"Make Me." My Bratty Employee Finally Takes Things Too Far [M40/F20][Brat Taming][Office Setting][Dom/Sub][Under-desk Blowjob][Performance Review][Creampie]

I just want to start by stating for the record that I did not hire her. Cassidy was a fixture of the office before I arrived during the restructure that brought me over from the Denver branch.

On my first day, I was introducing myself to the team when I noticed one of my new employees looking at me a little strangely. Specifically, she was staring at my left hand, where my wedding band gleamed in the fluorescent lights of the conference room. As I continued talking, I watched her out of the corner of my eye. She licked her lips, and I couldn't help but notice that her hands had suddenly disappeared between her legs.

I forced myself to look away, quickly wrapping up my introduction. As everyone else filed out of the room, she stayed, pretending to be fiddling with the buckle on her shoe.

"Hey boss?" Her voice was warm, like she was greeting an old friend. At the time I thought it was just her being friendly. Now I know better.

"Yes?"

"How long have you been married?"

"Oh," I paused, a little taken aback by the personal nature of the question. "Almost nineteen years now."

"Wow," she breathed, standing up now so that her full figure was on display– a figure that was only enhanced by the tight blouse she wore, complete with a pencil skirt that framed her ass so well that I could see the curve of it even looking at her from the front. A black choker around her throat completed the ensemble. Her green eyes met mine boldly.

"That's a long time. Almost as long as I've been alive."

She grinned impishly at me, winking before turning on her heel and moving toward the door, leaving me with my mouth agape and feeling like I'd just entered a game where I didn't know any of the rules.

I'd watched through the conference room windows as she returned to her desk, trying to ignore the way my body reacted to the motion her hips made as she walked, trying to figure out why my brain had just gone into overdrive.

That's how I met Cassidy.

___

For the next six months, things were almost normal. There was the usual settling in, learning the strengths and weaknesses of the team I was leading, that sort of thing. Everyone did their best to make it work.

Except Cassidy. She was testing me. Her official title at our company was "executive assistant", which basically meant that she was the one who kept the day-to-day of the office running. She made sure there was coffee in the morning, made sure the printers always had ink and paper, made sure that my appointments always made it onto my calendar.

She was good at it too– in the six months since I started, I didn't have a single complaint about something coming up missing or running out of supplies. The office hummed along like a well-oiled machine.

Except for when she did things for me. She'd intentionally not quite finish a task, and when I asked her to please do so, her answer was invariably the same:

"Make me."

The first time she said it I'd looked up in shock to see her sticking her tongue out at me. She'd winked again and scooted the folders I'd asked for over to me.

"Just teasing you boss."

She'd sauntered out of my office, her hips swaying with each step as I tried to figure out what was going on.

The "teasing" continued, never rising to the level of outright insubordination, but always simmering in the background. Every morning my coffee would be placed just outside of reach, forcing me to either stand up to grab it (with Cassidy always standing right next to the cup so my hand would brush her hip as I did), or to ask her to hand it to me herself, which would result in her using her new favorite phrase on me.

For months this continued. It seemed like no matter what I asked, I always got the same response:

"Cassidy, could you please order food for the meeting this afternoon?"

"Make me."

"Cassidy, can you call corporate HQ and see what the plan is for the retreat?"

"Make me."

"Cassidy, would you run over to the bank and deposit these money orders?"

"Make me!"

More often than not her teasing was accompanied by her tongue sticking out at me, or sometimes by a long glance that lingered until one of us looked away– usually me.

It was around this time that I'd also started to really focus on my health, working out more and eating better, and Cassidy wasn't shy about letting me know that she at least noticed the changes in my body.

"Looking good today boss! Those biceps are getting out of control!"

"Cassidy, you can't… you should stop saying things like that."

"Hmph! Make me!"

I was the only one subjected to this bratty kind of teasing– everyone else loved Cassidy, and as I've said before, she was an invaluable part of our office, handling all sorts of problems both large and small with grace and care.

It's also true that part of me enjoyed the attention too, even if it could be infuriating at times. After nineteen years of marriage, things between my wife and I had gotten stale, and both of us were clinging on to the marriage more as a polite fiction than out of any real romance.

So when Cassidy started wearing tops that showed off more of her cleavage and skirts that went from business professional to something you might see at an office-themed stripclub, who was I to complain? She was a beautiful young woman after all, and if she wanted to show off her body, that was her right. As a man basically double her age, I shouldn't be commenting on her fashion choices, even if there were times when I'd have to keep sitting at my desk for a few minutes after she'd left until I was confident I wouldn't be showing off a certain part of my body to the office.

And so it happened that late one evening I found myself working well after the office had closed for the night. It's quiet, and as far as I know I'm the only one there. That is, until Cassidy waltzes in, carrying two cups of what smells like caffeinated heaven.

"Hiya boss! Figured you could use a little pick-me-up after working so hard all day!"

