Archive of Our Own ^beta

Chapter Text

***

Dean didn't date highschool girls.  He was twenty, living on his own, and didn't want the drama teen girls always seemed to draw.  Or invent.  However, Anna Milton had something Dean wanted.  

When her family had moved to town six months ago, she pursued him, the resident bad boy.  She was always walking around wearing short shorts and low cut tops.  She was a shapely girl, nice C cups and well rounded ass.  Dean ignored her all summer.  It wasn't until late September when she came around looking way older than sixteen, practically spilling out of her anime schoolgirl outfit (highly inappropriate and inadequate for the season), with her little brother in tow.

Dean took in the sight appreciatively, licking his lips.  He called to his boss that he was taking a break.  He walked around to the corner of the building and leaned against the brick.  

"Hey, Anna," he said with a smirk.

"Hey, Dean," she said, her voice low as sidled up close.  She was working it hard today. 

"Who's that?"  Dean thrust a chin at the gangly boy looking confused by the soda machine.  

"My stupid brother, Cas.  Mom made me take him with me today."  Anna frowned, but smiled coyly up at Dean and, unsubtly, clasped her hands behind her back, making her shirt gap open.

"Hmmm."  Dean made it a point to look down and admire her soft mounds bulging out of her too small shirt, her areolas showing through the white fabric, and her nipples hard in the chill of early fall.  He rested a finger on the v of her shirt where the button was straining to keep her nonexistent modesty intact.  "Damn, no bra?"

"Nope."  Anna's breathing quickened as Dean ran his other hand down her back and up her too short skirt, exposing her ass to anyone who went by.  She placed her hands on his chest, but not obscuring his view to her chest.

"No panties?  Fuck girl."  His eyebrows went up.  "You want me, bad."

She jumped a little when he rested a finger in her crack because he could and she made no move to stop him.

"Can we go somewhere more private?" she asked, trying to step away.

"No."  Dean held her firm, glancing at Cas trying to get the soda machine to work.  "Why did your mom make you watch him?"  

A slight twist of his finger and thumb  and that straining button came undone.  He slid a finger into her top and brushed the nipple, not caring his hands were staining her shirt with grease and oil.  Not when the prize was so close.

"Cas doesn't need a babysitter."  She bit her lip and shivered, leaning closer.  "He's thirteen, for shit's sake, but my mom insisted."

"Thirteen's an innocent age."  Dean pushed her away enough to lean down close to brush a kiss on her neck.  He undid another button, slipping his hand on her ass lower, his finger probing her crack.  "You are a good girl for bringing him."

Anna was practically humping him.

"Yeah," she breathed, biting her lip again.  "I'm a good girl."

"So fucking good," he whispered, looking at her brother.  Cas was still trying to work the broken machine and was getting frustrated.  His cheeks were flush and he pouted.  

Hard in his jeans, Dean exposed Anna's tit, cupping it in his hand.  He was not surprised she let him with weak protests, considering he was fingering her asshole for all to see.  He leaned down and licked the nipple.  He chuckled when she jerked and clutched his arm.    

Pleased he could confirm his initial impression of her, he stepped back releasing her.  She did nothing to cover up, just looked at him with lust.  Perfect.

"Come to my house and bring Cas to meet Sam.  I live there."  He pointed to the peeling white house on the corner.  "I'll be home at 5:30."  He left the flustered girl to finish his shift.

He was twenty minutes late getting home because he had to convince Sam to actually come.  As predicted, there was Anna, looking like a bitch in heat, and Cas looking confused.  He introduced them to Sammy and told him and Cas to play in the backyard.

He sat down on the couch and proceeded to finger fuck Anna and suck her tits, all the while watching the boys out back.

---One Month Later 

"Dean, can you come over?  My parents are gone and I'm having to babysit my stupid brother again."

"Of course, Anna."

Within moments of arriving they were on the couch and Anna moaned wantonly as Dean kissed her, his hands up her shirt.  He trailed kisses down her throat and swiftly lifted off her t-shirt.  

"Dean," she gasped with a little giggle, playfully covering her tits.

"No shirts," he whispered before stripping off his own.  He grabbed her wrists, pulled them away, and licked her tits, one then the other.  Slipping one hand down into her soft pajama pants, he fingered her.  "When will your folks be home?"

"Ten.  You make me feel so good," Anna moaned.  Her overly excited, inexperienced attempts at rubbing his crotch were easily ignored.

Dean sucked her nipple, squeezing the tit.  His lower fingers breached her causing her to gasp again.

"Your folks know I'm here?" Dean whispered in her ear. 

"No, suppos-- AH! Be alone."  She arched her back, her hands rubbing and grabbing at him, not knowing what to do.

"You bad girl."  Dean thrust his fingers inside her, thumbing her clit.

