Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/ works/2295698. Rating: Explicit Archive Warning: Underage, Rape/Non-Con Category: M/M Fandom: Teen_Wolf_(TV) Relationship: Derek_Hale/Stiles_Stilinski Character: Derek_Hale, Stiles_Stilinski, Sheriff_Stilinski, Ennis_(Teen_Wolf), OFC Additional Tags: Alternate_Universe_-_Mob, Loan_Shark_-_Freeform, Alpha/Beta/Omega Dynamics, Mating_Cycles/In_Heat, Omega_Stiles_Stilinski, Alpha_Derek Hale, First_Kiss, Loss_of_Virginity, Anal_Sex, Knotting, Claiming, Collars, Dubious_Consent, PWP, It's_mainly_smutty_smutty_porn, those_darn heats_make_everyone's_brain_useless Stats: Published: 2014-09-12 Words: 4890 ****** Damn Fine Insurance ****** by kits_lightning Summary He couldn’t believe he was fucking collateral for a loan shark. What the fuck had his father gotten himself into this time? Stiles had no clue where his dad would come up with twelve grand but he knew his father wouldn’t leave him with a pair of criminals. Well, he hoped. Notes The Underage warning is because Stiles is 17. If you want to know about the non-con/dubious consent you can check out the end notes!! Please heed the warnings before you read! This is un-beta'd so please forgive any mistake you notice. Enjoy! See the end of the work for more notes “Well well, if it isn't the Sheriff’s son. Damn, I didn't think I’d ever be glad that someone couldn’t pay but you…” The huge alpha loomed over him and grossly eyed Stiles from head to toe. Stiles did his best to not gag. “You look like some damn fine insurance.” He couldn’t believe he was fucking collateral for a loan shark. What the fuck had his father gotten himself into this time? “Look, Ennis, its Ennis, right? My dad said he'd get the money.” Stiles had no clue where his dad would come up with twelve grand but he knew his father wouldn’t leave him with a pair of criminals. Well, he hoped. “Oh he better, otherwise I’m going to sell you to the highest bidder to make up the money he owes me. And kid... I know some people who'd kill to break your pretty little omega ass in two.” Stiles swallowed audibly at the man’s words. The loan shark grabbed his ass and pushed him back into a corner of the room. “Now stay there and don't bother anyone.” With a flash of his red eyes, Stiles sunk down to a corner of the room and hoped his father would show up soon. *** “You’re eight grand short.” Ennis huffed from behind his desk. “You only gave me 10 hours! Give me a few days and I can get the rest.” The Sheriff looked panicked and tried to explain to the alpha that he had other sources to get the cash but Ennis didn’t seem to be listening and Stiles was shooting worried glances over to his father. “That wasn't the deal, Johnny. The deal was twelve grand and you get your kid back. Now, you didn't keep your end so I’m going to have to take the rest out of your kid’s ass.” Oh no, oh no no no no no. Stiles felt his stomach drop as the alpha gave his father a shit-eating grin and the Sheriff shot forward but Ennis’ crazy girlfriend kicked the officer in the gut before he could reach him. “Dad!” Stiles tried to reach his father but Ennis grabbed him by the collar of his hoodie and pulled him back. His father was on the floor gripping his abdomen and coughing roughly and every inch of Stiles’ body was blaring that he needed to help his father. He needed safety and pack. “He’s only seventeen, don't do this!” The Sheriff wheezed, kneeling in front of the female beta. “Well you should've thought of that before you defaulted on your loan.” She told him in a bored tone. Stiles wanted to punch the bitch’s face. “Please. I can get the money, I swear!” The Sheriff kept trying to reason with Ennis even as two other men came in the room and started dragging him away. They can’t do this. This cannot be happening right now. “Dad? Dad!” Stiles stood and before he could take a step forward the alpha’s mate got in his way and crossed her arms over her chest, blocking his way. This bitch was getting on his last nerve. “You can’t keep me here!” Stiles shouted at her and tried to shove past her screaming for his father but the woman was holding him back. “DAD!” The alpha walked over to them and with pure command to his voice told Stiles to shut up. The omega felt the order shake him to the bone and he quickly bared his neck to Ennis. Stiles sunk to his knees and stayed there in silence even though his whole body was vibrating with a mix of frustration, anger and fear. Stiles began to take deep breaths to calm down and find a way to get out of this situation but the conversations his captors were having caught his attention. “Who's going to pay eight grand for this kid?” The she-bitch