Elaine’s work email inbox pinged late Monday afternoon with an email about upcoming new hire headshots. Skimming it, she read that a photographer would be there Thursday to take headshots of all the recent new hires, like herself. She wasn’t one to spend a lot of time on her appearance, she liked to think of it as “prioritizing beauty sleep” over spending an hour in front of the mirror. She had perfected the dashboard-heater-blow-dry method during her commute, which was the extent of her hair care routine, and occasionally adding some lipstick in the parking lot.
But her new company featured their staff proudly on their website. Even the executive support staff, like herself, were posted. The last headshots she’d had taken were probably from the year she graduated college. She didn’t love them; she thought she looked too plain. Elaine typed “blow out near me” into her browser search bar and sure enough- there was a salon just down the street from her work with an 8am opening.She booked it, figuring that the one-time cost would be worth it if it resulted in a gorgeous headshot. What could it hurt?
The next morning Elaine and her coffee were the first ones to the salon. The stylist, after taking one look at her thick, long hair, made the executive decision that today they were going to “go big”. When she left the salon at 9am, gorgeous long curls framed her face, cascading down her Shoulders like an auburn waterfall. The stylist had taken a few minutes to apply some makeup too, foundation, eyeliner, mascara, and a touch of eyeshadow to highlight her hazel eyes. Then a little bit of bronzer, and the perfect shade of lipstick to compliment her complexion and outfit. The transformation from girl-next-door to office bombshell was complete. Elaine, delighted with the results, tipped extra and bought a tube of lipstick in the same shade from the stylist. She wanted to look like this every day if she could!
Walking in to work, Elaine turned more than afew heads. She was already the “new girl” so she was a bit of a curiosity. But because of the makeover, all the extra attention didn’t both her. If anything, she found herself enjoying the spotlight, she felt freer and more confident. When it was time for her headshot, posing for the camera felt natural. She couldn’t quite be sure but she got the impression the photographer took a few extra snaps.
Whether it was the makeover that broke the ice or not, Elaine was finally invited to eat lunch with a group of her coworkers. So, instead of passing the hour reading a novel in the quiet of her car, she and her turkey sandwich joined a group of sales and support staff in the company lunchroom. Then, by the end of lunch she was invited out for drinks after work.
At drinks, she found that conversing with her new colleagues was surprisingly easy, especially outside of work. She was also surprised because quite a few members of the Executive team were there, though they arrived sepaRately from the larger group. Even the CEO joined the group. And the entire party, whether a member of the C-suite or not, all seemed to get along well and enjoy each other. That was a good sign, she thought to herself, this is hopefully going to be a fun place to work.
Elaine had left her last role, a remote position where she was the executive to the CEO, because she realized that working remotely as a young, single girl was not all that it was cracked up to be. She liked the occasional work from home day, but for a naturally quiet person like herself, work was basically the only place she was likely to make friends. Or even to meet anyone. She hadn’t had a serious boyfriend since college, and her mother was beginning to joke that if she got another cat she would stage an intervention.
There was a lull in the conversation just as the cocktails hit her bladder so Elaine exhausted herself to the ladies room. As per the custom, a couple other women decided to join her. One, Kristi, was an executive assistant, like herself. Kristi supported the CEO, while Elaine supported the less important COO. Miranda came too, Elaine thought she worked in the Sales Department
“You know what they say, a girl can’t go to the ladies’ on her own!” Kristi joked as the women navigated the crowded bar towards the restrooms. Elaine scanned the room on the way, thinking of the possibilities. Who knows, maybe she’d meet a sexy stranger tonight?
In the restroom, the women each did their thing with Kristi chatting a mile a minute. Currently she was on the topic of each of their co-worker’s office dating histories, which Kristi seemed to have a keen interest in. Up until today the woman had barely spoken two words to Elaine, but for whatever reason she wouldn’t shut up tonight. Maybe it was the drinks, she’d had more than a few. Or perhaps she finally considered Elaine as “part of the club”.
