Yet, still, Castiel was speechless. So Dean took to continue his talking. “I touch myself here sometimes,” he spoke directed away from Castiel so the voice sounded a little distant, “but I’m too scared to penetrate completely. I wouldn’t want my fingers to be the first,” Dean admitted. Cas didn’t know how much longer he was going to last. He was edging off of his chair and gazing at Dean’s ass like if he blinked it might all vanish and he’ll wake up. “D—Dean,” he finally stuttered. Dean hummed in response. “Do you realize what you’re doing right now? What you’re doing to me?” Should I send him home? Should I tell Mary or John? Dean just giggled. “Yep,” he said lightly, wagging his ass in the air. “Seducing my old perverted neighbor.” He gulped. That was exactly what he was. “Don’t be down about it, Cas!” the brunette boy exclaimed, turning his head so that he could look back at Cas. “I mean, I’m practically throwing myself at you right now, you know…” Honestly, Castiel couldn’t decide whether he was thankful or not for the ring of the doorbell. “Fuck, Dean! Get dressed! I’m not going to prison—!” not today at least.       xXx He had insisted. Full on begged. So now he was working the non-motored lawn mower across Cas’ back yard. He didn’t exactly have a front yard except for the shrubbery and cobblestone path to his front door. He had taken off his shirt and the sweat on his back and front were very evident of his hard work. Castiel couldn’t tell if this was another one of Dean’s tricks to get into his pants or if he genuinely wants to pull his weight around here. He’s been coming over for almost three weeks now and this is probably the first time he picked something up and just started doing it. So Castiel was thankful. He sat on his back porch with a glass of scotch and another glass of lemonade for Dean when he got thirsty. He was half reading a magazine, half watching Dean use his surprisingly developed arms to push the lawn mower. The teen got about three quarters done with the lawn and he trotted over to a semi-hard Castiel. “Am I doing a good job, Sir?” Oh, fuck you, Dean. “Brilliant, Dean.” Dean absolutely beamed. “Thanks! Is this for me?” He picked up the glass of lemonade and brought the pink straw to his lips, taking a long suck. Castiel watched as his cheeks hollowed out for a moment, but then threw his head the opposite way. “Little tease…” Cas muttered under his breath. Dean in turn, hearing this, set the drink down and climbed onto Castiel’s sturdy lap, wrapping his arms around the older man’s neck and leaning in to hug him. Castiel was hit with the scent that was Dean Winchester—green apple, sweat, and maybe a bit of cinnamon. “But I like teasing you, Cas.” He began to rut his thin hips into Cas’ crotch, the raven-haired man groaning all the while. “Please…” Dean wasn’t exactly sure if that was a plea for more or a big red stop sign. So he leaned in close to Cas’ ear and whispered, “I’m turning seventeen in a week. I want to get fucked before then.” “Dean, you’re way underage—” “I want it!” Dean growled, lower and huskier than Cas had ever heard from the boy’s lips. “I’m not a top, Cas. All I want is to get fucked so hard I won’t be able to walk straight for at least two days. I want you to lick me open and scissor inside of me; I want to feel you tear me apart from the inside out.” Right now Cas was sporting a full on boner and it was rocking right against Dean’s less impressive one. Without leaving his eyes, Dean reached down and unbuckled the man’s belt, sliding it through the loops and tossing it into the grass somewhere. He snapped the button and ripped the zipper down, not caring how much the stupid slacks cost. “Dean, we can’t…” the man tried pleading again, but his voice broke and both males knew that Cas wasn’t as supportive of abstinence right now as usual, what with him thinking with his downstairs brain. “I can, and I will,” Dean said forcefully, standing up off his lap—Cas immediately missing the warmth—and padding over to the bench next to the backdoor. Without looking in Cas’ direction, he began to strip his tight jeans and plaid boxers, stepping out of them neatly. He sat down on the flowery designed cushion and spread his legs wide, leaning his head back against the house. “Dean…” he said in a warning tone again, but it would be the last time. “Please come here and eat my sweet ass out,” he said with a smirk and one eyebrow cocked, slipping his ass off the side of the bench and presenting his little hole to Castiel, “Sir,” Dean purred. Castiel almost tripped getting up in his haste. He ended up on his knees anyway right before Dean’s ass, leaning in and taking in the boy’s scent once again, but it was different down here, more sweaty and heady. Absentmindedly, the older man held his hand out for Dean to take