Submissive Assistant Gets Personal

Just after their last tryst, in horny hopes of tethering the best sex she'd ever known, she set a web alert dedicated to her notoriously off-grid Sir. Despite CEO status with a company due for a publicized update, he maintained his man-of-mystery mode as weeks dragged on. The alert remained dormant, soon forgotten. Months collected and still her sexual appetite subsisted solely on recalling their taboo adventures - a reel she played less often as she lost hope they'd actually play with each other again.

Time trudged on and changed much, but the sudden flash of a screen notification dominated by his name unexpectedly reminded her that one thing certainly hadn't; his power over her instantly, and quite literally, flooded her system. A deluge of delightfully dirty sexual souvenirs overwhelmed her mind and the torrent quickly spread to her sex. Her eyes withdrew from light as her nose drew a calming breath, pausing at the top with a grin forced by the thought of his long-missed musk. Pheromones of an adored lover combined with the perspiration of their exertions had a way of driving her mad every time, but his neck as they hugged goodbye remained her favorite intoxication. Her gut twisted with base desire to withhold her lungs their desire for oxygen, just as her pussy had been denied his cock. Recollection always left her breathless in attempts to hold him - his scent, his voice, his cock, his cum - inside her longer, and she suddenly felt desperate for the spell he cast over her body. Completely humbled by the excitement he could still effortlessly provoke, she forced renewed breath and opened her eyes to the notification.

Sir was looking for assistance again, but this time it was official and posted for anyone to apply. "CEO - Personal Assistant - Pay Commensurate to Experience - 24/7 Position." She didn't need to see the full company post to read between the lines. He's still spending too much time in work mode; he's still willing to generously reward those he deems worthy; he's now openly admitting he needs assistance, apparently at all hours of the night, she mused. Feeling primal urges taking over, she silently debated if he seriously needed a PA or if this was some sort of half-hearted signal meant to lure her back in. Avoiding her own work, she followed the link like Alice down a rabbithole. It cheerfully redirected to his company website Careers page, unsurprisingly populated with postings for engineers and account managers, but asterisks bound the position she found most alluring.

Clicking further down the rabbithole, she found a disappointingly standard list of qualifications and tasks asked of any executive assistant in a big city. Under Driver's License and Passport Required, read the only obviously personalized line: "The perfect candidate will find pleasure in completing arduous and menial tasks for a dedicated CEO without a moment's notice and often late into the evening." How playfully dominating, she laughed to herself before societal conditioning corrected her thought; how creepy and rude, she bemoaned. A quick copy/paste search failed to yield on the top job posting sites. Sir must have realized how questionable that sentence would seem to most anyone else, she surmised. After verifying the company site still showed him as CEO - paired with the unchanged image of his mischievous blue eyes and a perfectly groomed beard framing an ever-charming grin - she salaciously pondered his dick. Her pussy lusted. She glanced back at his job posting and quickly located her admin-related resumé. So far, she hadn't found any new positions worthwhile, but she had to admit that nothing sounded more promising than being his personal fucktoy.

Salivating at the prospect of dedicating herself to his pleasure at a moment's notice, and again being generously rewarded by Sir for such personal attention, she got three pages in before realizing she probably shouldn't submit any damning evidence. She wanted to see him again, but certainly didn't want a paper trail. Refreshing the page, starting over, she watched the cursor blink in the Applicant Name field. Landing on a pseudonym, realizing she gave herself some arduous and menial tasks to legitimize this new self, she laughed to herself, giddy with anticipation to serve Sir again.

-

"Alright, Natasha, thank you for your time and honest answers to my inquiries. Do you have any questions for me while we're wrapping up?"

"Just one: what type of arduous and menial tasks will be asked of me?" She wanted his silence that followed to serve as an answer, but chose to illuminate the voice on the other end of the line. "The posting specifically noted 'arduous and menial tasks'... and late nights... Just curious if you could clarify, in case I had experience in such tasks."

Cooper chuckled, "Ah, sorry. You'll have to ask the CEO that... not sure what he meant."

She tried to calm her voice before responding, "Oh, no worries!" Still came out as a squeak in her timid excitement. She swallowed hard before continuing, "I really appreciate your time today, but I hope to have the opportunity to learn more about the position from him in person!"

