Fatal Mistake
by Octavia Love
Jenny Houston is one mishap away from losing her job as personal assistant to Derek Stein, the demanding CEO of a prestigious firm. Her legendary clumsiness and forgetfulness have become office lore. But nothing could prepare her for the disaster that unfolds one late night when, in a haze of exhaustion and distraction, she accidentally sends a series of nude photos meant for her boyfriend... straight to Derek. Mortified, Jenny braces for the worst — resignation letter drafted, boxes mentally packed. But what she doesn’t expect is...
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Chapters: 53
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About the author

Octavia Love
The rumors are true: I write all my love scenes during thunderstorms. Everything else comes from eavesdropping in coffee shops and public transportation. If you've had an interesting conversation in Chicago in the last five years, check my books care...
Digital Disaster
"Houston!" Derek Stein's voice booms through the intercom, making me jump so violently I knock over my coffee. Perfect. Another stain on my already questionable work attire—the third silk blouse this month ruined by my trembling hands.
I've been called clumsy since kindergarten, but that label feels like an understatement. I'm practically a walking disaster zone with an employee badge.
Dabbing at the spreading brown puddle with tissues, I take a deep breath. When Derek uses my last name, it means I've screwed up. Again. When he uses my first name, Jenny, it means I'm doing something right—which happens about as often as solar eclipses.
"Coming, Mr. Stein!" I call back, abandoning the coffee cleanup. The stain can wait; Derek Stein cannot.
I hurry toward the conference room where I know he's waiting, mentally cataloging what I might have messed up this time. The list of possibilities is embarrassingly long.
When I push open the glass door, I find not just Derek but the entire executive team seated around the table. Six pairs of eyes turn to me, but only Derek's steel-gray ones make my stomach twist into knots. His tailored navy suit stretches across his broad shoulders as he leans forward, the silver watch I’ve seen him adjust a dozen times glinting under the harsh lights.
"Ms. Houston," he says, his voice deceptively calm. "Would you care to explain why Eddie Chen just called me asking if I was planning to cancel our partnership meeting?"
My heart plummets. The meeting with Eddie Chen from Apex Solutions—the one Derek specifically asked me to confirm yesterday. The one I was supposed to reschedule after Derek canceled his dinner with Valerie Hurst.
"I—" My voice catches. "I can explain."
Derek's jaw tightens. "Please do."
I can feel everyone watching me, their collective judgment making my cheeks burn. "When you asked me to call Valerie about canceling your dinner, I got caught up in that conversation because she was... upset." That's putting it mildly. Valerie had practically threatened to burn the building down. "And then Janice from Accounting needed those expense reports immediately, and I—"
"Forgot to call Eddie," Derek finishes for me, his voice flat.
"Yes, sir." I stare at my shoes, wishing they would swallow me whole.
Derek dismisses the other executives with a curt nod. As they file out, some offering sympathetic glances, others smirking, I remain rooted to the spot.
When the door closes, Derek stands and walks toward the window, his back to me. The silence stretches until I notice his reflection in the glass—eyes tracing the curve of my hips before snapping back to my face. "Jenny, this is the third major oversight this month."
"I know, and I'm truly sorry. I'll call Eddie right now and—"
He turns, cutting me off with a raised hand. "I already spoke with him. He's rearranged his schedule to meet tomorrow."
"Oh. That's... good." I shift my weight nervously, hyperaware of his gaze lingering on the undone top button of my blouse.
"No, it's not good. It's damage control." He steps closer, stopping near enough that his cedar-and-bergamot cologne wraps around me. "I've been patient because you're excellent at many aspects of this job. Your rapport with clients is outstanding, and your organizational skills are impressive—when you actually apply them."
I nod, hope flickering faintly.
"But I can't have an assistant who forgets critical meetings." His thumb brushes a stray coffee droplet from my wrist, sending an unwelcome shiver up my arm. "This is your final warning, Jenny. One more significant mistake, and I'll have to let you go. Do you understand?"
My throat tightens. "Completely, Mr. Stein."
"Good." He glances at his watch, the movement pulling his shirt taut across his chest. "The Chen meeting is rescheduled for tomorrow at 2 PM. I need you to prepare the quarterly reports and have them on my desk by noon."
"Yes, sir. I won't let you down."
His expression softens fractionally. "I hope not. I'd hate to lose you."
That tiny glimpse of humanity makes this somehow worse. Derek Stein isn't a monster—he's a reasonable boss who's put up with my mistakes longer than most would have.
I retreat to my desk, determination burning through me. No more mistakes. I can't go back to being a barista at The Daily Grind, where customers snapped their fingers at me and left zero tips. I'd rather eat glass than return to that humiliation.
For the rest of the day, I triple-check everything. By the time 6 PM rolls around, my eyes are strained from proofreading and my fingers ache from typing, but the quarterly reports are flawless and sitting in Derek's inbox.
"You look like you've been through a war," my roommate Zoe comments as I trudge through our apartment door.
"Corporate battlefield," I mutter, dropping my bag and collapsing onto our sofa. "I nearly got fired today."