asked Ennis while sizing up the teen. Ennis shrugged and sat back on his chair as the beta went to sit on his lap like if this was the most ordinary conversation ever and not, oh I don’t know, Stiles’ life. “Meh, the Hales probably, they have a thing for twinks. Deucalion's always an option.” Stiles felt his heartbeat increase at the man’s words. The Hales? The fucking mobster family, Hales? The Hales that show up on the evening news with a new murder tied to their organization, Hales?! “Ok, which of the Hales? There’s like 20 of them.” The woman asked while rubbing the alpha’s shoulders. “Awww yeah, right there, babe. Uhhhh Peter or Laura. They’ll pay top dollar, especially for a virgin omega. Just call Derek and he’ll make sure everything’s set.” Stiles looked down at his hands and noticed they were sweaty and shaking. He felt queasy, lightheaded and he couldn’t take the easy tone they were using while talking about selling him. Peter Hale was a top lieutenant in the Hale’s criminal organization; the man was known to be ruthless, cunning and basically Satan in a V-neck. Stiles’ father had been tracking that family's activities for years and has never been able to physically tie them to anything. Any witnesses or potential victims who decided to come forward either disappeared or suddenly developed a case of amnesia. Laura Hale was set to inherit the whole thing from her mother, Talia, once the matriarch retires and her twin brother, Derek, was their best enforcer. The Sheriff believes that Derek has been the cause of all the deaths and disappearances of top members from rival packs over the past few years, and the guy never leaves a fucking trace. And Deucalion? Stiles had only heard that name twice and both times it was when whole packs disappeared. Rumors say that he has the power to make alphas turn and kill their pack. Either way, Stiles is going to die a horrible death. Great. “Hey! I’m right here you know! You—you can’t just sell me!” His voice was shrill and he was about thirty seconds away from having a full-blown panic attack. Ennis picked up his mate and placed her on the desk as if she weighed nothing and crouched in front of him. “Told you, kid. Your dad can't pay so a big bad wolf is going to take your pretty little virginity and say goodbye to anyone who'll want you after that.” Crazy bitch started laughing at that. “A defiled omega? Baby, your life is over.” Stiles tried to ignore them but his chest felt too tight and his vision was swimming. He couldn’t seem to catch his breath and he could barely focus his eyes with all the dark spots clouding his sight. The last thing he saw before passing out was the couple laughing at him. *** When Stiles came to, he was in another room. His chest ached but that was something he was used to after a panic attack. He rubbed his torso as he slowly sat up and noticed that he was no longer at Ennis’ office but in a living room in an apartment. A very nice apartment. It seemed spacious and he was facing a glass wall that held an amazing view of a forest. Where the fuck was he? The bar where Ennis kept him was somewhere downtown of Beacon Hills and there wasn’t a forest for miles. His heart began to pound as he suddenly remembered everything that happened before he passed out. His father, the Hales—fuck! The Hales! They lived on the preserve, hundreds of acres of land for their pack to run in and also to bury bodies in. Shit. A cool breeze made him shudder and as he wrapped an arm around himself he realized his clothes were gone, he was only wearing his black boxer briefs with the Aperture Laboratories’ logo. When he looked down he felt like something was around his neck and realized he had a collar on. “What the—” Stiles’ hand shook as he palmed the band. It felt like it was made of leather, it wasn't too tight but the omega felt his face heat at having been collared while he was unconscious. His father told him that you only get collar by your mate and Stiles was still months away from being formally offered to an alpha. “Do you like it?” A voice from behind him asked. Stiles jumped at the sound, tried to turn around too quickly and almost fell of the couch at the shock. Derek Hale was lounging on a love seat a few feet away with an amused smirk. Stiles recognized him from the pictures the Sheriff’s Department had pinned up on their boards when dealing with cases that could be related or tied to the Hales. He’s as intimidating in person as he is in the pictures but his eyes seemed different. Focus Stilinski. “Where am I?” His voice came out much meeker than he intended. Fuck this is it isn’t it? He was going to die. A totally horrible death—granted, by the