"Yes," Anna fairly squeaked.  She moaned and asked,  "When are we going to have real sex?"

"Where's Cas?"  Dean ignored her question, slowly pulling off her pants.  He draped her legs over his shoulders and licked her pussy.

"He's-- oh!"  Anna grabbed his head.  "Up-- upstairs… a-Ah--asleep."

Dean chuckled, licking her clit fast as he thrust two fingers inside her.  He always fucked her fast.  She was quite lively as she writhed on his tongue and fingers.

"Too fast."  Anna pushed at his head, her legs trembling on either side of his head.  

He hummed and held her thighs apart to keep from getting his head crushed.  For a sixteen year old girl, she was surprisingly strong.  He kissed back up to her tits.  He loved tits.  He suckled each one, squeezing them in turn.  He could suck them for hours.  One time he made her come just from doing that. 

Dean fingered her fast, brutalizing her clit, squeezing a tit, and kissing her hard on the mouth until she arched her back and let out a strangled scream.  Dean chuckled as she twitched, riding the waves of forced orgasmic bliss.

"That was so fast but incredible," horny, sweaty Anna said with a sigh.  

"Seven minutes, a new record."  Dean nuzzled her neck and helped her lay down on the couch. 

"We have hours," she said, sleepily, "we don't have to go so fast."  She was fading fast.

She was so beautiful laying there naked and completely fucked.  He thought about jacking off on her, but instead he covered her with a throw and waited until she was thoroughly asleep.  He was so happy she slept afterwards.  He didn't want to have to waste his stash.  

Now for the real fun, he thought, smiling and rubbing himself.

***

Chapter Text

***

"Hello, Dean."

Dean's dick filled at the sound of that voice.  He closed the door of Cas' room and went to the bed.  He kissed Cas, drawing him close.

"Cas."  Dean swiftly unbuttoned the boy's shirt and slid a hand on his soft skin.  The thirteen year old was smooth and a bit pudgy, and felt like heaven.

"I missed you."  Cas sat back to pull off his shirt and wiggle out of his pants.  "You taste funny."

Dean licked his fingers and grinned.  "I just had a snack before coming up.  Lay down."

Dean shucked his clothes quickly after a glance at the clock, 8:23.  Anna usually slept for about an hour after frenzied activities.  He pulled the lube out of his pocket, laid down next to Cas, and squeezed some out on his fingers.  He kissed Cas again, spread his legs, and slid his slicked fingers to his tight hole.

Cas flinched but didn't break the kiss.  He spread his legs further and tilted his hips.  Cas gasped and let out a long breath when he was breached.

"That's right, relax."  Dean raised up to look at the smaller boy.  "You are so tight."

Cas smiled, practically beaming.  Dean worked his two fingers in and watched as pain and pleasure played across the teen's face.  He rushed the prep because he was getting blue balls.

"I love how tight you are."  Dean kissed him working in a third finger.  He pumped him, finger fucking him fast while he flinched and whimpered.  He licked down the boy's chest then took one of Cas' nipples into his mouth.  He chuckled when Cas jumped, gasped, and moaned at the same time.

Alternately licking and biting until the nub was hot and hard, he switched to the other with Cas holding onto his shoulder and arm.  The porn sounds this boy was making had him ready to explode.  He pulled off before the firecracker went off and kissed him again.

"That got you going."  Dean smiled, ignoring the boy's dick, and moved, getting between Cas' legs.  "Ready?"

With a flash of fear and excitement, Cas nodded uncertainly.  Dean knew he needed a more prep, but he had waited long enough, and, most importantly, he didn't want to stretch him out too much.  Dean was ravenous for him.  

He pulled out his fingers and smeared the lube on his throbbing dick.  He pressed against Cas' hole letting the boy anticipate the pleasure.

"You're my best friend, Cas."

"You're my best friend, Dean."  Cas' face brightened and Dean pushed.  Cas slapped a hand on his mouth as he arched his back and screamed.  

Dean laughed, feeling the rush of euphoria soared through him and Cas via the tears that formed and fell.  He moaned as Cas' body shook and clenched around his dick from the sudden intrusion.  Dean watched as the thrill of excitement, the pain of reality, and the anticipation of pleasure crossed Cas' face; not unlike their first time.  Cas bawled for an hour afterwards.  Dean held him and petted his hair and told him he was gorgeous in how the boy made him feel.  He loved the way virgins would cling to him, wanting to please him, worshiping at the altar of Dean.  Their fragile psyches needed to be validated making them so easy to manipulate.  It made it all the more enticing.  

He promised to go slow, but he lied and he began thrusting.  He would either get used to it or not, Dean needed to move.  Cas whimpered and squeaked with Dean's thrusts, his trembling body rocking under him.

"Damn, Cas, you are so damn tight."  Dean closed his eyes and planted his hands beside Cas' head, looming over the boy, dominating.  He snapped his hips viscously, having to exaggerate his movements in the vise of a hole.

