Chapter Text
“Daddy? What are you doing?”
“Shhh,” Dean whispered, moving his hand lower to cup his son’s ass, loving how firm and round it was, how small. “Quiet down, angel. Let daddy touch.”
Cas whimpered and tried to pull his towel down to cover himself, but Dean was too strong. He lifted the towel up and away until there was nothing Cas could use to keep Dean from seeing his private areas, completely clean and bare after his bath.
Dean leaned forward and smelled his angel’s neck, catching the whiff of fresh baby wash that seemed to always cling to Castiel. Dean couldn’t imagine a more erotic scent.
“Daddy,” Cas whispered, his words coming out shaky in a way that should have made Dean back off, but all that came to mind was the image of his angel whispering Daddy, Daddy, please on his cock, words coming thick and heavy from the large member thrusting in and out of him. “Daddy, please,” he whispered, completing the fantasy.
Dean groaned and allowed his finger to slip between the two round cheeks of his son’s ass to circle the tight virgin hole he wanted to claim.
“Quiet, angel,” Dean said. “You remember what I said about being a good boy?”
Cas choked out a sob, but he nodded and stayed quiet otherwise.
“That’s right. I want you to be good for me now, Cas. Open your legs.”
Cas held them together stubbornly, not wanting his daddy’s hands to keep going. He was scared, more scared than he remembered being in his life, and the hands on his bottom felt uncomfortable, wrong.
“Open your legs.”
This time it was an order, and Cas couldn’t stop the tears from falling as he obeyed. Dean’s hand came down on his rear, smacking hard enough to have Cas sobbing.
“You listen the first time I ask,” his daddy said.
“I’m sorry,” he whimpered. The finger around his hole pressed harder.
“I forgive you, angel” Dean said, distracted by the little whimpers his son was letting out at the contact. “I’m doing this for your own good. Just need to check and make sure you’re healthy.”
Cas bowed his head in shame. His daddy would never do anything to hurt him. Why did he even think he would?
“Get on the bed. I think I found something.”
Found something? Was that bad? He didn’t want something bad to be happening to his back parts. Cas was confused, but he did as his daddy asked, sitting down on the bed even though he was still naked.
His daddy smiled at him and shook his head, obviously amused by whatever he’d done. “Not like that,” Dean said. “Up on your hands and knees. I need to be able to see you.”
Cas blushed and turned around, hiding his head in the pillows, ashamed as his backside was completely exposed to his daddy.
“Good boy, Cas,” Dean praised.
Cas shivered at the thickness of his daddy’s voice. He’d never heard it like that before, but it sounded like he was crying, like whatever he saw was really bad.
“I’m gonna do something, angel,” his daddy told him. “It’s gonna feel cold, and it’s gonna make you feel full, like you want to get rid of it, but I need you to hold it, okay? We have to clean you out.”
“Okay,” Cas answered, bracing himself.
Something small and hard probed his hole, slipping inside just barely before he understood what his daddy meant. He cried out as he was filled to the brim with cold liquid, wanting to do just what his daddy said not to.
“That’s a good boy. You’re doing so well.”
“Daddy,” he sobbed.
“I know. Just a little bit longer.” Dean was mesmerized with the sight. His son’s hips twitched as he took ounce after ounce of the enema fluid, sobbing loudly, making Dean swear he could hear it slosh inside of him even though he knew it was impossible. “Almost done.”
“Please.”
“There you go.”
“Daddy.”
“All done. Hold it in, angel.” Dean removed the nozzle from his boy’s tight hole and smiled wide when his son did as he asked and squeezed his hole closed to keep the fluid in. “Good boy. You took it so well.”
Cas couldn’t stand it. He sobbed into the sheets, burying his head in so that his daddy wouldn’t hear him cry. It hurt so much that Cas was sure he’d never felt anything like this before. He wanted whatever was inside of him out. But his daddy’s hand was rubbing circles onto his back, and it reminded him that he was just making things worse. His daddy was trying to help him, and all he could do was cry about it. His daddy was soothing him, trying to make him feel better even though it was his fault in the first place.
“Stand up, Cas. Off the bed.” The words were calm, soothing, and Cas did as his daddy asked.
It was even worse standing up. He could feel the fluid inside of him move, pressing against his rim, wanting out, but he knew he couldn’t let it.
