How to Please the Boss Ch. 01

In comparison to the majority of jobs he'd interviewed for this future working space was spacious and bright. It offered a stunning view through the large open windows showcasing the beach. As well as offering ample sunlight it also offered opportunities for ogling attractive women in their bikini's, which was better than his previous job where the bloke opposite him had been known as fat Dave.

Before his imagination got too carried away, he instead focused upon the sharp-looking woman before him, who continued fiddling with several papers before her before speaking.

"So," she asked, "you are happy with the offer?"

Nodding, Victor couldn't quite believe the salary and benefits that went in it for what, on paper, appeared to be a basic receptionist position.

"Very," he admitted, "but I am confused by the generosity of the offer. Apart from my degree, I've only got two years experience working..."

"The Directors are aware," the woman interrupted, "but as is mentioned in the contract there are several special requirements that, if not followed, do reduce your pay to a base level, as well as the first six months being probationary. The expectation is that you follow any and all requests of both Directors, although you will be exempt from anything other than polite courtesy from the remaining managerial team. You answer to Director Manning and Director Donaldson only."

"Anything you can tell me about these special jobs?"

Smacking her lips, she seemed annoyed by the very question.

"Legally, not until you've signed the contract, as it binds you to an NDA."

Concerned that this job would lead to his involvement in illegal activities, Victor knew that if he turned down the offer he'd probably never get the opportunity to earn this much again. Being an insurance business, surely there wasn't too much illegal that he could be asked to do. Was there? According to the job specifications, he was barely going to be involved in that side of things anyway, rather being focused up sorting appointments and keeping the two directors happy as the bulk of the work.

Having met both Directors earlier he surmised that Director Donaldson was late forties, early fifties if he was any judge. She wore basic makeup and plain clothing over her frame, while her face was that of a teacher he once fantasized about. Sharp, prone to scowling, but when she finally smiled it caused shivers down certain organs. It didn't hurt that her hair was closer to silver than grey, attracting him like a bird to shiny things.

On the other hand, Director Manning was younger, in her mid-thirties, with dyed bright blonde curly hair, she was tall and curvy, wearing light blue shirts that clearly revealed her hefty bust. Her plump lips were bright red and her blue eyes sparkled, yet he felt like there were hidden depths not yet revealed.

Both of them, when they'd had brief conversations in their individual offices located directly next to the other, had been polite but stern.

If he took the job, Victor would be working for them, a necessary cog in their machine, but not a unique cog. They had been quite clear that, if he wasn't willing to put in the effort, there were others who both could and would.

"Then," Victor smiled, looking over at the sharp-faced woman, "if you're happy, I will sign."

"Good," she nodded, clearly happy even if she still didn't smile, "you will not regret it. If I didn't need to move in with my mother in Wales I wouldn't leave. I'm glad that both of them will be looked after by someone competent and able. Although," she admitted quietly, lowering her voice, "when they chose your application between them I was surprised. You'll be the first man in this position since it started a hundred years ago. Not," she raised an eyebrow as if imparting a secret, "that Directors Manning or Donaldson were around then, no, they are of course more recent. but historically, it's very strange."

"Colour me surprised," Victor smiled weakly. Putting down the pen, his signature on the contract, he couldn't get his mind off what had been dangled before him, so he asked once more.

"What exactly are these special jobs?"

------

Upon learning the content of the jobs, his eyes froze upon her face.

"Really?" He asked stiffly, "I'm expected to..."

"Yes," she confirmed, "the instructions are as I have informed you. Each office has a different manner to inform you if they require your services. Director Manning will call you in for a 'special meeting', while Director Donaldson presses her call button three times."

"That," Victor gulped, "is not what I, I must admit I don't, well, I didn't think..."

"It would be a shame if you changed your mind now," she warned him, "as you may find it difficult to find a job elsewhere, especially if any of the information you have just been told was leaked. It would be denied of course, the torrid revenge story of a man who was never offered a job in the first place. Or," she added, finally smiling, although it could have been smirking at Victor's discomfort, "you can turn up on Monday, get paid generously, and gather valuable experience as you do so."

