A Very Personal Assistant [MF]

“It’s very nice to meet you, Sir. I’m confident I’m the woman for the job. And I’m glad to say HR thinks so too. Please! Let me take your coat.” She slides the coat off his shoulders, running her hand down his arm slowly before she pulls away. “Since this is my first day, you may need to show me the ropes a little, but you can rest assured I catch on very quickly.” She hangs the coat on a rack in the corner. “I’ve taken the liberty of scheduling your meetings so you can have fifteen minute breaks between them, as well as an hour for lunch.” She puts up a hand. “Before you protest, I think you’ll see that relaxation will boost your productivity. You also have twenty minutes now before your first engagement to gather your materials, make calls, and enjoy some coffee. I have a fresh cup on your desk along with this morning’s Times. So, please relax, and let me know if there is anything else I can do for you—and I mean anything.”

A few minutes after entering his office, he hears a small thud and peers out his doorway. She is on her hands and knees under her desk, retrieving something. Her gray pencil skirt is stretched tight across her ass, and her heels are lightly waving in the air. She realizes she is being watched, turns her head, and locks eyes with him just as he has begun to mentally undress her. “I apologize! I just dropped something under my desk. I didn’t mean to disturb you.” She scoots back and turns around, still on her knees. Her blouse has shifted from the commotion and settles, leaving a gap over her cleavage.

During his first meeting, he is a bit distracted with the mental images from earlier in the morning. As one of his clients is giving a pitch to him and his colleagues, he reaches to play with his pen and knocks over his coffee mug, spilling its contents onto his tie and shirt. He excuses himself and hurries back to his office. He opens the door to the anteroom and finds his new secretary sitting on the corner of her desk with her skirt hiked up mid-thigh. She is applying clear nail polish to a run in her hose. She looks up, momentarily flustered, until she notices his shirt. “Oh no! We have to get you into some new clothes. I’ll take these to the dry cleaners right away, no worries.”

She bustles ahead of him into his office, opens a bureau, pulls out a spare shirt, tie, and slacks, and turns to find him standing in the doorway. She strides over, closes the door, and begins untying his tie. She slides it from around his collar with a quick motion and casts it aside. Before he can reach up to unbutton his shirt, her hands are fast at work. She seamlessly unseats each button, getting lower and lower toward his belt. Before pulling the shirt up, her gaze wanders a little lower to the growing bulge in his trousers. Her eyes flicker up and meet his gaze. She blushes, untucks the shirt, leans forward almost against him to slide it off his arms, and then notices the coffee soaked through to his undershirt. She pulls it up slowly, sliding her hands up against his torso, and pulls the shirt off with one hand, leaving the other on his chest. They are both breathing quickly in the closeness. She pauses, her mouth open slightly, quivering at the tension. Her eyes trail down over his stomach to the bulge growing beneath his belt. She lightly rubs her hand up and down on his chest, and his bulge twitches a little. Taken off guard, she shifts her balance, stumbles, and falls into him, pushing him against his desk. He catches her so she does not hurt herself, but now her hip is resting firmly between his legs; and her ample breasts are pressed against his chest. After a moment, they break apart, blushing slightly.

He digs some bills out of his wallet and instructs her to take his dirty clothes to the dry cleaners and to pick him up some underwear. He throws a few more bills on the pile and suggests she fix her own wardrobe malfunction and buy some new stockings for herself for her trouble. He shoos her out to go to the store so he can finish changing. She weakly protests that she should wait outside in case he needs help tying his necktie.

He assures her he has been doing this for himself for years and will be fine. He closes the door and sighs. It is no longer clear how much of the wetness on his pants is from the coffee spill and how much is pre-cum. His cock is so hard it is practically throbbing. He drops his pants and give it a quick stroke, thinking about her ass bent over in her skirt, her cleavage, her skirt pulled up over her thighs, her body pressed against his. Within seconds he feels close to cumming, but he stops. He shouldn’t do this. She is his employee, and if things keep going the way they are going, he might get sued. He quickly gets dressed, going commando. The fabric of his spare trousers uncomfortable on his aching cock. He walks back to the conference room, trying to use a newly acquired clipboard to conceal what his suit pants are not doing a very good job of hiding.