"Well, I have a few other calls to make, but I think it's safe to say we would like to have you in for the second phase interview. I'll have Sophie call to coordinate. Thank you Natasha!"

Hanging up the phone, she couldn't help but happy dance. It was a short interview that seemed to go well, with all the hallmarks of a real company looking for a real hire, which she found both appealing [she wanted a new position] and frustrating [she wanted a position under Sir more]. The first phase interviewer had peppered in a couple odd questions with the standard ones, but nothing struck her as a red flag Cooper regarded her as anything other than a good girl looking for a stable job. Good thing admin positions were still low on the list for HR background checks, she scoffed to herself. Deducing all signs strongly suggested the PA duties weren't [just] the kind of personal she craved from Sir, she resigned that a second phase interview still offered her a chance at seeing him. If she wanted any personal attention herself, she'd need to make a good impression and that would take the perfect attire.

-

Adjusting her skirt - the length of which fell somewhere between short and sinful, but ramped up to slutty when combined with black fuck-me stilettos and a sheer blouse - she walked the few blocks to the officespace. While teetering across the sidewalk, she found herself instantly wet and flushed thinking about the last time she'd been in this building with him. She'd ended up face down and ass up with fluorescent overhead bulbs lighting her bare and spread holes while he used her furiously until they both came hard, her for at least the third time in an hour. She shook her head to rid the thought; no time for that now.

Gathering herself with a deep breath, her lust for his scent growing stronger with every intake, she opened the door and met a smiling receptionist. Taken aback, she stutter-stepped, pulling her shoulders back in a quick attempt to ensure the edges of her bra weren't peaking out. A employee welcome shouldn't have been a surprise, but the last time she was here the CEO gave her a personalized, after-hours tour.

"Hi, I'm here for an interview for the CEO PA position... My name's Natasha." She ended up giving a slight questioning inflection to her name because she momentarily forgot her pseudonym as the receptionist offered an earnest but very blank stare. After clearing her throat, "I spoke with Cooper on Monday and Sophie told me today at 4:30pm would be best?" The questioning inflection remained as she squirmed in her attire.

Still unresponsive, the receptionist gave a shrug, picked up her phone, and dialed an extension. "Yes, Sir, I'm sorry, I have a Natasha here, she said- Okay, yes, will do boss!" Overhearing the conversation, she could feel her eager pussy clenching. So close to finally seeing him again, her body could barely contain the excitement and she grew nervous about her wetness traveling down her thighs.

The receptionist guided her up a stretch of stairs that tested the discrepancy between the height of her heels and length of her skirt, and down a long hall and through an arch, veered a quick left across another threshold and was introduced to... Cooper. Disappointed, but trying her damndest not to show it, she gave the man a handshake and introduced herself while taking stock of his looks. To his credit, he was handsome, tan, tall - but not Sir tall - and generally what good girls go for these days. She wasn't good, and she wasn't looking for just anyone, or just any type of fuck. She needed Sir.

Wrapped up in comparisons and disappointment, she realized Cooper had also been silently surveying since she walked into the private office. He had remained propped against the main feature of the room - a large carved wooden desk - as his eyes reached hers in assessment. Something about his eyes made her cower a bit before submissively asking if she could sit in the modest chair well within reach but seemingly on another planet in this space. Both he and the desk stood demonstrably commanding.

To her surprise, Cooper didn't hesitate with his response or blush at its abrasiveness. "No," as he coolly leaned against the desk, shook his head, and raised his hand to twirl his index finger indicating a spin. He offered a calm "please" - a command, not request. To his leering but somehow unoffending evaluation of her, she coyly twirled around for him - her eyes downcast so he could feel free to let his wander - before smirking his way. "Please stay standing." She suddenly felt like a little girl waiting to be chastised, and stood still and quiet, quite unsure why. She didn't want this man, but his energy still screamed safe space. Her weight shifted on the stilettos as she patiently waited for his direction.

