Who's the Boss?
If given the chance, I would fuck you hard against water cooler until you howl. I would bend you over my desk, lift your skirt, untie that tight bun in your hair, and push my dripping cock into you until your pleasure starts fracturing the syllables of my name.
The first time you walked into my office, I didn’t think I’d be able to keep my hands off you. Hiring you as my general manager was the best bad decision I ever made. You were brilliant, of course, I couldn’t not hire you, but I also couldn’t stand to be within a ten-foot radius without sporting a ridiculous erection. If you knew how many pieces of furniture I rearranged to keep you from noticing, you'd probably quit.
You carried that holier-than-thou tension in your shoulders. It made others fear you. It also made you my perfect right-hand woman. I had a reputation as a risk taker. I was overly casual, personable to a fault. By contrast, you were calculated, strategic, methodical, and formal. Even when everyone else called me Al, you always opted for Alejandro.
You didn’t make friends easily, and you expected people to earn your trust. You might've been the only person that didn't try to suck up to my assistant. As a result, I trusted your advice more than I'd ever trusted any of my executives.
But you were an interminable professional. With everyone else, I understood. But even with me you wouldn't let your walls down. I wanted to erase that clear line you drew between the professional and the personal. I wanted to peel back the layers--the cardigans, the silk blouses, the unlined lacy bras--until I discovered just how dirty you were. And I knew you had to be dirty underneath those perfectly pressed pencil skirts. Call it a predator's sixth sense, but I could smell the seduction coming off you. I wanted to tease it out.
Over the first three weeks we worked together, we ended up in six awkward positions, and I had forty-three fantasies about you. I'd started to develop this bad habit at night. I couldn't fall asleep until I'd jerked off to one of my fantasies about you.
Your office was right next to mine. I'd started leaving my door slightly ajar at all times so I could catch glimpses of your feet sliding out the back of your heels, your thighs crossing under the desk. I don't know what killed me more, the times when I could see the outline of your underwear under your skirts or the times when I couldn't find even a trace of a line.
“Alejandro, you should go home,” you said at a quarter past nine p.m.
We had an eight a.m. deadline and half a proposal. You knew the night you were in for when one of the manager’s turned over a rough draft at four o’clock and called it good.
It was the first chance we had to be totally alone. Maybe you thought the glass walls of the conference room would ensure things didn't get out of hand. But I knew the cleaning crew's schedule. I knew where all the security cameras pointed, and I think you did too. You had the information, at least.
“Your family will worry,” you said.
“Unless you’re referring to my fish, I don’t have anyone at home worrying about me.”
You didn’t smile or laugh. You just nodded and kept digging through the numbers on the screen.
“How about you? Anyone I should send Uber Eats to as an apology for monopolizing all your time tonight?”
“No. I'm still trying to figure out why these numbers don’t add up. Come and take a look at this.”
I leaned over your shoulder. The smell of your shampoo had been agitating me for weeks. I wanted to pull your ponytail out and massage your scalp. I wanted to lick along your neckline just to have that taste on my tongue.
I gripped the back of your chair to stop myself from tracing the soft fabric plunging down your sternum. You were wearing one of those chiffon blouses that framed the small triangle shape of your breasts. I swear, you were trying to torture me.
You shifted in your chair as I tried to focus on the screen, opening your legs, crossing them, squeezing them together. If I didn't know better, I'd swear you were rubbing your pussy against that chair.
“Do you see?”
You pointed at the screen and looked up, catching me staring at the lap of your skirt. I stepped away and rubbed my eyes.
“Sorry. I must be getting tired after all.”
You stood up to stretch.
“My back is killing me from hunching over this laptop all day,” you said.
“Hang on. I’ve got a fix for that.”
I unlocked Frank’s office and grabbed a handheld back massage wand from his desk. When I returned to the conference room, you were stretching at angles that should've been illegal in that tight pencil skirt.
I paused at the door, clearing my throat. You stood up quickly but didn't apologize. That's how I knew my instincts were right. You weren't prudish.
I set the massager on the table and unwound the cord, plugging it into the laptop outlet in the middle of the table.
“What the hell is that?” you said.
“Frank’s back massager. Thought it might help your back.”
