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Good Grief Dean Winchester

Summary:

Dean has a kink he's been exploring for some time, but what he'd really like is to take it to the next level. He wants a twenty-four-seven relationship with a special someone. It's hard though. Dean still struggles with some aspects of his kink. He wants to be pushed, but that means more vulnerability, and going toward his limits.

Enter Cas, who is exactly what he needs. Stern, no nonsense, and totally, fucking hot. Dean's about to embark on some 'little' adventures, that will take him deeper than ever before. Plus, Dean is a super adorable little, which just needs to be said.

Notes:

(See the end of the work for notes.)

Chapter 1: Big Brother Dean

Notes:

April 25, 2020
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Hello everyone! It is I Mock, finally bringing you some comfort food in the form of words. If I may have a moment of your time, I want to relay that I have been writing my fingers off and the #Mockmachine is still at full blast.

But here's the thing. I have decided to tackle Finding Sammy, which was an even bigger job than I had anticipated. Partly due to the content, as it's heavy stuff that's hard to traverse at this time, and partly due to structure, the way I have to lay the pieces down for the plot is complicated and even having an outline (which I never use, but attempted for this) was unhelpful. It's not just a matter of knowing where events go, it's an art, so that I can make sure the story is told in an exciting way.

The good news is, I've written nine and a half chapters for Finding Sammy, which includes the final chapter. I've made good headway, but I can't start posting all the chapters yet. I might be able to finally post chapter 14. I'm going to do a read over and see.

But for now, we have this series because Mock needed a break from the heavy. This chapter is all cutesy and fluffy, which I dunno about you, but I needed.

Speaking of needs, I dunno about you guys, but exercising had been my savior through all this. It releases all the anxiety and tension I feel and makes me feel so powerful. Because of all the anxiety and stress, I don't do super intense workouts at this time (this is actually better for a stressed-out nervous system), but I do enough for a light sweat and I feel fabulous after. I have worked out every single day since I've been off work. I mean, I have always worked out and a lot, so this is no new thing, but it's easy to forget how much these things improve mental health. I hope you all have something too. xoxoxo

This is my good habit. My bad habit is that I dowdloaded a video game to my phone called GardenScapes which is a HUGE time waster and I will be deleting it... eventually, Ha! So bad. Mock never does this, but the distraction is addictive. But it gets deleted after this weekend... probably. *sly face*

In the meantime, I have been blogging in case you missed:

 

APRIL 3

 

APRIL 12

 

 

I will blog again either today or tomorrow. I will post chapter 2 of this story tonight or tomorrow morning. Enjoy and much love to you all! xoxoxo

Chapter Text

Deans loves Sammy, but sometimes little brothers can be annoying. Uncle Gabe’s asked Daddy if Daddy can look after Sammy. At first, Dean’s super excited to get to play with Sammy all of Friday night an all-day Saturday, but once he realizes how much he has to share Daddy and his toys, he gets upset and throws a fit. “That’s my toy, Daddy. I didn’t say he could play with it,” Dean complains when Sammy grabs for Professor Norris. Dean swipes him up before Sammy does.

“It is your toy, and I won’t make you share your really special toys if you don’t want to, but you’ve got to let him play with something.”

“Professor Norris and me are gonna play with the blocks. He can play something else.” In other words, Sammy can take a hike. Dean can tell Daddy doesn’t like the road he’s headed down.

“Come here, little boy. We’re going to have a chat,” Daddy says taking him by the hand and leading him to the couch where Daddy can still see Sammy – who digs into the toy box without Dean’s authorization of what he can touch and what he can’t – but far enough away to give the illusion of privacy. “Dean, I know it’s hard, because you haven’t got to play with your toys all week, but I still expect good behavior. I want to see you making effort to be a good big brother to Sammy. Understand?”

Yeah, Dean understands, but he wants some time to play with his blocks alone and then to have Daddy all to himself for just a moment. He’s used to their routine. Having to share is a whole new challenge. “I can play with my block with just Professor Norris for a little while, Daddy? Please?”

“There’s my nice boy with his nice manners. Thank you. You can do that, but you’ll tell Sammy nicely, and not to worry my sweet boy, you’ll have Daddy all to yourself all tomorrow night and all day Sunday,” Daddy says with knowing eyes, a small bit of amusement playing there.

Daddy. Knows. Everything. “Okay, Daddy.”

