Kinktober 2022 | Day 10/11/12 – A Twink And A John

Pairing: Dean x John (Daddycest)
Rating: 18+
Tags: Daddycest, Dean’s age is unspecified, imagine whatever you want, crossdressing, forced feminisation, name calling, humiliation, Dean as bait, case fic, angst, Dean’s self-loathing, pining, not mutual, hero-worship, hint of touch starvation, implied oral sex, orgasm denial, cock worship, semi-public / public, plot twist
Kinktober Prompt – (10) Forced Fem / (11) Orgasm Denial / (12) Humiliation
Word Count: 2.3k

A/N: Also written for Syn and Alex’s ‘Fool Us Twice’ challenge!

“Dad,” Dean whines, tugging at the uncomfortably tight shirt that John has made him put on over the uncomfortably poke-y bra that he’s had to stuff to get it to look like he’s got tits. They still look like the smallest tits on the planet, Dean grimaces as he looks at himself in the foggy bathroom mirror. His legs are cold where the skirt has his skin on full display, but his whole body feels scorching hot with embarrassment. 

“Can it Dean, you know this is the only plan we’ve got. Even if it’s not ideal,” John grunts from somewhere in the main room of the motel. 

“I don’t look like a girl, I just look fucking ridiculous,” Dean gripes, trudging out of the bathroom to rejoin his father now that’s he’s donned the “disguise” for their hunting operation. 

“You’re not supposed to look like a girl,” John huffs without looking up at his son, pouring over some print-outs of information they’d gotten from the library earlier and scribbling some notes into his journal. “You’re supposed to look like a boy dressed up like a girl. Which is–” the elder Winchester’s voice dies when he does tear his eyes away from their research to glance over his son’s outfit. 

“Which is…” John mumbles again, eyes combing over every inch of Dean, from head to toe, and then again. And again. He clears his throat. “Which is exactly how you look. So…good job.” He nods stiffly, pulling his eyes away from Dean and forcing them back onto his journal. 

Dean can see the muscles of his dad’s eyelids twitching, like there’s a magnet trying to draw his gaze back up. He’s clearly fighting some kind of impulse right now. Dean wonders if he really looks that bad. Sure he’s uncomfortable as hell, but he hadn’t actually thought he looked entirely unfortunate in the get-up. The tight, feminine clothes, with the dark smudge of eyeliner and the bit of lip oil he’d put on… he’d thought he looked okay, at least. 

But his heart sinks as John continues to avoid looking at him as they pack up their gear and head out to the club that their monster has been stalking for the past few weeks. 

They don’t even know what it is yet. Their best guess is some pagan spirit, but there isn’t really a whole lot of lore on monsters that target crossdressing twinks. It’s a pretty damn specific M.O. If it hadn’t been for the disappearing-into-piles-of-dust element of the case, Dean would have said it was more likely to be some wacko serial killer, but he doesn’t know any humans capable of disintegrating people, no matter how sick they are. So, off they go to the gay club, Dean posing as John’s boytoy, because they hadn’t been able to come up with any other plan. Lucky Dean. 

“Put your arm around my waist,” Dean mutters to John while they wait in the line to get into the bar, shuffling along past too many curious eyes. 

“What?” John looks down at him, expression practically offended that Dean would think to give him an order like that. 

“I don’t like the looks I’m getting from these people, and I don’t want to be fighting off regular horny people once we’re inside,” Dean mutters. “Whatever we’re hunting probably won’t care if I look off-the-market, but it will stop civvies butting in and distracting us if they know I’m unavailable. So put your damn arm around my waist, and act like you actually like me,” he hisses, his frustration with being forced to dress up like this and his despair that John apparently finds him even more unappealing than normal seeping into his tone. John raises an interrogatory brow at his son, the shadow of a challenge, but he does as Dean asks and slips his arm around the boy’s waist, pulling their hips close together. 