Crying out with each thrust, Cas clutched at Dean, searching for purchase while he got plowed.  At one point Dean had to hold onto Cas' hips to keep him in place because his powerful thrusting was pushing the boy away.

Cas' expressions ran the gamut of pain to confusion to pleasure, and everything in-between.  His sex sounds were so yummy, he'd bet a porn star could take lessons from this boy.  Dean kissed him when he got too loud, stifling his whimpering cries.  He loved to hear the boy's painned pleasure.

Oh yeah, he had his tits downstairs and this juicy ass up here.  No vagina ever felt as delicious as a pubescent boy's ass.

After pounding that ass for a good while and Cas sobbing beneath him, Dean had reached the pinnacle height of pleasure, teetered on the edge of explosive pleasure and utter deviation, he came with a truncated roar, pushing himself deep and wrapping himself around Cas, holding him tight against his chest, pumping him full with every jerky thrust, until his orgasmic flinches stopped.  Rolling over and out of Cas, he threw an arm over his eyes.  

"Fuck, that was..."  Dean gasped, breathing in deep the smell of their sex musk.  The stench of lust laced with fear and pain always sated him.

"Was I better?"  The quiet, hitched, insecure question sent a thrill through his gut.  

Dean leaned up on an elbow and touched Cas' face, gently wiping away a stray tear.

"Yes, Cas, you were better."  He tilted his head, brushing the hair from Cas' face.  "You were quieter, but I see you still cried.  I mean, you're not a virgin."

Cas' face crumpled.  Dean enjoyed watching as he tried to salvage something of his worth with trembling hands swiping at his face.  Dean kissed his forehead and brushed fingers along his cheek.

"You feel good, don't you?"

"I feel--"

"I mean, how could not feel incredible?  You feel incredible, don't you?"  Dean fell back down.

"I guess--"

Dean sat up and stretched.  "Exactly."  His body felt so relaxed and the memory of that orgasm gave him a shiver.  "Never thought I would keep coming back to you.  Damn."

Cas sniffed and said, "I've been practicing."  He leaned over with a pained hiss and pulled something from the desk drawer.

Dean let out a burst of laughter.  "Where did you get that?"  He regarded the tapered, black thing with a round knob on the end.

Cas blushed, making his flush face redder.  "It's from the blender."

Dean threw back his head and laughed, shaking his whole body.  "You are a clever little dude."  He got up, wiped himself off with Cas' pajama top, and pulled on his clothes.  "Don't practice, you know I like you tight.  It's the reason it feels so good."

Cas smiled, wiping his nose with the bed sheet.  "I'm trying to get used to it."

"That is my job.  Did you come?"  Dean asked offhandedly, pulling on his boots. 

Cas shook his head looking sad.  "It hurt too much."

"What have I told you?"

"Stop focusing on the pain."

"Exactly.  Pain is part of it.  It hurts like a bitch when I push in your tight little hole, but I push past it.  I move so I can get to the good stuff."

"I know, but--"

"You reach for that pleasure I am pumping into you and you will come, Cas," huffed Dean, acting put out.  He rolled his eyes as Cas slumped and looked at his hands.  "I know you feeling, I feel it."

"You do?" said Cas, his face and voice earnest.

"Of course, Cas."  Dean brushed his fingers along his jaw and kissed him on the forehead.  "It will get easier.  I promise.  You just need to focus."  He sat on the bed and shook his head.  "We've done this a few times, I have faith that you will get it right soon."

"This is our fourth time."  Cas looked so proud of himself for remembering.

Dean remembered each time like the first, licking his lips, pushing down the flush of arousal.  Unlike the others, he kept coming back.  Normally, when the boys became experienced, they failed to excite Dean.  Cas kept pulling at him, kept drawing him to him with his innocent demeanor that didn't seem to diminish after their first time.

"I bet next time you'll do it."  Dean pulled down the sheet Cas had covered himself with and palmed Cas' soft junk, working him until he was hard again.  He stopped and held his dick lightly, not letting him move.  "When you come, it will be fantastic."  

Dean never let the boy come while he fucked him.  He didn't want to spoil Cas.  He learned his lesson.

"Remember, don't tell anyone.  It's our secret."  Dean stuck a finger to Cas' lips who obediently took it in his mouth and sucked.  He smiled and stood up, slipping his finger out of that sweet mouth. 

"I made a promise and I keep my promises."  Cas' innocent seriousness always made Dean hard.

"Good.  Now don't get mad that I have to date Anna."

"I know."  Cas pouted and looked down at his hands.  "It's so mom and dad don't keep us apart."  He peeked through his eyelashes.  "Do you have sex with her?"

