Den of Random Iniquities
Fic: Summer Vacations Suck

I know, it’s a horribly uninspired title.

The prompt for this is over here. Dorian is a Goddess at coming up with awesome story ideas, and I strive really hard to write the story she wants. I felt like the first one went over really well, so I hope this one doesn’t disappoint.

Summary: Summer vacations suck, and Cas seems bent on making it awkward for Dean.

Pairing: Dean/Cas
Rating: NC-17
Length: ~4,500
Warnings: There is an age gap here that I suppose technically makes the sex illegal. Dean is 16, Cas is 21.
Other kinks: rimming, denied (delayed) orgasm, use of cock ring, handcuffs, and gag. Deep throating. Mention of breath play. Did I forget any? I usually forget one…

Dean wakes up and has the room he’s sharing with Castiel and Sam all to himself. He can hear Sam and Anna laughing outside and the steady rumble of Castiel’s voice is laced with it. This registers on one important level to Dean: it means he doesn’t have to sneak to the bathroom to take care of his morning wood. He can take his time and do it the way he likes, with his legs spread, knees slightly bent, and a finger in his ass. It’s fantastic. Probably the only part of the entire trip he’s enjoyed. If only his family would let him stay inside the cabin all day, masturbating his brains out, cycling fantasies of busty cheerleaders, with the football players and their tight asses, with all of them at once. But the family won’t let him stay inside long. Something about bonding.

Family vacations simply suck. Family vacations with the Miltons, in grubby cabins along mosquito ridden lakes suck more. Dean can think of so many things he’d rather be doing. Like making out with said cheerleaders and/or football players instead of just fantasizing about it. Maybe finally getting laid. But he’s 16, and he wasn’t given a choice. Not like that asshole Castiel, whose 21 and didn’t have to come, but chose to anyway. The last three years in a row Castiel had been away at college and his exam schedule conflicted, not that Dean missed him being there or anything. This year his exams didn’t conflict, but that doesn’t explain why the dark haired -look at me I’m perfect- arrogant prick would decide to come. He didn’t have to.

All Cas does is sit on the beach in his swim trunks and read, like he’s so much smarter and more sophisticated than everyone else, like his three years at college have made him some high-class intellectual who actually likes books and reading, and everyone else is just a dumb hick. Like it justifies him going off to school and leaving behind everyone else.

Sometimes, though, he plays with Sam and Anna (13 and 12 respectively) and they laugh and love every minute of it, like Cas is the best older brother ever. Normally Dean would have a huge ass problem with this, because he is the best older brother ever damn it, but it also leads to one very fortunate thing.

It makes it very easy for Dean to sneak away.

He has this awesome spot behind the cabin where no one can see him, where he likes to sneak off to after he’s stolen a beer from a cooler, to light up a cigarette from the pack he hid the second they got to these bug-ridden woods.

He’s sulking in that spot now, leaning back against the cabin and scratching absentmindedly at a bug bite on his arm in between puffs off his cigarette and pulls on his Bud Light, when he hears the crunch of footsteps on forest floor. Before he can think to put the cigarette out, Castiel has turned the corner and that’s it. Cas knows.

Cas keeps walking to him, like he’s completely unsurprised to find Dean smoking and drinking, and that’s a little infuriating. Still, Dean freezes, unsure of what to say. Would Cas tell on him? Probably. Castiel always was a goody-two-shoes, and now he’s also a prick.

Dean watches with trepidation as Cas saunters up to him, clear into his personal space, and plucks the cigarette from his fingers. He catches Dean’s eye with his piercing blues as he drags a slow puff off it, before throwing it to the ground and stomping it out. He leans forward, his body almost flush against Dean now, pressing him into the wall, before slowly blowing the smoke across Dean’s ear. Dean shivers as he feels blood rush down to his crotch. He feels Cas’s fingers next to his own as they wrap around the beer bottle.

Cas’s lips tickle his ear, Dean growing harder every second, as he whispers in that absurdly deep voice of his, “Little kids shouldn’t play with big boy toys.”