“Go to the restroom, angel,” Dean said. “Let it all out.”
Cas looked up at him with red-rimmed eyes, unsure of what he’d heard.
His daddy smiled. “Go potty, Cas. I’ll be right here when you’re done.”
Cas bolted to the restroom and Dean couldn’t help but shiver as he thought of how clean his son would be inside and out, and just how much fun it would be to make him all dirty.
It took a minute for Cas to finish, and in the meantime, Dean grabbed some supplies. Lube was a priority. He may have been sick for wanting his son this way, but that didn’t mean that he was completely depraved. He eyed the condoms in his bedside drawer, but thought better of it. He wanted to feel that tight heat around him, stuff his angel full of come. He didn’t want or need a condom for that. Besides, that wasn’t what he had planned.
He watched his son walk hesitantly out of the restroom to stand at his daddy’s side.
“Just two more times, angel,” Dean said.
Cas bowed his head and kneeled like he was supposed to, crying as he was filled to the brink again. It felt like more and more fluid was added each time, that he could feel it stretching out his stomach with how much there was, like he would choke on it if he breathed too deep. But just as it started getting too bad, his daddy would stop and send him to the potty so that he could be emptied. By the third time, it was easy to get the fluid out of him, and he felt better than he had in a while.
Cas came out of the restroom looking happier now that they were done. The tenseness in his shoulders was still there, but it wasn’t as pronounced as it had been before.
“You ready, angel?” Dean asked, holding up a different bottle than before.
“Th –there’s more?” His angel sounded so distraught that Dean felt the urge to bury himself in his son’s tight ass right then and there, but he held himself at bay. “You –you said… You said only two more times.”
“I’m sorry, Cas, but I just needed you clean. I still haven’t gotten a chance to inspect you yet.”
Cas began to cry, harsh sobs that shook his entire frame, and every single whimpering noise that came from his mouth went straight to Dean’s cock until it was hard in the confines of his pants.
“Come here, angel,” Dean beckoned, and Cas charged him, running across the expanse of the bedroom to bury his face in his daddy’s soft t-shirt.
“I –I don’ li—hic—like it.”
“I know, Cas. I know.”
“Th –then why?” he sobbed.
“Because I have to make sure you’re okay. I want my little angel to grow up big and strong. Don’t you want to grow up big and strong?”
Cas couldn’t speak through his hyperventilating, so he just nodded against Daddy. He didn’t know what was wrong with him. His daddy was just making sure he was okay. There was no reason to act like this, but he couldn’t help it. The touches were strange, not horrible, but not good either. He wasn’t sure he liked them, but when did he ever like things that were good for him?
“You’re so strong, angel,” his daddy praised, and Cas couldn’t help but feel better at it. If Daddy thought he was strong, then maybe he could do this. “You’re doing such a great job. I just need to finish checking you out, okay?”
Cas got his crying under control and whispered, “o—hic—okay.”
“That’s a good angel. Back on the bed.”
Cas didn’t sit this time, already knowing that his daddy wanted a view of his hole.
And, damn, was it a view. Dean licked his lips at the sight of the puffy pink hole that he knew would be a stretched out red by the end of the night. Dean coated his finger in lube and began teasing his boy, just touching.
The finger that circled his rim was cold and wet, and it pressed against him hard, making him gasp. “Daddy,” he cried out.
“Shhh,” Dean soothed. “It’s okay, angel. Daddy’s here.”
That calmed him down a little, but the finger was still there, circling, circling.
Then it slipped inside for a moment, making Cas choke out a sob in surprise, but it was gone before he could really protest, circling the rim again. It became a pattern—circle, circle, slip, circle, circle, slip. Each time the finger slid inside, it went deeper and deeper until his daddy’s entire finger was nestled in him and he was crying outright at the sensation.
His daddy stayed there, deep inside of Castiel’s hole, until the cries turned to small hiccups and the muscles inside relaxed enough that he could thrust freely.
Cas didn’t expect it when his daddy pulled his finger out suddenly, or when he thrust it back inside, repeating the sensation over and over again to watch the pucker twitch around thin air, expecting his finger to still be inside.
“Daddy!”
Dean didn’t respond. He continued with his thrusts, basking in the tight heat that enveloped his thick finger, clenching and squeezing in all the right ways. He knew it would feel so good when it was surrounding his cock. Even so, he knew that it would be a while until his son was ready. But he had all the time in the world.
