BossX shy assistant
1646 Words
Sage.
I pinch the bridge of my nose, willing away the headache building behind my eyes. Third time this week she's messed up my coffee.
The coffee on my desk looks like someone melted a bag of sugar into it.
“Hailey,” I mutter, reaching for the phone.
A moment later, she walks in—skittish as usual, like I’ve got a gun under the desk. Dressed like someone’s lost grandmother again. An oversized skirt hanging off her hips, a cardigan that looks like it belonged to a scarecrow, and those ridiculous, massive glasses sliding down her nose. To top it all off, a beanie pulled low like she’s hiding from the damn IRS.
I pay her very well. There’s no excuse for… whatever this is.
“Do you have a vendetta against me, Hailey?” I ask, holding up the cup like it’s exhibit A in court.
She blinks. “What?”
“My coffee. It tastes like you drowned it in sugar and hate.”
Her mouth parts, those wide brown eyes doing that panicked goldfish thing. “I… forgot.”
“You forgot,” I repeat flatly. “To not poison me with liquid diabetes.”
She shifts nervously, tugging her cardigan tighter like it’s going to shield her from my irritation. “I’ll get rid of it.”
“Please do.” I wave it off, watching as she hurries to snatch the cup and bolt for the door.
As she twists away, I catch it—a glimpse beneath the grandma disguise. Hips. A surprisingly full, round a$s under that tent of a skirt.
I lean back in my chair, eyes narrowing slightly as the door clicks shut. There’s a woman hiding under all that fabric. Who knew.
My gaze drops to the itinerary on my desk—the business trip to Miami. I tap my pen against it.
Picking up the phone, I call her back in.
She reappears like a nervous rabbit, already looking like she regrets existing.
“Trip to Miami,” I say. “We leave at seven.”
She stares at me. “We?”
“You’re my assistant. You’re coming.”
Her face twists, that startled deer in headlights expression blooming. “I… I can’t. I didn’t plan to— I booked a one-room suite—”
I shrug. “You could just quit if you’d like.”
“No,” she finally says, chin lifting just enough to make me want to smirk. “I’ll be ready by six.”
“Good girl.” The words slip out before I can stop them, low and amused.
Her cheeks flush scarlet as she turns and flees again.
I lean back, a slow grin curling at the edge of my mouth.
~~~~~
The suite is… nice. Not surprising.
What is surprising is Hailey’s face as she steps inside, eyes wide like we just walked into a damn palace.
She does a slow circle, mouth parted, gawking at the marble floors, the floor-to-ceiling windows overlooking Miami’s skyline, the king-size bed.
I fold my arms, watching her.
“It’s a hotel room,” I say dryly.
She blinks, flushed with embarrassment, caught ogling like a small-town tourist. “It’s… nice,” she mumbles, tugging at her cardigan sleeves.
I pull my phone out as it buzzes.
“I’ve got to take this,” I tell her, already turning toward the adjoining room. “Don’t get lost.”
She makes some noncommittal sound as I disappear to handle the call. It drags on—contract negotiations, board members whining, the usual.
By the time I hang up, the suite is quiet.
“Hailey?” I call, stepping back into the main room.
Nothing.
The bathroom door’s cracked open, warm mist curling out. I frown, curiosity pulling me closer.
The moment I step inside, I freeze.
Behind the glass shower door is a silhouette—a woman, her back to me, delicate curves outlined in the fogged-up glass. Her hair’s down, clinging to her damp shoulders as she hums softly to herself, completely unaware.
And her body…
Not a damn grandma in sight.
Full hips, a narrow waist, long legs, perfect ass. All those ugly cardigans and oversized skirts? Just camouflage for this?
I can feel the heat crawl up my spine, settling low as my c0ck hardens beneath my jeans. My eyes locked to the glass like a starving man staring at dessert.
I was right. Those clothes have been hiding a bombshell this whole time.
I drag a hand down my face, cursing under my breath.
~~~
The online meeting is still going, but I couldn’t tell you a damn thing about what anyone’s saying.
All I see is the image burned into my head—Hailey, naked, glistening with steam curling around those curves in the shower.
I rub the back of my neck. The tension’s been building since we landed, and that little shower surprise pushed me over the edge.
