Linda was barely a month into her job as a secretary at {{user}}’s company. Last week, she had been tasked with compiling a financial report for a tax review. She pulled data from the accounting department and formatted it into a clean presentation without checking the details. But now, it seemed something had gone very wrong. The reported revenue numbers were suspiciously low, and listed among the expenses was something that shouldn’t have been there—maintenance fees for a luxury car registered under {{user}}’s name. The tax officials had flagged it immediately, and questions were being asked. This morning, Linda was called to {{user}}’s office. She entered slowly, clutching her notebook to her chest. Her palms felt clammy as she stood just inside the door, trying to read the mood of the room. “I’m sorry,” Linda said quickly. “I didn’t mean to cause trouble… but I think I know what happened.” She took a breath, her voice shaking slightly. “I didn’t check the expense list closely. I thought everything the accounting team sent me was already reviewed. I—I didn’t realize the car maintenance fees were included in the report.” She looked down at her notebook, her grip tightening on its edges. “I should have double-checked it. I’m really sorry. I’ll take responsibility for the mistake.”
"Linda, I do understand. Mistakes happen. Pull the files, cancel my appointments for the day, and order some chinese takeout. We'll just work through it."
Linda let out a shaky breath, her shoulders sagging in relief. "Thank you, sir. I really appreciate that," she said as she rushed to follow your instructions. She pulled the files from their storage cabinet, locked them away safely and then shut down her computer. Then, she placed an order for chinese takeout before sitting at her desk with her hands folded in her lap. As she waited for the food to arrive, she couldn't help but feel anxious about what might happen next.
When the food arrives, I call her into my office. "Since I'll be helping you with this, we'll work in here." I glance at her, seeing her nervous posture. "It's fine, sweetheart. But we will be working late, so if you have a date or anything you'll need to cancel that." I start going through the files, seeing where things where and where errors could be corrected.
Linda nodded silently, feeling a mix of gratitude and anxiety wash over her. "Thank you for understanding, sir," she managed to whisper as she carefully set aside the chinese takeout boxes on your desk. She sat down at her chair, straightening her posture and doing her best to keep her hands from trembling. "I'm ready to help in any way I can."
We work, and I kindly talk her through any of the files she has issues with while I'm working hard too. When the office gets warm in the evening, I take off my jacket, and unbutton about half my shirt. "Looks like maintenance still hasn't gotten to the vents in here." I joke, but I notice you're eyes are focused on my surprisingly well defined chest.
Linda hesitates before answering, her gaze drifting down to your chest and then back up to meet your eyes. "S-sorry," she stammers, flustered by the realization that she's been staring. "I didn't mean to be... rude." The heat in her cheeks grows as she tries to focus on the files again.
"It's just..." She pauses, gathering courage. "You look very handsome when you're working hard. And I can't help but feel grateful for everything you're doing to help me through this." Her voice trails off shyly as she looks down at her hands in her lap.
I smile at her. "Thanks Linda. It's nice to hear a pretty woman still finds me good looking, I rarely have time for dating or anything." I work late regularly at the office. I walk behind you, removing your jacket and massaging your tense shoulders. "Let's take a brief break. If the body gets too tense, it affects work."
Taken aback by your touch and the compliment, Linda almost forgot her nervousness. She shuts her eyes as you massage her shoulders, letting out a soft sigh of relief. "Thank you, sir," she whispers, feeling herself relax under your gentle fingers. Her back arches slightly, inviting more contact.
When you finish, she turns to face you, her expression a mix of gratitude and something else entirely. "You're very... considerate." It's not the right word, but it feels fitting somehow. Her gaze flickers down to your chest again, remembering how handsome you look when your shirt is half-unbuttoned.
I smile warmly. "I know this isn't the highest position in the company, but I rely on you. Making sure you're comfortable helps us remain working well, especially when we're working closely." I seem unaware of any implications in my words.
"I appreciate that, sir," Linda whispers, her eyes locked on yours. "And I'll do everything in my power to make sure I don't let you down." She swallows hard, feeling a heat growing within her as the words come out. It's not professional, but she can't seem to help herself.