Castiel is gone before Dean realizes he took his beer.

That asshole, Dean repeats to himself over and over again while he jerks off quickly into the cabin’s toilet. Who does he think he is?


Things pretty much go downhill from there. Cas comes out of the lake in nothing but his swim trunks, water running down his perfect, flat stomach and over the peak of hip bones, the sun glinting off the wet skin, making Castiel fucking glow, and in fucking no time, Dean Jr has come to full attention against Dean’s direct orders.

It’s awkward and embarrassing, and Dean curses at Castiel the entire time he jerks off in the bathroom.

And you would think, YOU WOULD THINK, eating lunch should be safe. One should be able to eat their PB&J without fear of a raging hard on. Then Castiel is plopping down at the picnic table with one of those throwback Coke bottles. And Dean, Dean ignores him. Why the guy couldn’t drink his pop somewhere else is beyond him, why he had to ruin the comfortable solitude Dean had temporarily found. But it doesn’t matter, he’s going to enjoy his peanut butter with extra jelly like the most gorgeous man in the world hadn’t just sat down at his table. Because Castiel isn’t. The most gorgeous man in the world, that is. Cas only thinks he is. Clearly.

That works for Dean for a few minutes. Until he glances up, and Castiel has finished his Coke, and is currently working his tongue all around the lip of the bottle, fucking lapping at it. It’s obscene, and suddenly Dean’s completely forgotten about his treasured sandwich. He’s too busy watching Cas make out with a Coke bottle.

Then Cas glances up, catches his eye, and smirks. Dean stops breathing as Cas begins sliding the bottle into his mouth. And that, that is not fair. Dean watches that bottle slide over Castiel’s full lips much further than should ever be possible, watches Castiel fucking swallow around it, and Dean’s done. He bolts from the table so fast he knocks his chair on the ground and the sandwich goes flying.

When he beats off to this one, one hand pressed to the wall above the toilet, one hand on his dick, it is with the knowledge that now Castiel is definitely fucking with him on purpose. And that quite properly pisses him off.


With knowledge comes power, right? Well. Not to Dean. Castiel is hell bent on torturing him and there’s nothing he can do about it.

So they need to go to the grocery, right? There’s a Wal-Mart in town, because there’s a Wal-Mart in every town, even if it’s a 45 minute trip. That means a long trip in a very cramped car. And with Sam and Anna, it means a very noisy car, because the two never shut up, and so Dad cranks the Kansas to drown them out, and then of course Mom has to shout at Dad, and the whole thing is just ridiculous. Dean tries to get out of going, but apparently he’s the “muscles” or some shit like that, so he’s resigned to a long, annoying trip.

Then Castiel’s opening the door on his side.

“You coming Cas?” Dad asks from the front.

“Yes, I have some things to get.”

“Shame, there’s no room,” Dean is quick to point out, relieved to have a ready excuse for keeping Castiel and his teasing, pretentious self at bay for at least a shopping excursion.

“That’s okay Dean, I can just sit on your lap. You don’t mind, do you?”


But Dean doesn’t get his full rebuttal out before Castiel is sliding that nice, tight round ass across his thighs and settling in.

Dean looks around, panicked and seeking help- surely this is absurd, there has to be a better solution than this, but his Dad just shrugs, and no one else is paying attention. He puts the car into drive, and their off. For 45 minutes. Of Castiel’s ass grinding into his lap. Great.

Castiel doesn’t waste the opportunity. Of course he doesn’t. Every bump in the road he exaggerates, bouncing against Dean. And when he isn’t bouncing, he’s grinding, shifting his hips back and forth. Dean’s harder than he can ever remember being in his life, and there’s just no way Castiel can’t feel that against his ass cheeks.

“Jesus Dean,” Castiel says at one point, in a totally normal voice. “Your legs are so boney.”

Dean grits his teeth. “Maybe if you sat still, that wouldn’t be a problem.”