“Come here. You need a hug, don’t you?”

Maybe. It was a long week. Originally, he’d looked forward to this weekend with Sammy, but now, he just wants his soother and Daddy and snuggles. “Here,” Daddy says, pulling a soother from his pocket and popping it into Dean’s mouth.

Dean looks up to him with big eyes that say, in your pocket?

Daddy gathers him into strong arms. “I realized having a Dean means carrying one of those in my pocket.”

Dean loves that, loves how much his daddy thinks and prepares ahead for him. He sinks into the hug, sucking his soother, happy Daddy understands him.

“All right, you go play and come join us when you’re ready.”

Daddy takes Sammy to a corner of the living room where they can play with the train together, but Sammy’s just a baby, so Daddy has to do everything for him. Dean can’t help but notice their game, and overhear that Daddy’s not playing it right. Sammy’s smiling, because he’s polite and well-behaved (most of the time), but he’s not laughing. Dean makes his way over. “I’d better do it, Daddy,” he tells him.

“Oh, Mr. Bossy I see. Daddy’s not doing it right?”

“You’re not. Sorry Daddy,” Dean says with a shrug he can tell Daddy thinks is adorable. Dean’s very adorable and sometimes Daddy has a hard time resisting him.

“Very well. You can take over and I’ll make you boys a snack. It’s going to be an early bedtime for you both.”

When Daddy heads over to the kitchen Dean assures Sammy he’ll work on the whole bedtime thing. “We’ll worry about that later. I’ll get Daddy to let us stay up later than whatever he’s planning.”

Sammy laughs at that. See? Already he has Sam laughing. Dean’s a total ham.

Daddy totally kyboshes Dean’s plans though, not letting him get a word in edgewise when the prophesized, early bedtime rolls around. “Little boys who have tantrums about bedtime, will get bedtime spankings,” Daddy says using his strictest tone.

“Not a tantrum Daddy, I was just gonna ask—”

“—you’re not staying up later. Absolutely not. Move it, Mister.” Daddy gives him a get going spank to his rear, which is only covered by thin, little boy shorts.

“Ow!”

“Well then, behave yourself.”

Dean grumbles to himself, which Daddy allows, so long as he makes his way up the stairs. Daddy changes them both and Dean’s a bit fascinated, watching Daddy change Sammy’s diaper. Sam’s got long legs, and for some reason – Dean may never know the reason – that Sam is a grown man, getting his diaper changed like he’s a baby turns him on more than he can tell you. Sammy’s legs have been waxed long enough by this point they are free of hair. Dean knows Sam plans to have laser hair removal done to make it more permanent. Will Daddy want that someday? Dean’s not sure, but Dean’s said Daddy can make those kind of decisions whether Dean wants that, or not.

It will be totally up to Daddy.

Aside from all the things that turn him on about watching Daddy change Sammy’s diaper, there’s a beautiful sweetness to it. Sam’s really good at dropping like an anchor into head space and docking there. Right now, he really is Sammy, sweet baby Sammy who’s enjoying the wonderment of what Uncle Cas is cooing at him. His happy smile relays pure bliss and the innocence of being little, of having no cares, or worries.

Sammy’s an exploratory infant. His excited squeals when Daddy tickles his thighs are genuine, and it warms Dean’s heart that Sammy can have something like this, a place where he can let go and live out this part of himself.

“All right, Dean’s turn,” Daddy says, pulling Sammy up by his arms and helping him down off the changing table. Sam’s an athletic and agile guy, but Sammy is a wobbly, baby with serious need for some vestibular training. It’s super cute.

Dean feels that familiar bubble of excitement and embarrassment when Daddy tells him it’s time to have his diaper changed. He gets up off the ground with the exuberance of a little kid, and races over to Daddy. “Dean’s turn,” he squeals, getting into it. Maybe Sammy being here is exactly as good as I thought it would be all week.

“You waited so patiently like a good boy, I think the first thing we’ll do in the morning is give you a new sticker.”

Dean gets shy about that. He loves earning good-boy stickers for his chart, but it’s still embarrassing as hell, which is part of its purpose. Daddy always seems to know the exact right things that will give him all the feels.