Dean became rougher and rougher with his thrusts, forcing his finger past the tightening ring of muscle until it was accepted without protest. Cas’ sobs died down, his entire body lax with the knowledge that his daddy wasn’t going to stop even though it hurt so bad.
One finger became two, and Cas cried out then, a hoarse scream at the intrusion, but his daddy didn’t thrust anymore like he did the first time, so he quieted down soon enough, telling himself that it wasn’t so much that it hurt as it was that it surprised him.
Dean crossed and uncrossed his fingers inside his son’s channel, spreading them out every so often to stretch the tight muscles. Cas was being quiet now, so he didn’t worry so much about hurting him. He was careful enough that he knew his boy wouldn’t tear and that there would be no permanent damage. The small amount of pain that existed now would shadow in comparison to the pleasure he would bring his boy later.
The pain dimmed almost immediately for Cas. Not even a minute passed with his daddy’s two fingers inside of him before he no longer wanted to protest. It still wasn’t pleasant, but it was tolerable. When a third slipped inside, Cas hardly mumbled a complaint. He was stretched out further than he’d ever thought capable, the sensation nearly the same as the fluid that had been inside of him, except this was much more solid, and the movement was something to get used to.
The fingers were gone suddenly, and Castiel breathed a sigh of relief. If the fingers were gone, that meant that his daddy was surely done inspecting his hole. Maybe it wasn’t that bad. Maybe that was it.
But then he felt something else at his hole, something harder than his daddy’s fingers, something thicker, and it forced it’s way inside, stretching him out all the way until he could feel it deep inside of him. His hole clenched tight once it was fully nestled, but his insides were still wide, trying and failing to find a comfortable place for it.
“That’s a good boy.” Then the hands were gone completely, no longer soothing him, and his towel was put back in his hands. “Now go get dressed,” his daddy ordered. “Uncle Sammy is gonna be here in ten minutes to watch the game.”
Cas nodded and moved to leave the room, wincing when every movement jostled the thing inside of him.
“Don’t take it out. I found something, and it’s pretty deep. We’re gonna need to fix it later, once you’re stretched enough.”
Cas didn’t have it in him to cry anymore. His tears had dried up while his daddy’s fingers probed at his insides. “Okay, Daddy,” he said instead, trying to be a good boy for him.
Castiel walked into his own bedroom and closed the door behind him. Uncle Sammy was coming soon, which meant that he needed to dress quickly. He opened his closet and frowned at the array of jeans and dress pants—both of which were too scratchy against his skin or too hard to put on in his current predicament. It seemed as if even lifting his leg had the thing pressing against him in a spot that made him flinch, though he didn’t know if it was pleasure or pain. Strange is what it was, and he ruled out both sets of clothes immediately, going toward his dresser instead to slip on a pair of loose sweatpants that possibly wouldn’t touch the thing in him at all, let alone move it.
Any t-shirt would do after that, so he chose one at random and slipped it over his head just as the doorbell rang, signaling his uncle had arrived.
“Hey, Sammy,” he heard from his bedroom.
Cas tried to ignore the sensation in his rear that demanded attention and went out into the living room to greet his uncle.
“Uncle Sammy!” Cas called, excited despite himself.
“Hey, Cas!”
Cas went downstairs as quickly as he could, wincing with every step, until he was tight in his uncle’s arms. “I missed you,” he said.
“Yeah. Sorry I can’t be around so much. Palo Alto isn’t close.”
“It’s okay,” Cas said, forgiving him instantly.
“I brought you something though,” his uncle said with a smile.
Dean smirked as Sam unexpectedly picked Cas up and held him on his hip. He watched his angel’s mouth part in a tiny gasp, tears threatening to pour as the anal plug was jostled inside his son’s ass. Sammy didn’t notice anything amiss, too busy pulling something small out of his pocket and handing it to his nephew.
“What is it?” Cas asked, taking the book that was just small enough to fit in Sam’s pocket.
“That, Castiel, is a one-of-a-kind book, just for you. It’s a book of angels, but more important, it all of the angels that are supposed to be in the Angel Castiel’s garrison—your garrison.”
“Mine,” Cas whispered, cradling the book to his chest. He still felt the thing inside of him—it was hard not to with his uncle moving his arm so often to readjust him—but the feeling was overshadowed by the book he held in his hands.