Castiel doesn’t respond, other to roll his ass backwards, harder into Dean’s erection.

Dean really wants to reach up and grab Castiel’s hips to hold him still, but he can’t. No one is paying them any attention, and no one can hear a damn thing over all the noise, but if Sam or Anna glanced over and saw him holding Castiel’s hips, there’d be no explanation to cover that. So he’s balling his fists at his side, and biting his lip to hold back a groan, while Castiel keeps on shifting.

He’s getting close to coming. He shouldn’t be. He’s got four layers of clothing between him and skin, but his dick doesn’t seem to care.

“Cas,” Dean leans forward a little bit to whisper panicked in his ear through clenched teeth. “Please. Stop. I’m…”

“You’re what Dean?” Castiel asks, not so innocently, rolling his hips hard.

“Stop it, you know-“

“Know what Dean?”

He bites his lip. It’s too late. He moans into Castiel’s shoulder, trying to muffle the sound, as the orgasm that never should have been washes over him.

Dean’s never been so mortified in his life. His parents, his little brother, and the girl he thinks of as a little sister are all in the car with him. No one noticed anything, but still. He has to rush to the bathroom when they get to the store before that fact changes and take care of the problem.

Cas is definitely an asshole.

Fortunately for Dean, Anna volunteers to sit on her big brother’s lap for the ride home.

“What was so important you had to come along Cas?” Dean asks with a disgruntled tone, earning him a sharp, questioning look from Sam.

“I needed batteries.”

“What the hell did you need batteries for?” Dean asks. It’s a good question. Nothing runs on batteries any more. Everything charges.

Castiel just smirks, and Dean has a feeling that’s not a good thing.


Later that night, Dean finds out what the batteries are for.

Everyone is feasting on the marshmallow, chocolate and graham cracker goodness they got at the store that day, gathered around a campfire and singing stupid hokey campfire songs. Dean thinks it might be a good opportunity to sneak off, so he does.

He’s lying in his bunk on the bottom, the sheets he used to make curtains out of pulled tight around the bed, debating about whether he wants to get off before calling it a night, (he’s most certainly not thinking about a certain jerk with blue eyes and dark hair and an ass that could –and nearly did- kill), when he looks down and sees the strap of Castiel’s bag sitting on the floor next to the bunk. Well, the guy had been an ass to him all day after all, so Dean doesn’t have to feel bad if he lets curiosity take over does he? He wants to know what Cas keeps in his bag. Maybe he’ll find something he can use against Cas. So he slides his hand through the sheet curtain to pull the bag closer and take a look.

Whatever he was expecting, a small blue vibrator was certainly not it.

And there’s lube next to it.

And a now open battery pack.

Fucking hell.

Dean’s dick gives an interested jerk, and that answers the question about whether he should beat off tonight or not. The thought of using Castiel’s vibrator on himself is too good to ignore. The fact that Castiel would use it later, after it’s been in Dean…

Dean strips quickly out of his boxers, leaving himself completely naked, and opens the bottle of lube. He pours some over his fingers and quickly slides them around his balls and against his hole. He plays with his dick lightly while he eases himself open. The vibrator isn’t a large one (which Dean is grateful for, he’s never had more than a few fingers in his ass before) so it doesn’t take long before he judges it good enough. He turns the vibrator on before letting it trace down his cock and over his balls, letting it tease at the sensitive rim of his hole. He slides it in slowly and groans hard.

It feels incredible. He gets it deep enough that it’s vibrating right against his prostate, and Dean doesn’t know how he doesn’t come from that alone. He starts fucking his fist slowly, feeling the vibration run through his cock, while his other hand keeps the vibrator in place, jerking and thrusting it slightly.

He’s panting hard. God it’s a good thing they’re being so loud outside. He’s building up to the best orgasm he’s ever had, and nothing is going to keep the sounds he makes when that happens in check.

Which is why, of course, Castiel picks that moment to throw open the makeshift curtains.