As much as she hoped to fit in, Elaine also didn’t enjoy gossip. She zoned outKristi’s words as she washed her hands and touched up her lipstick. Her blowout was still holding strong. Once everyone seemed ready, Elaine led the way to the door. She was anxious to escape the bathroom and finish this conversation. Stepping out, she exclaimed as she came into contact with what felt like a brick wall. To her horror she had barreled into the company CEO, Chris Connery, who must have been trying to walk past the women’s room on his way to the mens’.
“Whoa, where’s the fire?” Chris exclaimed while feigning injury. At least she hoped he was faking, she had definitely made some solid contact so perhaps he really was feeling it too.
Elaine began trying to apologize. Just when the night was going so well, then clumsy, awkward Elaine just had to butt in. By body slamming her new. hot. Boss. If it wasn’t so mortifying it could be funny, considering how he towered over her, taller by at least a head.
“It’s ok…” he replied quickly, waving off her apologies.He sounded sincere at least “I’m Chris, and you must be… the Incredible Hulk?”
Great, cute AND a sense of humor. Was he flirting?
“Yep that’s me, after a couple of cocktails then no one is safe!” She flirted back. Where was this banter coming from? Certainly not her. But she could feel her mouth was moving, and yes, that was her voice. And he was laughing!
“You should see what’s left of the bathroom attendant.” She quipped.
“Well then I guess I’m lucky.” He told her with a smile while leaning in towards her. “I’d rather run into you than Bruce Banner seven days a week.”
OK yes, he was definitely flirting. But he probably does that with everyone, she told herself. Realizing that Kristi and Miranda were stuck in limbo in the bathroom doorway behind her, Elaine had to move even closer to her boss in order to pass him in the narrow hallway. As she brushed by him, his hand encircled one of her wrists, causing her to pause, their bodies almost touching, her face inches from his.
“It’s Elaine, right?” He queried. “I mean to ask you actually- there is something we need to discuss tomorrow. Come to my office, say 4:45pm? It won’t take long, I promise.”
Elaine blinked slowly, the thrill of flirting replaced by racing thoughts. What could he possibly want to discuss with her? She thought and thought but came up with nothing. She just prayed she wasn’t getting fired already. Maybe if they did they would at least send her her headshot so she could use it on the next job search. Since it had proven such good luck here, clearly.
Elaine wasn’t even sure what exactly she said, but she knew that she had agreed to the meeting. The entire walk back to the table was hazy too. She spent the rest of the night pretending to follow along with the conversation, but in reality she was just waiting for someone else to call it a night, so she could cut out, too. While nursed the melted ice of her remaining drink she tried not to despair. MercIfully someone finally called the first Uber, and soon after Elaine followed suit, saying goodbye around 9pm.
The next day at work each hour seemed slower than the one before. On Fridays her executive apparently liked to keep her schedule light, and Elaine’s tasks were easily done by noon. She spent the rest of the day trying to look as busy as possible, hoping not to draw attention to the fact that she didn’t have much to do.
By 4:30, Elaine had discretely organized her desk, in case she had to pack all of her belongings when she returned to it. Then she had just enough time for a glass of water and a bathroom break. At 4:45 sharp Elaine knocked on the CEO’s wooden double doors.
“Come in!” She heard him call. “Don’t worry, those doors are Hulk-proof!”
Elaine opened the door closest to her, stealing a quick glance back towards Kristi’s desk. The executive assistant to the CEO sat at her desk, headset in place, typing rapidly. Besides a curt nod, Kristi hadn’t acKnowledged Elaine’s greeting when she’d checked in a few moments before. The silence was particularly awkward given that Elaine still had no idea what this meeting was for.
She wondered if Kristi knew the reason for the meeting. When people were getting fired, the EA usually had a heads up. No doubt whatever went down, Kristi would know, or pretend to know, the entire scoop so she could share on Monday.
Elaine brushed aside these thoughts as she entered the office. The heavy, “hulk-proof” door closed with a thud as she took in his office. The space fit the high-rent style of the rest of the firm, and was private except for the floor to ceiling windows overlooking the city below. Chris was leaned back in a chair behind a heavy gray washed wooden desk, his attention glued to the monitors before him. She could tell he was still on a call. After a moment he motioned for her to sit in one of the ox blood leather armschairs opposite his desk.