Cas threw his arms over his uncle’s shoulders and held him in another hug. “Thank you,” he whispered.
“You’re very welcome,” his uncle replied, like always.
“Alright, boys,” Dean called, pulling them away from their chick-flick moment. “Game time.”
Sam smiled and set Cas on his feet—something the child appreciated immensely, even breathing a sigh of relief that wasn’t caught by either adult—and followed Dean into the living room.
Cas stood awkwardly by the couch, watching the game, listening to the catcalls when the cheerleaders danced, the cries of anger when the other team scored, and the cheers that erupted when their team won. Three hours passed as Cas stood around, trying his best to ignore the stretch of his hole and the flush of his little prick that wouldn’t go down as hard as he tried.
“Cas?”
It took a second for Cas to realize someone was saying his name. He turned his eyes toward the sound, surprised when his uncle Sammy was right in front of his face.
“You okay, Cas?”
Fine, Cas tried to say, but all he could get out was the letter F and a low moan.
“You’re not looking so good,” his uncle worried. “Dean, I think something’s wrong with Cas.”
Dean held his smirk at the concern in Sam’s voice and pasted the best caring father expression he had on his face. “You alright, angel?” he asked.
Cas shook his head, no. He knew that it was whatever his daddy had found in his rear that was making him like this. Nothing else would have made Uncle Sammy and Daddy worry so much, but Cas couldn’t even speak out enough to tell them that. All he could do was pant and whimper, hips twitching whenever he accidentally jostled the plug.
“Come over here,” Dean said. “Come sit on my lap. I’ll make you feel better.”
Cas shivered as that tone entered his daddy’s voice. He must have been really worried if he sounded like he was going to cry again. Cas walked to his daddy and crawled gingerly onto his lap, careful of the thing inside him, but unable to keep it from pressing deeper.
“You sure he’s okay, Dean?” Sam asked.
“No problem, Sammy. Here,” Dean lifted Cas’ face up to meet his eyes. “You wanna go sit with your uncle?”
Cas didn’t want to, but he knew that Dean was testing. He nodded and scoot over until his backside was directly on his uncle’s moving thigh, causing him to gasp as the plug moved inside of him.
Sam held his nephew tightly, a slightly confused expression on his face that had Dean unable to hold back his smirk. Sammy’s hand slid down the small of Cas’ back to cup his ass, no doubt feeling the plug he’d put in his boy.
“Dean?” Sam asked, voice shaky.
“Yeah?”
“What…?”
Dean grinned. “Thought we could play, Sammy.”
Sam groaned, noting immediately when his nephew stiffened in his lap as he toyed with the plug. He wasn’t able to do much more than that before Dean was calling out, “c’mon, Cas,” and leading them both to the master bedroom.
“Daddy?” Cas questioned, extremely shy now that his uncle was there to bear witness to his humiliation as well.
“Your uncle is here to check and make sure I don’t miss something. We have to have a second opinion in case I’m wrong.”
Cas nodded as if it made sense—in that childlike mind of his, the explanation probably did—and climbed on the bed with the same amount of trepidation as he had the first time.
“Be a good boy for me, angel,” Dean whispered.
He began pulling at the toy, stretching his son’s hole around the base of the plug only to force it back inside. He basked in the glory of his son’s pitiful cries as he continued the assault, knowing full well the conflicting sensations that were flowing through him. There would only be pleasure by the end of the night, but they were still a ways from that, and Dean knew that, for now at least, Cas had to be feeling the stretch.
“Daddy,” Cas choked out, trying to get his daddy to hurry up so that he wouldn’t have to feel that painful stretch that made his little prick leak, wanting to be touched too.
“Your daddy found what it is, Cas,” his uncle said, breaking his focus. “It’s real deep. He’s gonna have to go inside you to help.”
“I –inside?” he questioned, trying his best not to begin crying again.
“Yeah, Cas. He has to fill you up all the way. If he can’t, then you’ll stay like this.”
Then Cas did start crying. He didn’t want it to stay—didn’t even know what it was, but he knew it had to be bad for it to feel like this. He didn’t know what they wanted from him, didn’t know what he was supposed to do. He let one of the sobs out of his chest just as the plug disappeared from his loose hole, and then hands were on him, big and warm and not his daddy’s, but offering comfort nonetheless.