When they’re both ready for bed, Daddy tucks Dean into his big boy bed, and Sammy into Dean’s crib, which Dean is mostly okay with, but he has to have a chat with Daddy about it to make sure of something. “That’s still for Dean, Daddy?” He asks the question, even though Dean knows it’s a ridiculous question cerebrally. The ‘big’ part of him isn’t absent, but being ‘little’ is about feelings and it feels a bit like Daddy gave his crib away to the baby even though that’s not what he did.

Daddy pulls the covers up over him, since Dean can’t, buckled in with his arms at his sides like he is. “Daddy didn’t give your crib away. Sammy’s just going to use it for the night and nap time tomorrow, because he’s too little for a big bed, okay?”

Dean glances over to Sammy cuddled up with his favorite blanket, the one with the puppy faces all over it, sucking away on his blue soother, his long strands of hair feathered over his face and Dean’s heart squeezes. Yeah, okay, he can use it. Not that Daddy’s asking, but Dean’s okay with it now. “Okay, Daddy.”

“Have sweet dreams, sweet boy. Daddy will see you in the morning.”

~**~

It’s Saturday morning and Daddy’s in the kitchen making them breakfast. Dean’s been charged with entertaining his little brother until Daddy’s ready for them. Dean’s good at this, Dean’s got this. He sets up his usual towers, ready to knock them over for Sammy and make him laugh, but Sammy does it before he gets the chance. “No, Sammy. You’re not ‘sposed to do that. Dean does it,” Dean explains. He’s super annoyed.

Sammy just laughs though, like he’s the funny one. “’gain,” he says pulling out his soother.

“Okay, fine. I knock it over though,” Dean says.

Daddy doesn’t much care for Dean’s tone, sensing trouble. “Dean, do you need a time out to cool down?”

“He’s wrecking everything, Daddy, and not playing the game right.”

“Sammy’s just a baby. You’re the big boy. You play nicely, Mister.”

Dean glares at his blocks, he doesn’t dare glare at Daddy since he knows where that attitude gets him. Sammy points to the blocks. He’s a bit more talkative and – Dean assumes – that Sammy’s feeling better today. Things can come up when you’re in your little headspace, things you didn’t remember were there, which is often the case for Sam and some of the reason he can get quiet. “I can try, Dean?” Sammy asks.

Dean has a major soft spot for Sammy. “Yeah, you can try.”

Dean continually sets up blocks for Sammy, so Sammy can knock them down. Uncle Gabe left special instructions for Sammy, which included wearing his special baby mitts all weekend long. Dean has to set things up for him, because Sammy literally can’t. He can only knock things over with the cumbersome things on. Dean’s rewarded doubly for his efforts. The first when Sammy smiles so big at him, kinda with awe actually, like maybe he’s thinking he’s got the best big brother in the world. Next when Daddy walks over and sees him playing, so nicely. “What a good boy I’ve got. Thank you for entertaining your little brother for me. I think that deserves another sticker.”

Dean has a love-hate relationship with the new chart thing-y Daddy started for him. When he’s well-behaved, he gets a sticker, when he’s naughty, he still gets a sticker, but it’s a frowny face which means not-good. Not only is he punished for each time he earns a frowny face, but too many frowny faces in a weekend, and no sexy fun times for Dean. Sometimes even, Daddy will decide Dean needs an extra spanking at bedtime if he gets too many frowny faces in a day.

On the flipside though, the good boy stickers are fun – Dean gets to pick from a large selection – and he gets nice rewards when there are enough in a weekend, including, but not limited to sexy fun times. Just earning one sticker can be a highlight, it makes him feel so fucking good.

“Which sticker would you like, sweet boy?”

Daddy has the sheets of stickers spread out and Dean can’t help it, he really likes the shiny, unicorn sticker with the pretty hair. “That one please, Daddy.”

Daddy helps him peel it off and stick it on the reusable white board next to the wizard sticker he chose earlier that morning he earned from last night and then tousles his hair, proud of him. Dean is fucking ecstatic. Next, Daddy gets them both situated at the table, where things go a bit downhill. Dean’s left to use his hands to eat the breakfast Daddy made for him, while Sammy gets Daddy’s attention, since Daddy has to feed him, Sammy unable to do such things with the mitts on. “Daddy, you can feed me too?” Dean says.

“I thought you were Daddy’s big boy today? C’mon now, eat your eggs and some fruit.”

Dean does, but he’s not happy about it. This isn’t fair. Sammy gets to be fed and Dean doesn’t. “Good Lord, Dean. Usually you want to feed yourself,” Daddy comments.