Dean freezes completely, right on the edge of coming his brains out. He simply blinks up at Cas’s smirk with wide, deer-in-headlight eyes, feeling his heart pound right out of his chest.

Then Cas is reaching down and wrapping his fingers around the base of his cock, chocking his impending orgasm right off.

Dean, to his unending embarrassment, fists the sheets, throws his head back and whines.

“Cas, fuck!” he finally says, when Cas doesn’t do anything else. “Cas please, damn it, let me come!”

Dean’s reaching for his cock, half unconsciously, but determined to get off, when Cas says, “No Dean, I don’t think so. Not until I say so.”

Dean whines again. Not that he would ever admit that.

“Please Cas.”

“Knew you wanted it,” Cas says in the most cocky tone Dean’s ever heard. But at this point, Dean doesn’t care.

“Yes. Yes, goddamn it Cas, yes. Just let me-“

“I said no.” Castiel says, keeping his grip on Dean’s cock. He reaches down and fishes around in his bag for a second before coming up with handcuffs. Dean’s eyes go wide. “Can’t have you touching yourself now can I?”

Before Dean can even process it, he’s handcuffed to a beam above his head. It hits him then, how vulnerable he is. Arms raised, and secure, and he’s still got a damn vibrator in his ass. It really, probably shouldn’t be as acutely arousing as it is.

“Fuck Cas, fuck.” Dean says, meeting his brilliant blue eyes. “Yes, yes, god yes. Fuck me, whatever… whatever you want. Just let me come. Damn it I’m so close Cas-“

Dean had been hoping that the dirty talk, the begging, would win Cas over, convince him to finish Dean off at least. But he breaks off when he sees Cas fish a neat little ring shaped object from his bag.

“You seem to be in danger of coming too soon, Dean,” Cas says calmly. “It’s okay. I don’t blame you. You’re new to this. But I can’t have that.”

“Fuck you Cas, I’m not some-“ Dean protests as Cas slides ring down his penis, but breaks off with a choked sound when it is snug around his base. Dean stares wide eyed at the bottom of the bunk above him, torn completely in a thousand different directions of emotions.

“Dean look at me.” Cas commands while he strokes Dean’s penis lightly. Dean looks because he has no brain capacity to do anything else. “Do you trust me? Trust me, Dean. You’re freaking out on me here. I need you to trust me. I will give you the best orgasm you will ever have, but you have to trust me.”

Dean suddenly remembers that this isn’t just some random jerk that went away to college. This is someone he’s known his entire life, someone he’s always wanted like this, if he’s being honest with himself. Someone he does and has always trusted completely.

Dean nods and arches into Castiel’s hand.

The feral smile that passes over Castiel’s face has Dean doubting that decision for a second. But only a second.

Castiel slides his hand down Dean’s cock to the vibrator, letting his fingers ghost over the end of it. “Now. Who said you could play with my toys?” Dean swallows hard. How do you justify taking someone’s vibrator? Then Cas chuckles. “Relax Dean. I left it there for you to find.”

“You what?”

“I didn’t need the batteries either. You think I’d come unprepared?”

Dean groans. “Cas you are one evil-“

Dean’s cut off with a whelp as Castiel grabs his hips and turns him 180 degrees on the bed in one quick, dirty motion, the chain of the handcuffs just long to twist with it. Dean’s barely adjusted to the abrupt change in position before Castiel is settling himself between Dean’s legs, pulling his hips up and maneuvering Dean until his ass is up in the air and he’s propped up on his elbows with his wrist crossed at the handcuffs. Dean thought he was vulnerable before? The vibrator is still in his ass, he is still handcuffed, only now his ass is in the air, just waiting for whatever Castiel has planned. He shudders in anticipation.

Castiel runs his hands lightly down Dean’s back and sides a few times before they settle on Dean’s ass. Dean feels his cheeks spread, and then there’s a wetness sliding around his hole, next to the vibrator.

“Fuck!” he moans in shock, pulling lightly at the handcuffs. “Is that your tongue?“ The wetness disappears and Cas pops into the side of Dean’s vision as he rustles in the bag again. “What is this? Castiel’s endless bag of kinky sex objects?”