“Shhh,” Uncle Sammy whispered. “You’re such a big boy, Cas. It’ll feel better in a minute, I promise.”
Cas screamed again, this time in pure pleasure as something soft and warm and wet flicked over the sensitive outside of his hole. “Wh –what was that?” he asked, scared.
“It was your daddy,” his uncle answered. “He’s trying to make you feel better.”
Cas nodded and accepted his daddy gratefully. His uncle was right; it made him feel much better. He gasped as his daddy took another swipe at his rear, wetting it even more than it had been. Whatever he was doing felt good, and he surprised himself by pressing back into it.
“Good boy,” his daddy praised. His voice was garbled, like he had his mouth full, but he knew it was his daddy nonetheless.
Cas beamed, shivers of sensation rolling through him.
Dean could feel his son’s arousal against his tongue. The soft pucker of the hole in front of him twitched with every slow glide against his perineum. He pointed his tongue and slipped it past the stretched out ring of muscle, loving how easily his boy parted for him.
Unlike the last time his daddy was in his rear, there was no pain, no confusion. His daddy was helping him, making him feel better. Cas pressed back against the sensation, wanting it to go deeper like the other thing that had been in him, but it didn’t, just stayed on the surface, making him frustrated with how much he wanted it.
“You ready, Cas?” Uncle Sammy asked, eyes glued to the sight of his brother eating out his nephew. “Your daddy is almost ready.”
Cas nodded, unable to keep from swaying his hips.
Dean pulled back and swiped at his boy’s hole one more time before grabbing he lube and slicking himself up. He pressed the head of his cock into his son’s heat, clenching his teeth to keep himself from coming. It had been so long since he’d felt anything that tight.
“Cas,” Dean whispered as his boy’s hole convulsed around him. His channel tightened with every inch he forced into him, and Dean couldn’t do anything but gasp as he pressed inside.
He was so caught up in the sensation, that he couldn’t even hear the low whimpers his son let out. The thing inside of him was much bigger than the plug, stretching him wider than he thought possible. His hole hurt, but there was something inside of him that tingled with the contact, so he focused on that, trying his best not to cry out or scream, wanting to be a good boy for his daddy.
“You’re doing great,” his uncle praised. Then he leaned down and captured Cas’ parted lips, kissing him.
Cas accepted it gratefully. It felt nice, reassuring. Uncle Sammy was there for him, trying to make things better just like Daddy.
Dean’s breath hitched in his throat when he saw the two boys kissing. Cas looked so innocent, even with his daddy’s cock buried in his ass as he made out with his uncle, plush red lips parting just right, letting out the cutest little whimpers that Sammy swallowed right up, tongue darting inside to taste his nephew.
Dean pulled his cock back slightly and pressed in again, testing the waters. Cas moaned, but didn’t protest, his lips still interlocked with his uncle’s, so Dean repeated the action, pulling back a little further and pressing in harder.
His angel looked like he could take it, so he pulled out to the tip and pounded his boy’s ass, loving the mixed cries of pleasure and pain that he drew with every hard thrust.
Cas could feel the cock inside of him, throbbing as if fucked in and out of his hole. Before that day, nothing had ever been inside of him, but now he couldn’t even remember what it felt like to be empty. Cas couldn’t move, was frozen in place by his daddy’s hard cock, though he could still feel Uncle Sammy’s lips, pressing light kisses to his parted mouth.
“I found something else, Cas,” Uncle Sammy whispered against him. “It’s in your mouth.”
Cas shivered. If it was in his mouth now, that meant it wasn’t getting better. It was spreading. He whimpered at the thought of it being everywhere, not just in his rear and his mouth, but it his prick too, and he couldn’t help the tears that formed with the thought.
“It’s okay. I know how to make it better. I have some special medicine that’ll make it go away. It’s what your daddy’s going to give you too, but I’m gonna give it in your mouth, and all you have to do is swallow it, okay?”
Cas nodded gratefully, thanking his uncle without words for helping him. He wanted to speak, to thank Uncle Sammy out loud, but the only sounds he seemed capable of producing were whimpers and moans from his daddy’s large cock, making him tingle inside and out.
Sam unzipped himself, taking his cock out to bob up against his stomach. He’d been rock solid since Dean was tonguing Cas’ little hole, and the relief he felt was unparalleled.