“He gets all the time with you,” Dean admits.

“Do I have a jealous boy?”

Yeah! He is a bit jealous. So be it. Dean nods and crosses his arms.

“Can I bribe you with another sticker if you eat all your breakfast by yourself like a big boy?”

Hmmmm. That’s a big offer. Normally, it means a spanking if he doesn’t finish rather than a reward for finishing. “Any one I want?”

“Any one you want,” Daddy assures him.

“Okay.” It feels good to complete a task for Daddy even though Daddy spends his time feeding Sammy. Dean’s delighted when he gets another sticker. He chooses the singing frog with the guitar sticker this time.

When Daddy has to clean up the kitchen from breakfast, he opts to put Sammy in the play pen. Dean still has no idea where Daddy got the play pen from. He keeps forgetting to ask. It’s large and wooden for starters, which leads Dean to believe it’s a specially ordered piece, or someone made it. The wood sections fold out to form a pen large enough for bigger babies like Sam and Dean and it closes with a latch. Daddy always lines the bottom with a large, soft mattress, covered with a blanket and lots of pillows.

Dean watches as Daddy props Sammy’s head up when he’s lying on the mattress and then gives him his bottle. “Papa says you need some quiet time after breakfast,” Daddy says. “Drink your bottle nicely, Sammy.”

Sammy looks at Daddy with big eyes and gives a nod, holding his bottle with both mitted hands, sweetly sucking. He looks comfortable. Daddy closes him in, and Dean can’t help sitting next to the pen cross-legged, watching over Sammy. Dean holds onto the bars from the outside and Sammy turns his head to look at Dean. “Daddy, he’s in there?” Dean says.

“Yep. He’s having his quiet time. Do you want to come help Daddy? Daddy can give you all his attention now.”

All Dean’s wanted is all Daddy attention since he got here, not to mention, Daddy doesn’t invite him to help often; cleaning the kitchen is for grownups. But now he thinks he’d better stay here. “No thank you, Daddy. I’m gonna watch over, Sammy.”

“Okay, but no pestering him.”

“Dean is not a pest, Daddy. I won’t.”

Daddy chuckles. “Okay.”

Dean watches Sammy some more from the outside, taking note of things like the way Sammy lays, his movements baby-like, even the way his eyes wander looking at this thing, or that with the same awe as a little person. Wow, Sammy can sure go deep. Dean’s gotten pretty good at it too, thanks to Daddy, but he isn’t like Sammy yet, and Dean’s fucking impressed.

Sammy’s got his cozy, blue onsie on, the one that even covers his feet. It’s got long sleeves and puppies on it to match his blanket. Sammy loves puppies. Dean’s glad Daddy thought to put Sammy’s blanket in with him. Eventually, Sammy finishes his bottle and he sits up then crawls over to where Dean is. “Out?” Sammy says.

Dean can help! “Daddy, Sammy wants to get out please.”

“Thank you for using your nice manners. Daddy’s going to finish this before he gets Sammy out, though. Sammy, you need to finish having quiet time.”

Sammy sits back on his diapered bum, pouting. “I’s sorry, Sammy. Daddy says no.”

Sammy stands up to lean against the sturdy play pen. It’s tall and comes to the bottom of his ribcage. He could climb out, but he would be in big trouble for doing that – it’s dangerous for little boys! Instead he reaches for Dean, who can’t stand the forlorn expression in his eyes. “S-Sammy wants to come out, Dean.”

Dean looks up to Daddy. Mean Daddy keeping Sammy locked in the playpen. “I’ll get you outta there, Sammy.”

Dean knows Daddy will have his eyes on them both, so he’s got to make his way over to the latch slowly. Dean saunters, like he’s not doing anything important, while Sammy gets back down on his hands and knees, following him around to the latch. Dean doesn’t have mitts on, so it’s easy for him to lift the latch and aha! Sammy is free. He pulls the door open while Daddy isn’t looking and Sammy escapes.

“C’mon Sammy. Let’s go up to the nursery.” Daddy can’t be too mad if they’re playing, so nicely, right?

Wrong.

They don’t get far. Daddy is there and he’s the most unimpressed Dean’s seen him in a while. “Did you let Sammy out?”

Dean covers his bottom with his hands, instinctively. “Yeah, but you’re mean locking him in there!”

“Good grief, Dean Winchester. Go to the corner, now,” Daddy says when Dean doesn’t move.

