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?"

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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.

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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.

"Stand."

He stood.

"Wank yourself off."

Spitting on his hand despite feeling dry from his analingus adventures, he did just that. His balls already felt tight, he couldn't take his eyes off of her until she stood up and walked behind him. Feeling close, he began to gasp.

"Stop."

Despite feeling so close, he did just that, standing there with pre-cum leaking from the end of his swollen cockhead.

"Wank."

He began again, focusing upon the shaft. It wasn't long before a familiar sensation occurred once more. his breathing ragged as he was so close.

"Stop."

He followed instructions, yet couldn't prevent a small amount of his cum from exiting his slit, sliding out and dropping onto the carpet.

"Close," she laughed, "you must be desperate." It wasn't framed as a question, but a self-satisfied statement. "If I made you wank again," she asked, "do you think you could stop yourself from properly spurting?"

With his cock still twitching, Victor knew that he wouldn't.

"No, Director." He answered.

She didn't reply as he stood there, pre-cum slowly dripping from the end of his twitching cock. He had no idea what she had planned, but knew he wouldn't last any more torture. Eventually, new instructions were given.

"Take your clothes," she commanded, "and get dressed at your desk."

Picking his clothes up, he could see the Director had used the time to dress herself. Despite having cum mere minutes before she looked immaculate.

Walking to his own desk, he hid behind the solid structure as he dressed. The door to the room was locked, but there were opaque windows that could offer other staff members a view of his nudity.

Unlocking the door and removing the signs, Victor noted the time. Four forty. He'd twenty minutes to finish up the emails and calls he's undoubtedly got, and had to do so while his boxers rubbed upon his incredibly sensitive stiffy. He could feel cum leaking onto the fabric.

To his relief, the emails and messages didn't appear to be too urgent, so he focused on what he considered the most important.

At five pm exactly, he heard Director Manning's door open and he stood, his erection thankfully reduced so he wasn't saluting his boss.

"It is five," she informed him as she stood in her doorway, "your day is over. Both Director Donaldson and I find your progress appropriate. We hope you will return tomorrow."

"Yes, director," he replied politely, "thank you for the opportunity."

A sly smile appeared to play across her face, although Victor assumed he might have imagined it. With a nod, she returned to her office and Victor closed his work. Leaving the building, he received the odd nod from other staff yet walked to the bus stop mostly in a daze.

What had just happened? Had he really spent a day doing paperwork and eating pussy? And ass, he interjected to his own thoughts. Was he really going to go back?

Feeling his balls twitch, desperate for the release he was planning the moment he returned to his flat, knowing he'd probably never get another experience quite like working in that office. So, despite his concerns, he knew he'd never forgive himself if he left now.

Returning to his apartment Victor didn't even bother to load porn up on his phone or computer. Just imagining Director Manning and Donaldson, nude and beautiful, doing unthinkable things to him was enough to cause him to spurt within a minute of using his pocket pussy. Filling the fake cunt, he felt relief like no other, shooting a gigantic load inside the soft interior. He had thought of the Directors sucking him, wanking him, fucking him, yet he had no hope that it would ever happen in reality. But who knew? A week ago, he couldn't have imagined giving oral sex at work, never mind in an official capacity. He could only hope.

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Months passed and each week, every Monday to Friday, Victor ate the pussy of Director Donaldson while scrunched up beneath her desk. He had sped up the process by figuring out her preferences, but it was otherwise the same activity every day. The order in which he serviced them differed, although there was always one Director in the morning and the other in the afternoon, clearly pre-arranged between themselves, but Director Donaldson never differed. He entered her office, he crawled under the desk, she came, he left, they got on with work. He came to admire her as a person and a boss. She knew what she wanted, and she took it.

Director Manning however, liked to change things up each and every day.

On Victor's second day after she had called him in for a 'special meeting', she had answered the knock instantly while wearing a white, latex nurses outfit, complete with little hat and stockings. Pulling him into the office by his tie, she had pushed him onto the sofa and commanded him to stay before sitting in her office chair.