into his hot mouth. The boy seemed to know exactly what Castiel wanted and he slipped the first three digits past his lips and sucked on them, swirling them around his tongue and letting them go with a pop. “Do you do this with other boys your age?” Castiel asked, hoping that the boy was a virgin. Please God, oh please. Dean shook when the dark haired man’s first finger breached his hole, just one tiny tap inside and his semi was rock hard. “I have a few friends,” he admitted. At this, Castiel pushed his finger in all the way to his knuckle. Dean’s ass tightened and convulsed, trying to push the foreign digit out, but Cas only added another. “What do you do with your friends?” he inquired, pressing a kiss to Dean’s balls and sucking one stinky one into his mouth. It tasted exquisite. Cas felt his eyes roll back into his head for a moment. “They fuck my mouth a lot; I’m really good at giving head,” Dean said with a smug smile. “I’ll have to remember that for future references, then, huh?” Cas said before he could stop himself. This one time was already enough, there would be no other time, he thought to himself dejectedly. Whatever, he might as well make this one last. Besides, Dean had made his life a living hell for the past few weeks. Why not make this one lazy afternoon as painful and equally delicious for the boy in return? Castiel thought deviously. “Yeah, I’ll suck your dick anytime, Cas,” Dean said, the smirk gone when another finger penetrated his ass and he felt so full. All three were in. “Are you going to fuck me?” he asked, suddenly all innocent and shocked. This made the older man cock a brow. “You seem surprised,” he said with a small grin. “I’ve wanted this for such a long time,” Dean admitted, spitting into his hand and slicking up Cas’ hard cock. Castiel looked up and Dean met his eyes at the exact moment, a hot blush forming over Dean’s freckled cheeks. “Now, uh, just stick it in…” he said awkwardly, looking anywhere but at Castiel. “Cute, acting all coy right when I’m giving it to you, little prick,” Castiel teased, smacking Dean’s small cock against the younger boy’s flat stomach. Cas positioned his cockhead right at Dean’s entrance before he could whine about Castiel making fun of him. Castiel realized with astonishment that he wanted to see Dean squirm. He wanted to get back at the little troublemaker for punishing him for so long. “’M not going to start until you work for it,” Castiel declared. “Tell me what a bad little boy you are; how bad you want this.” Dean sobbed. “Cas pleeease, my ass is twitching I want you inside of me so bad—I’m sorry I’ve been so naughty I’m sorry I acted like such a little slut I just wanted to make you look bad losing your cool because of a little dweeb like me—just fuck me and I promise you won’t regret it, okay?” The boy’s delirious face was enough for Castiel to smirk and ease his head inside of Dean’s pretty pink little asshole. Dean screamed, of course, at first. Tears sprung to his eyes and Castiel had to shush him because they were on his back porch and it would not do to collect attention around the neighborhood. “Gotta be quiet, sunshine.” “Kee—keep going, Cas, please oh god it’s so fucking good,” Dean babbled, but the look on his face said otherwise. He was in pain and Castiel felt a twinge of remorse for putting the boy in this situation. So he leaned in and pressed their lips together to take Dean’s mind off the pain while he pushed the rest of himself inside of the teen. “You’re being such a good boy, Dean,” Castiel acknowledged, smiling as he kissed the red faced and panting boy. The porch bench began to creak as Castiel rolled his hips into Dean’s for the first time and they both groaned aloud. “Yeah?” Dean asked but he didn’t sound to sure of himself. “Yeah.” Castiel pressed their lips together as he continued to rock into the boy. The pace was a little slow for him but he would hate to make the boy’s first time a painful memory. “Make me want to take you in to my classroom and show you off to all my students,” he began. “Mmm, yeaahh?” Dean encouraged, biting his lower lip and squeezing his eyes shut in bliss when Castiel hit that magic button inside of him, gasping when Castiel didn’t decrease the pressure. “I’ll wait until they all leave and lock all the doors and lay you out all over my big desk and open you up slowly. So slowly you’ll be crying and snotty by the time I get you ready enough.” Castiel roughly thrust up into Dean. “I’ll fit your small prick and balls into my mouth and suck you until you want cum. Of course you’ll be wearing a cute little pink cock ring that won’t allow you.” “Cruel!” Dean declared, raising both hands behind his head and getting a grip on the house behind him. Castiel’s pace had definitely picked up and neither male could stop himself. “I’ll