Dean heads over to the corner. He hears the sounds of Daddy putting Sammy back in the play pen. “You’re having your quiet time, mister. Understand?”

“Uh-huh, Uncle Cas,” Sammy says.

“I am going to have to tell Papa about this. He’s not going to be pleased.”

“Nooooo!”

Dean can hear Sammy having a bit of a tantrum, but that’s the least of his worries for the moment, Daddy comes over and takes his hand. “Time to deal with you, little boy. That was very naughty.”

“I needed to help, Sammy.”

Daddy brings him over to the couch and stands Dean between his knees as he starts pulling down his little boy shorts. “I understand that’s how you feel, but when Daddy says Sammy needs to have quiet time, it’s for a reason, not because I’m trying to be mean. You need to follow Daddy’s rules, little boy.”

Daddy untapes his diaper and pulls it off and then he’s put over Daddy’s knee. Daddy’s hand feels very slappy as he spanks and spanks. It stings a lot. Dean finds he has to kick his legs and he even tries to put his hand back, which Daddy grabs and pins to his low back. “Ah! Oooow! Ah-haouch! I’m sorry. Sorry! Dean’s sorry!”

But Daddy keeps on spanking. “When Daddy gives you instructions, you follow them young man. I’m disappointed that you didn’t obey, Daddy.”

Daddy spanks his bum until it’s throbbing and sore. Daddy pulls his shorts and diaper the rest of the way off and stands him in the corner again. Dean’s got tears running down his face. “No touching your naughty bottom. You think about how you’re going to listen to Daddy, Daddy’s giving you a frowny face sticker on your chart.”

Stupid chart.

Dean stands in the corner, miserably, while his bottom stings and he does think about how he will behave. He wants another fun sticker, but it’s hard sometimes. When Daddy calls him out, he runs to Daddy. “I’m sorry,” he says.

Daddy gathers him into his arms. “You’re a silly, billy. Be a good boy. Daddy would much rather give you fun stickers.”

Dean sniffles. “Yes, Daddy.”

Daddy gets him back into a diaper, and Dean looks over to check on Sammy who looks wretched. Least he’s got his soother now. “Yes, I know. He’s not happy at the moment, but he needs his quiet time. Another thirty minutes or so. I would prefer to be able to leave you here with him. Can I do that, or do you need to go in your highchair while I finish the kitchen?”

No way! “I will behave, Daddy.”

“Good. How about sing him a song. He’ll like that.”

Daddy leaves Dean in just a diaper and his t-shirt that says ‘Daddy’s Boy’ on it. Dean makes his way over to Sammy who’s lying on his side crying softly into his blanket. “Daddy says you come out soon, okay?”

Sammy sniffles into his blanket, but then nods. “Dean. Your daddy’s going to tell Papa,” he says around his soother.

What they did he means. “Yeah, I’m sorry.” The impending doom sucks, because no one likes to disappoint their daddy or papa, but Dean knows Uncle Gabe always takes good care of Sammy, so he doesn’t worry about it too much. “You want me to sing you a song?”

“Yeah.”

Dean runs through all the kid songs he knows. When Daddy comes over, Sammy’s smiling. “You ready to come out now, Sammy?”

Sammy nods, sucking his soother. Daddy opens the latch and Sammy crawls out with his blanket looped around his arm so he can drag it. Dean’s excited, now they can play! They do. They play the morning away, but then it’s ruined when Daddy tells them, “okay you two, naptime.”

“But Daddy, none of us are tired,” Dean says on both their behalf.

“He says, every naptime. Come with me you little monkey. You’re both having a nap.”

Dean pouts, but he follows Daddy and Sammy up to the nursery. Daddy gets Sammy into his crib, which Dean isn’t sure he’s crazy about. He loves Sammy, but it’s his stuff and he already slept there last night. Daddy notices his scrunched-up face. “Where do you expect him to sleep, hmmm?”

“I don’t know.” Dean guesses it’s the only place, but still.

“Besides, you’re big enough to sleep in your big boy bed,” Daddy says closing Sammy in. “Here you go, sweetpea. Close your eyes and go to sleep. You, come with me.”

Daddy takes Dean to his bed and opens the covers for him. Daddy puts the white, leather mitts on him, with their covers as Dean’s yawning. “Not tired, huh?”

“Maybe a little.”

“Go to sleep my adorable little nuisance.”