I glance up from the spreadsheets that have been consuming me all afternoon to see she's holding two mugs of coffee against her chest in such a way that I can't help but notice the breasts behind them are nearly falling out of the sage green top she has on. Her black choker is in the usual place around her throat, joined today by a pair of gold hoop earrings that send sparkles of light skittering around the room as she moves. Her skirt is a deep green that nearly matches that of her eyes, and her fiery hair is pulled back in a loose ponytail.

"I thought you left hours ago. Thanks Cassidy, you're an angel." I reach to take the coffee from her, half expecting her to play some trick on me, but she hands it over without protest. She walks around my desk and sits on the edge, sipping her own coffee as she takes a peek at the numbers.

"Looking like we'll close the sale?"

"Looks that way– nearly done now, just a few more things to double-check."

"That's good– you've really done a good job letting people here take charge of parts of it. Shawna and Elias were both saying how much they appreciated getting to take point on some of the presentations– looks good on their resumes I guess."

"Oh," I say, caught a little off-guard by the sudden revelations. "I believe in delegating– no sense in having me do all the work!" I chuckle self-deprecatingly.

"I'm sure you could handle it," she says sweetly, scooting a little closer on the desk so that her thigh is nearly touching my arm. "How's married life, by the way? Still good?"

"Uhhh…" I pause, glancing over at her. Her eyes are fixed on me, studying my reaction. "I should really finish looking over these numbers, Cassidy."

"Sure! Just asking– be sure to let me know if something changes, ok? It's my job to take care of you, after all." She squeezes my arm and my muscles flexes involuntarily. Cassidy makes a little noise of surprise as my bicep grows in her hand. A rush of heat washes through me– I haven't made a woman make a noise like that in years.

"You really should stop," I say softly, nodding to where her hand is still on my arm.

"You want me to stop talking, or stop touching you?" Her bold gaze holds mine, her hand unmoving on my arm.

Neither, some part of me cries, a part of me that hasn't felt wanted like this in too long.

"Both," I finally manage to say in a strangled voice that must make it all too clear how hard it is for me to do.

Her eyes glint with something more than humor this time– a recognition that the game we have been playing for half a year is rapidly coming to its conclusion.

She leans in closer, her pouty lips parting.

"Make me. Please. Make me."

Something inside me snaps. I growl, taking her arm and pulling it free of mine. Pulling her to my lips instead.

"If you insist…"

The first kiss is hard, my mouth overwhelming hers as she melts into me, pressing herself against my suit. Even through all the fabric I can feel the heat coming from her, can feel the softness of her skin as her breasts rub against my chest.I stand, cupping her jaw with one hand as the kiss deepens. She sighs as I run my other hand down her back all the way to the curve of her ass, grabbing a handful of it to pull her off of the desk.

"These reports are due in ten minutes," I rumble, pulling away from the kiss. "Think you can be quiet while I finish them?"

She bites her lip and I know what her answer will be before she even says it.

"Make me."

I am already pulling her down, one hand ripping her top open, scattering buttons across my carpet, the other on my belt, unbuckling it and shucking off my pants.

"Under the desk."

She crawls into the tight space as I sit back down. She has my cock in her hands before I can even reposition my chair.

"Fuck boss, it's huge," she gasps. Her breath is hot on the tip of my cock as she examines me.

I guide her mouth to me, taking her ponytail in one hand as she takes me between her lips. The numbers on the screen blur as Cassidy starts to suck me, the first time a woman has done something like this in over a year now. I try to focus on the reports, but I keep glancing down, watching as her mouth bulges each time I pull her to me, her choker stretching as my cock fills first her mouth and then bulges her throat. If she has a gag reflex, I certainly can't tell.

I pull my eyes back up to the screen with a superhuman effort, trying not to be too distracted by the eager slurping noises coming from under my desk as Cassidy gives me the most enthusiastic blowjob I've ever had. It's no use. Her mouth feels too damn good.

"Fuck it, this is fine," I mutter, hitting send on the message that will seal the contract for us. Cassidy hums as she hears the email leaving my inbox.

"You know you really are a little brat," I say, looking down again to see her mouth stretched around my shaft. "Teasing me for the last six months. Making me pretend like I didn't notice the way you were flirting with me. Showing yourself off for me…"

Her chin is coated with spit and precum and she smiles around my cock as I speak, clearly not in the last bit sorry for her actions.

She gasps as I pull her head back, my cock slipping out of her, leaving a line of spit connecting us.

"What are you gonna do about it boss?" She gasps, her chest heaving as she catches her breath. Even on her knees, her eyes still flash a challenge as she looks up at me.

I stand up, motioning for her to do the same.

"I think it's time for your six month review, since you're clearly so eager for suggestions."

Her face lights up as I grab her hips, picking her up so that she is back on the desk again. This time though I lift her skirt up as well so that it bunches up around her waist.

Technically, Cassie is wearing underwear, but the tiny white thong is so soaked that it's practically see-through in places. Her breathing grows heavier as I look over her nearly-naked body.

"Don't get too excited," I warn her. "I have some disciplinary actions that we're going to discuss in depth…"

"Oh no…" she purrs, spreading her legs wide. "I hope it's nothing too bad?"