Sitting before him se had put on a show, touching herself, pulling at her breasts and nipples, filling her pussy with her fingers. Only when she was dripping did she knely over him and command he eat her out. He had obeyed instantly and she came not long after, this time letting out a scream as she squirted over him, covering his face and shirt as she shook and quivered from the intensity. Yet as quickly as it had started she ended it with the same speed.

"Leave," she gasped, still clearly feeling the effects of her orgasm.

Walking out of her office and closing the door Victor didn't have a clue what to think or feel. He also didn't know what to do about his shirt and tie, covered in her ejaculation and still barely ten in the morning. Looking at the clock, he realised the entire thing had taken less than ten minutes. Shaking his head, he headed to the bathroom, where he washed his face and tried to dry his shirt under the hand dryer. Failing the latter, he returned to work as if nothing had happened.

The next day, it had been leather whip and riding crop, the day after she copied Director Donaldson's approach down to a tee having somehow had a replica of her co-director's desk inserted in her office, while on Friday she merely got him to watch her masturbate with a bright pink vibrator. Even within a week, watching one of his bosses masturbating had been relegated to an 'only'.

For months and months this remained Director Manning's routine, constantly chopping and changing, never the same thing. In a way he grew to enjoy the variety, but that remained the only thing he 'enjoyed' in the office.

Never once was he allowed to use his cock to fuck either one, nor had he been allowed to cum. There were one or two times where Director Manning, doing similar to his first visit to her office, caused him to shoot without pleasure, his disappointment and discomfort seemingly causing her to smile and laugh more heartily than he'd ever seen her. So, the day something finally changed, he hadn't see it coming.

Kneeling between the legs of Director Donaldson he licked and sucked as usual. He'd been there for nigh on six months but, for the first time, he heard the Director stop typing without her reaching orgasm.

"This isn't working," she informed him brusquely. "I need you to sit on the sofa."

Surprised, by the time that he had managed to extract himself from under the desk she was already waiting for him by the sofa, customary pencil skirt removed. He could see her engorged pussy, but was more amazed by how large he could see her ass was. Under the pencil skirt you wouldn't have known she had a perfect bubble butt, but here and now she was tapping her foot. Noticing this he hurried over where she handed him a small item.

"Trousers off and put this on."

Taking the condom from her, he followed her instructions, rolling it down over his erect length before sitting upon the cold leather sofa. To his surprise, Director Donaldson spat upon her hand before rubbing it over his covered length. Turning around, she moved to sit reverse cowboy style, placing her wet cunt above his cockhead. As she slowly lowered onto him, he gasped as he felt the tightness of her cunt.

It wasn't long until she began to bounce rhythmically upon him, his whole length embedded with her, his eyes focused upon her amazing ass bouncing upon his lap. What surprised him most was, as she began to speed up, she began to speak to him.

"Yeah, you like that don't you?" She continued to fuck him, yet periodically talking to him. "You like fucking me? Does it feel good?"

Several minutes of this and, with her gasping and moaning, Victor was struggling. He'd never fucked anyone quite like her before, and he didn't mean her age. She might be around fifty but she fucked like she had the energy of a twenty year old. It was to his relief she finally pressed down, her cunt clenching upon his length as she came. Her mouth opened but no noise came out, although her arms, either side of Victor, shook as she held herself down upon him. Eventually she stood, breathing heavily.

Except, as she looked down at him it was clear he was close, breathing through pursed lips, his length swollen and hard, his balls tight.

"Are you close Victor?"

He couldn't speak fully as he tried to prevent himself from moving too much, worried that anything too overstimulating could cause a problem, but as he tried not to stare at the bubble butt that he was pressed against Director Donaldson offered him some rope.

"If you are close to ejaculating, you are welcome to finish. I recognise that my," she paused, "struggle, to reach my own orgasm may be causing you to reach your own. Would you like to keep going?"

Unsure if this was a test, Victor was too close to his own orgasm to try fight it.

"Yes, Director."

