Smart Girls Give Head to Get Ahead

It all started because of her new hire headshot. Elaine was notified by email late Monday afternoon that a photographer was coming in Thursday to take headshots of the new hires. Normally she was unconcerned about her appearance, gladly choosing a few extra zzzz's over waking up early in the morning to spend an hour in front of the bathroom mirror. The full extent of her current hair care routine consisted of blow drying her hair with her car's heat on high during her commute, before hastily applying some lipstick in the parking lot and heading into work.

The company she had just started with, SG Industries, featured photos of all of their staff on their website. Even the executive support staff, like herself. She thought about the last headshots she'd had done for her last job. They were just meh, so Elaine typed into google "blow out near me" 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 in 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 Elaine left the salon at 9am, gorgeous long curls framed her face, cascading down her shoulders like a brunette 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 pale complexion and her outfit. With that the transformation from girl-next-door to office bombshell was complete. Elaine was so happy with the results that she bought the tube of lipstick from the stylist- she wanted to look like this every day if she could!

Walking in to work, Elaine turned more than a few heads. She was already the "new girl" so she was a bit of a curiosity. Instead of feeling the usual discomfort she was accustomed to when in the spotlight, she actually felt freer and more confident. She found herself posing with ease for the camera and the photographer definitely took a few extra snaps.

Her colleagues noticed, and she was invited to eat lunch with a group of them. That is how she found herself instead of reading the novel she had tucked in her purse at lunch from the safety of her car, she joined a group of sales and support staff in the lunchroom. And it was there that she was invited out for drinks after work with the "in crowd", who were all headed to a trendy downtown bar that had strong cocktails and tiny servings.

At drinks, she surprised herself further by speaking animatedly, and she soon found herself the center of attention with her colleague. She also felt the attention of other bar patrons, both men and women. She could scarcely glance around the room without her gaze being intercepted, met with either a nod or a wink, and even the occasional stare. Whether it was the conversation, the attention, or the cocktails, Elaine suddenly felt a bit overwhelmed. She excused herself to go to the ladies room.

To her dismay, a colleague of hers elected to join her. Kristi was an executive assistant, like herself. Kristi supported the CEO, while Elaine supported the less important COO.

"You know what they say, a girl can't go to the ladies' on her own!" Kristi joked as the women navigated the crowded path to the restrooms. Even as they walked, Elaine felt eyes on her, and she found herself enjoying it, shaking off her prior unease. Who knows, maybe she'd meet a sexy stranger tonight? Maybe her life would change forever.

In the restroom, the girls each tended to their needs with Kristi chattering a mile a minute. The girl didn't usually pay much attention to Elaine, but for whatever reason she wouldn't shut up. Maybe it was the alcohol, or maybe she just regarded Elaine as "part of the club" finally.

Elaine zoned out Kristi's gossip as she washed her hands, and the girls left the restroom together, Elaine in the lead. As she stepped out, she barreled into Chris Connery, the company CEO, who must have been walking towards the men's room. Elaine apologized profusely, stammering over her words. This was her first close encounter with the "Big Boss" and she was mortified to have essentially body blocked him. Which was laughable, because he towered over her 5'3" frame, making it all the more embarrassing.

"Oh it's alright," Chris smiled down at her and he placed a hand on the small of her back with a sexy familiarity. "You're Elaine right? I was meaning to ask you- there is something I'd like to discuss with you tomorrow. Can you come to my office at 4:45pm? It won't take long, I promise."

Elaine blinked slowly, racking her brain to think of what he could possibly want to discuss with her. She came up with nothing. Hopefully she wasn't getting fired. Maybe they would at least send her her headshot so she could use it on the next job hunt. Finally Elaine nodded to the CEO and said, "Yes, Sir, of course I can do that." She didn't recognize the voice that came out of her mouth as her own. Elaine and Kristi returned to where their table where the group was still going strong/

Elaine didn't remember too much else of the conversation that night, except that Kristi was quieter than usual. She nursed her remaining cocktail, and tried not to despair. She didn't want to be the first to leave, and thankfully someone called the first Uber, and soon after Elaine did the same, saying goodbye's around 9pm.

The next day at work each hour seemed slower than the last. Friday's her executive took it easy, and she completed her work easily by noon. She spent the rest of the day looking as busy as possible, trying not to draw attention to the fact that she didn't have much to do. Finally it was time, and 4:45 Elaine knocked on the CEO's heavy wooden double doors. "Come in!" He called. Elaine pushed open the doors and glanced briefly back towards Kristi, still at her desk wearing her headset. She seemed to be gathering her things to leave, though slowly. Elaine wondered if Kristi knew the reason for the meeting. When people were getting fired, the EA usually had a heads up. No doubt Kristi would want to know the entire scoop so she could share on Monday.

