Chapter Tags: flirting, teasing, spanking, dry humping, heart to heart, angst
Chapter WC: 2061
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Jensen’s POV
As Jensen steps into Y/N’s classroom he finds her sitting at her desk, staring down at her phone with a concerned look on her face. She looks up when she notices him, and drops her phone to her desk, sighing heavily.
“What’re you up to?” he asks casually, standing in the doorway, pushing his hands into the pockets of his slacks.
Y/N sighs, shrugging. “Thought maybe I was feeling brave enough to ask Drew for my stuff back. Dad offered to go and get it for me.”
Jensen nods his understanding, stepping further into the room and pushing her door closed. He’s pleasantly surprised to find the key in the door, and turns it to activate the lock.
“What are you up to?” Y/N returns the question, hesitation in her voice.
Jensen once again digs his hands into his pockets and starts to walk closer to her, casually.
“I happen to know that you have a free period right now, and I happened to be between tasks. And I also happen to know that you left for work this morning in a very tight skirt, and I haven’t been able to stop thinking about that.”
He smirks as he stands directly in front of her desk.
Y/N laughs softly, her eyes glancing to her locked classroom door and she bites her bottom lip.
“It’s just a skirt, Jensen,” she counters, sitting back casually in her chair, a glint in her eye. Jensen’s eyes unashamedly drop to her cleavage, the way her blouse just about flashes it, and he smirks harder, his cock slowly starting to harden in his slacks.
“Then you don’t mind me doing a random uniform check,” he asks.
“Uniform?” she scoffs. “I’m not your student anymore.”
But Jensen remains quiet, cocking an eyebrow at her challengingly. Y/N can barely wipe the smirk off of her face as she slowly rises to her feet, pushing down that tight fitted skirt to cover a little more leg. She grabs her phone and then begins pointing it at him, before rounding the desk and standing in front of him.
“What are you doing?” he asks, his eyes landing on her phone.
“Just making sure this uniform inspection is going to be above board,” she teases. “Do I pass your test, Sir?”
Jensen isn’t shy about letting his eyes rake up and down her body several times, no doubt giving away how eager he is to rip those very clothes off of her.
“Hm,” he ponders, “that blouse has one too many buttons undone. I seem to remember that being an issue when you were a student.”
Y/N reaches up, but instead of doing a button up, she pops another one open. “And I seem to remember you loving that,” she purrs seductively, playing with the neckline of her shirt to flash more of her bra.
“That skirt is a better length than the ones you used to wear, but it’s a little tight, doesn’t leave much to the imagination.” Jensen steps forward and reaches for her cell, turning the camera around to aim at her instead. His eyes leave the screen and land back on hers. “Bend over, I want to make sure that the students won’t get an eye full.”
Y/N smirks, licking her lips, but slowly turns around, bending herself over her desk seductively, her ass now on full display for him. Her skirt is long enough that he can’t see a flash of panties, but he’s sure he can remedy that. He steps even closer, pointing the camera down and starting to push her skirt up her legs, over the round apples of her ass. He spanks her once, watching the flesh jiggle with the impact, the skin turning a darker shade.
“Ow,” she complains, wiggling her ass back all the same.
“I seem to remember you used to like that punishment,” he hums, letting his hands smooth over her soft skin, palming at her ass.
“And just what have I done to be punished for?” she sasses.
“Oh I’m sure I can think of something,” Jensen chortles, pushing his crotch against her ass. “Making me hard at work is one.”
Y/N grinds her ass back against his cock, making Jensen moan softly, and he stops the recording before things get too explicit, putting her phone down on her desk and making use of his now free hand to rub his fingers over the damp crotch of her panties. Y/N moans, bucking her hips back to meet his touch, pressing the side of her face down onto the desktop.
“Maybe I should fuck you over this desk, let you teach your next class with my cum dripping down your thighs.”
“Fuck,” Y/N whimpers, bucking her hips harder, and Jensen chuckles at how needy she’s growing. But then her phone starts to ring, and Jensen looks to see Drew’s name on the screen.
She grunts, frustrated, and instantly presses reject. Jensen returns to what he was doing, and Y/N starts moaning again, but Drew calls once more, and she only gets more frustrated, standing up, which pushes Jensen away slightly.
“Sorry,” she sighs, once again rejecting the call.
The moment is well and truly gone now, and they both know it. She turns around to face him and looks up at him apologetically.
“Hey, it’s okay,” he reassures her, reaching up to stroke his fingers down the side of her face. “Probably not a good idea, anyway,” he relents. “We can finish this later.” He flashes her a wink and then leans forward to kiss her lips softly. “Block his number,” Jensen jokes, making her laugh slightly.
One Week Later
“Nervous?” Jensen asks, placing a large scotch down in front of Jared.
He sits on the chair next to him, looking around the fancy hotel bar a little.
“Just a bit,” Jared admits, nodding his head. “The last time either of us did this, it didn’t end well,” he reminds him.
Jensen nods his understanding, taking a sip of his own scotch.
“Well, the last time wasn’t the right time,” Jensen argues. “This place is nice, much nicer than where we got married.”