She didn't reply after that, just immediately sat back down on his cock and returned to bouncing upon his lap, his length filling her cunt. Unable to stop himself, it was barely ten seconds before his balls tightened. Instinctively holding onto her hips, he thrust upwards as he shot his load within the condom. Only his nightly masturbating prevented it from being a flood, yet it was still a large amount.

Director Donaldson waited until it was clear Victor had finished before standing carefully. To his surprise she inspected his spent cock and the full condom. From his position upon the coach, her face close to his, he could see red cheeks beneath her long silver hair. Her unusually unbuttoned shirt revealed a good-sized chest, although it remained contained in a white lacy bra.

"I am glad to see that you clearly required the release," the Director spoke to him, lifting the full end of the condom as if intrigued by the liquid contents. "Just be aware such an event will not become frequent, so do not expect things to change. Is that clear?"

"Yes, Director Donaldson," Victor gulped, still feeling sensitive from his recent ejaculation, "I understand."

"Very good," she nodded, "now do not let me keep you."

"Yes, Director Donaldson."

Standing stiffly, he gathered his clothes and, returning to his desk put on his trousers before heading to the bathroom to remove and empty the condom. As he emptied it down the toilet, he considered that her requirements for the use pf a condom was likely to be in case he had any diseases rather than pregnancy considering her age, but he did briefly consider how she would look pregnant as she bounced upon his cock...

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It had been six months of employment before either of the Directors had requested he fuck them, and it was roughly another similar length of time before it occurred again. Once more, oral hadn't been enough for Director Donaldson and again his only clue had been that her typing stopped before she commanded him to stand.

As he clambered from beneath the table the Director undid her dress and, instead of heading to the sofa bent over her desk, where her slim fingers pushed a silver packet towards the edge.

"Until I come, Victor."

Unable to believe his luck, he picked up the condom packet, ripping it open eagerly.

"Yes, Director Donaldson."

Keen to fuck her while her watched her bubble butt bounce, he forced himself to retain a professional attitude as he rolled the item over his length. Although she was already well-lubricated, he spat on a few fingers and inserted them within her, his fingers curling gently within her soft, warm walls, eliciting a quiet moan of either contentment or pleasure as he did so.

When he felt she was ready he removed his digits, instead sliding his wrapped cockhead across her slippery hole a few times before inserting himself into her cunt. He did so an inch at a time, not wanting to cause the Director any discomfort, not that he was likely to bottom out, but this was about her pleasure, not his.

Thrusting at a steady pace, he was surprised when, within moments of starting, the Director began to moan and push herself backwards to push him deeper in. Taking this as a signal, he held onto her hips not only to make it easier to increase the speed but keep it rhythmic.

After barely a minute of doing so Victor felt her cunt grasp onto his length, her legs bending from the intensity as her orgasm hit. His arms held onto her waist, preventing her from falling from her legs giving way.

Taking deep breaths, it was a good minute before the Director was able to both support herself fully and speak in complete sentences.

"Are you close, Victor?"

As he'd thrust, her ass had bounced like a porn star, while her gasps had been like sweet nectar to his libido. Despite this, he knew he wasn't going to cum quickly.

"No Director Donaldson, I'm afraid not."

Not only was it probably the first time he'd heard her laugh, but as she gently shook he could feel it as he remained deep within her.

"Afraid not?" She chuckled, "I assume that is because you would like to ejaculate within me?"

"I would Director Donaldson," he agreed, "but I'm not close."

"Then why are you afraid you are not close?" She quizzed, bending her neck to see the man inside her.

"Because I'm enjoying both the view and the sensation, Director Donaldson."

"Hah, yes," the Director rolled her eyes as she spoke, "I used to find my suitors enjoyed the size of my posterior, not that I know why. I have been unlucky enough to be cursed with such a size, no matter whatever diet or exercise I am suggested."

"Yes, Director Donaldson." Having not been directed to remove himself from the director, Victor wasn't keen to lose the feeling, so was determined to wait for the instruction, as he had done so for the last year of his career within the company.