Dean smiles as he drifts off to sleep.

When Dean wakes up, he notices he’s already peed and will need Daddy’s help, but then he remembers Sammy’s here! Maybe he’ll go see if he’s awake first. Only, Dean knows the rules well. He’s supposed to wait for Daddy to help him. No problem, he’ll investigate Sammy first then climb back in bed and call for Daddy. Easy, peasy.

Even with the mitts, Dean’s able to climb around the guard that keeps little boys from falling out of bed at night, and slide off the back of the bed. He creeps over to the crib where Sammy is still sleeping. Sammy’s hair is fanned out around his face and he sucks his soother gently in his sleep. Dean wishes he was awake, but he should probably leave him be. Before he can turn back to his bed and get away with his mischief consequence free, Sammy’s eyes pop open and he gets scared. He spits his soother out and cries for Papa.

Shit!

Dean doesn’t have time to make it back to his bed or try to calm Sammy down. Daddy’s there and he sees his mischievous boy. He gives Dean his I’m unimpressed with you little boy look, as he helps Sammy out and leads him over to the rocking chair for cuddles. Dean feels bad he scared the crap out of Sammy, but he didn’t mean to. He knows what Daddy will say though, “you shouldn’t have been out of bed, Dean Winchester.”

Tentatively, he crawls over to where Daddy and Sammy are. Daddy’s getting Sammy settled down, but he’s still upset. “It’s okay Dean, you can come over here,” Daddy says, seeing how slowly he’s crawling.

Dean makes his way over to Daddy’s feet, near where he’s rocking Sammy. “I, I didn’t mean to, Daddy.”

“I know. You don’t mean to get up to half the mischief you do, which is why you need to listen to Daddy’s rules. They’re for a reason, which we’ll be talking about.”

Dean nods. He needs some comfort too, so he tries to put his soother in his mouth but can’t with the mitts on. Daddy reaches down to help him. “Tank you, Daddy,” he says around his soother.

Eventually, Sammy calms down and Daddy lets him sink to the floor. His face is wet. “Hi Sammy. Sorry, I scared you.”

Sammy nods and he’s smiling. He dives for Dean, hugging him. Dean squeezes back.

“All right you two, diaper change time and then lunch and then Papa will be here, Sammy.”

“Papa!” Sammy lights up.

“That’s right, Papa will be here to get you.”

Daddy gets Sammy changed, but when he gets to Dean, Dean knows it’s time for him to be punished for earlier. “This is the second time today Daddy has to punish you for not listening. Daddy’s going to take off your diaper, clean you up and then you’re going to bend over and touch your toes.”

Oh God. Just the thought of that has Dean’s cock hardening. Daddy doesn’t just take his diaper off though, he removes Dean’s shirt to, so he’s totally naked in front of Sammy. It suddenly feels a bit cool in here and the hair on his legs, prickles. Sammy’s watching him and he recognizes the hooded look there, Sammy’s turned on too. “Bend over and show me your hole. You’re getting a good spanking,” Daddy says. “But first a little deference will do you some good.”

Holy shit. Dean bends over to touch his toes. The position is utterly humiliating. Both Daddy and Sammy can see everything. “Spread your legs wider, little boy.”

Ugh! Dean does, making himself obscener. Daddy’s really dragging it out, so he has to spend more time in the position. His balls are hanging down and his hole is on display. “Little boys who don’t listen to their daddies get big spankings, don’t they, Sammy?”

“Uh-Huh.” Sammy has to clear his throat and though Sammy is still deep in headspace, Dean can pick up some of his ‘big’, alter persona. He’s enjoying this.

Dean hears Daddy go to a drawer he knows too well. It’s one of the drawers Daddy keeps his implements in, ones you most definitely wouldn’t use on a real little person. They’re for big, little boys. “You’re getting ten of these right on your naughty hole,” Daddy tells him showing him the whippy little cane.

Fuck that’s gonna suck.

But Daddy’s not ready to start, he reaches out to grab Dean’s balls, which feels oh so good. Dean moans and his cock is already leaking, thinking about himself in such a position, ready to be spanked in the most embarrassing way ever. Daddy starts circling Dean’s pucker with his finger. “Do you want Daddy’s fingers in there?”

“Please, Daddy.”