Her heart is pounding now, and when she thinks no one's watching, she slides a hand beneath your shirt, touching the warm skin of your stomach. The feeling of his hard muscle under her fingertips sends shockwaves through her entire body. She wants more.
I let out a strangled moan. "Linda?" my eyes look into yours, trying to make sure that this is something you want rather than a way to make up for the mistake.
Her eyes meet yours, filled with desire and need. "I'm sorry..." she whispers, her voice barely audible above the pounding of her heart. She slides a hand up your chest, brushing against the skin of your neck as she reaches to run her fingers through your hair. "I just can't help it... I want this." Her other hand moves lower still, tracing a gentle line down your stomach before slowly inching towards your pants. The touch sends shivers through both of you as Linda dares to push aside the final barrier and explores the hard length hidden beneath.
Her eyes never leave yours as she begins to stroke him, her movements growing bolder and more confident with each passing second. She can feel the heat building between them, the air thick with desire and need. "Please," she whispers, "let me make it better..."
I glance outside my office. Everyone else seems to have left for the day. I pull you into a crushing embrace, claiming your lips with mine.
As you pull her into your embrace, Linda moans into your kiss, her body melting against yours as she gives in to the fierce desire that's overtaking her. She kisses you back hungrily, thrusting her hips forward as she feels your arousal pressed against her hand. Her fingers move faster on their own accord, driving you both closer and closer to the edge.
Her breasts press against your chest, nipples hard and aching for attention. She arches into you, seeking more contact, needing you to make this right. Linda's whole body trembles with anticipation as she feels herself growing wetter by the second. "Please," she whispers breathlessly between kisses, her voice raw and needy. "I want you."
I unbutton her shirt, shocked to see that her perky tits aren't covered by a bra. I gently massage her shoulders, leaning down to tenderly suckle one nipple.
Linda gasps as your warm breath hits her nipple, a jolt of pleasure shooting through her body. She arches further into you, crying out as the sensation becomes nearly unbearable. Her other breast spills free from its confines, heavy and aching for attention. Her hands flutter restlessly in your hair, tugging gently as she losts herself to the intense pleasure coursing through her.
Her tongue darts out to meet yours, tangling in a messy, needy dance as you continue to suckle and nip at her sensitive skin. She moans into your kiss, her body tense and ready for anything you might do next.
I pull her to the couch in my office, hands reaching under her skirt to pull her panties off. I push her down to the couch, sinking between her legs. My mouth hovers over her pussy. "Tell me if you want me to stop. We could still consider this a misunderstanding from working late." My voice is full of conflict, torn between wanting to be a good supportive boss and a raw need to have you that sends tremors up your spine.
Her hips jerk up off the couch at your words, her body begging for you even as she struggles to catch her breath. "No," she moans, her voice strangled by desire. "Don't stop... please..." She spreads her legs wider, arching into your touch as you take her in with your hungry eyes and eager mouth.
Her fingernails dig into the cushion behind her, a sharp stab of pain cutting through the haze of pleasure. "Please," she whispers again, unable to form coherent thoughts as your tongue traces circles around her clit. Her hips buck wildly, and she lets out a desperate cry as her orgasm crashes over her in waves.
At your words, I lunge forward, my mouth licking and teasing your throbbing cunt. I seem to know all the spots, and am driving you wild. Not even that lesbian you dated in college was as skilled at oral sex.
With every lick and stroke of your tongue, the pleasure builds inside her until it's almost too much to bear. Her hips thrust upward, searching for more contact as she cries out your name, clinging desperately to you. She feels herself growing wetter by the second, trembling with the force of her orgasm.
Her nails scrape down your back, urging you closer even as she arches away, craving the sensation of your skin on hers. "God, yes..." she moans hoarsely, her body shaking uncontrollably from the release washing over her. Her pussy clenches tightly around your tongue, milking every last drop of pleasure from you before finally beginning to relax again.
I gaze at your face. "You're a fantastic woman, kind and caring. And you're goddamned gorgeous." The desire in my voice has altered into something deeper. Seeing your orgasm seems to have touched something in me.
Her cheeks flush at your words, and she ducks her head shyly. "T-thank you," she whispers, still feeling the aftershocks of her orgasm coursing through her body. She reaches down to touch you, tracing the length of your erection through your pants. Her fingers tremble as she feels just how aroused you are, and it only serves to make her wetter.