After dropping the clothes off at the dry cleaners, she hurries to a department store to find a new pair of hose. She makes it to the lingerie section, and the hosiery display is nearly empty. All that is left are white, bright navy, or fishnets. She sighs and spot a pair of black hose laid on the next rack by the clearance items. She picks them up and finds they are her size, but only thigh highs. She glances over and spies a couple garter belts. She grabs one, ensures it would fit, and beelines for the register. After checking out, she make sure it is alright to use the dressing room to change into her purchase. Once in the stall, she kicks off her shoes, unzips her skirt, and shimmies out of the ruined hose.

Her mind wanders to the events earlier. Of course he can tie his own tie! There is a line between being helpful and domineering, and she had crossed it. Her cheeks flush, and she slumps down on the corner bench in the stall. She puts her hand to her face and is reminded of the moment he and she had pressed together—her breasts against him, her hip nestled between his legs against that bulging hardness. She spreads her legs and places two fingers against herself through her thong. She closes her eyes and begins massaging, imagining what it would have been like if he had let her help him out of his trousers—looking him in the eye as she unfastened the button, watching him watch her as she slowly tugged on the zipper, feeling his hips and pressing her palms against them as she slid his underwear—oh shit! The underwear.

She looks down and notices her wetness has soaked through her thong and is beginning to run down her thighs. She slips out of the thong, grabs the ruined hose, and cleans herself up the best she can. Not knowing what to do with the thong, she tucks it into the corner zipper pocket of her purse. She puts on the garter belt and stockings and secures her skirt. She inspects herself in the mirror and sees everything looks presentable. No one could tell she is not wearing full hose, and the lack of underwear lines is the same as if she were still wearing her thong. She throws the ruined hose in a trash can just inside the dressing room lounge.

She hurries to the men’s department and freezes upon reaching the back wall. What kind of underwear? He did not specify. Boxers? Briefs? She berates herself for taking so long. All this time he has had to go without underwear. Her mind automatically wanders and starts undressing him—no, no time for that now. She settles on a pair of gray boxer-briefs made from incredibly soft fabric. Hopefully he likes them. She imagines them on him and how his bulge would look in them. She bites her lip.

“Ma’am?”

She jumps. A sales associate checks to see if she is finding everything alright. She assures him that she is and heads to a checkout kiosk. She then hurries back to work, hoping to make it to the office before her boss is out of his second meeting and off to lunch.

When he breaks for lunch, he finds his secretary has returned. After politely sending off the clients, she discreetly passes him a shopping bag and waits looking at him expectantly. He checks the contents and assures her they are to his liking. He asks if she had much luck for herself, and she swings her legs out from under his desk. They look very smooth and sleek. He congratulates her on her good taste. As she returns the change from the shopping, he notices it seems like a bit too much. He asks to see the receipt. Sheepishly, she hands it over. Upon inspection, he finds she only bought one pair of stockings, and some greatly marked down ones at that, despite his instructions to stock up for emergencies. He returns the money and congratulates her on her bargain hunting but gently reminds her that despite today’s excitement, always looking presentable and professional is a key part of the job. She is to take the rest of the cash and stock up on several pairs to be kept at work at her earliest convenience, and also to go get them lunch.

She protests and tries to pick up her purse, but he doesn’t trust her not to pay for things herself, so he insists she leave it behind and spend his money. Lunch and “office supplies” are business expenses, and he will cover them. Once she is out of sight, he can relax. The receipt showed a garter belt too. That revelation had him starting to tent again at the thought of her now in stockings instead of pantyhose, her thighs presumably bare under her skirt. Just as he is about to head back to his office to try on his new underwear, his mind wanders to her purse. She seemed awfully concerned about it, so he should put it somewhere safe while she is gone to be sure nothing happens to it.

As he picks it up, he notices something red poking out of a pocket. He goes to stuff it back in and the touch of his fingers discovers the object is lacy. And damp. He discreetly pulls it out to investigate, knowing full well he should put it away and forget about it. The mystery is too exciting, and he unfolds the fabric already guessing what it might be—a pair of thong panties. But he is surprised to find them completely soaked. Once again, despite his better judgment, he holds them up to his nose. Fortunately the wetness is not urine, but a woman’s excitement. She must have been very excited to leave these panties in such a condition that they should not even be worn anymore.

Suddenly, the image of stockings, garters, and a naked soaked pussy under that tight skirt crashes into his mind. Maybe she put on a new pair? No, there were no panties on the receipt, and all the cash was accounted for. His cock, already restless, has woken up. It then occurs to him that the most logical explanation was that their little mishap earlier is what got her going. The totality of the situation has his mind racing and his cock aching. Does he put them back and try to move on? Does he take them? Surely, even if she suspected him, she would be too embarrassed to ask and would probably just think they fell out somewhere. He really wants to go back into his office and jerk off while smelling them and using them to soak up his cum. That is too much, he thinks, and too far even if he needs the release.