He felt like he waited forever while the Director seemed to deliberate on what to do now, but in reality it was mere moments.

"I have an important report to finish Victor. While I apologise for not being able to finish to completion, I must return to work. You may return to your desk."

"Yes Director Donaldson," he replied politely although disappointment filled his veins Removing his cock from her slick hole had the emotional destruction of being dumped, but he had spent a year following instructions and no way would he ruin the opportunity to work in a job that allowed him to give oral sex to two stunning bosses.

Returning to his desk, Victor removed the condom there and then, popping it into the bin. Not being full, he didn't see the point in heading to the bathroom for a wash, especially as he hadn't worked up a sweat. Yet as he headed to the office door to remove the sign, his phone rang despite the re-direction, meaning it could only be one of two people. Surely Director Donaldson hadn't changed her mind? From the other side of the desk he was unable to see the caller ID but answered politely.

"Yes Director?"

"Victor," a rich purr came through the phone, "come to my office for a special meeting, will you?"

"Of course, Director Manning."

Putting down the phone, Victor was confused by the timing. In almost a year never had both directors called him in at the same time of day, so either this was something else, or his boss's communication was deteriorating.

Knocking on her door, Director Manning answered almost immediately.

"Come in."

Opening the door, Victor walked in, and shut the door without looking at the Director. He got halfway before it became apparent something was off. Sitting at her desk as usual, yet rather than working or glowering at him as if he were a nuisance, Director Manning was sitting at her desk relaxing in her office chair, not unusual in itself, but sitting on the desk before her was a rubber ass.

"I heard that Director Donaldson required your other skills," she sounded bored as she spoke, still typing, "but was unable to finish the job. To help, you can fuck this." She directed Victor's attention to the life-size model of an ass on her desk which he could see had two holes, a bottle of lube standing behind it.

"Director Manning," Victor blurted out, "there's no need..."

"Nonsense," his boss interrupted, finally looking him in the eye, "you need a release, and we have one for you. So get your knob out and get to fucking."

Never disobey an order. Never disobey an order.

With this mantra running through his mind, Victor removed his cock from within his trousers while the Director returned to whatever she was doing on her computer. Lubing himself liberally, he didn't quite know where to start. He owned what he called a 'pocket pussy', a fake, light-pink hued masturbator based upon the 'perfect' look of a vagina, essentially the equivalent of the average vibrator, but this was well beyond that. This had a puckered asshole and a vagina with clearly defined details, positioned to look as if he were fucking someone doggy style. The two perfect butt cheeks either side of it even gave Victor something to hold onto as he fucked. The only issue was that it had been positioned so he would be looking directly at Director Manning as he did so.

From an aesthetic viewpoint, this wasn't an issue, as looking at a beautiful and buxom blonde while he got his rocks off was never going to be a negative, but despite showing plenty of cleavage Director Manning had never shown any real interest or appreciation for anything Victor had done, so how would she react to him essentially wanking himself before her?

Placing his still erect cockhead, now lubed up, against the 'vagina', he began to play in and out of the hole, getting a feel for the cold and rubbery interior. There being a slight too much friction, he removed the inch or two from within it and applied lube to his fingers before, well, fingering the cunt to lube it up. Focused on what he was doing, he almost jumped when he heard the director speak.

"That's the stuff," the Director laughed, "don't you know you need to get a girl ready before you stick it in?"

"A woman, yes," he replied while still fingering the vagina, "but this, well, it's a new feeling."

"Just pretend it's Director Donaldson," Director Manning continued authoritatively, "it's barely different from what you were doing in her office."

Not sure exactly how much the Director knew what he'd done next door, Victor didn't answer, instead returning the tip of his cock to the now well lubed cunt.

Sliding in, the suggestion to consider Director Donaldson floated to the front of his mind, although as he thought of her considerable ass, he realised the cheeks before him were nowhere near the same size. Hers rippled and bounced freely while this just moved with his thrusting, and last time she'd even dirty-talked him. Not this most recent time, he admitted, but that was because she'd been too busy gasping and moaning from the build-up to her inevitable orgasm.