Elaine walked through the doors, releasing the heavy door. It closed loudly behind her, and Chris motioned for her to sit in one of the seats opposite his desk. His attention was fixed on the monitors in front of him as he finished a call. She sat down quietly, self conscious of the knees peeking out of the hem of her skirt. She smoothed the hem of the skirt and tried to not appear as anxious as she felt. Before long she heard the familiar closing comments as Chris tried to wrap up the call. He glanced at her for the first time now, and while making an impatient gesture with his hands, as if the person on the other end was holding things up. And then the call was done and his intense gaze was immediately upon her.

"So." He started in, "You've recently started with us, correct?"

"Yes, Sir."

"And are you happy here?" He interrogated further. "Do you like supporting Samuel? Things are going well?"

"Yes, of course!" Elaine answered, cautiously optimistic that her 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 Samuel. 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? Seemingly oblivious to her 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 grow. And what I like more than anything is to see 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. But enough about me,?"

Elaine didn't have to think twice. This was her dream job, her dream company, and her dream opportunity. She could scarcely believe this was happening- it felt just like whiplash. Finally she found her voice.

"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 it wasn't someone else's livelihood they were discussing.

"There is, however, one condition of your promotion, and I'm afraid it is non negotiable." Chris told her, still from behind.

Elaine swallowed. Chris still had one hand on her shoulder and he kept it there as he adjusted the chair next to her so that it was facing hers. Then he sat down, taking one of her small, delicate hands in his.

"Our dynamic needs to be one that is deep and fluid, and it needs to be built upon trust and a high level of communication." He began. That was logical, Elaine thought to herself.

"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 couldn't quite comprehend what he was saying to her, so she just nodded wordlessly, her eyes wide. The hand holding hers suddenly felt less comfortable and friendly.

"Starting today, and every Friday afternoon forward, you will serve me, submit to me, sexually, right here in this office." He continued. "You are so sexy, so beguiling, 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 felt like it was the polite thing to do, especially when she was being complimented so heavily by someone in power over her. But 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 easy.

"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 compensated extra. 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 what he was proposing 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. It was as if he brokered promotions for sexual favors every day of the week. Who knows, maybe he did? The CEO leaned back comfortably in the chair. "Now I want to see what you have to offer me, young lady. Stand right here for me, and strip everything off, slowly."

Elaine stood at once, for him. Something came over her as she mentally prepared to take her clothes off, for her boss, revealing her stunning body, and taking one step closer to the job of her dreams. Ordinarily, she would feel shy and uncomfortable when getting naked for the first time with a new man, and she'd never been with a man as sexy as the CEO was. He was probably late 40's, early 50's, and fit, with a perpetual 5 o'clock shadow and a sprinkle of silver to his hair. But the way he had spoken to her just now, and the needs he had described had turned her on. She felt desired, alluring, and she felt like showing off, maybe even being a tease.

She met his piercing gaze with an intensity of her own as she took off first her blouse, then unzipped her tight pencil skirt. Elaine took her time folding each nicely and laying them on the chair beside her. She felt his hunger to see the rest of her with each slow and deliberate step, she felt his desire, and it was intoxicating. Finally when she was clad only in her nude pumps, a black lacy thong and a black bra, she pointed her eyes down at the ground as she unclasped her bra, releasing her full, beautiful tits, which were met with a sharp intake of breath from her boss. Buoyed by his approval, she looked right at him now as she shimmied off her panties, stepping carefully out of them in her heels, before tossing the panties at him and placing a hand on her svelte hip. She felt like a supermodel, naked in her boss's office, except for her high heels.

Chris was visibly affected, Elaine could see the bulge in his suit pants. He got to his feet and approached her, 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 against one perky pink nipple, his other hand tracing the delicate line of her opposite collarbone. He breathed in the floral scent of her hair, still wavy from yesterday's blow out.

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, parting her labia slightly, and making her moan. Embarrassed, her hands covered her face, and Chris chuckled as he probed further to find her wet, warm center. With his fingers now naturally lubricated he explored the folds of her labia, teasing her sensitive clit before taking his hand away. Bringing his hand to her mouth, Elaine instinctively opened for him, and his fingers went roughly into her mouth. He groaned with satisfaction and ground his pelvis into her ass as he forced her to taste herself for him.

Tasting her own flavor was so forbidden, so sexy that Elaine could barely conceive of it. Yet she hadn't even thought twice before opening her mouth for him. What was happening? She felt unrecognizable, like a slut. And it turned her on.