Once the meeting’s done, I toss my laptop aside and head for the bathroom. A cold shower? Useless at this point. I need release, plain and simple.
When I’m done, towel slung low on my hips, I step back into the room—only to nearly collide with Hailey.
She gasps, eyes wide as they snap down to my chest, then lower—to the towel—and back up again.
Her cheeks flush a furious red. “M-Mr. Jacobs, I— I’m sorry. I… uhmm… shouldn’t look…” she stammers, spinning on her heel so fast it’s almost impressive.
I smirk, keeping my expression flat as I watch her retreat. Back in full disguise now—oversized cardigan, shapeless skirt, beanie pulled low, those ridiculous glasses sliding down her nose like we didn’t both know what’s hiding underneath.
Shame, really. Those curves deserve better than cotton and wool.
I change quickly, tugging on a shirt and sweatpants, then step out into the living room where she’s perched awkwardly by the couch.
“You booked one room,” I remind her, raising a brow. “Which means we’re sharing the bed.”
Her eyes widen like I suggested murder. “I’ll… like sleep on the couch.”
“It’s a king-size bed, Hailey.” I gesture toward it. “I’m not going to jump you.”
She hesitates, still hugging that cardigan like a shield. Eventually, with visible reluctance, she creeps toward the bed, climbing in fully clothed with glasses still on.
I shake my head, amused, settling on my side of the bed.
Sleep comes easy… for a while.
When I wake, it’s to the distinct sensation of someone hovering over me.
I crack one eye open—and nearly laugh.
Hailey’s leaning over me, her face inches from mine, glasses gone, beanie abandoned, her curious brown eyes locked onto me like I’m some wild animal in a zoo exhibit.
For a second, she doesn’t notice I’m awake.
Then I shift slightly.
She jolts, scrambling back to her side like a kid caught sneaking cookies.
“S-sorry! I… I was just curious! There were—uh mosquitoes! I thought— maybe— didn't want it to bite you sir.” she babbles, voice cracking.
I chuckle, unable to help myself. “Mosquitoes?”
She groans, burying her face in her pillow. “Yes, kinda. I dunno.”
I grin, stretching an arm behind my head. “Relax, Hailey. Next time you want a closer look… just ask.”
The mortified whimper she lets out is the best thing I’ve heard all night.
The bed dips as she curls up on her side, facing away from me, probably still mortified by the whole "mosquito" situation. I stretch beneath the covers, but something feels… off.
I glance down, tugging the blanket higher—and freeze.
The oversized cardigan? Gone. That ridiculous skirt? Nowhere in sight.
Bare shoulders, smooth and exposed skin like a lot of it.
I pull the covers back just enough to confirm what I already suspect—and yeah, there it is. She's na.ked.
Well, well…
“Hailey,” I say, my voice low with amusement, “you planning to tell me you’re naked under here…?”
She stiffens, shoulders hunching like she can vanish into the mattress. “I— sleep bare,” she mutters, eyes fixed on the wall.
I chuckle, pushing onto one elbow to get a better look at her. “Shy now, are we? That’s why your cheeks are the color of a stop sign?”
She tugs the blanket up to her chin. “It’s just… embarrassing,” she mumbles. “I’m…”
I lean in before she can finish whatever lie she’s about to sell me.
“Shy,” I echo, lips brushing close to her ear. “Sure. That’s what this is.”
I shift over her, the mattress dipping as I cage her in, one arm planted beside her head, her wide eyes finally meeting mine.
The covers slip down, exposing more of that warm, flushed skin. She’s damn beautiful under those grandma clothes.
She swallows hard, blinking up at me.
My hand slides along her cheek, thumb brushing her bottom lip. “You’ve been driving me insane all week,” I murmur. “Those ugly clothes, the attitude, the mouth… and this is what you’ve been hiding under all that?”
Her lips part, but no sound comes out.
I lean down, closing the distance.
The kiss is soft at first—her lips warm, surprised, but she melts fast, fingers curling in the sheets, breath hitching as I deepen it.
By the time I pull back, her eyes are h
azy, lips kiss-swollen and cheeks blazing.
“Still shy?” I tease, hovering above her.
She groans, covering her face with her hands.
I laugh quietly, dropping onto my back beside her.
- Writer