The friendly, flirtatious colleaguess from the night before was gone, and today’s CEO was in full business mode. From his side of the conversation, whoever was on the other end of the call had fucked up. Chris mentioned this fact, frequently, as he lit into the unfortunate individual, demanding accountability and a solution.
Elaine sat down quietly, thankful she wasn’t on the receiving end of this tirade. While smoothing the hem of her pencil skirt, and wishing Suddenly that it covered her bare knees, Elaine tried not to appear as anxious as she felt. Before long she heard the familiar closing comments as his call wrapped up, punctuated by a few more f-bombs. As soon as the call ended, the CEO’s eyes were on her.
“So.” He started in, with the same authoritative tone from the conference call. Hopefully she wasn’t about to get cussed out too. “You’ve recently started with us, correct?”
“Yes, Sir.”
“And before S&G you were with Prather, correct? In their Denver office?”
“Umm, yes sir. Remote,but yes Denver was my home office.” She responded, unable to hide her surprise. How did he know that? He must have reviewed her CV.
“It’s been a week. Enough time to form a first impression.” He interrogated further. “Do you like supporting Samantha? Things are going well?”
“Yes, of course!” Elaine answered, cautiously optimistic that her prior fears were unwarranted. Perhaps this was just a typical new hire check in?
“Ok. That’s good to know.” Chris was looking at her even more closely, if that was possible. “Because I have to be frank with you, I have some concerns. I think you may not be a great fit with Sam. Other people have expressed the same concerns, too.”
Elaine’s heart dropped. She had been right- how could she lose her job just as things were starting to go so well? Oblivious to his subordinate’s racing thoughts, Chris jumped up from his seat and went to look out the window before continuing.
“We need to make an adjustment, and soon. I’d like to offer you the opportunity to move into the role of my EA, with a clear career path to Chief of Staff.”
Elaine’s despair turned to confusion. But something inside held her back from speaking, and when she didn’t respond, the CEO walked behind her and placed a hand on each of her shoulders.
“You have what it takes to really excel in this role. And what I enjoy more than anything is watching my Employees blossom and grow under my guidance. I need an assistant who is an extension of me, my right hand. Someone who I trust to keep my confidence, and to follow my every lead. Even if it’s uncomfortable, I need a deep level of trust from my assistant. I’ve been looking for a long time, and from what I see, you are about as close to perfect as one could be.”
Elaine could hardly believe her ears, but she also didn’t have to think twice. She was driven, intelligent, and it was true that she was overqualified for the role she’d been hired for. She’d just been so desperate for something new when she was interviewing, so she’d settled for the assistant to the COO role..
But what he was offering, this was her dream job, her dream company, and Chief of Staff was her dream opportunity. She could scarcely believe this was happening.
“I would love the opportunity to support you.” She spoke earnestly. “And to move into Chief of Staff one day. That has always been my end goal.”
But then she paused. “But what happens to Kristi?”
“Oh you don’t need to worry about that, this conversation is just about the relationship between you and I.” Chris told her, waving her worries off as if they weren’t discussing someone else’s livelihood.
“There is, however, one condition of your promotion, and I’m afraid it is non negotiateable.” Chris told her, still from behind her body.
Elaine swallowed. His hands left her body as he circled her chair before taking a seat in the chair beside her. Now they were eye to eye, and Chris took one of Elaine’s handsbetween his own. If the hands on her shoulders had been borderline appropriate, hand holding was definitely crossing the line. As uncomfortable as she was, she also realized with surprise that she didn’t want him to let go of her hand.
“Our dynamic needs to be one that is deep and fluid, built upon both trust and honest communication.” He began.
Elaine nodded, but stayed silent.
“The best way to establish this type of relationship, I’ve found, is through sex. Specifically, D/s style sex. Is that something you have heard of before?”
Elaine hear his words quite clearly, but for some reason her comprehension was delayed. She simply nodded her head slowly, her eyes wide. Inside though her thoughts were racing. Sex? D/s? Did he mean BDSM??? Suddenly an image of her boss, clad only leather assless chas came to mind. Was he going to like, spank her if she overbooked his calendar? Flog her for a missed email? She stifled a laugh, as uncertain as she was about where this was leading, she could tell that to her boss, this was not something to joke about,
“Starting today, and every Friday afternoon forward, you will serve me, submit to me, sexy, right here in this office.” He continued. “You are so sexy, so begining, and not only do I want you to be my right hand in work, but I want, No, I need to use your sexy body to get me off.”
