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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Jensen’s POV
“You know the drill,” 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 – teasingly – 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 he’s standing, and they’re 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 Jensen’s 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 it’s 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.
“Twenty today,” he informs her.
“Yes, Principal Ackles,” she replies obediently. She’s 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.
“One,” she counts.
“We haven’t started,” 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 Jensen’s cock swelling quicker than before.
“You know, it’s not a very good punishment if you enjoy this so much, baby girl,” he hums, letting his fingertips dance along her heated skin, towards the damp patch in the crotch of her panties.
“You enjoy it too,” 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. “Now, sweetheart, Daddy didn’t say you could touch.”
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.
“Please, Daddy, please, fuck me.” Jensen reaches down for the lump in his slacks, palming over it slowly as he watches her slowly losing her mind.
“I’m not done with your punishment,” 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.
“Please,” she sobs, “please fuck me.” 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, he’s deep inside her.
Jensen’s 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, he’s 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 doesn’t matter how much he rubs, the image of Y/N bent over that desk with her ass on display won’t budge. What’s worse, is the image isn’t even of the white silky panties she’d had on in the dream, or even any of the other panties she’s worn in all the other dreams he’s been having. Oh no, the image he can’t 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 he’s getting more and more tired as time goes on; he’s barely had a decent night’s sleep in the eight weeks since that afternoon. He’s 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. He’d never planned on actually making her bend over the desk, and then he’d never planned on actually hitting her – and he’d 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 couldn’t 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 wasn’t 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 shouldn’t have let it get that far and he certainly shouldn’t have enjoyed it. And then he saw the woman she’d 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. He’d made her feel that way.
Jensen clearly had a problem, and he’d made sure to distance himself from her since. The only silver lining to the entire situation was the fact that for several weeks she’d been actually keeping her head down. He’d heard no complaints about her uniform or skipping class, or even her making inappropriate comments to teachers. Her grades aren’t perfect, or even close to what Jensen knows she’s capable of, but at least she hadn’t been causing trouble, either. That was until about a week ago. Jensen should’ve known it wasn’t going to last forever. First she’d skipped Math, then Jensen got a complaint from Mr. Gardener about her uniform.
He’s been trying to turn a blind eye, not trusting himself to spend any amount of time alone with her again. While it’s not exactly great that she’s skipping classes and wearing her uniform inappropriately, she’s also not really putting herself or anyone else in danger, so it’s not the end of the world that he pretends to forget to discipline her. At least, that’s what he keeps telling himself. He’s just lucky she hasn’t told her Dad – or anyone else for that matter. It doesn’t matter that Jensen knows her personally, he’d 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 it’s the final day of school before Christmas break. He’s 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 he’s got to go home and pretend everything is fine and normal. And he’s going to have to lie to Jared about how Y/N has been getting on. At least telling him that she’s been settling in and keeping her head down the last several weeks won’t be a total lie, even if he can never say why. He just prays Y/N doesn’t say anything, either. She’s always loved waving these things in her father’s face, but she has to recognise that this is different. Jensen can only pray.
First period hasn’t even begun when Michaela knocks on Jensen’s door unexpectedly.
“Everything okay?” he checks, not really looking up from his laptop.
“Holly Kimble has asked to speak with you,” 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 it’s probably about Y/N. What if it’s about what he did with Y/N?
“Send her in,” he commands softly. Michaela smiles and nods in understanding.
“Principal Ackles will see you now,” 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.
“Holly, to what do I owe this pleasure?” He links his fingers in his lap, telling himself that her roommate is probably the last person Y/N has told about what happened.
“It’s about Y/N,” she tells him timidly. “I know that you’re like… related to her or something,” she blushes.
“What about Y/N?” Jensen presses, now more concerned for Y/N’s wellbeing than saving face. Holly chews her bottom lip, starting to play with her fingers in front of her, which makes Jensen increasingly nervous. “It’s okay, Holly, you can tell me.”