Dean chuckled and shook his head.  "Of course.  How am I supposed to keep up appearances?  You understand, don't you?"  The fact he hasn't had vaginal sex or even let her blow him was beside the point.

Fresh tears fell, but Cas nodded.  Dean kissed him lightly on the lips, pulling away when Cas tried for more.

"If it makes you feel better, I am thinking of you while I'm fucking her.  Plus, you don't have those gorgeous tits."  He pinched Cas' nipples, holding them after Cas flinched.  "Mmm, I could suck them all day."  He closed his eyes and licked his lips.  He waited for a moment before looking down at the devastated boy and released him.  

"Listen to me, I only do what I have to so I can be with you.  Trust me."  He poured sincerity into his voice and face.  

"I trust you, Dean."

"Go to sleep."  He tousled Cas' hair and left after turning off the light.  Back downstairs he found Anna dressed and eating a slice of pizza in the kitchen.

"Hey, what happened?  Cas okay?  I heard noises."

"Cas had a nightmare."  He shrugged.  He stepped up close and raised her shirt over her tits.  "What did I say about shirts?"  He thumbed her nipples, cupping her tits.

"No shirts."  She giggled.  "Thank you for helping Cas.  I don't understand his nightmares.  He didn't have them before we moved here."  Anna kissed him.  "You are so good with him.  I am glad he responds to you."

"We're best buds, BFs, or some shit."  Dean smirked and squeezed her tits.  "I appreciate you giving us privacy so I can take care of him."  He kissed her slowly.

"It must have been intense, you're sweaty."

"Yeah, I fucked Cas'," he kissed Anna deeply, pinching her nipples, "demons in the ass."

Anna laughed and shivered again.  Dean lifted her to sit on the counter.

"Stop wearing shirts when I come over."  He latched on and sucked, tickling her nipple with his tongue and teething the areola.

She moaned, carding her fingers through his sex-sweaty hair.

"I would love to, but I don't want Cas coming downstairs and seeing.  Can't have him telling."

Dean laughed.  "Can't have that."  He gave the other tit the same treatment.

"I don't want you to stop, but it's nearly ten, you should go."  Anna looked sad with her tits glistening with his spit on her hard, prominent nipples.  "Oh, can I ask a favor?  I have a late practice, can you pick up Cas tomorrow after school?"

"Sure, I'll give Cas a ride."  Dean smirked at his cleverness.  

***

Chapter Text

***

Dean leaned back on his couch and moaned.  He held onto the boy's head between his legs letting him move slightly.  His mouth was so warm and his tongue was the right amount of soft and firm.  He wiggled his hips, swirling the head of his dick in that luscious mouth before releasing the hair.

"Your mouth is so good, Cas."  

Cas' eyes smiled up at him.  He had to use both hands to stroke Dean as he tried to take in as much as he could into his mouth, which was only a little over an inch. 

"Fuck, I wish you could do that all day."  Dean shifted, making Cas move to accommodate. 

Cas did his best, but he really did suck at this and not in a good way.  His mouth wasn't big enough.  His tongue felt amazing on his head, but the rest of his dick was left wanting.

"Stop, up."

The naked boy scrambled up to Dean's lap.  Dean kissed him deeply, maneuvering his legs so Cas straddled him.  He rubbed his throbbing dick along the boy's crack, getting ready to impale him.  

"I missed you," Dean kissed down the boy's chest, raising him up by his waist.

"It was only last night."  Cas giggled when Dean licked his belly.  

"Stand up, feet on either side."   Dean held him by the backs of his thighs, sliding one hand up to tickle his asshole.  "Beautiful.  You can put your hands on my shoulders.  Remember, don't touch my hair."

Cas' little boner was at the perfect height for Dean to take into his mouth.  He allowed Cas to thrust into his mouth slowly.  Dean was happy he was small for his age.  It was one of the features that drew him to him.  He looked more like ten than a teen.  His body was just beginning to go through puberty.  His hair had come in thick, but he kept himself shaved just for Dean.

Dean hummed, making Cas gasp and flinch.  Dean laughed, lapping at this dick so it wouldn't come out.  He could almost take the whole thing into his mouth, but he didn't as a matter of principle.  He sucked hard and then settled into an easy rhythm.  He slid his hand up further and breached the boy dry.  He enjoyed the hiss of pain.  He pushed in, loving the little jerks Cas did to stifle his pain and continue his pleasure.  Dean told him if he pulled out for any reason, Dean considered that action to mean Cas didn't want it.

Cas cried out when Dean forced in another finger, but remained thrusting into his mouth.  Maybe Dean would finish him if he stayed through the entire prep.  He doubted he would make it.  Cas' legs were trembling and his ass was clenched so tight it was hard to get his fingers in.