As he fucked, Victors eyes glazed over as he considered pounding Director Donaldsons cunt, so he didn't notice that Director Manning had stopped typing and was instead looking at him intensely. Her gaze was focused upon his face rather than his cock, yet for once her expression wasn't judgemental, instead more understanding and caring. Despite the lack of lust within her gaze, she undid a couple of buttons of her top, exposing the small lacy bra that precariously held her large breasts, and whether or not she'd intended it, the revealing of extra flesh coincided with Victor returning to reality, continuing to pound the rubber as he noticed the Director looking at him intently. As he pounded, he asked a question.

"Is there... anything else... I should... think about... Director?"

She didn't answer immediately, her eyes searching his face, but she smiled softly as she considered her answer.

"Perhaps you'd consider fucking Director Donaldson in the ass?"

His eyes opening wide, Victor didn't argue, instead immediately slipping out of the rubber cunt, placing more lube on his fingers and inserting them into the toy's asshole. Even with just two fingers he could tell this would be tighter. Before placing his swollen head against the asshole, he placed more lube on his fat, swollen cock, only then slipping into the tighter hole.

"Does that feel good?" The director asked softly. "Does it feel good to fuck her tight asshole? To hold onto her fat ass and just use her, to slam yourself inside her as her ass bounces and wobbles, watching and feeling it again and again and again, until your balls tighten, your cock twitches and you shoot rope after rope of hot, white cum inside of her?"

Her words lit a fire within Victor, his mind filled with visions of his boss. Despite being in her fifties, he'd had multiple wanks thinking of how it would feel to shoot a load in that asshole, or how it would look if he tried to cover her ass with his jizz, not that he'd ever shoot enough to cover more than a single percentage. As those images were placed in his head he immediately began to feel his balls tighten. He gasped involuntarily as he pulled back, not wanting to shoot his load so quickly, yet Director Manning had other plans as, without him noticing, she was standing behind him.

"Now, we can't have you stopping," she purred in his ear, "not to deprive Director Donaldson of a hot load."

Without saying anything, she pushed herself against him, her breasts pressed against his back before wrapping a hand around his length and beginning to stroke him hard and fast.

"You're so close," she taunted, "so close, come over her ass, you know you want it."

Blood rushing away from his brain, Victor knew he moaned something but couldn't figure out what, the intensity of the handjob overloading his bodies senses.

Unable to stand the sensation any longer, with a guttural moan his balls tightened, his cock pulsing within Director Manning's grip. The first jet not only covered the ass, landing over both the asshole and the cunt, but was powerful enough to reach the back of the director's monitor, while the second covered the table between him and the simulacrum he'd been fucking. He could sense the Director's delight as she milked him for all he was worth, the last few drops falling onto the carpet directly before him.

"You weren't joking when you said you wanted to cum over Director Donaldson's ass more than anything," she spoke admiringly, "I'm going to have a fun time cleaning that up. Now," she released him from her grip, "go back to work. I will still expect you here for our session this afternoon."

Nodding wordlessly, Victor barely remembered to do up his trousers before leaving her office. He'd worked here a year, but she still knew how to surprise him.

He was fairly certain that Director Manning's preference was anyone without a cock, but moments like that always threw him. Did she actually enjoy playing with his dick, or was it the control she enjoyed?

Sitting at his desk, feeling the cum from his cock pressing against his boxers he knew one way or the other he wasn't going to argue.

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

As Victor took the call from Director Donaldson, he knew something was up, especially as mere moments before, he had just seen Director Manning enter her counterpart's office. In the almost three years he'd worked for the two of them, he'd seen and done a lot of things. For one he'd eaten both of their cunts five days a week the entire time he was here, he'd even fucked Director Donaldson several times, and Director Manning had done something different every day, the most imaginative of which had involved a female dwarf and a bag of skittles. But never in his time had he ever been called into a meeting with both of them at the same time.