Finally, "The CEO prefers to preemptively manage certain personality quirks, and has particular physical attributes he requests of certain employees," Cooper clarified. "Those qualities," he continued, "can be a delicate matter to properly ascertain sometimes, so he asked me to personally and privately screen-" something behind her caught Cooper's eye "-his search for a PA." He finished a bit louder, "And I've been happy to help him," with a wink - not at her, but just past.

Reeling from an unwanted assessment from a stranger while standing in far too minimal fabric, her heart plummeted and her mind raced. Either Cooper knew something of her identity and was toying with her, she deduced, or they were actually looking for a suitable PA and this guy was taking advantage of the applicant pool. She instinctually tugged her skirt down with one hand and put her guard up. "I'm sorry, are you saying I flunked this interview because of seven seconds of physical assessment?"

"No, he's saying you instantly passed."

She didn't need to turn around to know the reassurance from behind belonged to her Sir. His voice instantly bolstered her courage, but until she was sure of the hierarchy of those present, her body froze and clenched in eager anticipation. Her torso twisted as her eyes followed the blonde stranger out of the room, quietly wringing out a sigh of relief as she found Sir in the doorframe smiling her way. He didn't take his eyes off her as his hands directed Cooper.

"Thank you, Coop. I'll take it from here," as he stepped into the room and Cooper wordlessly removed himself, "I'll see you in tomorrow morning's prep," as he closed and locked the door behind. His office was all theirs now. He was all hers now.

"Hello Sir," she smirked, as she extended her right limb for a handshake.

-

"Savannah," he almost whispered, "It's good to see you," and he looked like he meant it as his shoulders dropped and eyes sparkled.

Hearing her real name flow from his lips again, her heart quickly melted and joined the hurricane gathering between her legs. Relaxed with his presence and literally dripping with desire, her body initially sought out his with a leap up onto him, but she managed to suppress the urge. Although her pussy would soon betray her particular need, she found herself far too grateful for his time today to not follow through with the pretense. She reminded herself, interviewees don't jump into the arms of the prospective employer. Ceasing her internal debate, Sir pulled Savannah in for a hug, resting his chin on the top of her head. Although comfortable to stay there hugging him forever, she knew they had limited time with an undisturbed locked office.

She wiggled out of his hug far enough to connect with his eyes, and stated as coyly as she could muster, "I believe I have an interview for the position of your personal assistant." He chuckled softly while letting her go.

"Yes, it seems you do," as he stepped away from her and further into the room - or lair, considering the couch and vice cart in the corner that would make madmen jealous. "I was curious when I saw Natasha's resumé slide across my screen," as he sat back in his executive desk chair, comfortably settling back into the role of superior. "The wording was... suspicious," as he opened his laptop and shifted his gaze to it instead of her. "I asked Coop to verify before I wasted any time on it," he continued with eyes preoccupied by the screen.

Savannah didn't quite understand what he meant, but chose to assume Sir simply trusted Cooper to manage the situation until he was sure it was indeed her. She let out a breath in relief and took a chance with her next, "So you were hoping to use me again!"

"No," he stated with more seriousness than she had expected of him, even after all this time living separate lives, "I really do need a personal assistant." A small, quiet "oh" escaped her. "And," still not looking her way, "honestly," making her sweat, "I'm upset that you thought it would be totally fine for you to come here under the guise of an absurd pseudonym."

She couldn't help but laugh, if only to hide her disappointment. He was right, of course; this was absurd, and she hated the thought of upsetting him. With her eyes downcast, she muttered a soft, "I'm so sorry." His eyes darted her way. Suddenly feeling very silly standing in front of him in her short skirt and thin blouse, she bent to gather the bag she had dropped at her feet. "I shouldn't have come here," as she finished her apology, "and compromised your position," as the bend only exposed more skin.

"Yes," he scoffed, "this could look really bad for me." He closed his laptop and redirected his attention. "Even if we ignore the half-assed application and fake identity," his tone grew more serious, "and forget how bad it would be if someone recognized you," as his eyes traced the curves of her body, "the extremely slutty attire alone is wildly inappropriate for a serious interview," as his eyes met hers, "Savannah."