“What are the odds that Frank only used this on his back?”
“I did spot a bottle of lube in his desk.”
“Joking.” Not. “But you’re clothed, and I wiped it down in the bathroom, so your chances of getting pregnant tonight are minimal.”
You eyed me like you could see right through me. It was the first time you let slip that you could read my intentions toward you. That pregnant comment had your wheels spinning. And, darling, if you'd like me take you without a rubber, I'd put a baby in you in less than ten minutes.
We'll call that fantasy forty-four.
“I really need to spend less time at work,” you said.
But you picked up the massager and turned it on. You turned it off after half a minute and set it down.
“I don’t think this is a one-person job.”
“Want some help?”
“Would you mind?”
I turned one of the armless office chairs around, picked up the massager, and gestured to the chair.
“Your makeshift massage chair, madame.”
You huffed out half a laugh and lifted your tight pencil skirt up your thighs to straddle the chair. Just seeing those two extra inches of skin tightened my balls.
“This isn't workplace appropriate, is it? I bet you didn’t anticipate massaging my back when you hired me,” you said.
If you only knew what I’d imagined when I hired you, you never would have walked into this conference room with me.
I turned on the massager and rolled it over your neck and shoulders. You rested your head in your folded arms and relaxed under the vibrating pressure. You fell into such a still state, I thought for a minute you'd fallen asleep.
But then you said, “You know, when I first met you, I thought you were intimidating as hell."
“Why is that?”
“At the time, I thought it was your aura, but maybe it’s just the suit.”
“I guess my tailor is doing his job. You know, I thought you were intimidating too. That’s half the reason I hired you.”
“You’re still intimidating as hell, Joanna.”
“Don’t be too intimidated, Alejandro, I’m drooling on myself down here.”
I rested my fingertips on your mid-back. You moaned. I rolled my knuckles along your spine.
"Jo," I whispered.
“Whatever you're doing with your hand, yes!" you groaned. "Harder. Lower.”
Those words were all it took for the blood in my hands to rush to my cock.
I turned off the massager and tried to calm down. You turned around to see my erection at eye-level.
You bit your bottom lip in a way that made me consider unzipping my pants and sliding my cock past those incisors. You didn't pretend you hadn't seen it, but you didn't make a move either.
“I’ll be back in a minute.”
“Where are you going?” you said, as if you didn't know.
I was already too far gone. My hard on was not going down. I had been too pent up, working too many hard, long hours beside you without taking a break to fuck. Hard, long hours. Hard, long. Fuck. I should’ve grabbed Frank’s lube when I was in his office.
I closed my eyes and thought of you, thought of your perfect, thick inner thighs, your fleshy lips, your tight back relaxing around my touch, your petite breasts shaking under my tongue.
And was it just my imagation, or did I hear your footsteps coming down the hall to find me? Did I hear your breath on the other side of the door, listening to me beat off? I placed my hand on the door as I groaned through the misplacement of pumping into my fist instead of your pussy. I imagined sliding into you from twenty different angles. I imagined what your pussy would look like, taste like, feel like. But it wasn’t enough.
I secured my hard cock under my belt, washed my hands and face, took a deep breath, and opened the door. You weren't there.
When I reached the conference room, I heard the massage wand. I glanced above the line of glazing on the glass wall. You were rolling the massager over your lower belly, grinding your pussy across the chair like it was a rocking horse.
My erection was ready to snap the leather of my belt to get to you.
I gripped the head of my cock and tried to breathe. You slid the massager up your skirt. You didn’t take it easy. You were grinding against that vibrating head like it owed you an orgasm. I couldn’t let you finish like that, I couldn’t let you finish without me.
The gentleman in me would’ve snuck back down the hall and returned loudly so you’d have a chance to stop. But you knew I hadn't gone far, and you knew why. The bastard in me refused to give you the gentlemanly courtesy. I opened the door.
“Shit,” you yanked the massager out of your skirt, dropping it to the floor. “Um, I was trying to get the spot without you.”
Like a bloodhound that had found its mark, I could smell your wet pussy in the air. It was even better than I'd imagined. I placed my hands in my pocket and pressed down on my balls.
“So … Did you get it?"