The gun-rough skin of his fingers catches on the sliver of Dean’s stomach that’s visible between the hem of his shirt and the waist of his skirt. Dean shivers, and not because John’s fingers are cold, even though they are. He’s incredibly regretful of the fact that he couldn’t wear boxers under this damn skirt because they’d show too easily. The skimpy underwear he had been forced to wear out–while technically from the men’s section–is little better than a pair of panties, with how little material they’re composed of. And they’re doing absolutely nothing to contain the thickening of his cock where it’s tucked between his legs. 

Once inside, Dean sets up shop at the bar as planned, and John does a scout of the perimeter and the exits one more time. They both keep their eyes peeled for anyone paying an unnatural amount of attention to Dean or any other boys dressed similarly. Tonight, for once, they’re in luck. Dean seems to be the only twink in a skirt and eyeliner in the whole bar. Of course, that means he’s also drawing quite a lot of eyes, most of which won’t be the supernatural ones they’re looking for. 

Dean is buying guy after guy drinks at the bar, pretending that he prefers to pay so that he doesn’t get taken advantage of. Batting his lashes, which have always been long and girlish, no mascara necessary, and making these guys fall for the whole innocent act he’s playing up. Really, he’s making sure to spike every drink he passes over with the charmed silver tincture he’s got hidden in the palm of his hand, waiting to see if any of his suitors react. 

Not a one does. 

Suddenly, John is sliding up beside him again and wrapping an arm possessively around Dean’s waist, smiling coldly at the burly, unshaven bear currently trying to chat up his son. 

“Sorry I was gone so long sweetheart,” John apologises warmly, dropping a kiss to the top of Dean’s head and giving his waist a squeeze. “Work call didn’t know when to quit.” 

Dean simply stares up at his father, struck dumb, wide-eyed. 

“You shouldn’t leave such a pretty little thing all on her own,” the man Dean had been trying to ease himself out of conversation with looks bitterly at John, clearly perturbed that Dean is spoken for even though he agreed to have a drink together. “Don’t want her giving someone the wrong impression.” 

“Thanks for the advice.” John’s voice is not at all thankful, and his smile doesn’t touch his eyes. “I’ll be sure to keep her on a tighter leash.” 

Dean feels his cheeks flame up in humiliation at being talked about like he isn’t even there, and being referred to as a girl the whole time on top of that. God, if this is how girls feel in bars all the time, Dean doesn’t blame them one bit for carrying pepper spray and tasers. He sort of wishes he had his gun right now, so he could shoot this asshole in the face. 

“What the hell was that?” Dean hisses in his father’s ear, pressed up on his tip-toes so John can hear his whisper over the music. To the casual observer, they must look like a couple trading flirtations. 

“I think he was right,” John turns his face to duck closer to Dean’s ear. The stubble on his chin skims over the curve of Dean’s neck, and the boy hopes desperately that John can’t feel how quickly his pulse has just shot through the roof. “I think I need to keep you on a much tighter leash, sweetheart.” 

“What the fuck?” Dean pulls back to look at John’s face, finding a heavy, lecherous expression that he’s seen plenty of times before. But never directed at him. No matter how many times he’s wished for it in the dark of an empty motel room; empty because John had gone home with somebody else. 

Whereas back at the motel, it seemed his father could barely stand to look at him, John is wholly focused on Dean now, his eyes wide and dark and hungry. 

“Dad?” Dean asks, and he’s surprised John hears him, the word had escaped his lips so breathlessly. 

“C’mon,” John smiles, sliding his arm from around Dean’s waist and lacing their hands together instead. Leading them away from the bar and towards the back of the building, Dean follows John like he’s in a trance, the crowds milling around them parting as easily as fog.

“Dad?” Dean tries again when they’re outside, in the abandoned, dirty alley they’d re-conned as a possible means of escape earlier that afternoon. 

John clicks his tongue, the sound smacking wetly off the surrounding bricks and damp tarmac, letting go of Dean’s hand to rest his shoulder casually against the wall, looking at Dean almost… pityingly. And that’s a look that Dean is more used to seeing directed his way, at least. Although there’s a different hue to the emotion in John’s eyes this time. 