Entering the office he could see Director Donaldson at her desk, while Director Manning stood beside her. As was customary, the expression of the former was neutral, while her companions were as dismissive of him as it ever was.

"Victor," Director Donaldson directed firmly, "take a seat."

Sitting in the chair opposite her, he took nothing from either of their demeanours and remained as confused as ever.

"In the one thousand and thirty-eight days you worked here, both Davina," she directed at Director Manning, "and I have been impressed by your exemplary work for us. I think it is fair to reveal you were not our first choice," she admitted with a wry smile," as never in a hundred years had the directors of this company previously chosen a man for your, special duties. Yet even Davina here has come to accept you, something I can assure you is a true compliment."

"The issue with your exemplary performance," Director Manning or, as Victor had just discovered after almost three years of work, Davina, interjected, "is that we are a small business, and your overachieving has caught the attention of several larger firms who work in a similar vein to us."

Director Donaldson nodded, and if Victor was any judge she actually looked sad.

"The Directors of one of these firms has offered you a position and, despite the disappointment this would bring to both of us, we both think you should take it." Sliding over a piece of paper, she nodded to Victor that he should pick it up. "These are their terms."

As he read it, Victor's eyes and mind boggled. The name stood out as one of their competitors, a larger London firm. Not only was the pay better but the firm would help pay for accommodation, a great help for a city as expensive as London. From what he could tell this would be dependent upon his continuing to provide 'special services' to his new boss.

As he looked at the two directors before him, he felt a pang of guilt and regret. These two had done so much for him, they'd introduced him to a world he'd never expected, even if that world had prevented him from starting any serious relationships, but he'd accepted the trade-off to do what he did. To leave now...

Seeming to sense his trepidation, Davina bent forward over the desk, accidentally revealing two of the reasons why Victor was tempted to stay.

"If you stay here, there is no way to progress. This is the job you will do until either one of us gets bored with you or, when a new director takes over from us, may even request a replacement. We admire the loyalty, but don't be a fucking idiot. Go for the interview and if you genuinely don't like it, I can only imagine other firms will come calling."

Nodding, Victor agreed.

"It's the best choice, Victor, I'm sure you'll come to see."

As Director Manning stood and left the office, Victor went to follow.

"While you are here, Victor," Director Donaldson added, "we might as well have our morning meeting."

Unable to keep the smile off his face, Victor agreed and was immediately on his knees, ready to crawl under her desk, but yet again the director surprised him by turning her chair so he wasn't cramped beneath her desk. As she turned he could see her skirt had been undone the whole meeting.

"For once I think I'd like to watch."

"Yes Director Donaldson."

As he knelt between her legs, he kissed her full lips gently before working his way to her cunt. As usual she was sat forward to allow access, and she was already wet, his tongue tasting the salty sweetness of her juices as he lapped away. Unusually, she placed a hand on the top of his head as he worked.

"Aah..."

Clearly happy with his work she released a contented sigh as Victor began to work on her clit, focusing upon her sensitive bud. The director reacted heavily and quickly to the attention; he could feel the muscles in her thighs tightening as well as increasing the pressure as she pushed on his head. He could sense it wasn't going to be long before she came, but he wasn't ready when she did

As her legs clamped around him, she pushed his face against her groin, his tongue slipping ever deeper inside her hole which, where damp was now flooding with her juices. The intensity of her orgasm leading to Victor being unable to breath, pressed as he was between the thighs he'd come to admire.

To his relief, as her pleasure subsided she released him, Victor gasping for air even as the Director seemed oblivious.

"That," she moaned in relief, "was amazing. I think I'll regret you leaving Victor."

Staring up at Director Donaldson with a full view of her sopping cunt, her heaving chest and her bright red cheeks, Victor knew that he felt exactly the same.

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

Looking across his desk, Victor had a sense of deja vu as he discussed with his replacement the duties expected of them. An attractive woman in her early thirties, she had a slight plumpness that gave her the outward image of looking like a kindly mother, the sort of person you'd expect to present children's television, all kindness and gentle. Knowing that, from next week, she was going to be eating pussy and maybe more regularly gave him a thrill. Finishing off the details of the job, he ended on a high note.