Cas gasped again, his knees bent but he remained upright.  Dean moved faster, swirling his tongue that pulled the most delicious moans from the boy's throat.  Okay, he deserved this.  Dean sucked harder, thrusting his three fingers into the boy's ass.  Cas squirmed, his fingers digging into Dean's shoulders.

"Dean," Cas whimpered before he orgasmed.

Dean drank down his jizz, sucking his tender and overly sensitive dick until he heard the strangled sob above him. 

"Please."

 Dean pulled off and helped Cas lay down on the couch.  Damn him, he looked so sexy all fucked out like that.  His hair was sticking out all over, his lips dick swollen, and his pupils blown wide, nearly blotting out the blues from the rare orgasm Dean gifted him.

"You are a treasure."  

Cas smiled sleepily up at him.  "I love you, Dean."

Dean grabbed the lube and smeared an extra generous amount on his dick and Cas' asshole.

"Please, I still hurt."  Cas put his hands on Dean's chest above him, his eyes now full of fear.

"I'll be careful," Dean lied.  "You can be as loud as you want here."

Dean lined up and smiled at the sharp intake of breath when the head of his dick touched Cas' asshole.  He kissed Cas lightly, then pushed in slowly until just the head was in.

"Dean!" Cas squeaked, arching his back and clutching the couch.

"That's right, let me in."  Dean shuddered as Cas' hole clenched around him.  He thrust in tiny movements to enjoy the tug, stimulating his dick with incredible jolts.  

Cas relaxed, his body melting at the sensation Dean could only imagine he was feeling.  He shoved the rest of the way in.

Cas screamed, arching his back and grabbing Dean's arms braced on either side of the boy's head.  Dean rode out the pure sexual thrill lancing through his body as that tight asshole squeezed his dick painfully.  He thought Cas was going to pinch it off, but soon it felt better and Dean sighed contently.  He began thrusting.

"Wait!"  Cas cried, his breath hitching as his body shook, struggling to accommodate Dean's huge dick.  He stifled a sob and he held on to Dean.  "Please."

Dean smiled and kissed Cas' sweaty forehead, slowing down his movements, letting the euphoric pulses crash through his body at a more sedated pace.  He closed his eyes, leaned his head back, savoring this delicious experience.

"Shh, shh."  Dean jerked three hard thrusts and Cas answered with three strangled cries.  "Damn, I love you are so tight."

Cas smiled as he rocked under Dean's thrusts, sweat glistening on his soft skin.  His face flushed red under the strain.  Dean leaned to look at his dick surrounded by Cas' overstretched hole.  Such a beautiful sight.

"You were made for me, Cas."  He put his hands under Cas and lifted him until he sat sitting with Cas straddling his lap.  He pointed, making Cas bend.  "See? My dick fits in your ass perfectly."  

"Yeah," Cas said, uncertainly, still trembling with effort.  

"That is a glorious sight."  Dean shivered and he snapped his hips again and again and Cas yelped in response.  He tried to hold onto Dean, but Dean held him away, guiding him up and down on his happy dick.  It made Dean want to plow that ass, but he held back.

"Shit, I could do this all day."  Dean laughed and bounced Cas on his lap, jolting mind blowing sensations though his body.  "I wish I could have you every day."

"Yes-s, D-Dean."  Cas was panting, the strain of taking Dean's huge dick seemed to be more tolerable.

He must have hit that balance between pleasure and pain.  Winking, Dean laid Cas back down on the couch and sped up, drawing out those cries of pained pleasure Dean needed to hear.  It told him Cas was feeling great too.

"Fuck, you are enjoying this so much.  Damn, to be you for only a moment, to experience how my dick feels in you.  Cas, you are so lucky!" Dean practically yelled he felt so wonderful.  And wonderful didn't seem like an adequate enough word to describe what Dean was feeling.  He blinked back his sweat and grinned down at the struggling boy and saw him grinning back and nodding in time with Dean's thrusts.

"Come with me, Cas.  I want to fill you up while you spurt all over me."  Dean pumped his hips so fast.  He reached between them and stroked the boy.

He came with a roar, pressing his dick so deep in Cas.  He panted, his breath wheezing in his lungs.  He laughed, guttural and primal.  Cas was his and he had marked his territory.

Dean rested on his elbows so as not to crush the boy and waited for his wild heart to calm down.  He watched the boy beneath him do the same thing.  He took a deep breath and gathered Cas in his arms and sat up on the couch, careful to not dislodge his softening dick.  He didn't want to leave that warm channel.

"W-was I be-better?"  Cas choked out, curled against Dean's chest.

Dean stroked his sweaty head and nodded.  "Yes, you were better.  Stay still."

Cas tried to shift which made Dean slip, but he held Cas still.  He rubbed the boy's back and listened to his orgasmic sobs.

"You came again, right?"

"Y-yes."  His voice was small.