"That remains to be seen. Let's start with the positives though. How would you say the job is going so far?"

I hook a finger into the fabric of her thong, pulling it to the side.

"I've been really… mmm… really enjoying it lately…"

I slide two fingers into her as she speaks, amazed at how tight she is despite being so wet.

"What's been the most difficult part of your job lately?"

My fingers work in and out of her, preparing her for my cock.

"I think… oh fuck, that feels good… Um… I think my boss and I have… haaaahhhh, yeah… different communication styles…"

Her green eyes go wide as I press myself against her, sliding my fingers out as the tip of my erection starts to part her folds.

"And do you think that… uunnhhh, fuck you're tight… that you and he can come to an understanding?"

"Oh yesssssssss…" she groans as I fill her, slowly working my cock inside her tightness. "I think we're… oh fuck… we're really making progress now…"

I start to move faster as she takes more of me with each stroke. I can feel every contour of her inner walls on my shaft as I fuck her. Her tits bounce in time with my thrusts and they look so good doing it that my hands naturally gravitate to them, feeling the way her soft skin moves up and down as I move inside her.

"Anything else you'd like to say?"

"Oh! Oh yeah, just like that…" her eyelashes flutter as I bottom out in her, stopping for a moment to let her get used to me.

"I'd just like to say that I'm really enjoying getting some experience… nnnyes… under your leadership…"

"Mmm, thank you. I think that concludes the first part of our review."

I slowly pull out of her, watching with halting breath as her pussy grips me the entire way. She looks up at me, mouth open and eyes going distant as my cock slides out.

This time when I lift her up, she actually moans, throwing her arms around me to feel my back muscles flexing.

"Fuck that's hot." Her breath is warm in my ear.

I turn her now so that she faces away from me, bending her over my desk so that my cock is once again lined up with her dripping sex.

"I'm afraid to say…" I grunt as I enter her again, a little more roughly this time. She groans as I fill her up once more, her hands moving to her ass to spread herself open for me. "...There have been a few instances where discipline has been… oh yeah, keep spreading yourself for me… has been needed but was not carried out…"

It's hard to speak, hard to think. She's tight in a way I haven't felt in a long time, and eager in a way that I've never experienced.

"Please," she begs. "Tell me what I can… nngh… can improve on…"

Smack!

My hand catches her by surprise and she squeaks as her right asscheek starts to redden a little.

"First, when you wear those slutty outfits, you need to give me plenty of chances to see you in them throughout the day."

My cock is harder than it's ever been, driving into her with every word. Her round ass cushions each thrust, bouncing back on my cock as she fucks me just as much as I am fucking her.

"Y-yes boss! I'll make s-sure you can s-see me all day long!"

"Good."

Smack!

Her left cheek joins its twin in having a red handprint decorate it. This time she expected it, and while she doesn't yelp, her pussy does clench around my cock in time with the impact.

"Second, when I'm working on a tough project, my assistant should be under my desk, making sure that I can stay focused!"

"Oh… yeah, keep fucking me, please… I'm sorry boss! I haven't been taking care of you like you needed. I'll do better, I promise!"

"I'm going to hold you to that."

I don't know how much longer I can last. Six months of teasing, of frustration, of angst– all of it is pouring out of me at once.

I reach forward, taking her ponytail in both my hands and lifting her head up off of the desk as I lean in closer.

"And finally," I growl in her ear as my cock continues to wreck her pussy, "you need to understand that from now on, when you say ‘make me'..."

I thrust hard into her. The desk creaks as it jolts forward a little.

"... I'm going to bend you over my desk like this again… and again… and again… until you learn to behave yourself, do you hear me?"

"Oh fuck…. Oh fuck YESSSSSsssssssss…"

Her cry trails off as I move faster now, her mouth falling open in a silent gasp.

"You want my cum in your tight little bratty pussy?"

"Yes! Please cum inside me boss… oh God it feels so good…"

"Are you going to cum for me, Cassie?"

"Make me… please boss, make me…"

"Do it. Cum for me, Cassie. Cum with your boss' cock buried in you!"

"I'm gonna… you're gonna make me… CUMMING!"

Cassie's body tenses as she orgasms underneath me and her climax is the catalyst for my own. As she screams out her pleasure, I erupt inside her, my cock pulsing as I release a massive load into her, six months' worth of tension leaving my body all at once. Both of us are panting, coated in a sheen of sweat.

"I can feel it spreading… inside me…" she sighs, still coming down from the high of her orgasm.

"Good. Let it be a reminder of what we talked about tonight."

"Mmmm, yes boss, s-sure thing," she pants. "Thanks for helping me… really stretch myself in this role."

"Of course." I pat her ass gently. "And if you need additional training, let me know and we can arrange for further sessions after everyone has gone home for the day."

"Mmmm…" she bites her lower lip as she looks over her shoulder at me, eyes already smouldering with renewed enthusiasm. I feel her pussy clamp down on me again, already begging for more.

"I hope you don't mind, boss, but I'm a bit of a slow learner…"