Chapter Tags: spanking, caning, fingering, p in v, angst, shame, guilt, inappropriate relationship, inappropriate feelings/thoughts, teasing, flirting
Chapter WC: 2975
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Jensenās POV
āYou know the drill,ā Jensen tells her as soon as she steps through his office door.
She smirks ever so softly and closes it behind her, turning the lock with a soft click, and then slowly makes her way over to the desk now in the centre of his room. Y/N takes a deep breath and then slowly ā teasingly ā bends over it, reaching back to inch her skirt up her legs and over her ass. Her panties are silk today from what Jensen can see from where heās standing, and theyāre a delicate white colour. Her ass swallows them, big and full and round, and there are traces from her last detention left behind, which makes Jensenās cock twitch. He licks his lips slowly and then starts to take his time approaching her, letting the tension build between them.
Reaching down, he palms gently over her soft skin to begin with, warming up the muscle, getting it prepared for the pain itās about to endure. Y/N murmurs ever so softly under her breath, readjusting her position slightly as she glances back over her shoulder towards him, her cheek pressed down into the wooden desk.
āTwenty today,ā he informs her.
āYes, Principal Ackles,ā she replies obediently. Sheās still gripping the hem of her skirt, keeping it bunched at her waist, and Jensen gives her ass a light spank to test the waters, making her flinch slightly and grip her skirt tighter.
āOne,ā she counts.
āWe havenāt started,ā he tells her, his voice gruff. Y/N licks her lips and swallows hard, taking another deep breath.
When Jensen withdraws his hand this time, he strikes it much harder against her skin, watching it instantly start to darken from the impact. Y/N whimpers and then composes herself, once again counting to one. Jensen pulls back and delivers a second crack of skin on skin to the opposite cheek, letting it heat up to match the first. He waits for her to count two before striking her a third time. Y/N starts to squirm, rubbing her thighs together, biting her bottom lip, and the sight has Jensenās cock swelling quicker than before.
āYou know, itās not a very good punishment if you enjoy this so much, baby girl,ā he hums, letting his fingertips dance along her heated skin, towards the damp patch in the crotch of her panties.
āYou enjoy it too,ā she sasses back, reaching out for his leg, rubbing her hand up to the noticeable bulge behind his slacks.
Jensen steps back before she can touch it, though, tutting and shaking his head disapprovingly. āNow, sweetheart, Daddy didnāt say you could touch.ā
Y/N snaps her hand away, and Jensen steps back even further, heading over to his desk to retrieve the cane. He smacks the palm of his own hand, watching Y/N flinch at the sound of the bamboo cracking against his skin and smirks, biting his bottom lip as his cock throbs in its confines. He brings the tip of the cane between her legs, using it to rub over her bundle of nerves through the silk, and watches as she desperately squirms and bucks her hips against the stick.
āPlease, Daddy, please, fuck me.ā Jensen reaches down for the lump in his slacks, palming over it slowly as he watches her slowly losing her mind.
āIām not done with your punishment,ā he reminds her, striking the entire width of her backside with the cane.
She screams out, but it chokes into a moan, tears filling her eyes.
āPlease,ā she sobs, āplease fuck me.ā Jensen grunts, using his free hand to tear her panties clean off, getting into his slacks as quickly as possible to free his aching cock.
He bends at the knee, rubbing the weeping tip of his cock through her dripping cunt, and then brings the cane to her face, forcing the bamboo between her teeth. He holds either end, forcing her to arch her back, and then in one hard thrust, heās deep inside her.
Jensenās eyes shoot open, landing on his alarm clock as it sounds out. He looks around the room to find himself in bed, alone, and his heart starts to slowly return to its normal rate as he realises it was only a dream. Fuck, heās gotta stop dreaming about Y/N like that. He rolls onto his back and stares up at the ceiling, reaching up to rub his face to try and help wake himself up. But it doesnāt matter how much he rubs, the image of Y/N bent over that desk with her ass on display wonāt budge. Whatās worse, is the image isnāt even of the white silky panties sheād had on in the dream, or even any of the other panties sheās worn in all the other dreams heās been having. Oh no, the image he canāt scrub out of his mind is the real one. The one from the time he actually bent her over her desk and spanked her. Fuck. Jensen pinches the bridge of his nose, feeling his cock is still semi hard in his boxers.
The nightmares are making him sleep restlessly, meaning heās getting more and more tired as time goes on; heās barely had a decent nightās sleep in the eight weeks since that afternoon. Heās still haunted by the memory of his resolve breaking so damn easily, enough to want to strike her like that. He just needed her to take him seriously, he needed her to stop. Heād never planned on actually making her bend over the desk, and then heād never planned on actually hitting her ā and heād certainly never planned on feeling the way he felt about it in that moment. The first strike had been satisfying, a little dose of relief from a lot of built up frustration, and then the second strike had been satisfying too, but in a way Jensen couldnāt put his finger on at first. It was the third that brought clarity. It was the third that made him realise that it was arousing him.
