I'm too old for this shit

Y/N starts to crawl under the desk until she’s kneeling in between his thighs. He rolls back a little to give her more room, which causes her to shuffle closer to him on her knees.

He reaches out to brush his knuckles over her face, painting a line from her cheeks to her lips with his thumb. She opens her mouth slightly to let him dip the digit in, her tongue licking at the pad. Dean doesn’t smile, he just looks at her with wide pupils and a lustful gaze.

There’s a lot of staring, with neither of them moving or saying a word, and she realizes that he’s waiting for her consent. She nods.

Dean nods back, “Go on, take it out.”

Popping his now wet thumb out of her mouth, Y/N slides both her hands up his clothed thighs, trailing her fingernails up his dress pants. Dean shivers as she gets closer to his crotch. She deliberately ignores his bulge, and instead starts to work on his belt buckle with deft fingers. Once she opens it, the metal clinks loudly in the otherwise silent room. Her fingers begin to work on the zipper next, and now she can’t avoid feeling the bulge pressing against it.

“Good girl,” he mumbles, more to himself than to her when she peels his pants apart and starts to lower the elastic of his boxer briefs. Only a little, just enough to take out his very impressive dick. It’s only half-hard but it’s beautiful.

There is coarse hair that leads from his belly button to his groin, not much, but enough for the sight to turn her on and for it to be endearing. But down there, Dean is well-groomed. Of course, he would be. His cock twitches when it is free from its confines. It is thick and pale with a blushing tip with some stray freckles on his shaft. Once she takes it in her hand, it grows a little more. Y/N wonders how big it will get once it reaches its limit, because it’s already big as it is. He wasn’t lying when he said women gag around his fat cock. And suddenly, she’s dying to be one of those women.

For a brief moment, she wonders what he meant by that statement anyway. She thought he was bi and was in a relationship with Mr. Winchester. Before she can think any more about it, his dick twitches in her hand, derailing her thoughts back to the present.

He’s hard now. The skin is soft but it’s unyielding. He growls when she tests the weight of it in her palms.

She’s drooling at the sight of it, and uses it right away, spitting into her hand and smearing it around his length. She begins to stroke him, causing him to grunt.

“That’s good, making it nice and wet,” he huffs, “good girl.”

God, praise has always been her weakness, and her body reacts to it on its own volition, causing wetness to gush around in her panties.

“C’mon, Y/N, it won’t suck itsel— fuck!”

Before he can finish his sentence, she sucks sharply at the tip of him, causing his words to die in his throat. Good. It’s surely a great way to shut him up. It’s also a win-win situation really because she likes the taste of him. He smells clean, a little musky from the day but it’s not bad. In fact, she could get addicted to it, which she hopes she won’t. Addicted to Dean’s dick, that’s the last thing she would need.

Next, she licks up his shaft before she accumulates more saliva. Leaning forward, she lets it dribble down from her mouth all over his cock, making it wetter. She jerks him off a little, the slick fapping sound lewd as it bounces off the walls. Y/N hums when she takes him into her mouth again. She moves her head further down and impales her face on his fat dick. Dean grunts above her, and when she takes him so deep that she’s practically retching and gagging all around him, he groans loudly.

When she comes up again, she gulps for air, swallowing it down greedily as she refills her lungs. His length is covered with her spit and his pre is running down to his balls and ruining his underwear and pants. Good. It’s a nice change to see him so messy, and especially to know that she’s the one who caused it.

After a couple of breaths to regroup, she moves down and takes him into her mouth again, bobbing her head up and down rhythmically. What she can’t fit in her mouth, she strokes with her hand. He’s really big and fat, already stretching her mouth so wide that Y/N isn’t sure she wants to imagine how much he’d stretch out her pussy. She can’t deny though, that the thought gets her all hot and bothered. Surely, he’d fill her so good and make the stretch burn a little, just the way she likes it.

“So good, baby, fuck—” his hand fists in her hair, fingers twisting around her locks as he starts to help guide her up and down his length while simultaneously canting his hips in order to reach deeper. She gags around him, but he keeps going, thrusting his cock into her waiting mouth — which is also fine by her. They don’t have a safe word, but she figures that if she drives her fingernails into his thighs, he’ll know. “Jesus— fucking walked out on me that last time, Y/N. You gave me blue. Fucking. Balls.” Dean punctuates each word with a thrust of his hips, causing her to choke around him before letting go of her head in order to give her time to come up for air.

His hand is still in her hair as he pulls at her scalp, making her look at him. She has tears in her eyes, and she can imagine that her mascara is running down her cheeks. Her lipstick is probably nonexistent, all the color now wrapped around his beautiful cock.

“Look at you, made yourself messy,” he coos with some sort of affection in his voice. “Looking so fucking ruined, Y/N, but it’s a great look on you.”

She can’t help but glow with the praise, wriggling on her knees as she brushes the back of her hand over her lips to get rid of some drool. She whimpers when he pulls harder at her hair.