"Good, didn't I tell you it would be fantastic?"  Dean laughed and leaned Cas back so he could look at him.  He was even more beautiful with tear tracks down his face, the red rims accentuating his deep blue eyes blown from his first sex induced orgasm.  "Tell me that wasn't the most fantastic thing you ever felt?"

"Dean-n, I--" Cas voice shook as he nodded, "it f-felt--"

"Fantastic, right?  Oh… Can you feel that?  I'm getting hard again.  You are so sexy, Cas."

He kissed the boy, long and slow, feeling his dick fill Cas again.  Damn, he wished he had thought to do this before.  It was an amazing feeling to grow hard inside an ass.  

"Awesome!  I have got to do this again."  He watched his dick expand that red rimmed asshole until the skin was white.  "Cas, you are still just as tight."  His eyes were wide in amazement.  How did Cas do that?  It's like he turned virgin after each of Dean's orgasms.  Maybe his dick was magic.  He laughed at that thought.

Dean stroked Cas hard and continued to stroke him until he was rocking his narrow hips on Dean's dick.

"Cas, that feels so good.  Do I feel good?  Tell me."

"Yes, Dean.  You feel good."  His voice was all low and dreamy.

"You want me inside you all the time."

"Yes, inside me."  Cas blinked slowly.  "This does feel good."

"One day you will get to feel what I am feeling and you will want to own it like I do."  Sighing at the eventual loss of thyos delicious child, Dean started to move him up and down.

"Please!"  Cas clenched and gripped Dean's arms.  Fresh tears fell down his face.  "Slower, please."

"Damn, Cas, you kill me with those lovely tears."

"It hurts so bad, Dean," Cas cried.

"I know, it hurts so good.  You feel that explosion of pleasure.  I like touching you.  I like making you come with my hand and mouth and now my dick.  I want you to feel as good as me."  Dean hugged him close as he thrust inside him.  He went slower because he felt tender.  He leaned Cas back and bounced him on his dick.  Dean loved the way Cas would cry out each time he slammed back down.

"P-please, De-ean, I h-urt r-real bad."

"Cas, do you not want to have sex with me?" 

"I do," Cas said in earnest.

"Then stop whining.  Let me finish."

Dean smiled when he nodded.  He fucked Cas faster and came with a more sedated groan before stroking Cas.

Cas writhed on his dick, moaning and groaning, whimpering, and crying.  He let out a long whimpering cry as he shot another load of jizz on them. 

"Gorgeous, Cas, just gorgeous."  Dean kissed him again and held him as he twitched and trembled.  When he had gone completely soft he allowed his dick to slide out of Cas' abused asshole.  Cas was limp in his arms when he shifted them.

"Damn, just like Anna."  Dean chuckled and brushed the hair from Cas' brow, kissing him lightly.  "You rest, Cas."

He laid Cas down and thought about covering him, but decided not to.  He didn't want to be denied the sight of this sweet boy.  Cas looked so sexy all boneless and fucked out.  He grabbed his phone and snapped a few more pictures to add to the hundreds he seemed to already have.  

Dean went to clean himself and get some water, he was damned thirsty.  A moment later he kneeled beside Cas, petting his hair and feeling his dick stir.

"You are mine."

***

Chapter Text

***

Dean touched Cas' skin, letting his fingers memorize the contours of the boy's body.  He frowned when he saw the bruises.  He traced the line of colors on his waist, followed it down to his hip, watching as the red marks deepened into blues and purples, Cas' flesh colored around his leg.  

He raised Cas' leg causing only a small whimper.  He saw more bruises, more colorful on the inner thighs.  He frowned, wondering what the hell happened, until he saw how his hand matched up one of the shapes.  He smiled to himself.  He never was around the others to see his marks on their skin, but here he saw the beautiful way these bruises told the world this boy was his.  

He raised Cas' small balls and looked in the fading light to see Cas' purple and red asshole all stretched out and gaping, leaking his cum. 

"Mine.  I did that, sweet Cas."  Dean carefully leaned forward and licked the rim.

Cas flinched but didn't wake.  Dean smiled and licked again, feeling how hot his trashed asshole was.  He pushed in one finger, only to find just a tiny bit of resistance.  

"I reamed you out good."  Dean chuckled, sliding two fingers in and out is Cas, enjoying the small grunts Cas made in his sleep.  He frowned.  "Why can't I quit you?  The others didn't last past the first fuck."

He licked around his fingers inside Cas, feeling how the skin puckered.   His dick stirred.  He wanted more, he needed more.  He began scissoring his fingers and added a third.  This was so easy as he was gaping already.  Cas was so much hotter inside, though, feverish and puffy.  Dean's dick had abused him but good.  He turned his hand and felt for that spot, that delicate spot… ah ha, there it was.  It wasn't as deep as he thought.  He toyed with it and saw how Cas' little penis was responding.