"So you're aware that certain, special jobs are expected of you?"

Nodding, Trudy went bright red.

"I, I am aware," she mumbled, "I'm friends with your predecessor," she revealed, "and, well, I'm quite looking forward to it to be honest. My husband's a bit of a dead fish."

"Just as long as you're aware you follow instructions to the letter. It's for the director's enjoyment, not yours."

"Of course," she answered, clearly flustered, "I shall do as I'm told."

"You've made the right decision," Victor smiled warmly before noticing three flashes," and with good timing." Standing, he held out his hand to shake. "As Director Donaldson is calling, we'll call this a day. Thank you for coming in, and I hope you enjoy your weekend Mrs Smith. Come Monday, you're going to find out if you're good enough to earn that paycheque."

As the woman left, Victor followed the instructions to lock up the office left for him one last time before heading straight in. He was pleased but not surprised to see both Directors standing by the couch, Director Manning holding a glass of something fizzy while Director Donaldson smiled at him.

"Victor, I hope the meeting with Mrs Smith went well?"

"She'll be fine," he admitted. "Just a word of caution: I think she's hoping to enjoy herself as much as you do."

"That," Davina smiled wickedly, "will be dealt with very quickly, don't you worry."

"Now," Director Donaldson walked towards Victor, "as it's your last day, we thought we'd send you off with a treat."

"And what could that be, Director?" He asked as the older woman pressed her body against him, wrapping her arms around his frame.

"Let's find out..."

With that, she pressed her lips against his, kissing him with real passion. Completely obsessed with her despite being over twice his age, Victor responded with vigour, holding her tightly as her hands began to caress his ass. Unable to stop himself, he found himself doing exactly the same.

When they finally broke apart, the Director pulled him towards the couch, fiddling with the buttons on his trousers as she did so. Already sitting there completely naked but still holding her glass of fizz was Director Manning, the fingers on her one free hand gently playing with a nipple as she stared, focused upon Director Donaldson who, to Victor's great delight, was pulling down his trousers and boxers together as she knelt before him. Already erect, his cock sprang out directly before the Directors face, who was licking her lips in anticipation.

"I've been wanting this," she smiled, gazing up at her secretary as she began to fondle his balls.

Licking his slit on his cockhead, she began to take him in her mouth slowly, adding him in centimetres as she took her time to lube him up with copious amounts of saliva. It was the sloppiest blowjob he'd ever had, made even better when Davina, finishing off her drink, began touching herself on the couch.

He stood there enjoying the sight, and when Director Donaldson paused to remove her shirt and bra revealing her breasts, he didn't even mind the interruption, especially as next to him he could hear Director Mannings short, sharp breaths as well as the wet squelch as she plunged several fingers within herself.

It took about five minutes of enjoyable effort, but eventually, Director Donaldson took him to the back of her throat, and as she removed him fully from her mouth, a string of saliva followed. Looking up at him he didn't see the fifty or so director whose body he admired; he saw a dirty MILF whose breasts were covered in saliva and, having managed to finally deep throat him looked the happiest he'd ever seen.

With a wink, she moved from kneeling before Victor, turning instead to kneel in front of the couch where she began to tease and kiss Davina's groin, quickly moving onto licking her clit while Director Donaldsons large ass perkily stared back at him. She licked cunt for a minute before she turned to look at Victor questioningly.

"Well Victor, are you going to fuck me or not?"

Unable to believe his luck, he began searching for a condom, but Director Manning wagged a finger.

"No condom..." she gasped from the sensation, "fill her raw."

Not needing a moment to consider, he fell to his knees directly behind Director Donaldson. Where he would normally have admired the perfect bubble butt that greeted him he instead couldn't wait, slipping his cock straight into her sopping wet hole.

"That's right..." Davina groaned, "pound her, make her cum so hard she screams into my cunt."