She calls ahead to a nearby bistro, and while waiting for the order, goes to another store for more stockings. She buys several pairs, including one with classic seams up the back. She smiles and decide that the garter belt is now part of her work uniform.

After picking up the food, she heads back to the office, pausing outside of the inner door past her desk. Her hands are completely full. She push the odor handle down with an elbow and eases the door open with her body.

She stops just inside the door, and it swings shut behind her. He is in his chair with his new underwear and slacks around his ankles. His head is thrown back, his eyes are closed, and he is stroking something against his throbbing hard cock. She must make a noise, because he opens his eyes to find her standing there with her mouth agape. She realizes then what he is holding against himself—her thong. She feels hot wetness leak out of her at the thought. He opens his mouth to speak, but she strides forward, places the bags on a side table, stands in front of him, unzips her skirt, and lets it fall to the ground.

His eyes wander up her legs to her little bush just above her pussy. He drops the panties, stands, steps out of his pants, and pulls her toward him by the hips. He guides her to the desk and seats her on the edge. He sits in his chair and rolls closer. She watches as he is transfixed by what is between her legs. She spreads them wide. He licks his lips, and she can hear his breathing is a little shallow. He brings himself just inches away and looks up at her. She meets his gaze and nods. She leans back on her hands, closes her eyes, and smiles.

As he inhales her intoxication, he shudders. He wants to taste her so badly, and her body clearly is ready. He leans in to her spread, dripping pussy and breathes her scent in deep. As he exhales, his breath across her exposed vulva makes her shiver. He licks one side and then the other. The taste is too much, and he cannot tease any longer. He buries his face into her, hands on her hips, pulling him tight to her. His tongue explores everywhere, from below her dripping opening to the little space above her clit. She writhes and mewls.

His tongue flickering and lapping all over her pussy is too much. She feels gobs of wetness leaking out. Her arms supporting her start to buckle. Pleasure is passing over her in waves. She wants him to see her, all of her. She sits all the way up, forcing him to pull away just a bit. He leans back and looks up. He pulls her blouse over her head and begins unhooking her bra. When she pulls her bra away, he raises his eyebrows. She slides off the desk and straddles his lap in the chair. She hovers just in front of his cock, no matter how badly she wants to feel it filling her. He cups her breasts in his hands and closes his eyes. His cock twitches and taps her clit. She lets out a small gasp. He wraps an arm around her waist and pulls her tight to him. His face is buried between her tits, and his free hand is squeezing and massaging one breast. She is pressed up against the tip of his cock. She moans and begins to work her hips up and down, sliding his hardness along her pussy.

He lets out a growl, grab her hips, and pulls her downward. She feels his cockhead kissing her opening. Her cheeks are flushed, and she is already breathing a little too quickly. His fingers tighten on her hips, and he presses her down harder, almost desperately. He pulls one last time, impaling her on his hard cock. She is naked except for garters, stockings, and heels. Her face is contorted by pleasure.

“Is this what you wanted?” he whispers.

“Yes,” is her meek reply.

He pushes her off, and she lets out a small whimper of disappointment. He turns her around, and bends her over the desk, moving behind her. “I want you too, not just as my secretary, but as my little slut. If you want to give yourself to me completely, spread that beautiful ass and tell me how you want me to fuck you.”

She hesitates just for a moment, then spreads her legs wide again for him, thrusting herself back, in the hopes of brushing her pussy against his cock. He roughly enters her from behind, going all the way in, in one plunge. He pauses for a moment to enjoy being completely inside her again, then gets to work pumping her sopping pussy at a steady pace. He bites his lip to take some focus off the incredible sensation of her wrapped around his hard cock.

As he pounds her, her ass ripples with each impact, the fronts of her hips being pressed against the smooth, hard desk. His hands move from holding her hips down to her waist, then up to the middle of her back. He holds her down as he fucks her, her tits spilling out on either side of her chest as her presses her onto the desktop.