hottest person he’s ever seen but still, he would’ve liked to live past seventeen. The enforcer leaned forward and put his elbows on his knees as he threaded his fingers together. “With me. Do you like the collar? Not too tight?” He didn't seem like a dangerous guy, Hale seemed genuinely concerned but Stiles knows what he's capable of and he needs to leave. Now. “It’s fine. Where am I?” He repeated with more strength to his tone. “With me. Come here.” The man leaned back on the love seat and patted his thigh. Stiles didn’t move. “Now.” Derek flashed his crimson eyes and Stiles scrambled off the couch over to his lap. He truly hated being an omega sometimes. The thought of disobeying an alpha fucks him up, if Stiles tried to disobey the simplest of orders he would feel extremely anxious and slightly nauseous. It was dangerous and annoying and it’s why the Sheriff kept him away from all alphas. The omega began to straddle the Hale enforcer and his heart was beating so hard he wondered if it was audible to the man in front of him. Stiles has never been this close to an alpha before, Derek felt solid beneath him, his thighs were warm even through his pants and Stiles put his hand on the alpha’s chest to steady himself and it was like touching a wall. The man was built with rock solid muscle. Stiles licked his lips and tried to ease his breathing, he could feel small drops of sweat traveling from his neck down his back. Derek's presence was intimidating and the intensity with which he was staring at the teen was making it hard to calm down. A wave of vertigo and heat swept through Stiles and he shook his head trying to clear it, which was a terrible idea because it made him dizzier. There was a scent in the air that was distracting him and he forced himself to look at the alpha and try to reason with him. “I- I’m Stiles.” He sputtered as he remembered his father telling him that criminals are less likely to hurt you if they get to know you and see you as a person rather than a target. “I know.” God, his voice sounded so nice and smooth, it wasn’t as rough and terrifying as he imagined. Wait. What? His voice? Did I turn into a twelve year old with a crush? Focus, Stilinski. “You're Derek Hale.” The alpha arched an eyebrow and whoa, those eyebrows were impressive as much as they were expressive. Damn, he was gorgeous and he smelled really good. Before the omega knew what he was doing his nose was against the alphas neck, inhaling that delicious scent. It was spicy and musk and he felt like rolling in it all day. “Glad you like my scent.” The alpha murmured with a hint of amusement. Stiles startled and pulled away quickly, he could feel his entire body burn with embarrassment. What the fuck is he doing? He tried to get off the alpha's lap but Derek was holding him still with one arm wrapped around his waist and his other hand holding his thigh. “I’m so sorry, I shouldn't have done that. I’m sorry, I’ve never been near an alpha before and you're like... It’s really hot in here. Aren’t you hot? I mean I know you’re hot—I meant your clothes! Not that you aren’t hot. I mean, you’ve seen you. Not that I—you know what? I’m going to shut up now before I give you more reason to kill me.” Stiles was strictly looking down at the alphas chest and avoiding his eyes, maybe that way he can actually focus. God, he was so dead. Who the fuck just dives into an alpha’s neck? Did he have zero self-preservation instincts? The not-going-to-look-at-you plan was going smoothly for all of four seconds before Derek put a claw to his chin and made Stiles look up and he was smiling. Well, at least he found Stiles' lack of social etiquette and word vomit funny. God, if he thought he was gorgeous before, his smile only made his hotness burn. Fuck. He was so fucking fucked. “You’ve never been near an alpha?” The enforcer asked in a whisper that sent a tiny shock down the omega's spine. Stiles shook his head. “My dad and my best friend Scott are betas. Scottie’s girlfriend is an alpha though, so we haven’t been able to hang out as much lately. My dad won’t let me near any alpha until I’m uhh... ma-mated. Until now, because here I am... near an alpha. Well, more like on an alpha and why aren’t you shutting me up?” He could still feel his blush cresting from the tip of his ears down to his chest. Jesus, the first time he's near an alpha—one who’s hotter than burning—and not only is he almost naked and collared, he's babbling and, oh right, the guy who's lap he's sitting on just happens to be a hit man for THE MOB. How is this my life? Derek's hands went from holding his thighs to cupping his ass and Stiles bit his lip letting out a whimper and his