The Boss Diaries

I slept like shit last night. Overthinking is one of my perks and I spent the whole night spiralling into thoughts about my new potential "training" routine. I wonder what he has planned for me. The sounds of his orgasm had haunted me on my entire way home, ghosted around in my brain, and kept me wondering how I ended up in this situation.

I wasn't exactly complaining about him finally finding his way into my panties but that wasn't how I expected it to happen if I had expected it to happen at all. Which I did not. Never would I ever have thought to be this close to him. To fuck with him. To give him a blowjob on my knees in the middle of his office.

A ping rips me out of my thoughts and a new message shows me that he might have stolen my phone number from my personnel file. "Do you own a anal plug?" is written all over my screen and my eyes roll naturally at his sharpened wording.

"Good morning to you, too. Why?" is my quick response.

"It's a simple yes or no question, Lara. Answer it. And... good morning." A grin spreads over my face.

"Maybe." I can practically hear him huff out in annoyance right now. Can imagine him being all unamused, huffing and puffing before my phone pings again.

"Wear it. I want you plugged today, squirming on your office chair not knowing what might come next. See you at the office." Well, I guess I'm doing him the favour and find my plug before I have to rush to work. Several minutes and many boxes later, I finally find it and it looks bigger than in my imagination. This has to do now. I grab the lube out of my nightstand and squad down while pouring a good amount of liquid onto the metal plug. Prepping it until it's slick and slippery, I reach down and insert it into my itching backdoor. The cold metal on that sensitive spot has me hissing in anticipation. I'm taking my time, tease my hole with the toy before inserting it completely. A small moan escapes my lips as I stand up and feel it settle in.

Pulling my panties and skirt on, easy access for him today, I scoot out of the door and straight to my car. The bumpy road feels more intense than it usually does and that's for sure fault of that toy that's stretching me out. Every hole in the street has me twitching and squirming in my seat.

Fifteen minutes later I enter the hall of the office building. The elevator brings me up to my floor and the first thing I see when the doors open is the handsome face of my boss. The scowl on his face turns into a filthy grin when he notices me and he licks his lips. I'm squirming instantly and when I feel the plug move with my movements I hiss and can barely keep my eyes from rolling backwards. His grin widens and the full lips of his mouth wish me a good morning. At least that's what I think he's said because the rushing of my blood is so loud to my ears that I can't hear anything else.

I nod into his direction before passing him quickly and basically running to my office, slamming the door shut behind me. My phone pings. "Good girl. Also, you look stunning in that sexy skirt of yours. Take off your panties. I want you bare and ready to bend over for me," he texts me, and my hands move on their own pulling my panties down and off my legs. My door swings open and he strolls inside, leaving it wide open. "Lara? A quick word please," he says and the wicked smile on his lips is anything but friendly. It's filthy and promising in the best way.

"How may I help you, Sir?" His eyes darken when he hears my way of addressing him. His pupils delay and the brown of his eyes is barely visible soon-ish later.

His hand shoots forward and a sharp "Give it to me" leaves no room for assumptions. The tiny thong dangles off my fingers as he grabs it and rips it out of my hands. "Good girl. I emailed you a file, please work on it and send it back to me right after. I'll have a look at it and we can discuss it further if necessary," says he and turns on the spot, leaving me behind completely stunned.

That makes one less beloved thong, but gives me an reason to go for a quick shopping turn in my lunch break. I sit down to check his mails and my eyes widen in shock when I notice the attached notes. He sent me several files of clients to check and that's nothing new to me. What is new, is the instructions added to the task.

• Rub your clit for 30 seconds with every paragraph you 've checked

• Push and pull the plug in and out with every file you finished

• Pinch your nipples, alternatively, every other 10 minutes -- I want them sore and sensitive by the time I'm coming to play with you

Part of me is excited and already eager to begin working, the other is shocked because I don't know how to concentrate while doing this. My juices are already leaking out of me. I can feel them covering the insides of my crotch, my thighs too. My backdoor throbs in anticipation in rhythm with my clit and my stiff nips perk through the thin fabric of my bralette.

Eagerness takes over and I begin to work on the files while keeping the tasks in mind. Three hours later I'm on the edge of cumming, worked up and uneasily squirming on my chair and my nipples are so sore that I can't bear to touch them anymore. I email the files back to him, thanking god that I'm finally done with them, when he orders me into his office.

I enter his office after a quick knock on his door and close it behind me. It's early Friday afternoon and most colleagues are already off duty but you can never know who is still around and those nosy people have their eyes and ears everywhere.

"Well done. See, that wasn't so hard, was it? You just needed a little... incentive." The smirk on his face shoots straight to my ovaries. I want to grab him by his short brown hair and pull his face between my legs to ride the grin off his handsome face. I don't reply anything, only walk closer to him. The plug massages my insides with every step I take and my butthole clenches around it, keeps it steady in his place while driving me insane. I need to get laid and I need it now.

He pats his leg just like he did yesterday, gestures me to sit down on his bulgy, muscular thigh. And so I do. I can feel how my juices instantly soak the expensive fabric of his suit pants and I couldn't care less about it at this point. He grunts. "Mmmmmh, fuck. You're so fucking wet. Did you do what I'd ask you to?" I nod. "Say it," he grumbles.

"Yes, Sir. I did. It's aching so badly. Please take care of it," the whiney undertone of my words makes me sound pathetic but I don't care. I'm absolutely overstimulated and I need the ache to go away. Everything south of my belly is in flames, and so needy that it literally hurts.