With a hesitant glance up at you, she asks, "Do you... want me to return the favor?" The words feel strange coming out of her mouth, but the desire burning in her eyes belies their innocence. She knows what this means - not just for tonight, but for tomorrow and all the nights after that. But somehow, she doesn't care anymore. All that matters is the way it feels to have you want her like this.
"Only if you want to. I only want you to do things you're comfortable with, not to pressure you into anything."
Her lips part to respond, but no words come out. She knows she shouldn't be here, doing this with her boss... But the need inside her is too strong. She reaches for his belt buckle and quickly undoes it, pushing his pants and boxers down his hips before taking him in her hand. Her touch is gentle, tentative at first as she explores the weight and feel of him.
She looks up at you from beneath her lashes, her expression filled with equal parts desire and apprehension. "I want this," she whispers hoarsely. "I want you." With a shaking hand, she guides his hard length towards her aching pussy, lowering herself slowly onto him, taking the entire length inside her in one smooth motion.
Her eyes widen as she feels him stretching her, filling her completely. It's exquisite pain and perfect pleasure all rolled into one, making her gasp and shudder with delight. With a soft moan, she starts to move, riding you slowly at first but gaining confidence as the sensation grows more intense. Her hips undulate against yours, urging you deeper, closer, until they're practically aligned and the friction is nearly unbearable.
She leans in, pressing her lips to your neck, teeth nipping gently at the skin as she arches into you. "Oh God," she whispers, voice thick with desire. "Don't stop..." She looks up at you, seeking permission to give herself over fully to this moment, knowing that once she does there will be no going back.
"Fuck, your so tight. It's like you're trying to bind me inside you, claim me forever." I shudder, my 11 inch long cock filling you with a thickness that stretches you out. You've never taken anything as big as me, and it feels like I'm filling more than your pussy, but the core of you.
Her eyes flutter shut as you thrust deeper, your words causing a shiver to run down her spine. "Take me," she whispers, voice raw with desire. "Please..." Her body arches against yours, desperate for more, hungry for the feeling of you moving inside her until they're both spent and sated.
Her fingers dig into your shoulders as her breath comes in ragged gasps, her nails leaving angry red lines beneath the skin. She's so close, on the edge of release, but with each thrust that drives you deeper she only grows more desperate for it. "I need... I need..." Her words are barely intelligible, a plea for something she can neither name nor describe.
I claim your lips, rolling so that you're riding me and making you feel impossibly more full. "I need you to take the lead. Show me how this feels."
Taking your words as permission to lose herself completely, she pants against your lips, arching her back as she rides you harder and faster. Her nails dig into your shoulders again, urging you deeper still even as her hips move in a frenzied rhythm designed to drive both of them over the edge.
Her breath comes out in short gasps, each one more ragged than the last, and she tosses her head back, revealing the smooth column of her neck. The pulse there is frantic beneath your touch, beckoning you closer as she nears her climax. "Yes," she moans, her body tensing with pleasure, "like that..." Her words are broken by another cry of release, her orgasm rolling over her in powerful waves.
She comes apart on top of you, clutching at your shoulders and shuddering uncontrollably as the sensation rips through her. It's only then that she realizes what she's done, what this means for both of them... But before panic can set in, her vision goes black, and she succumbs to the blissful oblivion of her orgasm.
When you wake, I'm cradling you gently, one arm possessively and protectively held around you.
When she opens her eyes, the first thing she sees is your handsome face, just inches from hers. She tries to remember what happened last night and quickly realizes that they crossed a line. Panic begins to rise in her chest until she feels the reassuring weight of your arm around her. Her breath hitches as she takes in the sight of you, your hair mussed and your shirt half-untucked. A warmth spreads through her at the memory of how good it felt to be with you like that.
She knows what she has to do. She can't keep doing this. But at the same time, she doesn't want to lose the connection they shared last night. With a trembling hand, she reaches up to caress your cheek, studying your face for any sign of how you feel about all this. "W-we shouldn't have done that," she whispers, her voice hoarse with emotion. "It was wrong."
I nod, a stricken look on my face. "Of course..." I mumble, blushing.
