(CEO) Caitlyn x (Assistant) Reader /wlw/age gap/slight angst/
------------------⁺‧₊˚ ཐི⋆♱⋆ཋྀ ˚₊‧⁺-----------------------
Heyyyy, this is my second post today because my last one floppeeeed, ALSO I've decided that I'll make this one series because Caitlyn. Does it need another reason? As always I'm happy for all the feedback ♡
“How many times do I have to tell you that this is extremely pointless?!”
Caitlyn Kiramman, CEO of KRMNN, standing at the head of the boardroom, voice sharp as a blade, slicing through the tense air. The unfortunate recipient of her wrath—a potential sponsor—looks ready to melt into his chair, fidgeting with the papers in his hand as if they hold the answer to saving himself.
You stand beside her, gripping the stack of documents she had handed you earlier, shifting your weight from foot to foot as the argument drags on.
This wasn’t anything new.
Caitlyn was relentless. She had to be. After her mother’s passing, she had taken control of the company without hesitation, stepping into the role that had once been shaped for her but never truly meant to be hers—not like this, not so soon. She was young, too young to bear this much weight on her shoulders alone, yet here she was, carrying it all without so much as a falter.
At least until you came along.
You had started this job for practical reasons. College wasn’t cheap, and being a personal assistant to a powerful CEO came with a paycheck that made the sleepless nights and overwhelming workload worth it. You were good at your job, too—so good that, at this point, the business felt partly yours.
But that wasn’t the only reason you stayed.
Miss Kiramman—Caitlyn, as she insisted (though you still struggled to say it without feeling like you were crossing some invisible line).
The sharpness in her words, the way she carried herself with such confidence, the fire in her eyes when she fought for what she believed in—it was impossible not to notice. Impossible not to admire.
And impossible not to find extremely attractive.
Not that you’d ever admit it out loud.
You were too busy trying not to stare, too busy trying to look professional while she absolutely owned the room, her rough British accent adding an extra edge to her frustration as she shot down the man’s weak proposal.
God, she looked good when she was mad—
Your train of thought derailed instantly as Caitlyn’s palm slammed against the desk, the sound echoing through the room like a gunshot. You flinched, gripping the papers tighter as she pressed two fingers to the bridge of her nose, exhaling sharply through gritted teeth.
A moment of stunned silence followed before the room burst into quiet movement. Chairs scraped against the polished floor, briefcases snapped shut, and people shuffled toward the door, eager to escape the storm before it could worsen.
You turned to follow them out, but before you could take a step, a firm hand caught your shoulder.
The heavy office door shuts behind the last person, leaving only you and Caitlyn in the quiet space. The weight of the argument still lingers in the air, but now, with no one else around, it feels different—more intimate.
Caitlyn exhales slowly, tilting her head back as if looking for answers in the ceiling. “God, I swear I could strangle half of them,” she mutters, rubbing her temples.
You shift on your feet, unsure whether to comfort her or let her be. Before you can decide, she steps closer—too close.
Her fingers reach for the papers you’re still gripping, but instead of taking them, she lets her touch linger against yours. The warmth of her skin against yours sends a shiver up your spine. You should pull away. You don’t.
“Why do you put up with all this?” Her voice is quieter now, low and smooth, the sharpness from before replaced with something almost vulnerable.
You could give her the practical answer—money, school, stability. But that’s not the whole truth, is it?
“I guess… I just don’t like seeing you go through this alone,” you admit, forcing yourself to meet her gaze.
Something flickers across Caitlyn’s face, too fast to catch. She doesn’t speak right away. Instead, she lifts her free hand—hesitant, unsure—before finally resting it against your forearm. A gentle touch, a test, a question.
“Alone is how I’ve always done things,” she murmurs, her thumb brushing absently against your sleeve. “But then you came along, and suddenly it feels different.”
Your breath catches. The space between you is almost nonexistent now, her perfume—subtle, elegant—wrapping around you like a cocoon.
“Different how?” you ask, barely above a whisper.
She lets out a small, almost bitter laugh, shaking her head. “You ask too many questions.”
But there’s no real bite to her words. If anything, she looks at you like you’re the only question she doesn’t have an answer to.
Then, before you can think, before you can talk yourself out of it, your fingers curl around hers. A bold move. A risk.
Caitlyn doesn’t pull away.
Her lips part slightly as her gaze drops—to your hand in hers, then back to your face. You don’t miss the way she sways just the slightest bit forward, as if caught in the same pull that’s been drawing you closer for weeks now.
The world outside the office doesn’t exist anymore. It’s just her, just you, just the unspoken words humming between you.
For a second, just one, you wonder if she’s going to kiss you.
But instead, she takes a breath, steadying herself, and squeezes your hand. “Take the night off,” she finally says, voice quieter, almost reluctant.
You should listen. You should step away.
Not until she looks at you again—lingering, longing. And then you know.
This isn’t over. Not by a long shot.
Your fingers are still entwined, neither of you making a move to pull away. Caitlyn’s grip is firm yet hesitant, like she’s fighting something within herself.