He smirks even more now. His one hand slips pass the rim of my skirt and gently pushes the plug, causes me to almost jump off his leg. His other hand finds me thighs and keeps me in place as he gently pulls the plug out of my hole just to let it snitch back in place right after. I moan. My head falls back and I expose my neck to him. He sinks his teeth into it just the second he pulls out the plug a second time, pulling it out a tad more this time, the girthiest part stretching me out. A whimper escapes me and I begin to squirm heavily until he sits the plug back into me.

"Sensitive?" He mumbles against the skin of my neck, scratching his teeth over it. The next second he pulls me up and bends me over his desk. I'm squeaking and attempt to wiggle out of his deathly grip but I can't move an inch away from him. His fingertips caress the plug that's now on full display since my skirt is nowhere near covering me up anymore.

The squeaking turns into moaning as he massages the toy inside my hole, and my forehead bumps onto his desk. I push my ass back towards his eager and promising hands and he stifles a laugh. "Just you wait. It's called patience. Try it." My middle finger shoots up and he giggles, right before he pull on the plug and lets it snap back inside. My other hand grabs the edge of his desk, clawing into it for dear life and the moan that slips out of my open mouth sounds animalistic.

He moves closer to me and his hard length presses against my bare ass. I moan, he groans. "What do you want to do to me?" My voice is nothing more than a whimper.

"I'm going to fuck that sexy, tight little ass of yours. I'm going to cum in it while you're cumming on my cock. And then, then I'm going to stuff that plug back in again before sending you home with my load still inside that tight little asshole."

A shiver rushes through my whole body, sending goosebumps all over me. A silent nod is all I can manage but it seems to be enough to encourage him to lose his pants. I hear a belt being opened, a zipper pulled down and then I can feel his bare cock against my naked flesh.

His fingers find the toy again, fumbling on it until I feel like I'm losing my mind. Mumbled curses escape me and he chuckles, then pulls it out in one quick movement. He smacks it onto the desk and his fingers slide down to my soaked centre. Collecting some of my juices, he slickens his cock with it before I can feel the crown of his dick on my tight backdoor. He pushes himself inside me, slowly, gently, but imperatively.

Inch by inch of his cock enters my tight hole, has me whimpering louder the more it gets stretched and yet this is exactly what I need. "Good girl. You're taking me so well. I'm almost all the way in. You can do it. You can take me. You were made so take my cock in every single hole of yours, made to be fucked by me, made to be mine. I knew I had to have you in any way possible the moment I laid eyes on you." His confession leaves me stunned. Sure, there was some tension between us from the get go, but I never ever would've thought he'd engage into something like this. And yet, here we are.

When his cock is all the way in and his balls press against my swollen pussy from behind, I exhale the breath I didn't know I was holding. He pats my butt cheek before he smacks on it heavily and makes it sting. I hiss back at him and he chuckles. "Buckle up, it's going to be a bumpy ride, Baby," and then he pulls himself out of me before thrusting back inside. I yowl, head thrown back into my neck as he grabs me by my waist and smashes into me until I see stars. I feel so full, so stretched and when his one hand sneaks up and finds my sensitive nipple I can't help but cry out in pleasure.

"Good fucking girl. Let everyone know what a good slut you are. That you're bent over your bosses desk and take it like you were born to be his perfect, little office whore. Show them how a perfect slut looks like, acts like, behaves like. I can feel you clenching around my cock, can feel you milk it. That's it, baby, milk my cock with your tight asshole." Each word brings me closer to the edge. I can feel my orgasm rush towards me and before I know what's happening, it washes over me. Teeth clenched together, I growl animalistically as I cum on his cock biting back the scream that wants to escape me. My backdoor cramps around his cock, pulls it even more into me, and he curses under his breath but doesn't miss a beat in his merciless rhythm.

He pinches my nipple, hard. "Again. Come again on my cock." His forceful command leaves me no room for backtalk and for once my pussy and I agree with each other and the next orgasm hits me like a train. I'm shaking, crying and it feels like my pussy is gushing too this time, as I ride out my climax and this time I'm taking him with me. He stutters in his moves and comes inside of me with a loud growl and constant cussing. His body shakes behind me, his hands grab my sensitive flesh so hard that it'll leave blue marks. My name is a prayer on his lips as he shoots his load deep into my ass.

After what feels like minutes of him spraying his cum into my body, he pulls himself out of me and reaches for the plug. He settles it back into me, keeps your load from dripping out of me, before he claps my bare ass gently and tugs my skirt back into place to cover my naked body part. He tugs his cock back into his pants and spins me around. His lips find mine and the kiss catches me off guard. I whimper into his mouth and he wraps his arms around me to pull me even closer. When his tongue touches mine I moan in awe. He pulls his head back and looks me in the eye, his lips still only mere inches from mine.

"You did so well. I want you to go home now, don't take the plug out before you get there. I want you to remember what I just did. I want you to relax on the weekend, this was only the beginning of your training." With those words he plants a quick last kiss onto my lips and lets go of me.

I'm blushed all over when I turn for towards the door before looking over my shoulder a last time. "Thank you for training me, Sir," I whisper, and when his eyes darken again I wink at him before heading through the door. His cheerful laughter follows me to the elevators until their doors have closed to bring me downstairs.