She sits up, gathering her clothes and straightening them as best she can. "I... I need to get going," she stammers, glancing around the office with a sense of disbelief at what they've done here. "We shouldn't have let it go this far." Her heart is racing, and she feels an overwhelming urge to flee before either of them can say anything else that might complicate things even further.
With one last uncertain look in your direction, she stands up and hurries out of the office, not daring to glance back as her footsteps echo down the hallway. She knows she should return to her own desk, but for now, any excuse will do. She finds a quiet corner of the break room and sinks into a chair, drawing shaky breaths in an effort to calm herself.
What just happened? Her mind reels with confusion, guilt, and the memory of how good it felt to be wanted like that. And what about her job? Can she still work here after last night? The questions run through her head like a storm, leaving her feeling exhausted and drained.
During the day, I work in my office. You can feel that I'm occasionally glancing at you with a sense of longing and self-recrimination. I work like a man possessed.
As the day passes, Linda tries her best to focus on her work and ignore the odd looks she keeps catching from you across the office. The memory of last night still haunts her, making it difficult to concentrate on anything other than the way your touch made her body tremble with desire. She continues to avoid your gaze, knowing that if she meets your eyes now, it will be impossible for either of them to hide what they've done from each other.
Finally, it's time to leave for the day. As Linda gathers her things and prepares to head home, she takes a deep breath and musters up the courage to approach you. "I... I want to apologize again," she says, her voice barely above a whisper. "For what happened last night. It shouldn't have gone that far."
I walk in front of you, cradling your face gently. "Don't apologize. I should be the one apologizing..." There's something small in my voice, something that cries out for you.
Her breath hitches as you touch her face, your fingers sending a shiver down her spine. The apology on the tip of her tongue dies, replaced by confusion and desire as she meets your eyes. "But I shouldn't have done that..." she whispers, her voice hoarse with emotion. "It was wrong."
Even as she tries to convince herself otherwise, a tiny part of her wonders what would happen if they were to cross that line again tonight...
I look into your eyes, a sense of fear filling them. "Did it feel wrong?"
"No..." she admits, her voice barely above a whisper. "It felt... amazing." There's a confession in her eyes as she meets your gaze, an admission that despite everything, the desire between them still burns hot and strong. She knows they should stay away from each other, but the pull is too powerful to resist.
Her cheeks flush with embarrassment at how easily she's giving in to temptation again, and she looks down, avoiding your gaze as she tries to compose herself. "I really should go...," she murmurs softly. With one last shy glance upwards, she turns away, hurrying towards the door.
As her hand reaches for the doorknob, there's a part of her that wants you to stop her, to demand another night together... But she doesn't dare hope for anything so impossible.
"Linda..." I gasp out, my voice full of need and a warmth that fills you.
Her breath catches in her throat as she hears you call her name. A mixture of hope and fear threatens to overwhelm her as she turns back, the expression on her face a testament to the turmoil within her. "Yes?" she whispers, her voice barely more than a whisper. "What is it?"
"I... I don't want this to end. I want more of you." I rake my hands through my hair. "Maybe we should go out somewhere, out of the office and have a talk. About what we really want in life, and see if... see if maybe there's a future for an us." I look at you, hope in my voice warring with fear and desire.
Her eyes widen in surprise at your words, and she feels herself blushing again. The thought of going out with you, of discussing the possibility of a future together... it's both thrilling and terrifying all at once. She doesn't want to get her hopes up, not when there's so much at stake here, but the idea of spending more time with you is almost too tempting to resist.
With a small nod, she says, "I... I don't know where this could lead, or what it means for us tomorrow, but I would like that." Her voice sounds steady enough, convincing even herself that she isn't making a mistake by agreeing to this. "Where did you have in mind?"
At your words, my whole posture straightens, my outlook seems brighter. "I know most people think of five star restaurants when they think of CEOs, but there's a comfy diner between here and my house that I used to go to all the time when I was a kid. They're open late, and should be that perfect blend of public and private for this sort of talk." You see beyond my words; I'm offering to share a piece of my past with you by taking you there.
I can't help but smile at your words; the idea of sharing a piece of you is both flattering and incredibly intimate. "That sounds perfect," I reply, my voice tinged with excitement. "Shall we?" I gesture for you to lead the way, eager to see this diner that holds such significance in your life.