Dean hears Daddy wet his finger and then he feels it slip inside of him. It’s really just torture. He knows Daddy’s not going to get him off during a punishment, and orgasms before Sunday are rare, but oh fuck he wants this. The fact he’s bent over like he is, with someone watching how dirty and naughty he is has him soaring with arousal.

“I’m going to plug this up,” Daddy says as he pumps a finger into Dean’s hole. “After you get your naughty boy spanking, I’ll put a nice plug in there, as a reminder to be a good boy.”

Sweet Jesus.

Daddy takes position in front of Dean, so he’s standing over his bare ass. “I’m going to need you to pry your cheeks apart for me and keep your hands out of target range, or that’s going to hurt, isn’t it?”

Dean tries not to grumble his answer. “Yes, Daddy.”

Dean thought this couldn’t get any more humiliating, but he was wrong. Now Sammy has a full view of his hole that’s about to taste Daddy’s cane; a few delicious shivers go through him, leaving a delighted buzz. “Good boy. Daddy’s going to start now.”

Dean hears the little cane whiz through the air with a mighty swish and then whack! on his hole. “Ooooowww! I don’t like that, Daddy!” Dean complains.

“Good. You’re going to be a good boy and do what you’re told after this, aren’t you?”

That means, Daddy has no intentions of stopping there, despite Dean’s complaints. “Yes, Daddy,” Dean says.

Dean gets the full, promised, ten. “Ow! Ow! Ooooouch!” Dean cries out at three in a row, but he manages to stay in position. Tears sting his eyes, because this particular cane is really stingy and the sensation reverberates through his body.

Daddy’s aim is true, as he carefully – if painfully – whips his hole with the cane, not even coming close to Dean’s hands. When the terrible spanking is finally done, Daddy tells Dean to stay and there’s no way Dean’s disobeying after that spanking. No way, no siree! Daddy’s back with the plug, which Dean can see is short, narrow at the top, getting wider and then widest at the base.

Daddy spends a bit of time lubing up his sore hole, with Dean giving grunts of protest. “Daddeeeee,” Dean whines.

“I know. You’ll be all right. Daddy’s just going to pop this in, and there we go.”

Dean feels the discomfort of the plug settling as Daddy stands him up and hugs Dean to him. “You’re so naughty sometimes,” Daddy says in a fond way as Dean sniffles.

Dean giggles, despite it all. He can be. “Daddy, it hurts,” he says.

“I know, but you need the reminder today. C’mon, let’s put your diaper on.”

If Dean’s honest, the plug doesn’t feel that bad, but he needs to state these kinds of things for the record. As Daddy re-diapers and re-dresses him in a t-shirt with a bunny on the front, he looks shyly over to Sammy. Sammy smiles back, biting his lip. Looks like he enjoyed Daddy and Dean’s little show, but damn, Dean needs to behave, or he really won’t be able to sit come Sunday morning. Also, he wants to come badly by this point and if he’s not careful, he’s going to lose those privileges. This definitely means another frowny face sticker on his stupid chart.

The late afternoon is spent showing Sammy how to do crafts, until his papa shows up to get him. As soon as Sammy sets eyes on Uncle Gabe, he cries. “Oh Button, you’re gonna break Papa’s heart with those tears. C’mere.”

Uncle Gabe gets on the floor, so Sammy can crawl to him and Uncle Gabe can gather Sammy into his arms. “Papa, I was a naughty b-boy,” Sammy gets out in between sobs.

Uncle Gabe looks over to Daddy, while Dean moves closer to Daddy’s leg, needing some comfort of his own, with all the emotional chaos he can feel in the room. Daddy reaches a hand down, tugging on him gently, signaling for Dean to come up on the couch with him. “They got up to a small bit of mischief when Dean unlatched the pen during Sammy’s quiet time and Sammy crawled out. I caught them and had Sammy settled back in before anymore naughtiness was wrought.”

Daddy explains all of this as Dean’s climbing onto the couch and situating himself, so Daddy has a lap full of Dean. Now that Dean’s been punished for all the mischief he got up to, hearing the stories about it, is funny. He giggles thinking about what the pair of them tried. “Oh, you think you’re funny do you?” Daddy says running a loving hand through his hair.

“Yeah, Daddy.”

Daddy rolls his eyes. Uncle Gabe is amused too. “It’s okay, button,” he says to Sammy. “You’re going to have to be spanked, because you know better, but that’s all. I’m not mad.”