Your eyes followed my hand shifting in my pants.
You grabbed the massager from the floor and turned it off.
I wrapped my hand over yours and slid the massager away from you.
“Let me finish what I started. You wanted me to go lower, right?”
I twirled the office chair so that you'd be facing the conference table again and stepped behind you, running the massager down your lower back.
“How’s that, Joanna?”
“Lower,” you whispered.
“Tell me when to stop.”
You nodded as I trailed the massager over your ass. You pressed your ass deep into it, rolling your hips like you didn’t care if I knew you were getting off from it. I slid it lower still.
“You know what you really need?” I said.
“Cock,” you said.
I nearly choked.
“I was going to say a deep tissue massage.”
You turned your neck and looked at my pants.
“So, give it to me.”
“I’m not qualified.”
“From the sounds you were making in the bathroom, I thought you were very qualified.”
I spun the chair around and placed my arms on the table, pinning you between my arms. My erection pressed into the back of the chair. I needed to read your eyes.
“Jo, are you asking …?”
"No one calls me Jo, Alejandro."
"I do," I said.
Try every time I've beat off to you since the day we met.
"Since now," I said and traced the V of your blouse, slipping it far enough back to see you weren't wearing a bra.
Right before I got to your nipple, you grabbed my wrist.
"Tell me what you want, Jo," I said.
“I want you to get me off, Alejandro.”
I couldn’t trust my ears. I was too aroused. My brain had put the words in your mouth. There was no way you had said what I’d heard.
“Let's just pause for a second."
I released the chair and paced the length of the conference room.
"I know everyone thinks I'm impulsive, but I am your boss, and I respect the shit out of you. Your work is top notch. It’s true, I’ve been … noticing you. But I swear I didn’t hire you because I expected something to develop between us. I don't expect you to reciprocate. I'll do my best to not let this ... attraction become a nuisance.”
"Do I seem like the type of woman that would entertain you because you want it? Have you been so busy staring at my ass for the last month that you haven’t noticed me staring at that permanent bulge in your pants?"
"Shit," I ran my hands through my hair. "This is a bad idea."
"I don't want to lose you. This company needs you. And I really respect you."
"You said that already."
"But the things I want to do to you, Jo, they're very disrespectful. And once I start, I don't think I'll be able to stop."
I traced every inch of you with my eyes. Your skirt was tightly pinched around the plastic spine of the chair, blocking the view I wanted the most.
You swiveled the chair back and forth, shifting your knees open as you moved.
“If you want something, Alejandro, I expect you to take it. That's your job.”
I gripped your bare knee, stopping your teasing movements.
"If I'm about to take something that will destroy us, I expect you to stop me. That's your job."
"I'm not stopping you."
"Then tell me why this is a good idea."
"Oh, it's the worst idea we've ever had."
You slid one side of your shirt over your shoulder, tucking the chiffon under your breast. Your breast perked out like the stiff peaks of a meringue. I kept my feet firmly planted as you slid your hand up your skirt. Your fingers were dripping when you pulled your fingers to your breast.
I grabbed your wet hand and pulled it to my lips, rolling your chair across the floor. I ran my tongue along the lines of your fingers, devouring every drop of honey.
You slid my hand up the lining of your skirt until I could feel that you'd soaked through the entire liner. I pressed through the material into your dark, damp heat and growled.
"Tell me to stop, Jo."
You slid back, leaving me standing several feet away.
“If you want it,” you said, scooting your skirt up until I could see your full bush. “Take it.”
“Stand up, Jo.”
You stood and your skirt dropped just below your pussy.
“Lift your skirt all the way.”
You slid it to your waist and backed onto the table, spreading your legs to show me exactly how aroused you were. Just that tease, just your excitement, and my mind was made up. I was going to take you. I was going to disrespect you so good.
I picked up the massager and stepped between your legs.
“What were you imagining when you used this?” I asked.
"Is this confession time?"
“I thought this conference room would be better, safer. But just the sound of your voice makes me wet, Alejandro. What was I imagining? I was imagining you using this on me, preparing me.”
I turned on the massager and pressed it against your perineum. You nearly jumped off the table with surprise.