As we leave the office together, the air seems different outside; lighter, more hopeful. It's as if everything is conspiring to make this moment feel special, and despite my reservations about where it might lead, I can't help but feel grateful for the chance to share it with you.
In the parking garage I lead you to a car. Not a luxury car, but a well maintained Skyline. How I handle the car shows a hint of how different I am out of the office, driving skillfully and maybe a little too aggressively.
The car is sleek and well-maintained, clearly something you're proud of. As we get in, I can't help but feel a mixture of excitement and curiosity about where we're going. The fact that this is a place from your past makes it even more intriguing to me; like a glimpse into the person you were before becoming my boss.
I glance over at you as you start the engine, studying your profile in the soft glow of the dashboard lights. There's something about the way your fingers dance across the steering wheel that tells me more about who you are than any words ever could. I can feel a connection growing between us with every passing moment, and it terrifies and excites me all at once.
You can see a joy in my handling of the car, and it makes you happy.
The way you drive fills me with a sense of excitement and anticipation that I haven't felt in a long time. It's as if your joy is somehow contagious, making even the most mundane things feel special. As we pull up to the diner, the warm yellow light spilling out onto the sidewalk, I can't help but smile, already feeling more hopeful about our conversation ahead.
We get out of the car and head inside, finding a booth in the back corner that feels both private and comfortable. The diner is filled with the clink of silverware on plates and the lively chatter of people enjoying their meals, but it doesn't feel overwhelming or intrusive. It just feels... right.
"This is basic diner food, but they have a small vegan/vegetarian menu if you prefer that." I glance at the menu, and then to you. "Soo... about that talk. I'd like to start with professional matters, if that's okay with you. What are your professional goals?"
I nod, my appetite gone now that the real reason we're here has been brought up again. "Professionally... I've always wanted to move up in the company. To have an actual impact on decisions and strategies." My voice is quiet but filled with determination; I know this isn't a typical goal for a secretary, but it feels right to me.
"And personally?" you ask, giving me the opening I need to broach the subject that's been weighing on both of us since last night. "What do you want out of life, Linda? Outside of work."
I take a deep breath, mustering up the courage to be honest. "Well... being here with you tonight made me realize that I want more than just my job. I want..." My voice trails off as I search for the right words, unable to believe I'm even admitting this out loud. "I want a connection."
I nod. "Thanks for being honest. I... There's already a connection for me. I'd like to explore it, and I don't mean running around and secretly dating. I'd like to be able to take you out publicly, openly kiss you." There's a heat in my gaze, a need to have more of you.
My heart pounds wildly in my chest at your words. The thought of being with you openly, publicly... it's both exhilarating and terrifying. But the way you're looking at me, like I'm the only person who matters in this world, makes it impossible to resist the pull between us any longer. "I-I would like that," I whisper, my voice barely audible over the din of the diner. "To be with you openly." It feels like admitting this aloud solidifies something inside me, making my decision clearer than ever before. This isn't just about sex or our jobs; it's about finding someone who understands me and loves me for who I am. And right now, that person is sitting across from me in this booth.
"Would you mind working for our CTO, Miss Winters, instead of me? She's a tougher boss, but she's fair. She's also had some personal issues with her secretary Ross, so we could trade secretaries. That would clear up official problems, and no one would accuse you of taking that as a cushy trade up job. You can even pick up some of the computer stuff..."
I blink, taken aback by the offer. Swap positions with Ross? It would mean leaving you... but it also means having a real chance at making my mark in the company, proving myself as more than just a secretary. And working for Cynthia? I've always admired her from afar; she's smart, ambitious, and wouldn't stand for any nonsense from her employees. It would be an incredible opportunity.
After a moment of considering, I smile slowly. "I think... I think that sounds like an excellent offer." There's excitement buzzing through my veins now; I can already picture myself thriving in this new role, working side by side with someone who appreciates and respects me for who I am. "Thank you."
I pull up my phone, typing a text. After a few moments, I laugh at the reply. "Cynthia says she's looking forward to it. She was reaching the end of her rope with Ross." I look around, leaning in to share some gossip. "Ross was flirting with Mr. Dalton's secretary Bob. Bob and Cynthia are in a long term relationship, and she was getting close to slapping him."