He let it get the better of him for a moment or two, forgetting who she is, forgetting who he is, forgetting everything else except the slow thrum of arousal making its way around his body. It wasnāt until she pushed up and looked at him that the reality of it all kicked in, hitting him straight in the gut. For a split second he saw the little girl he met at five years old, and he felt a twist of guilt in his stomach, because he shouldnāt have let it get that far and he certainly shouldnāt have enjoyed it. And then he saw the woman sheād become, and hated himself for every inappropriate thought and feeling that was trying to force its way into his brain. But it was the way she looked at him that haunted him the most. Pure shock and confusion, shame, even. Heād made her feel that way.
Jensen clearly had a problem, and heād made sure to distance himself from her since. The only silver lining to the entire situation was the fact that for several weeks sheād been actually keeping her head down. Heād heard no complaints about her uniform or skipping class, or even her making inappropriate comments to teachers. Her grades arenāt perfect, or even close to what Jensen knows sheās capable of, but at least she hadnāt been causing trouble, either. That was until about a week ago. Jensen shouldāve known it wasnāt going to last forever. First sheād skipped Math, then Jensen got a complaint from Mr. Gardener about her uniform.
Heās been trying to turn a blind eye, not trusting himself to spend any amount of time alone with her again. While itās not exactly great that sheās skipping classes and wearing her uniform inappropriately, sheās also not really putting herself or anyone else in danger, so itās not the end of the world that he pretends to forget to discipline her. At least, thatās what he keeps telling himself. Heās just lucky she hasnāt told her Dad ā or anyone else for that matter. It doesnāt matter that Jensen knows her personally, heād be fired in a heartbeat for spanking a student. If anything, his relation to her probably only makes it worse.
Jensen huffs as he rolls onto his side and gets up. His cock is finally starting to soften, thanks to where his mind has wandered to since his dream, and he stands up, heading into the bathroom, at least grateful that itās the final day of school before Christmas break. Heās almost made it a whole semester; Y/N has almost survived a whole semester. The only thing tainting that fact is that it means now heās got to go home and pretend everything is fine and normal. And heās going to have to lie to Jared about how Y/N has been getting on. At least telling him that sheās been settling in and keeping her head down the last several weeks wonāt be a total lie, even if he can never say why. He just prays Y/N doesnāt say anything, either. Sheās always loved waving these things in her fatherās face, but she has to recognise that this is different. Jensen can only pray.
First period hasnāt even begun when Michaela knocks on Jensenās door unexpectedly.
āEverything okay?ā he checks, not really looking up from his laptop.
āHolly Kimble has asked to speak with you,ā she tells him quietly.
Jensen looks past her out into the reception area to see Holly fussing with the end of her plait, looking nervous about something. Jensen frowns, wondering what issue Holly could possibly have, and then he gets a gut feeling itās probably about Y/N. What if itās about what he did with Y/N?
āSend her in,ā he commands softly. Michaela smiles and nods in understanding.
āPrincipal Ackles will see you now,ā she tells Holly.
Jensen closes his laptop as Holly enters the office and closes the door behind her. This makes him slightly nervous, but he keeps the smile on his face.
āHolly, to what do I owe this pleasure?ā He links his fingers in his lap, telling himself that her roommate is probably the last person Y/N has told about what happened.
āItās about Y/N,ā she tells him timidly. āI know that youāre likeā¦ related to her or something,ā she blushes.
āWhat about Y/N?ā Jensen presses, now more concerned for Y/Nās wellbeing than saving face. Holly chews her bottom lip, starting to play with her fingers in front of her, which makes Jensen increasingly nervous. āItās okay, Holly, you can tell me.ā
āY/N wasnāt in our room last night. I woke up to go to the bathroom around two and she wasnāt there, but I was tired, so I didnāt really think anything of it, I just went back to bed, and then she woke me up at four this morning, getting in. She was drunk, and she started talking about this man sheād urmā¦ spent her evening with. Now sheās passed out in bed.ā
Jensen stays quiet for a long moment, realising that not only is Y/N no longer keeping her head down, but sheās even worse than she was before the spanking. As far as heās aware, she hadnāt snuck out of the school grounds since the night she slept with Jeff. What is she thinking?
āIām really sorry, Principal Ackles. As the head of the dorm, I shouldāve notified you sooner, or at least informed someone when I noticed her missing at two.ā
āItās fine, Holly,ā Jensen reassures her softly, not wanting her to panic. āYouāve done the right thing by coming to me. Thank you for letting me know.ā
Holly seems a little less flustered and offers him a weak smile before nodding her head and leaving his office. Jensen stares at the closed door for a moment and wonders if itās too early for the whiskey in his bottom drawer, courtesy of Michaela as a Christmas gift last year. Itās not even nine am, so he decides it probably is and huffs.