He could leave. He could if he wanted to, and the special jobs... He was twenty-three years old! Was this really what he wanted to do? But also, he considered, he was only twenty-three years old. Did he want to lose his chance at such a role just because he lost his nerve?

"I'm in." He agreed.

Standing up to shake his hand, the previous receptionist smiled.

"You've made the right decision, Victor, and with good timing." This time her smile appeared genuine as lights flashed on her desks landline. "Director Donaldson is calling. Enjoy your weekend young man because, come Monday, you're going to find out if you're good enough to earn that paycheck."

Walking out of the office, removing the tie that was stifling even without the twenty-five-degree heat, unusual for spring. He walked along the beachfront, completely ignoring a gang of bikinied beauties walking before him. Even the sight of women essentially wearing thongs in public couldn't take his mind off his current worry.

Either he'd made the best decision ever, or the absolute worse. Only time would tell which.

----------------------

At eleven AM on a Monday morning, Victor felt that he was enduring a trial by fire. He'd arrived early at seven-thirty and was following the list of instructions exactly to the letter, yet it seemed like every five seconds there was either a new email or phone call to contend with, a new problem to manage, be it cancelled meetings, other managers concerns or just emails from countless other businesses either keen for a meeting with the directors or trying to sell something to them. So far, he'd managed to prevent any problems more serious than a smudge of coffee on his white shirt sleeve from occurring, which was in itself was irritating as he'd only bought the bloody thing from Marks and Spencer's on Saturday. Honestly.

Feeling overwhelmed, it was sheer luck that he noticed when three lights flashed upon his desk phone, which, according to the instructions, meant Director Donaldson was calling for the 'special meeting.'

Picking up the sheet of paper that carried the instructions for this particular job, he stared at it for a few seconds before dropping it to carry out the instructions in order.

1. Turn emails to 'Out of Office', and phone to silent. Lock office door, turning sign to 'Busy.'

Okay, done. He let out a breath. Now for instruction two.

2. Enter the office without knocking. Do not speak to Director Donaldson. Crawl under desk, complete task, return to desk.

His hands sweating, he almost immediately fucked it up by knocking on the door. He caught himself before he did so and, with sweaty palms, opened the door.

Walking into the office it was impossible not to be intimidated. Like his own, it contained a large window, although this room was decorated with antique wooden furniture, including a couch, a coffee table and her desk. They were surrounded by perhaps thousands of books covering the walls, with not a centimetre of empty shelf space available.

Director Donaldson's desk faced the door, yet she didn't bother to look at him. As instructed, he did not communicate with her, instead silently moving beside her before getting on to his knees. From here, her wire-framed glasses and tight white top became even more intimidating, especially as the desk was solid wood and didn't leave a lot of space in which he could get in front of her.

Having finally crawled under the desk he didn't use his time to admire the fine craftmanship of the expensive mahogany. Instead his eyes were affixed to the immaculately shaved cunt that greeted him between her thick thighs. From this viewpoint, he wouldn't have guessed she was about fifty, but instead barely thirty, all toned and young-looking. The appearance was a lot better than some of the mincemeat he'd took home after meeting in clubs, but when you were drunk by the time you finally saw the mixed meat delight you might as well just get on with it and get your rocks off. In the here and now, he was sober and surprisingly eager.

The enclosed space gave little room for him to move around, but he eventually managed to find a position where his feet weren't too cramped, even as the top of his hair brushed the underside of the desk. Moving his head into position, he could still hear her typing on her computer. Christ, was she still working even when she expected her pussy eaten? This was less romantic than his drunken fumbles.

From this angle, he could see that her pencil skirt had a hidden zip, allowing it to be parted to allow better access. Custom-made he assumed, and if you don't wear underwear, you're never going to have a visible panty line. Smart. To his surprise sat like this she appeared to be sitting upon a fair-sized arse, so perhaps not as average a build as he'd assumed after all, not that he'd had much time to ogle her lower half.