“If you’re looking for my clit, it’s the other way,” you said.
“I’m not going for your clit, Jo. A woman like you doesn’t want your orgasms to come quick and easy.”
“How do you know what I want?”
“Okay, maybe you want it quick and easy. But a man like me wants to give it to you slow. I want to draw this out until you're begging for it.”
Your lips were swelling with blood, your folds were filled with cream.
“I know you came to work with panties this morning, Jo.”
“How do you know that?”
“I noticed the outline when you bent over to fix the paper jam. What happened to them?”
"I've been, uh ..."
"They've only been making it half a day."
“From now on, when your panties get so wet you can’t walk around in them anymore, you bring them to me. Understand?”
"What are you going to do with them?"
"It's not what I'm going to do with them that you should be worried about. It's what I'm going to do with you."
You hooked a finger under my belt and pulled me closer. My cock was dripping through my shirt. You lowered your head and sucked on the tip of my cock right through my shirt. I nearly came right then.
I pulled your head back and panted.
"If you make me wait any longer for that cock, I might just come without it."
"Who's the boss here anyway? You'll come when I tell you too."
You unbuckled my belt and unzipped my trousers. My erection raged under my white dress shirt. You tugged on the ends of my shirt as I slid two fingers along the bundle of nerves at the bottom of your entrance.
“Unbutton my shirt, Jo. When you’ve gotten to the last button, I’ll make you come.”
You tore at the material, popping the bottom three buttons clear off my shirt. As soon as you saw my cock, your pussy clenched around my fingers so hard and fast, I thought you might come.
"You like cock," I said.
"I like yours."
I liked your eyes on my shaft, the way you leaned forward on the table and tried to pull me to you.
I slid you further back.
“Impatient much? I want to give it to you twice, Jo. First with my fingers, then with my cock. That way you'll know the difference. But if you pop another button, I won’t let you come until I’m balls deep in you.”
You growled and slowly worked at the buttons.
“I hoped you’d be like this,” you said.
“Demanding. Complicated. As big and hard as a drainpipe.”
As I slid my fingers deep inside, your pussy quivered. I pressed on your bottom walls, stroking your nerves awake. You were hungry for that deep pressure that only a cock could satiate.
You paused at the top button of my shirt and pivoted off the table, sliding the massager to your ass as you tried to take my fingers deeper.
“Tell me what you want, Jo."
“Harder, deeper. Up. Fuck. Not down. Up!”
I knew you wanted to feel me against the bundle of nerves on your top wall, you were clenching my fingers so tight.
“Men go straight for the clit and G-spot too often. Let me play a bit. Let me explore. I've been dreaming about this for so long."
“You want me to beg for your cock, is that it?”
“A little bit,” I smirked.
I turned off the massager and slid my finger along the rim of your anus. You grunted and pressed down.
“I’ll make you a deal. If we get the green light at tomorrow’s proposal presentation, I’ll beg for your cock in three languages right in front of everyone.”
"There's no way I'm leaving this conference room until I've been inside you."
You grabbed my shirt by the collar and pulled me to your lips. As I lapped my way into your mouth, you unhooked the last button. I slid your hips off the table, extending my fingers all the way as I pressed my thumb into your anus.
"Alejo ... Al ... andro ... oh God."
You bounced, riding my fingers to climax until your cream covered my hand. Your face contorted in the moment of ecstasy, and I nearly came right on top of your clothes.
You panted against me, then lowered your skirt.
“Not so fast,” I said, turning you around and pinning your hands to the table.
You stuck your ass out like you were desperate for my cock, but as I slid it up your leg, you reached down and blocked me.
“The tension will be good for the proposal presentation tomorrow.”
“Like hell it will. Shit, Jo, you can’t leave me like this.”
“That spreadsheet isn’t going to untangle itself. And it’s getting pretty late.”
You yawned. I groaned, but you weren't going to budge.
"Let me take you home," I said at last.
"That's not going to work for me."
"Not going to work for you?"
"If we go home together, there's no way we're getting any sleep tonight, and your presentation skills are shit when you haven't slept."
"You think I'm going to be able to go to sleep in this condition?"
"You'll work something out. Do you want to clean up that massage wand or should I?”