Dean’s ears perk up. Spanking? Dean would really like to see that spanking. After all, Sammy’s got to see him spanked all day. “Next time feel free to spank them both, Cas,” Uncle Gabe says. “If Sammy’s going to misbehave here, he can be spanked here.”

Then do it! Dean chants in his head, but Uncle Gabe doesn’t seem to be making any moves to spank him right now.

“Other than that, Sammy was well-behaved, despite this one,” Daddy says kissing Dean’s crown.

Dean pops his soother out. “I got lots of spankings today, Uncle Gabe,” Dean says even though it costs him some humiliation to do so. It’s a bit of a pleasant feeling, but also not. In any case, it gives him nice arousal throughout his body, not just his groin.

Uncle Gabe laughs. “Why am I not surprised?”

When Uncle Gabe and Sammy leave, Daddy announces he’ll be going in the playpen while Daddy makes dinner. Dean is not a fan of the idea. “But Daddy, I want to help you.”

Daddy gives him a serious frown. “I don’t think so. You’re adorable, it’s true, but you’ve been nothing but mischief today. Daddy can’t trust you won’t get hurt somehow. Now c’mon little man. In.

Dean crawls into the playpen, but not before Daddy casually sticks his hand down Dean’s diaper to check to see if he’s wet. Dean scowls up at him, but only because he’s not happy about this playpen situation. “Tell Daddy if he needs to change you,” Daddy instructs.

Dean nods, sucking his soother methodically as a last form of protest, before Daddy latches him in. Truly, Dean could climb out of the thing no problem, it’s a matter of standing up and swinging his legs over, but when you’re as deep in the headspace as he is, you really feel locked in which just makes you feel all the more little.

For a little while, Dean watches Daddy from afar, as Daddy gives him a kind smile, with that little sense of knowing behind his eyes. Daddy’s not stupid, he knows Dean’s put out with him for putting him in his playpen, but Daddy’s certain of his good reasons, so he simply enjoys Dean’s poutiness.

Daddy’s told him over and over how cute it is when Dean’s all pouty and that it gives him the nice feeling of non-sexual arousal, Daddy’s get to feel being a Daddy. Dean plays it up for him a bit, holding onto the bars, like he’s a prisoner, but then something catches his eye. To his right is that cool new box of blocks Daddy gave him. Daddy must have put them in here! He dumps them out, laughing when it makes a big mess.

“Are you making a mess?” Daddy asks from the kitchen as he slices carrots. Dean can tell Daddy’s not mad.

“Not a mess, Daddy. Dean needs to find the right blocks to make his playpen fortress.”

“Right, silly me,” Daddy says, but he’s not fooled.

Dean spends the time Daddy prepares dinner constructing a fortress out of blocks all around the playpen. By the time Daddy comes to fetch him for dinner, Daddy has the opposite problem of convincing Dean to leave the playpen. What? He’s complicated. “But Daddy,” Dean says legit tearing up like a little kid. “I made the Dean fortress and the T-rex is going to get in if I leave my post.” In this moment, Dean truly believes it.

“Hmmmm, that is a pickle, because Daddy says it’s time for dinner.”

Dean can’t believe he’s actually crying about this, but he is. He knows if Daddy says, then he has to do it, or he’s in trouble, but the stupid T-rex banging at his drawbridge with all his stupid threats.

“What if you left Professor Norris in charge? He could hold down the fortress while you eat.”

That’s, a really good idea, actually. Daddy’s really smart. “Okay, Daddy. I can do that.”

He stations Professor Norris in front of the drawbridge, with an army of other stuffies behind him to help, but now there’s the problem of getting out, without knocking everything over, since Dean built in front of the door. Daddy has a solution for that too. “Stand up,” he says. Dean stands and Daddy puts his hands securely under Dean’s armpits, like he’s a little kid he’ll lift out. “On three I’m going to lift and you’re going to do a big jump sideways up and over the playpen. You’re not to do this on your own, only when Daddy helps you, understood?”

“Yes, Daddy,” Dean says smiling around his soother, excitement dancing in his eyes. This is going to be really fun.

“Okay. One, two, three!”

On three, Dean jumps with his strong legs and with Daddy helping lift him and acting as support; there’s a moment when he feels like he’s flying through the air. He’s still laughing when he’s safely to the ground. “That was fun, Daddy! We can do it again?”

“We’ll do it again,” Daddy promises, and a Daddy promise is gold.