Unable to use his fingers without causing both himself and Director Donaldson discomfort, whom the latter Victor assumed to be a major no-no, so instead he began with focus upon her slit.

Having assumed she'd already be moist anticipating her treat, he was surprised to find that wasn't the case. He'd just assumed someone horny enough to call in their secretary for daily oral sex would already be eager, but he didn't mind the challenge of working her up from zero to sixty. This was why he was getting paid the big bucks after all.

His tongue, gently sliding up and down her slit had the intended effect, her pink lips parting from the increase in moisture. He continued this for a few minutes before he felt his tongue begin to cramp. Uncomfortable and painful, he had half-planned for such an eventuality, and moved onto her generous clit, sucking and kissing it as if he loved it. This appeared to have the desired effect as she began to moan appreciatively before moving onto light gasps. The time he spent 'kissing' her clit gave his tongue enough reprieve so he could return to licking, but even then it was touch and go that his tongue would last long enough until her orgasm.

To his great relief Victor felt Director Donaldson's thighs clamp around his head as he felt her body tense. She even stopped typing, letting out a shallow moan as she finally came, a small amount of liquid spilling over his tongue which was once again nestled with her cunt. He stayed that way for long enough to get short of breath but didn't dare react. To his relief she let him go before he passed out, but if he expected a thank you it wasn't forthcoming as she returned to typing.

Exiting in reverse to his entrance, he slid out of the narrow gap under the desk before taking in lungsful of fresh air. He stood and, without a word from the woman who'd just orgasmed upon his tongue, left the office.

Although not on the instructions, he took two minutes in the toilet to wash his face, sweaty from the environment under the desk, as well as rinsing his tongue, not because she'd tasted bad but because he desperately needed hydration. He was also aware that he was fully erect, uncomfortable in his smart suit trousers.

'Fucking hell,' he thought as he stared at the mirror, smoothing out his hair, 'did I really just do that?'

Returning to the office, he removed the signs and the 'not in office' messages before once again feeling swamped by the amount of messages for both of his bosses. Except, despite having a raging hard-on, he found the work to be less monotonous and difficult than this morning and, by one pm, had answered everything possible without further information.

Following the instructions provided, he made certain both directors had their respective delivered lunches before politely informing them that he was heading on break. There was a note regarding lunch saying, 'Expect the Unexpected', but as both just nodded before continuing with their work, he left their offices with a sigh of relief.

For his paid half hour he headed to the staff canteen where, taking an empty table he ate his home-made sandwich. Having felt like the world was his oyster in his new job he'd decided he could afford to include both ham and cheese the night before. Hell, his new job meant he could shop in Marks & Spencer's or Waitrose and buy whatever he wanted without checking his bank balance constantly. Next month he could afford caviar if he wanted, but for now, he was happy with what he had.

The other staff paid him little attention, either unaware of his new position or purposefully avoiding him. Either way, he didn't mind.

Returning to his office, he removed the same signs from earlier before checking in with the Directors, both of whom nodded politely but otherwise didn't specifically answer.

Between his return and four pm, by following the instructions Victor had managed to not cause any major problems. At two pm Director Donaldson's door had opened, and as per the instructions stood as she walked past, leaving her office for the remainder of the day for a meeting on the outskirts of town. Knowing that only a few hours prior he'd made her cum hard, he couldn't help but stare after her. Sitting on the chair had given her a fine ass, but the pencil skirt hid it well. Before she opened the door a thought seemed to strike her, and she turned to face him.

"You were good today," she told him breezily, "but do try speed it up. You still have work to do after all."

With that, she left, leaving Victor shaking his head before, bemused and amused, he returned to his work.

It was about four when his phone went, Director Mannings name appeared on his office phone's screen.

"Yes, Director Manning, how can I help?"

"Can you please come to my office for a special meeting?"

"Of course, Director."

Hearing a click as she ended the call, Victor began to sweat as he nervously checked the instructions for being called into Director Manning's office.

1. Turn emails to 'Out of Office', and phone to silent. Lock office door, turning sign to 'Busy.'

Following the instructions, he was aware that the following were different from this morning.