“What’s that?” He chuckles, “Does this turn you on, hhm? Getting your throat fucked makes you wet, sweetheart?”

“Oh fuck, yes,” she affirms, all pretense and shame flying out the window.

Dean smirks, “Go on, push your skirt up and grind your greedy cunt on my shoes while you suck me off.”

Y/N’s too desperate to even pretend to put up a fight, the need to get off overwhelming.

He watches as she pushes her skirt up around her waist, revealing her pink and very soaked satin underwear. Dean smiles when she positions her drenched pussy on his left shoe and begins to grind.

She moans at the friction. Who knew the expensive shoes could get her off? While she moves her hips, she gobbles him down her throat, causing him to growl. “Fuck, Y/N, can you see how we work much better together? Shit— always trying to fight me— just like that, yes, good girl, suck that dick— such a great little mouth, baby.”

Oh god, she’s so close already, completely turned on by his filthy language. It’s no surprise that someone like him is running a dirty mouth. She hums around him as she tries to take him even deeper, only to choke on it. But that doesn’t stop her either. Instead, it turns her on even more. Her hips work harder as she really puts her weight down to where her clothed cunt meets Italian leather.

“That’s right, you’re close, ain’t cha?”

“Mmmhh.”

“You want my cum, baby? Want me to come in your mouth?”

“Mmmhh.”

“Will you swallow it down, hhm? Take it down your tight hot little throat, baby?” His voice is strained when the words spill out of his mouth in a low growl.

“Mmhh.”

His grip on her hair tightens just so. “Then come. You have to come first, before I’ll feed you mine, Y/N. Be a good girl, baby. Show me you deserve it.”

Y/N grinds her clothed cunt harder down onto his shoe, moaning and shamelessly drooling down his shaft in the process, as she chases her orgasm.

When her peak hits her, she lets out a low whine around Dean’s dick.

He holds her steady by her hair, fingernails biting into her scalp as he halts her motions while he lets out a series of low deep grunts. Dean grits his teeth when he speaks, “Take it,” he pants, “Take it all, Y/N, but don’t swallow yet, you hear me?”

Dean growls as his dick twitches in her mouth and spills onto her tongue while she fights her own reflexes to swallow down his spend. He pulls her face away from his cock by her hair, again, blunt nails digging into her scalp on that right side of pain. His still half-hard dick flops out of her full mouth and is still twitching. It is covered in a shimmer of her lipstick and coated with a layer of come and spit. In other words, it’s messy, yet beautiful, and she wants him to shove it back down her throat.

“Look at me,” he commanded. His hand has released her hair and is now cupping her head gently while his thumb strokes at her jaw.

Y/N does.

Dean looks a little beat, pearls of sweat gracing his hairline. His cheeks are tinted pink, a sheen of sweat coating the bridge of his nose, causing his freckles to stand out. His breath comes out in long and heavy spurts. “Show me.”

Opening her mouth, she lets him see the pool of cum on her tongue, his scent encompassing her fully. She tastes him and smells him, and it’s truly intoxicating, causing her to get a little light-headed.

He dips his thumb into her mouth and into the cum before smearing it along her lips. “Good girl.”

God, she just came but with how he sounds and the way he looks at her, she could come again, right now. She definitely would if he tells her to, there’s no doubt about it.

Dean leaves her hanging there as he takes his time and tucks himself back into his pants. They are definitely ruined with her saliva. She feels a little proud of that.

Once he’s decent again, he looks at her, but instead of the hard gaze, she finds softness in his eyes. He nods, “Now you can swallow it, baby.”

Y/N does, like the good girl she is. It’s a bit harder to get it down after holding it in her mouth for so long and she grimaces and fights against her gag reflex.

“Stick your tongue out,” he demands when she swallowed it all.

She licks her lips, savoring the last taste of him before swallowing once more. Sticking her tongue out wide, she lets him inspect it.

“Good fucking girl,” he praises and pats her cheek twice. She smiles shily.

Dean leans forward to kiss her afterward, tongue invading her mouth. He groans as he tastes himself on her.

When he pulls away, he sits back up straight, holding out a hand to help her up. He even helps to tuck her skirt back down and she walks back to pick up her heels from the floor.

“Thanks for the stress relief,” he says, and it causes her to frown. He basically just threw her words back into her face. How dare he?

“What? What about the job?” Y/N asks, incredulous.

Dean leans back in his chair, the leather creaking under his weight. He stares at her as he worries his lips. Then he says, “You won’t get it.”

She has half a mind to throw her shoes at him and ruin his smug pretty face, but then she wouldn’t have footwear to go back home with, and somehow the thought of having to even walk to the next store in her bare feet in order to get new shoes makes her shiver.

“Fuck you,” she grits out before stomping to the door. She has it open and is ready to leave when she hears him talk so she turns around.

“No, I think next, I’d really like to fuck you. And please, don’t let the door hit you on the way out.”

Y/N slams it closed as hard as she can.

..to be continued

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