Jared also looks around and nods his head. “Yeah, it’s great,” he agrees.
The conversation seems a little forced and stilted for a second, which makes Jensen uncomfortable, because it’s never been like that with Jared before. But he supposes there are two very big elephants in the room right now, suffocating them. Jared however, only knows about the one.
“I’m happy for you, dude,” Jensen tells him, staring the lesser of the two evils straight in the eye.
“You are?” Jared almost chokes, clearly surprised.
“C’mon, man,” Jensen laughs softly, shrugging. “It’s been eight years, you two are happy, anyone can see that. I wouldn’t be a good friend if I wasn’t happy for the two of you.”
Jared nods softly, forcing a slight smile, and then he drinks more. “That means a lot, Jen,” he confesses, choking up a little.
“C’mon dude, suck it up, save it for tomorrow,” Jensen laughs, slapping Jared’s arm in a sort of manly affectionate way.
He takes another sip of his drink, glad that they got that out of the way. He really is happy for them. Clarissa was never the one for him, and it should’ve always been obvious, but now Jensen often wonders if everything worked out this way for a reason; so that he and Y/N could end up together. It’s unconventional, and it’s probably not something he should be proud of, but the bottom line is Y/N is the one for him, he’s absolutely certain of it. He’d be a hypocrite to get jealous or disapprove of Jared and Clarissa’s relationship. How could he ever expect Jared to accept how he feels for Y/N if he can’t even handle Jared’s far more conventional relationship?
“You and Clarissa are some of the best people I know. You deserve this… you deserve each other. I know you’ll never hurt her, I know she’s safe and happy with you. That’s all I want… for both of you,” Jensen adds, more sincerely.
It doesn’t help Jared’s tears as he tries to keep them in, silently reaching over and gripping Jensen’s shoulder in appreciation. Jensen gets the message loud and clear, not needing Jared to say anything else.
It’s quiet between them for a moment, and then Jared clears his throat.
“So, how’s your love life?” he asks. Jensen nearly chokes on his drink. “That bad, huh?” he laughs.
Jensen finally swallows and then plays with his glass. “There might be someone,” he replies carefully. “Well, no… there is someone.” Clearly the scotch is making him feel brave, because he shouldn’t be saying any of this.
“There is?” Jared asks, curiously. “What’s she like? She is a she right?” he checks.
“Yeah, dude,” Jensen laughs slightly. “She’s incredible,” he answers honestly. “And I think she’s the one.”
Jared instantly beams, which makes Jensen’s cheeks heat up.
“Jay, that’s amazing, I’m so happy for you. Why am I only just hearing about her?”
“It’s complicated,” Jensen explains awkwardly. “There are… complications,” he struggles, not knowing how else he can say it without just coming clean.
“Well, whatever they are, I’m sure you’ll work through them, if the relationship is worth it.”
“It is,” Jensen nods, smiling slightly. “I’m happy and she’s happy.”
“Then I’m happy, dude,” Jared insists, grabbing the back of Jensen’s neck. “Look at us, two failed marriages and finally finding happiness again. We did it, Stack, and we did it side by side.”
“Yeah, I think we did,” Jensen nods, hoping Jared still thinks the same thing when it’s finally time to come clean.
Jensen straightens his bow tie, checking himself over in the mirror. While he truly is happy for Jared and Clarissa, there are still a few nerves in the base of his stomach about the day ahead. No matter how okay with it he is, he assumes that it’ll always be a little difficult watching your ex wife marry your best friend. Jensen can’t help but think back to their wedding day, how he’d thought it was for forever. He remembers the necklace he put around her neck that she didn’t take off until the divorce. He thinks about Jared and Caitlyn sitting in the front row, Y/N between them. He thinks about May and Frank welcoming him to the family and immediately discussing grandchildren. He laughs slightly at that memory, shaking his head. Some things haven’t changed.
His smile drops slightly as he remembers Y/N stressing about the alibi she was going to have to give them as to why Drew wouldn’t be here, because she’s too afraid to tell them that she called off their engagement just yet. This family might be the most dysfunctional family he’s ever met, but he’s part of it. He could’ve gotten out, and he’d wanted that for a long time. But he’d take a thousand more dysfunctions if it means he gets to stay with Y/N.
There’s a knock at his hotel door, and he assumes it’s Jared, probably flapping about his bowtie or something about his speech, and Jensen reaches into his inner jacket pocket for his flask, ready to offer the poor guy a quick swig. But as he opens the door he’s faced with Y/N, staring at him wide eyed. He quickly steps to one side to let her in before anyone notices her, and once the door is closed again he’s able to take in just how beautiful she looks. Her dress is floor length, a deep navy colour, and her hair has been done up and her makeup is flawless.
“Fuck, baby girl you look stunning,” he finds himself saying, breathing out deeply.
“Thanks,” she replies quickly, glancing down at her own body before looking back at him. “I think we have a problem,” she adds, the fear back in her eyes.
“What? Why?” he presses, starting to panic just as much as her.
“Drew’s here.”
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