“Open wide, Cas,” Sam ordered, surprised when Cas did just as he asked.
Cas parted his lips, opening his jaw as far as he could for his medicine. He knew what was coming, but nothing could have prepared him for the thick member thrusting itself into his mouth. The pressure in his rear was forgotten as he tried to accustom himself to choking down his uncle’s cock, trying to make it fit somewhere it didn’t.
Sam gasped and groaned, trying not to thrust hard into his nephew’s mouth, but loving the friction that Dean created as he pounded his boy’s hole. “You have to suck it, Cas,” Sam said, panting. “The medicine won’t come out of you don’t.”
Cas swallowed and nodded around the cock in his mouth, sucking as much as he could. It was harder than he thought it would be. His daddy had him whimpering and tingling all over, and the thickness in his mouth wouldn’t give him enough room to suck as hard as he wanted to, but Uncle Sammy stroked his back in silent praise, and Cas figured that he was doing good.
A small glob of something came from his uncle, thick and bitter, and Cas figured that that was the medicine he was supposed to take. He swallowed it, shivering in distaste. He hated medicine.
His daddy thrust harder and harder, making it hurt again, before he stopped completely. Cas felt something wet deep inside of him, and he knew that that was what his uncle had been talking about when he said that Daddy had to fill him. It was probably the same medicine he was getting from Uncle Sammy. He swallowed another glob gratefully before his uncle pulled out with a smile.
Cas angled his head up, hoping for another kiss, and Sam granted it.
“Did I do good, Daddy?” Cas asked, voice hoarse.
“Yeah, angel. You did great. And you're going to be just as good for uncle Sammy, aren't you?”
“But…” he almost cried when he realized that he wasn’t done. “But I was good, wasn’t I?”
“You were great, Cas,” his uncle reassured. “But your mouth only needed a little medicine. I have to put the rest deep inside you like your daddy did.”
Cas could feel more tears pricking at his eyes in anticipation of taking his uncle’s length inside of him. It was big, much bigger than his daddy's had been, and it scared him to think that he would have to feel the stretch of Sam's cock inside of him so soon after his daddy.
"I don't want to," Cas whispered. "Please."
Cas looked up, eyes begging, to Dean's soothing expression.
His daddy petted his hair and looked at him sadly. “You can’t get better if you don’t take your medicine, angel.”
He knew his daddy was right, but even with the tingling, it hurt, and he knew that Uncle Sammy’s thickness would be more than his daddy’s.
"Come on, baby boy," his daddy pressed. "Get up on Uncle Sammy's lap."
"But..."
"Now, Cas," his daddy ordered, and Castiel had no other choice.
He straddled his uncle’s hips, feeling the thick member along his backside.
Sam rubbed an ungodly amount of lube on himself, not wanting to hurt his nephew any more than he had to, and pressed inside steadily, ignoring the cascading tears that his cock forced from his nephew’s eyes. He knew the boy was in pain with as big as he was, but that didn’t deter him in the least.
“It’s okay, Cas,” Sam soothed. “Move whenever you’re ready.”
Cas nodded, grateful for the period he was given to adjust. When his daddy gave him his medicine, he hadn’t waited, just made him take it. Uncle Sammy was letting him do it, and that made him want to be a good boy for him.
He lifted his hips up as high as he could go before his uncle stopped him, then slid down on his cock, surprised when it didn’t hurt as much as he thought it would. The tingling grew, making him pant and moan for a whole other reason, and he repeated the action. Up, down, up, down, he fucked himself on his uncle’s cock, hearing the squish of medicine inside of him, but that just made it better.
He could feel it leaking from him, dripping down his thighs, but for some reason, it just made him feel better. That had to be the medicine working, he decided. It made him feel real good.
Cas bounced on his uncle’s cock quickly, taking it deeper and deeper until he had the whole thing in him, something he never thought possible. His thighs hurt, his back hurt, his whole backside hurt, but he couldn’t remember ever feeling this good before, so he kept going, bouncing harder to increase the tingling.
There was a tap on his chin that had him opening his eyes lazily, only to glimpse his daddy’s leaking cockhead by his mouth. He didn’t even wait for an order this time. He opened his mouth and sucked like Uncle Sammy taught him, swallowing down glob after glob of bitter medicine that made him feel so good.
“Great job, angel,” his daddy’s praised. “Almost done. You ready for your medicine? I’m gonna give it to you all at once.”