She gasps as his hard cock pumps away at her. His thrusts become slightly shallower, quicker. She lets out a moan. He has found the perfect spot. Her legs are getting weaker. She can already feel herself getting close to cumming. She realizes she must be getting louder and louder as he has clamped a hand over her mouth. He is grunting with his thrusts, sounding more and more breathless. She realizes he is going to cum soon too. She moves his hand away from her mouth. “Are you going to, going to c—“ Her question is cut off by faster thrusting. His balls are slapping her clit with each motion of his hips.

“Yeah baby, I’m going to cum.”

“I’ve never felt—I’ve never been fil—“ She can’t finish a single sentence. If she keeps moaning, someone will hear. She presses her own palm to her mouth, trying to stifle her pleasure. It builds too high. She finds herself saying, “I’m coming!”
Each of his last thrusts is punctuated by him saying “Oh” and “fuck,” as he spurts, holding her hips impossibly tight to him. The pleasure is too much. Her muscles tense and flex inside of her. She squirts, cumming against his dick. She moans and grinds her hips back against her, reveling in being filled up by his cum. He lets out a gasp as her muscles squeeze his cock. They both pant, trying to catch their breath.

“I think,” he manages to gasp out between deep breaths, “I have found a very special personal assistant, indeed.” He collapses back into his office chair. He notices she has soaked him from navel to knees. “You agreed be my personal little slut. I will understand if that was just a passionate outburst in the moment, but I don’t think it was. From what you’ve done today, I think you need and want to please me. Clear my first appointment tomorrow, and we’ll talk about it then. I think we can do some great work together. Speaking of which, we need to get dressed and back to work. It will have to be a hungry afternoon.”

He passes her skirt to her. When she takes it, he covers her hands in his, pull her close, and kisses her deeply. He runs his hands up her back and grabs two handfuls of her hair. She welcomes his tongue into her mouth and sucks on it gently. They break their embrace and begin dressing again. He hands her her blouse and winks. “That’ll be all for now.”

. . . . .

The next morning, after bringing in his coffee, he beckons her to close the door and sit down. She sits on the edge of the desk, her hands gripping the edge of it, letting her arms push her breasts together.

“What we have so far has been fantastic, but if we are to continue, we will need to establish some rules. It is very important as we need to trust each other completely, and what I need is your willing submission of your own free choice. If you have doubts or anything that makes you feel pressured or coerced, we must resolve them if we are to go further than a few moments of passion. If you would like to stop, you can do so now or at any time without fear of professional punishment or consequences, but once it is over, it is over forever. I will not tolerate any ambiguity in this matter.

As my assistant and pet slut, that will be your role. To make sure my every need is always taken care of—professionally, physically, and sexually. You will always be ‘on call,’ although I will try to limit your time outside office hours. I will need you to be ready to pleasure me at all times. I might ask you to expose yourself for me, masturbate for my enjoyment, suck my cock at any time or place, fuck me or anything else I might think of. You should always be ready to beg for my cock and enthusiastically be prepared to cum for me or take mine.

From time to time, it might be necessary for me to correct or even discipline you, but please keep in mind I do these things to make sure you are the best possible slut you can be. You may even come to enjoy them, but don’t misbehave on purpose for attention. If you have a need, you can always ask nicely, and I will make sure it is fulfilled at an appropriate time.

When you are ready to submit, you may get on your knees and beg to suck my cock. When you swallow my cum, our arrangement will be sealed.”

She stands, unties her blouse, letting it fall open to reveal her bra, and steps forward so her breasts are directly in front of his face, daring him to look down at them. He swallows hard, keeps his gaze level with hers, and rises from his chair. After a few moments, she slowly kneels down. “Now please, Sir, may I suck your cock?” She presses the palms of her hands against the front of his slacks and rubs slowly, lingering a little over the stiffening bulge.

“That isn’t begging.”

“Please, Sir. I need to suck your cock.” She unbuckles his belt, slides it open, and undoes the button and fly to his pants. “I need to feel you in my mouth, filling me up.” She curls her fingers around the waistbands to his slacks and briefs and slides them down, freeing his cock. “I need to suck you off. Please Sir, please let me suck your cock so you can cum down my throat.”

A bead of pre-cum glistens at the tip of his penis. She tears her gaze away to look up at him. He smirks. “Are you sure you want it?”

Still watching him, she slips a hand under her skirt, then brings it out and grips his cock with it, coating it with her wetness. A shudder visibly passes over him. She licks his cockhead. “Yes, Sir.”

Source: reddit.com/r/sexystories/comments/586nzy/a_very_personal_assistant_mf