The way he said her real name again shook away most of her doubts. Loud enough for her to know he wasn't terribly concerned about sound traveling, slow enough to know he optimistically carved out time in his schedule for her. Glancing back at the door to verify it was locked, she stood tall again and took a bolder chance. "I'm sorry," as she began to unbutton her top, "of course you're right," as she tentatively stepped his way and met mischievous eyes again. Finally, she cheered to herself. "I shouldn't have come here," as she stripped the fabric off her skin, "and I definitely shouldn't have worn this."

Apart from a raised eyebrow, he remained unmoved when the blouse fell on his office floor. She slowly made her way around the desk to him as she continued to undress, moving her hands to unhook her bra and shimmy it off her breasts and onto his laptop. He didn't stand or speak, but feet had swiveled his chair her way as his eyes danced across her now half naked body. The want was there, but he often relied on need to spur action.

Growing nervous with his eyes on her, Savannah spun around to bend over at her waist while pulling her tight skirt up around her hips. She looped her thumbs around the exposed sides of her thong to slowly pull it over his favorite asset, down her legs, over her heels. She stayed bent over for him for a few heartbeats, but when he didn't move to test her wetness himself, she turned to find him leaning back with his hands behind his head, accompanied by an obvious hard-on and unrestrained smile.

Desperately wishing for his direction but finding little, she dropped to her knees before him, undid his pants, and found his cock with her mouth - all without a word from him, yay or nay. He was hard, but not the stiffness nor length she remembered. Maybe dicks do change, she lamented; or, maybe he's been dormant for too long, she hoped. Placing her hands on his thighs to better leverage her throat against his cock, she decided to give it her all. She figured she had already compromised herself being there, and although so far he didn't seem interested in actively pleasing her, perhaps she could get off with him anyways. She reacquainted her tongue with his shaft as she toyed with the head at her throat, deciding to make it vulnerable to his semi-hard cock.

At the moment she felt the head pop and slide into her throat, and forced her gag reflex to relax, she felt his hands in her hair. Suddenly he was gently holding her head, firmly pressing down. A wave of panic at the blocked airway gave way to immense pleasure in knowing he was enjoying this too much to let her up quite yet. She felt her pussy drip as his shaft grew harder and longer in her filled mouth. She couldn't help wondering if her heels would inadvertently catch evidence of her lust. She tried recalling the location of the nearest bathroom so she could clean up later. As she mentally traced back her steps, he finally spoke, but it felt more like a guttural growl.

"You think I'm so easily manipulated?" as he held her face down on his dick. "You think you can just saunter in here and I'll drop everything to make you cum on my hard cock?" Between the pressure on her throat and the shock of this sudden and aggressive - albeit ever accurate - assessment, she could barely breathe.

Let alone think.

She pooled remaining resources, shifted on her weakening knees, and held her breath. He guided her head back by a grip of hair near the nape of her neck. Before, he may have asked if she was okay with the brief lack of air. Now, domination swelled in him faster than affection. Her next heartbeat found his hands gently but firmly reversing his motion, forcing his rock hard cock across her wet lips and into her throat again. Savannah revelled in feeling him inside her again as her mind drifted to his intentions for her. He may not admit he missed her or needed her, but, she reassured herself, his cock sure betrayed him.

Before she could give serious thought to his machinations, he held her head down onto him and stated seriously, "I am not yours to manipulate and bend to your will." His dark tone tested the limits of the game as he continued, "I'm too busy with the actual needs of my company to waste time on discipline." She pressed her hands against his thighs and looked up at him desperately. "But because of our particular history, I'll take care of you myself," as he let her gag force his cock from her to gasp a breath, "if you'd like."

He had quite literally left her breathless, but he already knew the answer. She mustered a muffled confirmation, to which he commanded a necessary addition with a playful smile. He let her up just enough for her to now manage an eager "Yes, Sir."

-

With her consent given, knowing the no-means-no rule still stood for them as the effective admissible safeword, he took her by a healthier grip of her hair. "I've had a rough week," he asserted as he pulled her willing mouth up from his hard cock, "so I'm going to enjoy this," before grabbing her ass up and twisting her so she was bent forward over his desk. He pushed her left cheek to his desk and ordered, "Your face stays on this until I say otherwise." Determined to properly steady herself, she held the far edge of his desk as her back arched to keep her ass up and legs straight, slightly spread.