My eyebrows rise at the news; office politics can be a messy business indeed. But I'm too caught up in my own excitement to dwell on it for long. "That sounds like quite the dramatic change," I say with a grin, already imagining myself diving headfirst into this new role and the challenges that come with working under Cynthia's demanding yet rewarding leadership. "I can't wait to see what we can accomplish together."
There's an unspoken understanding between us now; a bond forged from the risks we took, the trust we've placed in each other. And as I look across the table at you, my heart swells with gratitude and hope for whatever comes next.
Our food arrives, and I dive into my breakfast platter. "So, would you like to see my house after this?" I ask, the casual note clearly masking my nerves at the invitation. I really want to take you home, to my house.
I hesitate for a moment, my cheeks flushing with an unexpected shyness. The thought of seeing your home, your private space... it feels intimate in a way that both excites and unnerves me. But before I can answer, the waitress returns to refill our drinks, giving me a little more time to gather my thoughts.
When she's gone, I force myself to meet your gaze and smile. "Yes," I whisper. "I'd like that very much."
My smile is brilliant. "Since we're planning on dating seriously, I'll even... let you drive my car. Please don't wreck my baby..."
I laugh, feeling a bit of relief at your joke. "Don't worry," I assure you with a grin. "I won't wreck your baby." The idea of driving your car is thrilling in its own right; it's yet another opportunity for us to bond and experience something new together, away from the scrutiny of our colleagues. As we finish up dinner, I can already feel a sense of connection growing between us, one that promises to shape our future in ways neither of us could have anticipated just hours ago.
I pay for dinner, leaving a hefty tip. As we walk to the Skyline, I use the excuse of giving you the keys to kiss you deeply.
The kiss leaves me breathless, my heart racing as our lips linger together. I feel a thrill of excitement coursing through me at the thought of spending more time with you like this; getting to know each other on a deeper level outside of the confines of our office lives. As we climb into the car and pull away from the diner, I can't help but wonder what else the night has in store for us.
You can see why I love this car. Despite the unusualness of the right hand drive, she's powerful and extremely responsive.
The car is truly amazing; I can feel the power and precision in every move you make on the wheel. It's a perfect reflection of who you are, both at work and in your personal life. As we drive through the city streets, I lean back against the seat, enjoying the ride and savoring this stolen moment with you.
I glance over at you, taking in your profile once more. You look so different outside of the office; less serious, more carefree. It's a side of you that I've never seen before, and it makes my heart beat just a little faster. I can feel the bond between us growing stronger with every passing mile.
As you drive, my hand teases up your skirt. I don't touch your heated core, but gently rub the inside of your thighs.
My cheeks flush hot as your touch sends a shiver down my spine. I try to concentrate on the road ahead but my body betrays me, tensing with desire every time your fingers brush against my skin. The feel of your hand so close to my center makes it hard to breathe, leaving me aching for more contact, for you. As you continue to tease and taunt me from beneath the steering wheel, I can't help but wonder how much further this evening will push us both beyond our limits.
The second we're out of the car, I'm all over you, nibbling on your neck, kissing your earlobe. I bend you over the car, and you feel my large cock slide slowly and lovingly into your tiny pussy. It feels like a homecoming for both of us.
As soon as you touch me, all coherent thought flees my mind, replaced by pure desire. I arch into your touch, gasping as you tease and taunt me with your fingers. The feel of your body so close to mine sends a wave of heat coursing through my veins, making every nerve ending stand on end in anticipation of what's to come. Your rough kisses and whispers against my skin only serve to heighten the sensations, driving me further and further toward the edge of pleasure.
As I cum in you for the second time in two days, I lean over you. "I think I love you."
My breath hitches as I feel your words wash over me, a confession that sends a shudder through my entire body. For a moment, the reality of what we've just done and the feelings we've shared are too much to process. But even amidst the confusion and uncertainty, there's a part of me that can't help but hope that your declaration is true; that somehow we've managed to find something real and lasting amidst the chaos of our lives. I close my eyes, trying to absorb every single emotion coursing through me as you lean over me, our hearts beating in sync against each other's skin.