head lolled to the side, baring his neck. The omega's head felt hazy, something smells really good and his lower abdomen ached slightly. Stiles is having a frustratingly hard time concentrating—not that that was entirely new to him—and the alpha is not helping the situation. Derek speaking brought him back to attention. “Have you ever touched yourself?” He asked while massaging Stiles' glutes. Stiles’ head snapped up and his mouth gaped in shock at the question. He could feel his whole face burning and he quickly looked down shaking his head. Stiles was forcing himself to stay still even though every fiber of his being wanted to push back onto the alpha’s hands and grind down. “Not even here?” Stiles felt a finger press up against his entrance and gasped as the feeling made him tense up, gripping the older man's biceps. The boy looked at Derek with wide eyes and lowered his head again. “Use your words Stiles and look at me when you answer.” Stiles lifted his gaze and the enforcer flashed his eyes again and Stiles' heart began beating quickly. He cleared his throat and licked his lips. “N-no. Uhh the doc- the doctor said that if I do I might trigger my heat.” Derek's eyes were really intense, what color is that? It’s not exactly blue and not entirely green either but there's some brown in them too, it's like an extreme hazel color combo. Another wave of lightheadedness hit him and he could feel his body perspiring. What was wrong with him? Stiles felt his body getting warmer and warmer and the feeling of Derek’s cool hands on his ass was refreshing. Derek straightened up and it made Stiles’—now stiff—cock touch his rock hard abs and it sent a jolt through his whole body as he moaned. The omega could feel his hole leaking, drenching the back of his shorts. Stiles couldn't keep a coherent thought for more than a moment. He needed Derek to touch him everywhere; he needed the alpha’s hands to cool him down. He felt empty and for some reason this was causing him anxiety and he couldn’t hold back the whimper that escaped him. “Shhhh I'm right here.” The alpha began to run his hands up and down his spine and leaned back so Stiles could fit more comfortably on his lap. Alpha At Derek's voice, the fear that was taking hold in Stiles dissipated and the omega buried his nose in the crook of the alpha’s neck, chasing that deep scent that enveloped him and made him feel safe and protected. “That right, baby, I got you. I’m right here.” Derek whispered in his ear while continuing to run his hands up Stiles’ back and through his hair. “Alpha.” He sighed. The enforcer chuckled and Stiles could feel the rumble of his laugh through his chest. “That’s right, Stiles. I’m your Alpha. Do you trust me to take care of you?” Stiles began to rub his cheek along Derek’s neck and shoulder. He wanted the smell of his alpha to be all around him, in him. The enforcer grabbed him by the collar and pulled him up and Stiles gave him puzzling look. “I asked you a question Stiles.” Derek’s voice sounded strong and steady as he gripped Stiles’ chin. “Do you trust me to take care of you?” The omega nodded and said, “Alpha.” He didn’t seem happy with that answer and Stiles became extremely anxious. Had he done something wrong? Was Derek going to leave? His vision started swimming and Derek pulled him forward and hugged him tight as he made reassuring noises and a deep purring began emanating from his chest. Stiles’ body relaxed and after a minute the alpha spoke again. “Stiles, I need to know that you want this. I need to hear you say that you trust me.” Stiles stared at the alpha before him, his earnest expression, his worried eyes, his air of determination and every instinct he possessed told him that he was safe. He took a deep breath of Derek’s distinctive aroma and nodded. “Yes, I trust you.” The smile that he was rewarded with was brilliant and he received his first kiss. Even sitting down he swayed, Derek tasted as amazing as he smelled, his lips were so soft and his tongue thrusting into Stiles’ mouth had the omega writhing on the spot. Derek grabbed the bottom of his thighs and stood up from the love seat. Stiles wrapped his legs around the alpha’s waist and immediately grabbed the back of the man’s shirt to hang on and continued to inhale as much of his alpha as he could. Being enveloped in that scent seemed to be the most important thing in the world at the moment. Stiles needed to smell like Derek, he needed to smell like the alpha inside and out. Needed to be filled by his alpha. The more he thought about it the worse the throbbing in his lower abdomen got. He felt empty and wet and he needed something—something to fill him. He was so