“Y/N wasn’t in our room last night. I woke up to go to the bathroom around two and she wasn’t there, but I was tired, so I didn’t 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 she’d urm… spent her evening with. Now she’s passed out in bed.”
Jensen stays quiet for a long moment, realising that not only is Y/N no longer keeping her head down, but she’s even worse than she was before the spanking. As far as he’s aware, she hadn’t snuck out of the school grounds since the night she slept with Jeff. What is she thinking?
“I’m really sorry, Principal Ackles. As the head of the dorm, I should’ve notified you sooner, or at least informed someone when I noticed her missing at two.”
“It’s fine, Holly,” Jensen reassures her softly, not wanting her to panic. “You’ve done the right thing by coming to me. Thank you for letting me know.”
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 it’s too early for the whiskey in his bottom drawer, courtesy of Michaela as a Christmas gift last year. It’s 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 can’t turn a blind eye to that. She’s putting herself in danger, and that’s something he simply cannot have. Anything could happen to her while she’s out there, and if he doesn’t know where she is, he can’t 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 he’s gotta do something about this, and that means confronting Y/N. Spending more than two minutes alone with her; something he hasn’t 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 she’s attended her remaining two lessons a little hungover ‘barely wearing a uniform’ 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 he’s gone, making sure all the girls leave safely by tomorrow evening.
Not that Jensen’s 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 he’s hoping Y/N won’t take too long to pack a couple of things to take home with her. He’s assuming she’ll have most things she needs at home already. By two, he’s 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 he’d touched her so inappropriately, but he’s going to have to have a conversation with her about how she chose to spend her night. And he’s going to have to have that conversation without sounding jealous.
Because he’s not jealous. That’s ridiculous. Yes, he got aroused by spanking her, but maybe he just likes spanking. He’s never really had a partner who’s been into it, so he’s never really explored it before. It wasn’t because it was Y/N. And he might keep dreaming about her, about spanking and fucking her, but that’s just his guilty conscience mocking him, wanting him to feel disgusting and perverted and even more ashamed of himself. And he’s only angry that she had snuck out because she’d put herself in danger, and definitely not because the thought of her fucking some guy that isn’t him makes him jealous. He’s just getting his wires crossed because of those stupid nightmares.
“Hey, I’m going now,” Michaela’s voice breaks through his inner turmoil, and Jensen forces a smile.
“Of course, have a wonderful Christmas, Michaela,” he tells her.
“Thanks,” she smiles softly. She steps up to him and hands him a small box, before leaning forward and kissing his cheek gently. “Merry Christmas, Jensen,” she whispers into his ear.
Jensen ashamedly relishes in the attention for a second, it’s 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.
“Y/N,” Jensen clears his throat, looking down at the box Michaela gave him and putting it in his top drawer. “Come in.”
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.
“I’m assuming you heard?” 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.
“What are you doing?” Jensen asks, swallowing hard at the very reminder of what he’d done to her on that desk.
“Preparing for my punishment.”
“Is that why you did it?” he finds himself asking. “You wanted me to punish you?”
She bites her bottom lip, turning around and leaning back on the desk, all long bare legs in her tiny skirt that Jensen’s only just noticing isn’t even the school uniform colours; it’s black.
“So what if I did?”
Jensen’s a little confused to say the least, she’d avoided him as much as he’d avoided her after what had happened, she’d even stayed out of trouble, so why is she looking for more now?
“That’s not going to happen again, it was a mistake,” he insists.
He doesn’t like the cocky grin that spreads over her lips as she pushes off of the desk and stalks towards him.
“I’m sure there’s more buttons I can press, Uncle Jensen, we’ll see how long it lasts.”
She reaches for his tie and straightens it, before leaving his office, and Jensen swallows hard. Now he’s just gotta survive three hours in a car with her, and something’s telling him that’s not gonna be easy.
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