“How ‘bout you try Daddy, Dean,” John suggests with a leering grin, and Dean feels his jaw practically smack the street below his feet. This can’t be happening. This can’t be real. John presses himself off the wall and is up against Dean, the edges of his leather jacket brushing over the fake tits protruding from the younger man’s chest. “I’ve seen the way you look at me,” John rumbles, his voice deep and seductive. Dean thinks he might be about to faint. “Don’t go coy on me now, baby girl,” he breathes, brushing the backs of his fingers up Dean’s arm, teasing the hairs into standing on end.

Dean feels a crushing weight settle on his chest. 

Of course. 

This feels a little more real now. 

He couldn’t believe that after all this time of lusting quietly after his own father – just about the worst thing he could ever imagine doing – Dean couldn’t fathom the idea of just being granted one of his greatest desires on a silver platter. But Dad doesn’t want him. Dad wants some pretty little girl – some version of Dean that’s done up, and soft, and tempting. Not the real him. Not the man John fashioned him into, who’s hard, and cocky, and never good enough in John’s eyes. 

It feels fitting, then, that the universe would take Dean’s wish and grant it in this twisted way that hammers home the fact that he will never be good enough for John. No matter how hard either of them try. And Dean, he’s weak–something else John finds occasion to scold him for at least once a week–he’s weak enough to not care how pathetic accepting John’s attention like this makes him. He wants, needs, so badly. He’ll take what he can get. 

Looking up at his father, willing the tears gathering in his eyes not to fall and smudge his eyeliner, Dean chokes back a whimper, sets his hands on John’s chest, beneath the lapels of the leather jacket that makes his dad look like an action hero to him, and he breathes the word ‘Daddy’. Testing it out. 

John’s smile is bright the way it is when Sam brings home a good report card. 

“That’s right baby girl.” John’s hand slides up Dean’s arm and settles on his collar bone, the pad of his thumb sitting in the hollow of his throat. Present. Heavy. It moves when Dean swallows, then settles again. “Daddy’s gotta remind you who holds that leash a’yours.” He presses down, Dean sinks to his knees, the bare skin pressing into the blacktop, sucking in the loose pebbles of tar, blackening his skin. His soul. He’ll never sink lower than this, he’s sure of that. 

“You’re not going to cum tonight,” John says, brushing a thumb tenderly over Dean’s cheek, dragging it to his lips and tugging them open. “Maybe I’ll let you, when I think you’ve learned your lesson about who you belong to. But you have to prove it to me first. You have to prove who you worship.” 

Dean nods, his dad’s thumb against the ridge of his bottom row of teeth. 

“Tell me who you worship, sweetheart. Who does your heart belong to? Your body?” 

“You, Daddy.” Dean’s tongue tastes the salt of John’s thumb when he answers. 

“Good girl,” John smiles, his other hand moving to the waistband of his jeans. 

John is walking around the bar steadily, but his heart is beating frantically against his ribs. He can’t see Dean anywhere. 

Last he’d checked, the kid had been at the bar, dropping silver in the drinks and clearing anyone who came up to talk to him. John had caught the look of someone suspicious, eyeing Dean but keeping his distance, and he’d tailed him for a few minutes. It became clear though that he wasn’t specifically interested in Dean, he was just after an easy target. When John saw him fiddling with a small plastic bag that kept disappearing and reappearing from his jeans pocket, he’d glanced up to check on Dean, seen he was fine–talking to some bear that didn’t look too threatening–and John had gone up front to tip off a bouncer about the creeper with the roofies. It hadn’t been that long of a conversation, but when John got back, Dean wasn’t at the bar anymore. Checking his phone, Dean hadn’t sent him their signal word to say ‘monster found’, and he hadn’t sent an SOS either. Hoping he’d just gone to the bathroom, John circled the room once more, keeping his eyes peeled. 

But no. No Dean, not anywhere he could see. Damn hero, where the fuck did he go? If John finds out Dean went off with the monster alone to try to get the drop on him, he’s gonna have the kid’s head.

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