"You naughty boy.  Ready for another round already?"  Dean kissed Cas' plump lips, savoring the tender taste of salty tears.  He trailed kisses down his chest, spending time sucking on the tiny nubs of his nipples.  He licked them, opening his mouth wide to tongue the areolas as well.  When they were kiss swollen and colored with hickies, he continued his trek down Cas' body.

"Why?"  Dean grabbed his own dick and stroked himself, looking at that perfect body of that wonderful boy.  "I should have shed you after I fucked you the first time.  You have me in your thrall.  Wrapped around your little finger."  He stroked himself and resumed massaging the boy's prostate.  Cas thrashed, whimpering in his sleep while his little dick stood at attention, neglected and wanting.

Dean couldn't help himself, he probed more, rewarded with tiny beads of precum.  He licked it and sucked in Cas' dick.  Cas' moans spurred him on, Dean stroked himself, pumped that ass, and tongued the boy's dick until Cas came with a weak whimpering moan.  He curled in on himself, still out but responding to Dean as if he knew.

"You do know, don't you?"  Dean licked his lips and stood.  "Fuck, I love you, you beautiful boy!"  He yelled, his confidence shattered as he spashed his cum onto Cas.  It should have almost drowned him, but he had already come twice this afternoon.

"Dean?" 

Dean jumped and turned toward the door.  Sam stood there looking lost and hurt.  Dean sobered and went to him, ignoring his nudity.

"What's wrong, S--"  His concern was brushed aside as Sam pushed past him to stand behind the couch.

"You said--"  Sam snapped, his face streaked with angry tears when he turned.  "You said no one would replace me."

"It's true, Sammy.  No one has replaced you."

"Then tell me what you were doing with him?  Pissing on him?"  Sam angrily swiped at his face.  "It sure as hell looked like you coming on him."

"Sammy."  Dean held out his hands, his voice soft and placating.  "It was just--"

Sam stepped back from the touch.  "How old is he?  Ten?"

Dean scoffed, offended.  "He's fifteen."

"There ain't no fucking way that is fifteen."  Sam went around the couch and crouched down.

"Sammy, look, I--"

Sam stood abruptly, his mouth agape in shock.  "It's Cas, Anna's brother.  He's barely thirteen!"

"It's consensual."  Dean shrugged, putting his hands on his hips.

Sam laughed, ugly and accusatory.  "Yeah, I know your kind of consent.  You buttered him up and gave him head and he was yours for the taking."

"Don't be so fucking dramatic."  Dean crossed his arms.

"You've fucked him, so your done with him, right?"  There was hope in Sam's expression.

"Not yet.  We're having fun."

"What, gonna string him along for a few months then dump him?  He's gonna be too old for you in a year."

"This is none of your business, Sam."  Dean glared at his brother.

"I know what happens after you are done.  Kevin had to move away.  Garth is anorexic.  Cole, hell, Cole got something done so he could skip his junior and senior years to join the Army early."  

"I am not responsible for what happens after a relationship ends," Dean scoffed, rolling his eyes.

"Do you really think when you dump someone, they can easily put it out of their minds like you?"  Tears filled Sam's eyes.  "That you are so easy to forget?  Do you?"

"Sammy," Dean said softly, dropping his arms.

"How can they forget you made them feel?"  Tears fell in tracks down his cheeks.  "How he felt loved?  How he felt wanted and not alone in the dark when Dad was gone for days on end? You think he can just turn off that urge to ride that dick all night making you come, orgasm after orgasm, until I can't walk the next morning?"  Sammy pushed Dean, his face a mask of fury and hurt.  "I haven't forgotten how you drew out the best orgasms I have had in my life.  You think I haven't wanted you, needed you so bad that I have jerked myself raw and only to feel so damn abandoned?   Do you know how many night my ass begs to be filled with your fucking cock and I am left empty and alone?"  Sam stumbled back.  "You think I can just forget?"

Dean stood slack jawed.  He never thought Sam still wanted him.  He told him to stop on his fourteenth birthday, so he stopped.

"Sammy, you told me to stop," Dean said, taking a step.  "I left you alone for three years.  What are you saying?"

"I'm saying you should have never fucked me!"  Sammy shook with emotion.  He was jealous!

"Sammy."  Dean shook his head.  "You wanted it as much as I did."

"I wanted my Dad home being a dad.  I wanted my big brother to protect me when I was scared.  I didn't want my virginity taken by my fifteen year old brother."

"You came to my bed, practically begging for it."  Dean picked up Cas' discarded shirt and wiped himself off.  He was getting itchy.

"I was eleven and scared of a fucking storm!"  Sam's eyes flashed anger, all sadness gone.

"You were willing every time we had sex. You enjoyed it as much as I did.  You told me how much you loved how I made you feel.  When you turned fourteen you asked me to stop, so I stopped.  I am not the bad guy."

