Chapter Tags: smut, p in v, fabric in mouth, oral sex, semi-public sex, risky sex, orgasms, degradation/humiliation, daddy kink
Chapter WC: 2243
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THREE MONTHS LATER
Your POV
Y/N: Well this weekend was fun 😉
Jensen: That’s what you get for being a good girl
You smirk at your cell as you make your way back to your dorm, already feeling a little pent up again even though you’ve only just left Jensen’s, but knowing it’s a Sunday night and there’s another full week of school ahead, means that you’re not going to get that itch scratched until at least Friday night. Jensen laid down a no sex at or during school rule pretty early on in your arrangement, and so far, he’s not gone back on that. So that leaves you with weekends, and the occasional evening that you don’t have homework or some test to study for so that you can spare time to sneak down to see him. Luckily, Holly doesn’t seem to question you spending so much time with the Principal, especially not after you gave her some sob story about feeling homesick sometimes and that Jensen helps you feel better because he reminds you of home. Though, Holly has been caring less and less about that stuff recently anyway.
Y/N: And what do I get if I pass my Math exam on Tuesday?
Jensen: Guess you’ll have to pass and find out
You blindly push the key into the door handle to your room and unlock it, opening it and looking up when you hear movement.
“Oh fuck,” Holly giggles, scrambling for bedsheets.
You raise your eyebrows for a moment, noticing her hair is a mess and she’s definitely naked.
“Did I interrupt special time?” you chuckle, turning around when you hear the bathroom door open behind you. You watch as some tall blonde dude steps out, dressed, but his hair is tousled and he’s turning a slightly darker shade of pink in his face. “Oh, hi.”
“Urm, Y/N, this is a friend,” Holly explains weakly, clearing her throat.
“I’ll call you,” he whispers to her, leaning down to kiss her.
“Yeah, sure,” she whispers back.
Holly reaches up to tame her hair again as the blonde leaves, and you can’t keep the smirk off of your face.
“A friend, huh? And where did you meet this friend?” you pry, crossing your arms over your chest.
“Just out,” she struggles, pulling the bedsheets up higher. “Do you mind urm… turning around?”
You laugh, “it’s fine, I’m about to take a shower. But can you stop being a slut for five minutes and help me figure out this biology work once I’m out? We have a test on Wednesday and I really need to pass it.”
“Well done, Miss Padalecki.”
You look down at the paper and bite your bottom lip, unable to hide the smile trying to force its way over your mouth. You’d never thought you’d be this happy to see a B on a test before. There seems to be a pattern with Jensen’s rewards; the better you do, the better he rewards you. And a B is the highest grade you’ve gotten yet in Math. You quickly load the camera on your cell and snap a photo of the grade, sending it to Jensen with an angel emoji.
You watch your screen for several minutes, and then a reply flashes up and you immediately bite your bottom lip and read it.
Jensen: Good girl, come to my office after school. Now stop texting in class or you won’t get your reward
You feel stupidly good about yourself at the validation, and no matter how hard you try, you can’t focus on anything but Jensen’s reward for the rest of the school day.
You clench your thighs together tighter, feeling your pussy practically dripping as you sit and wait uncomfortably. You keep looking at Michaela, and every time she notices you staring she clears her throat awkwardly and looks away. But you’re not here to terrorise her today, you’re over that. Jensen’s fucking you now, and as far as you know he’s never even fucked her once. The only reason you keep staring at her is because you’re waiting for those magic words, the ones that mean this teasing, agonising wait is over. Jensen no doubt knows what he’s doing – he loves making you desperate.
Her phone rings on her desk, and your heartbeat starts to quicken. You almost want to jump to your feet and head in there before she lets you, but part of the thrill – you’ve come to realise – is hearing those words. It’s almost like foreplay.
“Principal Ackles will see you now.”
You stand up immediately and walk over to his door, not even bothering to knock as you let yourself in and close it tight behind you so Michaela can’t hear or see anything. Not that anything ever happens in this room anymore, but there’s still the blind, naive hope inside you that thinks maybe this time he’ll crack.
“Hi,” you smile sweetly, moving to sit in the armchair opposite him, placing your bag beside you.
“A B in Math?” he questions, a small smirk on his lips.
“Yeah, are you proud of me?” you ask, biting your bottom lip.
“Very,” he confirms, “are you proud of yourself?”
“Sure,” you shrug.
Jensen spins in his chair, reaching for keys out of his pocket and unlocking one of his desk drawers.
“I’ve been waiting to give you this, for a time you’ve really impressed me,” he explains, pulling out a gift bag. You recognise the colours and logo to be from the lingerie store in town. Jensen rounds his desk, perching himself on the edge of it right in front of you. Slowly he hands over the gift bag and smirks. “Put that away somewhere safe, the only other person that’s allowed to see it is me.”
You take the bag from him and open it, peering inside to see deep red lace. You reach inside to touch, feeling how soft it is against your fingertips, and as you lift it out, Jensen glances to the door and pushes your hand back down into the bag to stop you. You smirk slightly.
“Thank you, Daddy,” you tell him quietly, indulging his paranoia.
“You can thank me this weekend.”
You watch as Jensen gets up and returns to his chair, and you bite your lip, deciding to push the boundaries a little. Clearing your throat, you place the gift bag down on the floor by your chair.
“It’s very kind of you to buy me new underwear, considering you ruin all my panties.”
Jensen’s cheeks turn a deeper shade of pink and he scoffs. “That right, baby girl?”