Turning her to face him with a single motion, Christ kissed her for the first time. He kissed aggressively, possessively. His lips covering hers, his tongue invading her mouth, and she knew he was tasting the flavor of her most intimate part, from own tongue. Delirious with desire, all she could do was hold on to his shoulders and kiss hungrily back as he tongued her mouth. His hands groped all over her body, as if he wanted to touch every inch of her at once. Time stood still until finally Chris broke the kiss, a fistful of her luscious dark hair in one hand. She felt him tilt her head back slightly and she looked up at him eager, but still unsure. "It's time for you to show me how you can be a good girl for your Daddy."

Fuck, fuck, FUCK. Elaine, more turned on than she could ever remember being, felt her pussy gush once more. Is this the kind of sex she'd been missing out on all these years? If she could feel like this every day, she would gladly wake up an extra half hour earlier to curl her hair. Fuck.

Chris guided her to her knees before him now, his hand still holding her firmly by the hair. As rough as it was, it helped to get to her knees without falling, because she was still in her heels. The CEO unzipped his pants and out dropped the most perfect cock she'd ever laid eyes on. If there had been a table, it would have made a thud. Up until now she had been worried there might be a catch, but he was bigger, thicker and somehow infinitely more attractive than any of the fumbling, dorky guys she'd been with before, she felt like this was a cock she could, and should, worship. Immediately.

Elaine's mouth opened instinctively, tongue at the ready, and Chris sighed with pleasure as he slipped his member between her lips. She was his property, and he wanted to try out all that she had to offer him. Focusing on the task at hand, Elaine focused on keeping her tongue on his cock as she moved her mouth up and down on his member, flicking the tip with each stroke as it came out, and focusing on keeping her full, thick lips tight to the shaft on the way in. She had always loved sucking cock- but something inside made her want to give this man the best blow job of his life, right there in his office.

Chris observed his new little fuck toy as she sucked his cock, allowing her to control the fellatio as long as he could stand it. Before long Elaine felt his cock starting to pulse urgently and she realized he was getting close to climax. Usually her partners would fumble at this point, and break the mood by apologetically asking if they could cum in her mouth.

But not her boss. With one hand fisting her by hair, he brought his other hand to grip her throat firmly and he began to fuck her face. All she could do was hold her mouth open, trying to relax her throat to accommodate him. Willing her stomach to behave and not betray her at this critical moment for his orgasm. Tears welled up in her eyes from the rough face fucking, dear god, please cum soon, she thought to herself.

His cock grew larger and harder as his orgasm neared and she couldn't help but reach a hand between her legs to furiously rub her wet little cunt. Chris noted this with amusement but he seemed to pay no mind, instead focused on pumping harder and harder until he finally succeeded in fitting his entire length down her throat with a quiet pop. Holding her head more tightly in place, he glanced down in satisfaction at her wide eyes. She saw only pure, primal desire on his face and she felt her cock throb and something slip down her throat. Elaine realized he was finally cumming.

With disappointment she discovered she could barely taste his cum as his cock was so deep down her throat, but she felt every spasm of his hard cock and he made the sexiest groaning noises she'd ever heard as he finished, withdrawing his cock partially. Finally she was allowed to breathe. Even as she gasped for air, Elaine felt her body start to erupt from the attention she was paying to her clit, she was such a slut that she was orgasming herself, so heavily turned on from the rough treatment he was giving her.

Chris ignored her orgasm. He knew that one day, she would only cum when he gave her permission. But there was plenty of time to establish that. Giving a few final pumps to her throat, he ensured he had fed her every last drop of his cum. No sense getting a drop on his suit, when he had the perfect whore in front of him to take all of his cum. Smiling down at her, he pulled as his cock from her mouth and appreciated the drool mixed with cum that dripped out with it. She wiped at it, seemingly embarrassed.

"My dear... that was even better than I expected." He told her as he zipped his fly. "Usually hot girls like you aren't that great at sucking cock."

Inwardly her eyes were rolling, though she smiled for him. She had the impression that he wouldn't appreciate a blatant eye roll, and he was, after all, her boss. Even if he'd just used her skull like a fleshlight. Self consciously, she tried to wipe the tears from her cheek and the drool and cum from her chin. Chris finished tucking his cock back into his pants before handing her a few tissues to clean up the saliva, cum, and tears from her face. She was glad she hadn't worn a lot of makeup today, not like yesterday at least. Hopefully there wasn't too much in need of fixing. Sensing it was what he wanted, Elaine remained before him on her knees. Chris took her chin in his hand, tiling her head once again up towards him.