Elaine nodded again, not really in agreement, but because she feel like it was the polite thing to do. Especially when she was being complimented so heavily by someone in power over her. Chris took her nod at face value. He was after all, a CEO, and he was used to getting his way, however peculiar the request.
“Good. This is the fastest way for you and I to develop the communication and working relationship we need, and for you to understand my needs and be under my control.” He spoke frankly now. “Every Friday. No excuses. There may occasionally be other times I need you, but you will be compensatedextra. And of course what I am offering comes with a decent bump too. Do you agree to this arrangement?”
Elaine could scarcely believe her ears, nor could she comprehend how her body was responding to his words. As crazy as his proposal sounded to her logical mind, the sexual side of her was extremely turned on. She could tell her panties were soaked. Could he tell? Elaine found herself nodding, then agreeing, albeit with a pink tinge of blush to her cheeks.
“Excellent!” Chris clapped his hands together and rubbed them in anticipation. Kind of like he brokered promotions for sexual favors every day of the week. Who knows, maybe he did? The CEO sat back confidently in the chair. “Now I would like to see what you have to offer me, young lady. Stand up, please, and strip everything off, slowly.”
Elaine stood at once for him, surprising herself. An air of confidence came over her as she steeled herself for what she was about to do. She’d agreed, sure. But once she took tHis next step, there was no going back. But for some reason she wasn’t nervous. Something in his speech had made her want to take her clothes off for him.
Ordinarily, she would feel shy and uncomfortable when getting naked for the first time with a new man. And the truth was, she’d never been with a man as sexy as him. He was probably late 40’s, early 50’s, fit, with a perpetual 5 o’clock shadow and a sprinkle of silver to his hair. But she suspected that what turned her on even more than his physical appearance, was his talk of using her, and of controlling her. The commanding way he ordered her to strip, and how she obeyed without thinking twice. It made her feel desired, alluring, powerful in her own right. And right now she wanted to show off, maybe even be a little bit of a tease.
Elaine met his piercing gaze with an open stare of her own, smiling slightly while unbuttoning her blouse, then dropping her gaze to unzip her tight pencil skirt. Taking her time folding eachitem neatly, then setting them on the chair beside her. She could feel his hunger to see the rest of her with each slow and deliberate step, could feel his desire, and it was intoxicating.
Now clad only in her nude pumps, a black lacy thong and a black bra, she looked down at the ground and unclasped her bra, revealing her breasts. The effect was a sharp intake of breath from her boss. Buoyed by his approval, she met his gaze While shimmying out of her panties, stepping carefully with her heels. Tossing the panties on the chair, she completed the pose a hand on her svelte hip. She felt like a supermodel, naked in her boss’s office, except for her high heels.
Elaine could see the bulge in her boss’s suit pants. Chris stood before approaching her with an air of appraisal, grazing a hand below her navel, his eyes slowly taking in every inch of her body. His body for the next few hours, his property.
Then he was behind her, towering over her as his fingers brushed againt an erect nipple, his other hand tracing the delicate line of her collarbone. He breathed in the floral scent of her hair, still wavy from yesterday’s blow out. Suddenly he cupped her breast in his hand and squeezed hard, and Elaine cried out softly in surprise.
Then his hand found her navel, pressing her body back against his, and Elaine felt the hardness of his cock against the small of her back, while his other hand slowly ventured down between her legs. He parted her labia slightly, making her moan. Immediately her hands came up to cover her face in embarrassment, and Chris chuckled as he probed further to find her wet, warm center.
With her natural luxury he explored the folds of her labia, probing gently. Elaine’s legs couldn’t help but bend a bit at the knee to open herself even wider for him. He rewarded her by teasing her sensitive clip for a moment, eliciting a moan, before taking his hand away just as abruptly.
Then his fingers were in front of her face. Elaine instinctively opened her mouth for him, and he rewarded her by shoving them roughly inside her mouth. He groaned with satisfaction while grinding his pelvis into her ass as he forced her to taste herself for him.
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