“You are much too loud, Dean.”

It’s all the warning he gets before there’s a slip of cloth sliding between his lips and a knot is tied behind his head.

“Mmmph,” Dean complains. Castiel ignores him.

Yes, it was definitely tongue, Dean decides as Cas goes to town. It’s probably a good thing Cas gagged him, if the sounds he’s able to make around it are any indication. Castiel works around the vibrator for a little while, but eventually slides it out. Dean’s gratefully for the reprieve from the constant onslaught of sensation when his dick feels harder and bigger than it’s been in his entire life, and yet utterly held back from orgasm.

But his reprieve is short lived. The vibrator is simply replaced by fingers, and they are doing everything possible to stretch Dean out as much as they can while pressing into his prostate and driving Dean mad.

“I was right, wasn’t I, Dean?” Castiel asks while he works. Dean struggles to hear it, the blood is pounding in his ears so hard. “I will be the first person to ever enter this sweet ass of yours?” Dean nods roughly. “I was hoping as much.”

The fingers are gone and Castiel disappears entirely for a moment while Dean hears him stripping. Then he appears again, rummaging in the bag. Dean watches him pull a condom out and quirks an eyebrow. “Yes, I had hoped I might get lucky on this trip.”

Castiel slips the condom on and moves behind Dean again. Dean feels hard bluntness press up against his hole, and then Castiel pauses. “Whenever you’re ready Dean,” he says with a trace of tenderness.

Dean can hardly speak around the cloth, so he indicates he’s ready, more than ready, in the only way left to him. He pushes back into Castiel, letting the Cas’s cockhead just barely breach him. He gasps hard at that, right around the gag.

Castiel’s hands are petting his sides, his back, and it helps ease the pressure, the newness of the moment. It’s so patient and tender and loving, Dean doesn’t know what to make of it. The guy has vibrators and cock rings and handcuffs and gags and god knows what else in his bag of kinky sex objects, and so Dean thought he was going to be taken roughly and forcefully. Why does he keep forgetting this is Castiel?

“I’m going to move in now, Dean. I’ll go slow,” Cas says.

True to his word, Cas pushes his way in as slowly as humanly possible. It’s a slow, bone deep burn, but Cas keeps one hand stroking him softly while the other reaches around to lightly caress his cock, and Dean is totally, completely overwhelmed. He’s never felt so many things all at once before. Cas is seated fully when Dean whines the overwhelming onslaught out. Cas seems to understand what it means.

He lets Dean have a few more moments to adjust to it all before he pulls out and pushes harshly back in.

“Fuck Dean,” Castiel growls. Dean’s not sure he’s heard Cas cuss before. “Sorry, sorry, I meant to go slower-“

Screw that. Dean shoves his hips back as hard as he can. Cas definitely understands what that means.

He growls again, sounds like Dean’s name if he’s not mistaken, and moves his hands to grip Dean’s hips tightly before pulling out to thrust hard again. And again, and again.

“Fuck. Fuck, Dean,” Cas says to him, “You’re so gorgeous. Always were. I go away, and when I come back you’re all grown up. Fuck, so hot. So hot Dean. God look at you, back arched like that, thrusting yourself backwards for me, so greedy for it.”

Cas moves one of his hands to Dean’s cock again and he moans his approval. Cas changes his angle just slightly, and the thrusts are now dragging across his prostate like there’s no tomorrow. Dean wants to come so bad. He would do fucking anything to come right now. The pleasure in his groin and the release he needs to go with it are the sole center of his universe.

Castiel must be able to hear his thoughts. “Gonna let you come Dean, like I promised,” Cas tells him at his ear, with a completely wrecked voice, “but you have to earn it first.”