If Y/N is starting to sneak out in the middle of the night again, meeting older men like before, Jensen knows he canāt turn a blind eye to that. Sheās putting herself in danger, and thatās something he simply cannot have. Anything could happen to her while sheās out there, and if he doesnāt know where she is, he canāt do anything to help her. Jensen would hate himself if anything bad happened to her under his supervision, and never mind himself, Jared would kill him. He takes a deep breath, knowing heās gotta do something about this, and that means confronting Y/N. Spending more than two minutes alone with her; something he hasnāt done since he bent her over her desk and spanked her ass raw. This should be interesting.
Y/N finally emerges from her dorm just after lunch, and apparently sheās attended her remaining two lessons a little hungover ābarely wearing a uniformā according to Angela Meek, her biology teacher. Jensen texts her to let her know that she needs to pack a bag and he wants her to come to his office after school. She replies with a simple Yes sir, which makes Jensen roll his eyes at his screen. Apparently her attitude is back in full swing, too. Jensen spends the remainder of his afternoon busying himself, tying up all the loose ends before finishing for Christmas and handing over to Keith to hold the fort while heās gone, making sure all the girls leave safely by tomorrow evening.
Not that Jensenās eager to get home, but he is eager to get on the road tonight, when traffic will be lighter before the weekend rush of everyone else travelling home for the holiday season. So his bags are packed and already in his trunk, and heās hoping Y/N wonāt take too long to pack a couple of things to take home with her. Heās assuming sheāll have most things she needs at home already. By two, heās feeling anxious about seeing Y/N again. Not only is he going to be stuck in a car with her for three hours after not really spending any time with her since heād touched her so inappropriately, but heās going to have to have a conversation with her about how she chose to spend her night. And heās going to have to have that conversation without sounding jealous.
Because heās not jealous. Thatās ridiculous. Yes, he got aroused by spanking her, but maybe he just likes spanking. Heās never really had a partner whoās been into it, so heās never really explored it before. It wasnāt because it was Y/N. And he might keep dreaming about her, about spanking and fucking her, but thatās just his guilty conscience mocking him, wanting him to feel disgusting and perverted and even more ashamed of himself. And heās only angry that she had snuck out because sheād put herself in danger, and definitely not because the thought of her fucking some guy that isnāt him makes him jealous. Heās just getting his wires crossed because of those stupid nightmares.
āHey, Iām going now,ā Michaelaās voice breaks through his inner turmoil, and Jensen forces a smile.
āOf course, have a wonderful Christmas, Michaela,ā he tells her.
āThanks,ā she smiles softly. She steps up to him and hands him a small box, before leaning forward and kissing his cheek gently. āMerry Christmas, Jensen,ā she whispers into his ear.
Jensen ashamedly relishes in the attention for a second, itās always nice to feel desired, and Michaela does that a lot, even if he never will reciprocate it. He does feel bad sometimes for that fact. Someone clears their throat behind Michaela and she pulls back abruptly, blushing hard before clearing her throat and turning and leaving, pushing past Y/N without saying a word.
āY/N,ā Jensen clears his throat, looking down at the box Michaela gave him and putting it in his top drawer. āCome in.ā
She just stares at him with a small smirk on her face for a moment, crossing her arms over her chest. Eventually, she pushes off the doorframe and heads inside.
āIām assuming you heard?ā she asks, almost cockily.
Jensen watches as she walks over to the desk she used to frequently sit at and pulls it further into the room, much like Jensen had done that afternoon.
āWhat are you doing?ā Jensen asks, swallowing hard at the very reminder of what heād done to her on that desk.
āPreparing for my punishment.ā
āIs that why you did it?ā he finds himself asking. āYou wanted me to punish you?ā
She bites her bottom lip, turning around and leaning back on the desk, all long bare legs in her tiny skirt that Jensenās only just noticing isnāt even the school uniform colours; itās black.
āSo what if I did?ā
Jensenās a little confused to say the least, sheād avoided him as much as heād avoided her after what had happened, sheād even stayed out of trouble, so why is she looking for more now?
āThatās not going to happen again, it was a mistake,ā he insists.
He doesnāt like the cocky grin that spreads over her lips as she pushes off of the desk and stalks towards him.
āIām sure thereās more buttons I can press, Uncle Jensen, weāll see how long it lasts.ā
She reaches for his tie and straightens it, before leaving his office, and Jensen swallows hard. Now heās just gotta survive three hours in a car with her, and somethingās telling him thatās not gonna be easy.
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