turn you over and, hmm, maybe we can role play. You can pretend to be a stupid little girl that’s failing my class and will do absolutely anything for an A. How cliché, huh?” Castiel growled, thrusting his hips into Dean’s. Dean gasped when that little piece inside of him was brushed again and he pressed back into the older man. “Yeeess, I’m such a fucking slut I would do anything for an A, Cas,” Dean said with his eyes shut tight. His mouth slackened and Castiel knew the boy was nearing his orgasm. He reached forward and clamped a hand down on his little dick and squeezed the base. “No cumming for sluts. Their sole purpose is to get their teachers off first. You want to pass, don’t you?” Castiel teased. “Open your eyes,” he ordered, his tone changing from playful to reprimanding in an instant. When Dean couldn’t comply so quickly, Castiel slapped his big rough hand across the boy’s freckled cheek and a clap rang out. Dean squawked and Castiel had to hold his hand over the boy’s mouth to keep him quiet. “What the fuck did I say? No yelling,” he commanded. The boy shook his head vigorously in agreement but Castiel didn’t let go immediately. Dean was short of breath but the man wanted to teach the boy a lesson. When he finally let go Dean was gasping and thrusting back on his cock like never before. “Oh really? Did you like that, Dean?” Castiel teased. Short little moans escaped Dean’s mouth at every single thrust now. It was the cutest thing Castiel had ever seen so he drove forward harder and his little twink boy pressed both hands against the wall behind him for leverage, pushing back so Cas could dig in deeper and deeper. “Fucking gorgeous,” Castiel declared, reaching between them and touching Dean’s steadily leaking cock. “You wanna cum now, sweetheart?” Dean nodded his head vibrantly. “Yes! Yes! Yes! Oh, Sir, please,” he begged. Castiel smirked and began fucking into the teenage twink even harder. He had just about lost his mind at the tightness of Dean’s virgin hole when the boy began quaking and shouting and Castiel didn’t have it in him to cover his mouth when Dean came all over his stomach and his own. There was just enough time for Cas to pull out of the brunette boy’s convulsing and addicting hole and bring his cock up to his face and ordering for him to “Suck. Now.” Obliging and seemingly half awake, Dean eagerly leaned forward and caught the cock in his mouth, sucking real good and swallowing around the thick head that was just thoroughly fucking his asshole moments ago. He apparently enjoyed the taste because he hollowed out his cheeks and sucked like it was a fucking lollipop and the man standing above him slammed his hand on the wall behind Dean’s head and fucked into the boy’s mouth. “Oh my fucking God, your mouth is fucking blessed, Dean, holy shit,” Castiel gabbed, feeling his eyes roll in to his head in pleasure as he came long, hot white streaks into Dean’s talented mouth. “Jesus fucking Christ,” he continued to blaspheme.  When the waves of pleasure began to wane, both males opened their eyes and gazed at each other as if for the first time. “Jesus fucking Christ,” Castiel repeated because Dean had the most beautiful and bright green eyes he had ever seen. Not only that, but he just fucked a minor. Dean slipped off the flower cushions that Castiel somehow in his daze remembered that Anna had bought for him a couple months ago and pulled his pants back on. "I'm a half hour late. My mom will be wondering where I am," Dean explained, his eyes on the ground by his feet. The lawn mower was abandoned in the middle of Castiel's yard but he didn't say anything about it. His azure eyes were trained on the boy in front of him that was shifting from foot to foot. "That felt really good, Mr. Novak. I'll be back tomorrow after school." And with that, he leaned in on his tippy toes and kissed his neighbor on his lips.  Castiel stood back aghast, not completely solid on what just happened. He remotely remembered kissing the boy to keep his voice down but that just now was something so much more chaste, so much deliberately sexy and secure that Castiel kind of stooped over the boy and pressed him against the wall behind his back and leaned in to take his lips against the man's own.  "I'll be waiting," he murmured seductively against Dean's lips.  "Ummm," the boy began to catch Castiel's attention. "I still get that A, right Sir?" Dean asked, cocking his head to the side in question. It was so innocent that Castiel could cry.   The man looked at Dean with wide eyes. Did he just...? He tried not to look too affected. "A-. You've got to work on your execution," Castiel said with a small blush on his cheeks. "But there's always room for improvement." Please drop_by_the_archive_and_comment to let the author know if you enjoyed their work!