Suddenly Dean is flipped back around, a condom makes a dull sound on the ground somewhere, the gag is undone and tossed aside, and Cas’s thighs are on either side of his head. He has one hand bracing him somewhere on the bed frame above Dean while the other is angling his cock to Dean’s mouth. “Swallow me Dean,” Cas says as he slides his cock past Dean’s lips. Dean, without hesitation, opens his mouth to take Cas in. It occurs to him that like this, Cas could fuck as hard and as deep into Dean’s throat as he wanted. Dean probably should not be aroused by that thought either.

Castiel does not fuck Dean’s throat, however. He was very, very close when he pulled out, and it only takes a few shallow thrusts and a few licks of Dean’s tongue before Castiel cries out and comes hard, spilling himself into Dean’s mouth as he swallows it all down.

Castiel doesn’t move away right away. He remains above Dean, panting. Dean wouldn’t really complain because the view is fucking fantastic and Cas’s softening cock feels good on his tongue. But hello, raging hard on with a cock ring wrapped around it. He thrusts his hips up in the air to get Castiel’s attention.

It works. Castiel smiles as he comes back to himself.

“Remember that coke bottle, Dean?” Castiel asks as he slides himself down Dean’s body. “I’ve had a lot of practice at college.”

Before Dean can begin to let the jealousy war with the arousal factor of those statements, Cas has slipped the cock ring off his erection and replaced it with his mouth.

Dean bucks his hips, tugging hard at the handcuffs. It doesn’t matter, he’s already fully inside the intense wet heat of Castiel’s mouth. He moans obscenely. He’s only been on the edge of orgasm for what feels like hours, so it might be a waste of Castiel’s obvious talent, cause it only takes a few thrusts of his hips, a few curls of Castiel’s tongue, a few flutters of his throat, before Dean finally, finally releases what had been building up more and more intensely this entire time.

Cas was right. He’s never come that hard before, and he can’t imagine he ever will again.

He collapses on the bed, only realizing then that he arched completely off the thing, handcuffs straining hard, and doesn’t ever want to move again. Or think, or breath. He wants to live in that orgasm for eternity.

Castiel chuckles. Damn cocky bastard. He undoes the handcuffs and puts them back in his bag before lying down on his side next to Dean. He props his head up on his hand so he can gaze down at Dean with some stupid look of fondness.

“Dean, you’re such a fucking idiot.”

Dean shoots him a glare, but then remembers he can talk again. “Yeah, well you’re a conceited-“

Castiel shakes his head. “That’s exactly what I mean. If you had gotten over this stupid anger you have at me, for what, going to college? Being five years ahead of you? We could have been doing this the entire vacation.”

Dean opens his mouth to retaliate, but he realizes he doesn’t actually have anything to say to that. “We’ve got the rest of the trip…” he says instead.

Castiel smiles. It the same light-up-the-world smile Cas had always had. It makes Dean feel warm inside. Then it falls into Castiel’s other classic face- the poker face. “I don’t know, apparently I’m some conceited asshole, I don’t think you should consort with me any longer.”

“Cas. Shut up. And no one says “consort” anymore,” Dean says. It’s the same kind of playful banter they got up to when they were younger. It feels good. “I’m trying to tell you I want to ‘consort’ with you again. Don’t be a dick about it.”

“Hmm,” Cas says thoughtfully as he leans down to Dean’s hear to whisper, “In that case, do you want to know what else I keep in that bag?”


The rest of summer vacation gets a lot more interesting after that. Castiel enjoys making Dean squirm, making him wear a butt plug when he’s outside the cabin, so that only Dean and Cas know it’s there. The cock ring makes more than one appearance as well, driving Dean insane. But it all more than worth it when Cas drags him to a secluded part in the woods, falls to his knees, and swallows Dean down his throat. Or when he takes Dean suddenly and roughly up against tree. Or when Cas gets real creative and chokes off his air supply, giving Dean the most unexpectedly mind-blowing orgasm of the whole trip.

Maybe summer vacations don’t suck so badly after all.

  1. girlwtuba reblogged this from girlwtuba and added:
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    You literally left my house 10 min ago. That was fucking quick girlwtuba
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