Zoe winces, handing me a glass of wine she apparently anticipated I'd need. "Stein again?"
"Who else?" I take a grateful sip. "I forgot to reschedule an important meeting."
"And let me guess—he gave you the 'one more mistake' speech?"
"Complete with the disappointed look that makes you feel like you've personally betrayed him and his entire ancestral line." I kick off my heels. "I need this job, Zoe. I can't go back to The Daily Grind."
"You won't," she assures me. "You're too good at what you do—when you're not being a walking disaster."
"Thanks for the vote of confidence." I roll my eyes but smile. "I'm going to change and then maybe we can order takeout?"
"Already ahead of you. Thai food will be here in twenty."
In my bedroom, I peel off my coffee-stained blouse and pencil skirt, replacing them with one of Kyle's oversized t-shirts that he left here last weekend. The soft cotton barely skims my thighs, and I catch my reflection in the mirror—the way the fabric drapes over my breasts, the curve of my waist visible when I stretch. Kyle and I have only been dating for about six weeks, but things have been going well. He's in his last year of college, which makes him three years younger than me—a fact Zoe never fails to tease me about.
Speaking of Kyle, I should probably text him. I grab my phone and see I already have several messages from him.
Hey beautiful, how was your day?
Mine was boring. Professor Wilson droned on forever about economic theory
Miss you. Can we video chat tonight?
I smile, typing back: Horrible day. Almost got fired. Would love to see your face though. Give me an hour?
His response is immediate: Absolutely. Sorry about work. I'll cheer you up ;)
That winky face makes me both roll my eyes and smile. Kyle is nothing if not predictable.
After dinner with Zoe and a quick shower, I settle into bed with my laptop. Kyle's face appears on screen, his sandy hair tousled and his grin infectious.
"There's my favorite corporate warrior," he says. "Want to tell me about your day from hell?"
I give him the condensed version, which still takes ten minutes because the day was that awful. He listens attentively, making appropriately sympathetic noises.
"Stein sounds like a hardass," he comments when I finish.
"He's actually fair," I find myself defending Derek. "He's put up with more of my mistakes than most bosses would."
Kyle shrugs. "If you say so. Hey, I've been thinking about you all day." His tone shifts, becoming lower. "Actually, I've been thinking about you in a very specific way."
I raise an eyebrow. "Oh?"
"Yeah." He bites his lip, his gaze dropping to where the neckline of my shirt slips off one shoulder. "I know we said we'd take things slow physically since we can't see each other that often, but... I was wondering if maybe we could try something different tonight?"
My stomach flutters with a mix of anticipation and nervousness. "What did you have in mind?"
"I’d love to see more of you," he says, leaning closer to his camera. "Maybe you could show me what you’re wearing under that shirt? Or better yet… what you’re not wearing?"
I hesitate, my fingers toying with the hem of Kyle’s shirt. "I don’t know..."
"Come on, Jen." His voice drops to a husky murmur. "You’ve got no idea what you do to me. Just a little peek—I’ll be good, I swear."
The heat in his words pools low in my belly. We’ve only slept together twice—both times rushed and fumbling in his dorm room—but the memory of his hands gripping my hips makes my breath hitch.
"Okay," I whisper. "But you have to promise this stays between us."
"Fuck yes," he breathes. "I promise, Jenny."
I take a deep breath and stand up, positioning my laptop so the camera captures my full body. With trembling fingers, I pull Kyle's t-shirt over my head, letting it fall to the floor. The cool air brushes my bare breasts, my nipples hardening under his hungry gaze.
"Christ," Kyle mutters, his hand moving below the frame of his camera. "You’re fucking perfect."
Emboldened, I turn slowly, letting him see the swell of my ass beneath my lace panties. His sharp inhale is audible. "Like what you see?"
"Are you kidding?" He laughs, low and strained. "I’m about two seconds from driving over there."
I sink back onto the bed, letting one hand trail down my stomach. "That’s all you get for tonight," I say, though my own pulse races at the power in his stare.
"Tease," he growls, but he’s grinning. We talk until my eyelids grow heavy, his voice thickening with sleep.
After closing my laptop, I feel restless energy humming under my skin. Standing before my mirror, I examine myself—the flush still coloring my chest, the way my curves catch the lamplight. On impulse, I snap a photo, arching my back to emphasize the dip of my waist, the shadow between my thighs just visible.
Something to help you sleep, I text Kyle, attaching the photo. Remember your promise.
I hit send and collapse into bed, exhausted.
I open my eyes some time later. Groggily, I check the time — 1:17 AM. Why did I randomly wake up at such an hour?
I grab my phone, expecting to see a grateful message from Kyle. Instead, I see that the last message sent from my phone was to Derek Stein. Huh?
Fully awake now, I frantically open the message thread and feel the room spin around me. There it is — my naked photo, sent not to Kyle, but to my boss.
My boss who just today gave me one final chance.
I stare at the screen in horror, my career and dignity simultaneously crumbling before my eyes.
I had sent the image to Derek Stein.