2. Knock on the office door. Only knock once. Enter when called.

3. Follow instructions to the tee.

4. Only leave when Director Manning gives you express permission.

Knocking on her office door, he found himself waiting for what seemed to be several minutes. The urge to knock again in case he hadn't been heard rose within him, but he remembered the note and refrained from doing so. Eventually, he heard her speak.

"Enter."

Relieved, Victor opened the door. Director Manning's office was in direct competition to her fellow directors, with minimal furniture and what there was of it black and silver, the same colours as the walls and carpet. A desk, a chair, a sofa, that and a single picture were the only items present. The picture was a photograph of a nude woman, clearly a woman even if her identity was hidden, yet despite the provocative pose nothing was revealed.

Victor paid no attention to any of that, as sitting on her desk completely nude with her legs crossed was Director Manning, her position lending weight to her voluptuous breasts, dominated by large, pink areolas.

Standing, she revealed a flat stomach and an hourglass figure, although he noted her ass didn't appear to be as large as Director Donaldsons.

"Strip," she commanded.

Without delay, Victor removed his socks and shoes before focusing upon the hastily bought shirt and the suit he'd owned since his University graduation, as well as the hated tie/ His boxers were flung off in haste, revealing a girthy five and a half inches that his delicacy told him to cover, but his instinct encouraged him to push forward.

"Not my usual," he heard the Director murmur as she walked around him, as if assessing him while her long, blonde hair fell down her back, "but it'll do."

Walking away, she bent over the back of the sofa and spread her legs looking exactly like a porn star, before instructing him in a similar manner.

"Eat me."

Following her, Victor tried not to stare too hard. She was, without a doubt, the sexiest woman he'd ever seen naked, possibly even including online, not that he could be sure he hadn't seen a similar video, but he needed to focus.

Kneeling behind her he began to tongue her shaven cunt, before Director Manning commanded him to stop.

"Not my pussy," she spoke mockingly, "eat my ass."

Swallowing while he moved up, he suddenly felt nervous. He'd never eaten someone's ass before. Hell, he'd never fucked an ass before. Would she be clean? How would he feel doing it? Would he manage not to gag?

Pushing these thoughts down, he stuck his tongue out and, closing his eyes, started licking around her ring, barely brushing over the hole. Feeling emboldened by the lack of disgust he opened his eyes before starting to dip his tongue in her anus slowly, advancing barely a millimetre each time. However, upon hearing Director Manning sigh in a clearly bored manner, panic set in and, holding onto her hips, slid it in as far as he could go before beginning to thrust with his head.

A sigh of relief followed and, so emboldened, Victor carried on what he was doing. In honesty, he didn't mind too much and even began to enjoy it. Feeling enterprising he even slid a finger up to her cunt and slid it in. With no complaints forthcoming he added another, beginning to fingerfuck her as he tongued her ass. As she began to moan and start rubbing at her clit, Victor increased the pace. A minute or so later he felt her sphincter tighten upon his tongue and her cunt upon his fingers as she came, yet he didn't stop, remembering the instructions to follow Director Manning's orders 'to the tee', and she hadn't said stop.

As she came down from her orgasm she looked back onto him, yet despite red cheeks seemed to look disappointed to see him, even his tongue continued to ream her ass.

"Stop." She commanded before instructing, "The silver toy, my top drawer."

Standing, his knees felt weak yet he followed instructions, opening the only drawer in the desk, he saw multiple sex toys. Pulling out the only silver item available, a butt plug, he closed the drawer almost reverently before returning it.

"Suck it."

Not keen, Victor did so, placing it in his mouth and covering it in saliva, ignoring the faint but odd taste.

"Stick it in. Slowly."

Assuming she added the last bit in case he was an idiot he did just that, taking his time as her ass puckered to take the toy, only the bulbous end visible. Like the rest of the toy it was silver, but contained engraving.

'For the bitch in my life.'

Wondering who it was from, Victor waited as she wiggled her considerable ass, trying not to focus upon his increasingly stiff cock.