confused and frustrated and he needed something! He didn’t even realize he was crying until Derek laid him down on a bed and caught his tears with his thumb. “What’s wrong, Stiles? You need to tell me.” The command in his voice rang loud and clear but the omega didn’t know how to say what he was feeling. Stiles opened and closed his mouth twice and shook his head. “Stiles, I want you to be good for me. Tell me what you want. I won’t do anything until you tell me what you want.” The alpha’s eyes remained clear but Stiles still felt the urge to tell him anything and everything to make him happy. “I-I don’t know.” He sobbed. After a few breaths he added, “I feel empty and I want to smell like you and I don’t know what do or what that means.” Derek looked down at him and groaned with a small smile that made Stiles chest tighten. “You’re beautiful and perfect and completely mine.” The last bit came out as a playful growl and the possessiveness in the alphas voice seemed to make Stiles leak more slick and he could feel it running down his thighs. Derek’s nostrils flared and his eyes shone crimson. Stiles could feel his insides burning, his hole ached and clenched around nothing and it was making him feel desperate. He began to pull the alpha over him but the bastard wouldn’t move. “Please, Derek, please make it stop. It hurts. Make it stop.” With every word, Derek leaned forward until his body was practically covering Stiles’. “Do you want me to take you, Stiles? Do you want me to fill you up until all you can feel, smell and taste is me?” “Yes. Yes, that’s what I want. Please!” Derek’s clothes felt too rough on the omega’s skin and Stiles wanted it off the alpha. He ached to feel all of Derek with no barriers. Without thought, Stiles began to push the alphas shirt up and tried to open it but his hands were shaking so bad he couldn’t work the buttons off and let out another desperate whimper until Derek put his hands over the omega’s to stop him. The large man stood up from the bed and the chill from the room hit Stiles and made him whine pitifully. Derek smirked as he undressed rapidly. Stiles felt so empty and his hole ached to the point where Stiles couldn’t take it anymore and shoved off his underwear and tried to stuff two fingers inside himself where he throbbed but Derek caught his wrist. “You’re so ripe, just begging to be filled.” He said, tone dark and lusting, sliding his cockhead up and down the crack of Stiles’ ass. “Derek, please…” He swallowed, his mouth open all wet and breathless. Stiles doesn’t even know what he’s begging for but he knew the alpha would take care of him. He needs the ache inside to stop, he needs to be full, to be wanted, to connect. “Shhh, I’ve got you.” The alpha whispered as he lifted Stiles up and laid him down on his stomach in the middle of the bed. The omega shifted up onto his hands and knees, making sure to bend his elbows and to rest his head to the side, presenting himself to Derek. He felt as much as he heard the howl the alpha released when the bed dipped and Derek grabbed him by the hips with one hand. After another whimper from the young omega, Stiles felt something hot and hard breaching him where he ached the most. He cried out as Derek began to push inside and Stiles could feel himself stretching, trying to accommodate the alpha’s girth and it felt amazing. It became easier to breathe with every inch of Derek that entered him. Stiles’ thighs were trembling and he couldn’t stop the full body shake and moan as Derek's length pressed against something inside him that made him shudder and momentarily lose control of his limbs. Derek filled him completely in one violent shove that made Stiles' muscles abruptly give, and the jolt of it made him come, arching uncontrollably and shooting stripe after stripe of come onto the bed. Stiles was limp, boneless, breathing raggedly and finally felt as if he wasn’t going to burn from the inside out but as rapidly as relief approached it quickly disappeared and the heat hit him at full force. “Please! More, Derek, more!” He begged as he felt his skin and muscles burn, only relaxing with Derek’s touch. Derek dragged Stiles' ass up and began to pound into it, repeatedly, making Stiles' eyes roll up as he buries his face into the bed, inhaling the scent of his alpha as he lets out low, near-soundless grunts at every thrust. Derek’s grip on Stiles’ hips tightens with a subsonic snarl that he buries in Stiles' sweat-slick nape, licking it, sinking stinging little lines into it with his fangs. Stiles just takes it, his ass feeling soft and wet and good, so good, the ache deep inside being soothed felt better than anything in the