“I should go,” you murmur, but neither of you step back.
Caitlyn exhales sharply, almost like a quiet laugh. “You always say that,” she mutters. “And yet, you never do.”
There have been too many nights like this—too many times you’ve lingered after hours, sitting on her office couch while she worked, sharing quiet conversations that were supposed to be professional but never quite felt that way. Too many stolen glances, too many moments that crossed the line between boss and assistant, yet neither of you ever acknowledged it out loud.
Maybe it was the age gap.
She was older than you, more experienced, hardened by the world in ways you weren’t yet. And you—fresh-faced, still juggling school with this job, still figuring yourself out—shouldn’t be standing here like this, heart racing in the silence of her office.
Caitlyn’s fingers twitch against yours before she finally—reluctantly—pulls her hand away. She clears her throat, straightening her posture, forcing back whatever had just flickered between you.
“This… isn’t a good idea,” she says, more to herself than to you.
Her eyes snap to yours. “You know why.”
Because she was older. Because you worked for her. Because there was too much at stake.
But the way she looks at you now—like she’s memorizing your face, like she’s weighing the risk in real time—tells you all those reasons aren’t enough to stop her from thinking about it.
“They’ll talk,” she continues, as if convincing herself. “If they haven’t already.”
You let out a small laugh, shaking your head. “Let them.”
Her jaw clenches. “You don’t understand.”
“Then make me understand,” you counter, stepping closer again, daring her to be honest with you. “Because I don’t think this is just in my head. And if it is, tell me right now, and I’ll walk out that door.”
The challenge hangs between you.
Caitlyn looks at you—really looks at you. Her throat bobs as she swallows, her fingers flexing at her sides like she wants to reach for you again but won’t let herself.
Finally, she sighs, running a hand through her dark hair before meeting your gaze once more.
“You’re young,” she murmurs. “You have your whole life ahead of you.”
Caitlyn exhales, shaking her head with a small smirk, but there’s no amusement in it. “I’ve already had my life planned out for me. This company, this world—it’s all I know. And the last thing I should do is pull you into it.”
You step forward again, close enough now that your shoes nearly brush against hers. “Maybe I want to be pulled in.”
Her breath hitches—so soft you almost don’t hear it.
For a moment, you think she’s going to close the distance between you, that she’s finally going to give in to whatever this is.
But instead, she takes a slow, steady step back.
“This isn’t a conversation we should be having right now,” she says, voice carefully controlled.
You know what she means. You know she’s trying to protect both of you.
But it doesn’t change the fact that, even as she turns away, she hesitates—just for a second—before murmuring,
And somehow, that feels more like a confession than a dismissal.
Because she doesn’t say, this can’t happen. She only says, not right now.
Your feet stay planted, even as Caitlyn turns away. She expects you to leave, to listen like you always do, to pretend like nothing ever happened.
Your heart pounds as you take a slow step forward, your voice soft but pointed.
You see it in the way her shoulders tense, the way her fingers twitch as if resisting the urge to clench into fists. Slowly, she turns back to you, but she doesn't meet your eyes right away. Instead, she stares at the desk, the floor-anywhere but at you.
"There is no 'last week," she says, but her voice betrays her. It's not firm, not confident. It's a defense mechanism.
You take another step. "So I imagined it?"
You don't let up. “Because I don't think I did. I don't think I imagined the way you kissed me in your car after that gala. The way you pulled me in, the way you—"
Finally, her eyes meet yours.
And damn it, they're burning.
Not with anger. Not with annoyance. With something else. Something she's trying so hard to bury, to ignore, to push away like it doesn't keep her up at night the same way it does for you.
But you're done pretending.
You take another step-close enough that you can see the way her chest rises and falls, how her breath is just the slightest bit uneven.
"Tell me you regret it," you challenge, voice quieter now, almost a whisper. "Tell me you didn't want it."
Her lips part, but no words come out.
You tilt your head, watching her carefully. "You can't, can you?"
"Because I did want it," you continue, your voice soft but insistent. "And I still do."
The last thread of restraint she's been clinging to snaps, and before you can process it, Caitlyn moves-closing the distance between you in one sharp, desperate step.
Her hands find your waist first, hesitant for only a fraction of a second before gripping you tighter, pulling you flush against her. You barely have time to gasp before her lips crash onto yours.
Like she's been starving for this, like she's spent every waking moment since last week pretending she didn't want to do this again.
You melt into it instantly, hands sliding up her arms, fingers clutching at her suit jacket as her lips move against yours-firm, demanding, like she's making up for lost time.
She backs you up against her desk, her hips pressing lightly against yours as her hands trace the curve of your waist, her touch just shy of desperate. When she finally breaks the kiss, it's only to rest her forehead against yours, her breath warm and ragged against your lips.
"This is reckless," she murmurs, but she doesn't let go.
You smile, tilting your head slightly, lips brushing against hers as you whisper,
Caitlyn exhales sharply, and then she's kissing you again-deeper this time, like she's accepted defeat. Like she's done pretending she doesn't want this.