"Yes, yes you are!" Sammy yelled, his voice breaking.  He wiped at his eyes and stomped up the stairs.

Dean started after him but was stopped by a tiny voice.  He turned 

"Dean?"  Cas was sitting up, clutching the back of the couch, looking at him with fresh tears streaking his face.  "I can't feel my legs."

"Hold on," he said dismissively.  He turned back to the stairs.  "Sam!"

"Dean, my butt hurts so much."

"Not now, Cas."  Dean took his three steps and backed down when he saw Sam coming back down.  "Sam, let me--"

"No,"  Sam said, his voice low and even.  He stepped around Dean. 

Dean grabbed his arm and spun him around.  "Okay, I get it, you're jealous.  That is no reason--”

"I'm not jealous."  Sammy jerked his arm out of his grip.  "Dean, you abandoned me three years ago.  Ever since that night you've ignored me.  You left me behind.  We never hung out, we never played video games any more, hell, we never even watched a damn movie together after that night."  Sam tossed a duffle bag on the floor near the door.  "I haven't gotten so much as a hug from you in three fucking years."

"Sam, you said if I loved you I would stop having sex with you."  Dean grabbed his jeans and pulled them on.  Shit, he needed a shower.  "I love you, but that doesn't mean I can't have sex anymore."

"You didn't have to stop being my brother."  Sam went over to the couch again.  "Come on, Cas, I'm taking you home."

"I can't move," Cas' voice cracked.

"I'm supposed to take Cas home at six."  Dean glanced at the clock.  "I have another hour with him."

"No."  Sam scoffed again.  "Get up Cas."

Cas cried out when Sam tried to pull him to his feet.

"Leave him alone, Sam."  Dean leveled a gaze at him which said more than his words.  "I get it.  You're jealous that I am having sex.  So you either tell me you want me back or you walk out that door and leave me and Cas alone."

"Or what?"

"Or nothing."

"I want to go home," Cas whined.

"Shut up, Cas."  Dean kept his eyes on his ungrateful brother.  

"You won't get away with this."

"I'm not doing anything wrong."  Dean took a step closer.  "Cas loves me and the way I make him feel."  He grabbed his crotch to make a point.  He loved his brother but he was stepping over the line.  

"The last time I looked, fucking a minor is a felony."  Sam straightened and looked much older than seventeen.

"Get out.  This is my fucking house and that is my fucking boy and this is none of your fucking business."  Dean pointed to the door, gritting his teeth..

Sam walked around the couch, gave Dean a wide berth, and picked up his bag.  He looked back at Cas and left.

Dean sagged against the back of the couch.

"Dean?"

"What?" he snapped.

"I'm bleeding."

Dean rolled his shoulders and let his head fall back.  He looked at the ceiling wanting a redo.  

"Dean?"

"No one cares that you're broken, Cas."

He shoved off and got a beer from the fridge.  He downed half the bottle before he went back to Cas.  He needed to fuck away these feelings.  He pulled off his jeans, letting his throbbing dick free. 

"Hey, I'm sorry."  He knelt down beside Cas and kissed him softly.  "Let's go one more time before I have to take your home."

"I hurt--"

"No, you don't.  Here."  Dean stroked his dick until it was hard.  "See?"

"I can't feel--"

Dean took the boy's dick into his mouth to shut him up.  He tongued the boy, ignoring his protests.  He sucked him hard and fast, pulling an orgasm from him before he sat up.

"Didn't that feel good?"

Cas was bawling again, his hands over his face bawling.  It was their first time all over again.  Dean rolled his eyes and spread the boy's legs to get between them.

"Cas--"

"Dean."

He stood, fury coating his features.  "I told you to leave, Sam."

"Yeah.  You can't ignore me any more."  Sam leveled a gun and fired.

Dean stumbled back, shock widening his eyes.  His mouth fell open and dropped his beer.  He looked at Cas who was screaming without any sound. He didn't remember him having freckles. 

The room spun and he fell to the floor.  Dean stared up at the ceiling not understanding what happened.  

"Sam?"

His brother's face appeared in the darkness falling around him.  

"Goodbye, Dean."  Sam shot him again.

***Epilogue (because I'm done)

Sam is arrested by police.  He tells them about trying to save Cas from his pedophile brother.  He tells them how Dean had sex with him from age eleven to fourteen.  He is held for psychiatric testing.  He ends up pleading manslaughter and gets sent to a mental hospital because he breaks down begging to die so he can be with Dean.

Cas has a ruptured disk in his back and his pelvis was cracked.  He was in surgery for a ruptured rectum.  He has chronic back pain.  He developed depression and tried to kill himself.  He finally ends up in a mental institution with Sam.

Cas and Sam developed an unhealthy, dependent sexual relationship as they try to cope without Dean.  They alternately love and hate him.