world. Derek’s hand reached his neck and Stiles let his head drop down and the alpha nosed the expanse of his throat. With a soft snap, the collar that sat on Stiles’ neck fell onto the bed. Stiles looked down at the strap of leather and didn’t understand what just happened. Why would Derek take the collar off? Why— “I’ll put it back on after, okay?” Derek was panting but his words were sincere. Stiles grabbed the collar and wrapped it around his wrist and turned to grab Derek’s hair and pulled him down to capture his alpha’s lips in a bruising kiss that left them both breathless. The omega could feel himself getting hard again and began arching into Derek’s thrusts. The alpha’s rhythm faltered momentarily before he growled menacingly and pistoned into Stiles, hitting his prostate with every other thrust. The omega was screaming in ecstasy as all his senses were filled with the alphas scent and touch. Stiles could feel Derek’s flesh expanding; the knot at the base of the alpha’s cock grew and began to tease the omega’s rim. “Mine.” Derek breathed. “Yours, yours. Just yours.” Stiles moaned. From this angle Derek was making him see stars but instinct told him that he needed more. “More, please Derek, more.” The alpha pressed Stiles lower back onto the bed and grabbed the back of the omega’s legs, pushing them higher on the bed, spreading Stiles before he shoved into Stiles’ hole again. The omega keened and thrashed on the bed as immense pleasure and pressure conquered his body. “THERE, THERE, THERE!” He screamed as his claws dug deep into Derek’s sheets. “Mine” Derek roared as he pierced the back of Stiles’ neck with his fangs, marking him, claiming him. Suddenly, all his muscles tightened up and his body arched off the bed as he clenched over the alphas cock. Derek’s knot slipped deep into Stiles and pressed up against his prostate and the teen’s body seized, hips lifting up and shaking in place, his nerves sparking, his spine stiffening and his lungs full of air but it’s not enough because he’s shouting, practically howling, and coming and coming and coming. The alpha barely slowed down as he continued to pummel Stiles through his orgasm. Derek arched his body down and buried his face in the crook of Stiles neck, breathing him in. “Mine.” He purred and it still sent a full-body shock through Stiles as he screamed Derek’s name, coming once more around the alphas cock and this time Derek’s knot had fully expanded, locking them together. The more Stiles moved because of his orgasm the more he continued to come and milk his alpha’s knot. “I-I can’t—too much—Der—I can’t—” He sobbed, begging for a respite. “You’re doing so well, baby. Just a little more, okay?” The alpha murmured gruffly in his ear and Stiles nodded. Derek caressed his arms and Stiles relaxed into him. After four more orgasms, Derek’s knot went down and the omega’s entire body went limp as he passed out. *** Derek has no clue how long they’ve been like this; it felt like weeks since they first fell into bed together even though it was probably just a few days. Stiles kept waking him up at random times to quench the heat when it took him over. He fed Stiles water and food whenever he let him leave the room and he vaguely remembers giving the omega bath at one point. Laura wasn’t going to be happy that Derek took Stiles for himself, but he couldn’t find it in him to care. Looking down at his chest, the alpha felt calm for the first time in too long. The young omega was sleeping soundly with Derek’s collar snug on his neck and had his nose buried in Derek’s sternum. Derek felt a smile tug at his lips at the memory of waking up to the omega straddling him, begging him to put the collar on him while he fucked himself on Derek’s cock. The alpha had placed the leather band back on the long length of his pale neck; fingertips pausing on the steady jump of a pulse beneath the ivory skin—so deceptively fragile. The alpha then took his time memorizing every inch of the teen, licking the pattern of moles that dotted his body until he had savored each and every one. Basking in the glow of Stiles eyes when they shone gold and getting lost in them in their natural amber hue. That time, when they had sex, their mouths never parted. Derek rumbled, a prolonged, quiet growl of satisfaction, and tucked Stiles closer to him as he drifted off to sleep. End Notes The non-con/dubious consent is because Stiles' heat had already started when he was asked to have sex, therefore he was not in the best state of mind to consent. I hope you enjoyed this story! Feel free to check out my tumblr! Please drop_by_the_archive_and_comment to let the author know if you enjoyed their work!