Cas nodded eagerly.
“Here it is.”
Cas held his uncle deep inside of him as a thick rush of medicine filled his mouth, choking him. He remembered to swallow at the last minute, but he couldn’t keep some from dripping out of his mouth. There was just too much of it.
Cas cried at the loss. If he didn’t get it all, then they’d have to keep going, but his daddy soothed him, petting his hair in a way that Cas discovered he liked immensely.
“What’s wrong, angel?” his daddy asked.
The thick cock inside of him twitched at the name, forcing a hiccup from him, but then it was still.
“I –I didn’t get i –it all, daddy,” he cried.
“That’s okay, angel. Daddy will give it to you.”
Dean wiped up the tendrils of come that coated his son’s chin and fed them to him. Cas sucked on the fingers gratefully, cleaning them off and swallowing every drop of come his daddy gave him.
“What do you say?”
“Thank you,” Cas whispered shyly.
“You’re welcome, angel. You still need to get the rest of your medicine from Uncle Sammy though.”
Cas nodded and lifted his hips once more to continue fucking himself on his uncle’s lap, but Sam stilled him. He looked at his uncle, confusion plain on his face.
“I’m going to turn you around,” Sam explained. He lifted Cas’ leg and maneuvered his nephew without removing the cock from his ass so that they were back to chest. Then he held the boy by the crease of his knees, legs together, and guided him up and down on his own.
Cas screamed when Sam shoved him down on his cock, but the sound was all pleasure. His little hole wasn’t so little anymore, and it could definitely take the pounding his uncle planned on giving him.
“Uncle Sammy,” Cas begged, and Sam knew just what his nephew wanted.
He repeated the motion, not letting Cas do anything but take the huge cock that thrust hard into his ass. Cas whimpered and cried, screamed every so often whenever Sam drove in particularly hard, but he was a mess of fucked-out pleasure by the time Sam filled his ass with come, watching it drip out of his gaping hole, too stretched out to keep it in on his own.
“Plug?” he asked.
Dean smirked and handed it over. Then Cas’ hole was filled once more, and both of their loads were sealed inside.
“Daddy,” Cas cried. “I need –need…” He sobbed in frustration.
Cas was crying then, and he didn’t know why. All he knew was that he needed something, but he wasn’t sure what.
“It’s okay, angel. Daddy’s here to take care of you, remember?”
Something hot and wet wrapped around his prick then, giving him something he didn’t even know he wanted. Like the pleasure he’d felt in his backside, the shivers reached up his spine and reverberated through him. His daddy sucked just a little, and Cas could feel something coming.
“Daddy!” he called. “I –I’m gonna…” He pushed down his embarrassment with a sob. He had to warn him. “I’m gonna pee.”
“It’s okay, angel,” his uncle said soothingly. “Go ahead. Your daddy’s waiting.”
Cas came with a shout right into his daddy’s mouth. Dean swallowed the small tendrils, sucking lightly as he did so to prolong his boy’s orgasm. When Cas collapsed against the bed, completely tuckered out, Dean knew he’d done good.
“Holy shit, Dean,” Sam said, staring at the fucked out version of his nephew like he couldn’t believe they’d done it.
“I know, right?”
Sam swallowed. He knew how this was going to play out. Cas thought everything was over, that he’d never have to take his daddy’s cock again, but Sam knew better. Have to do this regularly, Dean would say, or looks like it’s back. Then he’d pound into his angel’s tight ass, fucking the protests right out of him until it was such a regular thing that Cas wouldn’t even question it when Dean ordered him on all fours.
If things went well like they had just now, Cas would even come crying to Dean, Daddy, I think it’s back, or it hurts, Daddy. Please take care of me. And Dean would smile and nod and say, I don’t know, angel. I might have to inspect you first. He’d finger his son, but not more than that, and he’d refrain from anything of a sexual nature for weeks, months even, until Cas forgot. Then he’d start all over again. By the time Cas would realize what was happening, he wouldn’t care. He’d be begging for his daddy’s cock, coming just from having something filling him up.
Sam knew all of this from experience.
“I remember when you looked like that,” Dean whispered, turning lust-filled eyes toward him. It was the same look Sam remembered from his childhood, and it promised nothing but a pleasure he could only feel when he rode his daddy’s cock.