“You don’t believe me?” You press, sliding yourself a little further down the chair. You bring your feet up to the desktop and then slowly start to open your legs. “They get so wet that now I just don’t bother wearing any.”
Jensen immediately looks away, but only seconds later his green eyes are back between your legs, taking in the sight of your pussy no doubt shining with the slick he’s caused.
“Baby girl,” he warns quietly, clearing his throat and reaching up to rub a hand over his face. “Put that away.”
“That? Oh, you mean my wet little pussy? But you love it so much, Daddy.” Jensen readjusts himself in his chair as you slowly reach between your legs and start to let your fingers play with your clit. “Can you see how wet I am just from thinking about you all day?” You bring your fingers to your mouth and suck them clean. “Tastes good too, but you already know that, don’t you, Daddy?”
Jensen reaches for the phone on his desk and picks it up.
“Hey, you can go for the day… no no, I’m fine now. See you tomorrow.”
His eyes don’t leave your pussy as he talks, and when he hangs up you continue to play with yourself, rubbing in small circles, only making yourself so much worse. The fading of Michaela’s heels as she leaves the office finds Jensen visibly relaxing a little more. He glances to the door and then back at you, lifting his hand as he flicks his fingers towards him.
“C’mere.”
You smirk triumphantly, pulling your hand away and jumping to your feet, eager to round his desk and join him on the other side. You can see now that he’s painfully hard in his slacks, and he tears into them and pulls his cock out of the fly.
“On your knees,” he grunts. “Wanna put that slutty mouth to good use.”
You lick your lips, not minding the command one bit as you lower to your knees and eagerly take his throbbing length in your grasp, licking from root to lip and then closing your mouth over it, starting to suck the precum away.
“Atta girl,” he hums, his hand engulfing the back of your head. “Suck Daddy’s cock, good girl.”
After a few moments your eyes are watering and your chin is a soppy mess. You’re trying so hard to please him, hoping it’ll prompt him to give in and fuck you like you so desperately need him to, and eventually he pulls you up to your feet and throws you over his desk. You feel him remove your tie from around your neck. You feel the fabric starting to push into your mouth, muffling the moan that bleeds from it at his heavy handedness. You quickly glance over your shoulder just in time to see Jensen dropping to his knees, his large hands pulling your ass cheeks apart and then his tongue is inside you, thrusting as deep as it can get. You scream out, luckily not loud enough that anyone hears thanks to the tie, and start gripping the edge of the desk for dear life.
Jensen hums as he eats you out, fucking you with his tongue before swirling it around your bundle of nerves and sucking it between his teeth. You buck your hips back against his mouth, desperate for more, and Jensen chuckles against your heat.
“Look at you,” he mocks. “Maybe I shouldn’t give you my cock. Going around school without any panties on like a little slut? You should get detention.” You whine around the tie, bucking your hips once more to tempt him. Jensen chuckles at the attempt, standing up and spanking your ass softly. “Lucky for you, Daddy loves this pussy too damn much to resist it.” Your eyes almost roll into the back of your head when you feel the thick swell of his tip rubbing through your folds, nudging and teasing your clit. “Tell you what, baby girl, you can have Daddy’s cock inside you if you beg nicely.”
“Pl-s, Da-ee, pl-s,” you try to get out around your gag.
“What was that, sweetheart? Can’t understand you.”
You grunt, clenching your jaw. You try to tell him it’s not fair, but that doesn’t come out even a little distinguishable. You reach for the tie and pull it loose, dropping the wet fabric to the desk.
“Please, Daddy, fuck me,” you finally beg coherently.
Jensen chuckles, his hand pressing the side of your face down against the desk. “See, you are a clever girl.”
He slides inside, stretching your insides beautifully, and thanks to the way his mouth had been relentlessly teasing you just moments before, you’re already close to an orgasm. You try to tell him, but once more your words aren’t coherent, only this time it’s not because of a gag. Jensen seems to notice though, because he chuckles and rolls his hips in the way he knows gets you closer, fucking you slow but hard, making your whole body shake.
“Reach back, spread those holes f’me, let me see you cum.” You instantly reach behind you, spreading your ass like he’s instructed, whimpering at the way that simple act makes it feel better. “Creamin’ all over my cock like a slut,” he growls, reaching around your body to toy your clit, which gets you right there. “Such a good girl, aren’t you, baby? Such a good little whore for your Daddy.”
Everything stops; your breathing, your brain – the whole world, it feels – everything but the orgasm that’s now coursing through every inch of you, making your legs shake and your eyes roll.
“That’s it, fuck, you wanna see how good that pussy looks cumming around my cock,” he chuckles. He pulls out, sitting back in his chair, pulling you into his lap, sending his cock the whole way inside once more. He’s holding you tight to his chest, fucking up into you mercilessly now, until his phone starts ringing. “Fuck.”
Jensen stops fucking you, and you’re expecting him to pull out, freak out and tell you to go back to your dorm, tell you he can’t ever fuck you in his office again. But instead, his large hand wraps over your mouth, silencing you completely, and he clears his throat, calmly reaching for the phone.
“Principal Ackles,” he answers, his voice surprisingly steady. “Yes, I heard she did well in Math, I knew she had it in her… I agree, she’s really making good progress. Thanks for letting me know.” Jensen rolls his hips up, and you instantly reach up, digging your nails into his arm in a desperate attempt to release some of your pent up arousal other than screaming. Jensen pays it no mind, his cock now deep and still, but throbbing inside you. “Don’t worry Keith, I’ll think of something to encourage her to keep it up.”
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