Holding onto Director Donaldson's hips, he took only a moment to make sure she was comfortable before he started a fast but steady pace. Only then did he admire the ripple her cheeks made, any noises of contentment muffled by her fellow directors cunt who he could see was almost wrenching upon a nipple, clearly close to her own release.

With a open mouthed, high-pitched cry, Director Manning came upon the tongue of her fellow director, her eyes shut tightly as body tensed before finally collapsing back onto the sofa, not that her fellow director gave her any respite, seemingly unfazed by the hard cock pistoning out of her cunt she continued to lick and tease, even as Davina squirmed and gasped from the attention, her body extra sensitive.

The whole situation amazed Victor as he had never once seen Director Manning look so vulnerable. While she'd often cum hard on his tongue she'd always treated him like a nuisance and had always kept a wall between her pleasure and her personal life. Here and now, seeing her slumped on the sofa, sweat on her forehead and no longer pressing her breasts up so high, he could see the minor flaws.

Her face was over-botoxed, her flat stomach had a roll, and her breasts were far too symmetrical to be real, but for the first time he felt genuinely attracted to her. She was no longer a perfect doll but a real person who was able to enjoy herself in his presence.

Director Donaldson however with her naturally curvaceous body and her willingness to accept her flaws including her naturally silver hair had always turned him on, and as he continued to pound her delicious pussy, he couldn't help but already feel his balls tingle, desperate to shoot a load inside his true sexual fantasy, something that Davina clearly noticed.

"Come on boy," she gasped at him, still enjoying the attention on her cunt, "we both know what you really want to do to her. Just look behind you."

Still thrusting, he glanced behind him and only now noticed something on the coffee table. With a grin, Victor knew exactly what he needed to do.

Pausing only briefly to pick up the bottle behind him, he returned to fucking as he poured a small amount of the contents on the fingers of one hand. With a nod, Director Manning pulled Director Donaldsons head further into her crotch, and only then did Victor insert two lubed up fingers into her ass.

He heard the director cry out, but as her face was muffled by her colleague's cunt, he couldn't hear her say stop, so he began to fingerfuck her ass until both fingers were fully penetrating her, even as he continued to fill her pussy with his swollen cock. With the Directors mouth still occupied he added a third finger before beginning to alternate his thrusts, keeping either her ass or cunt full at all times, and as he did so he could feel her clenching her muscles around his length.

Without any warning he removed both his cock and his fingers, manoeuvring himself into his fat cockhead pressed against her stretched but still tight asshole. Using more lube, he covered himself before beginning to press forward, the tip of his head beginning to slide in.

It was only when Director Manning came again on her colleague's tongue that she loosened her grip, allowing Director Donaldson's head free. Looking back at her secretary, her eyes had a fire within them.

"Fuck me," she commanded, "and fill my ass. I want to feel your cum dripping OUUT!"

Her final word was more a cry as, feeling adventurous, Victor slammed his entire length straight up her arsehole before pounding intensely, desperate to do exactly that, to cream pie her ass, to leave her feeling full even when she wasn't filling by his cock.

Needing to feel deeper, he began pulling her hair, pulling her head backwards. Whether or not she enjoyed this he wouldn't know as, despite Director Manning's annoyed expression, the moment he did so his balls tightened and with a deep cry he came, emptying his load within the Director's bowels.

As he came, he could see her looking back at him, her mouth a small O as he shot several ropes within her. As he felt himself finish, he thrust several times to eke every drop out, in time to see Director Manning sliding down the sofa until she was kneeling before Director Donaldson. His cock still in her cum-filled ass, the two began to kiss intensely. As Victor watched, he felt that this must be a dream, as he was still feeling light-headed from his own orgasm.

As he began to remove himself from the Directors ass, Director Manning almost lunged towards Victor, although any hope she was going to suck his cock clean disappeared when she shoved him out of the way. He was not left disappointed though, as she bent over and pressed her breasts up against Director Donaldsons ass before she began to kiss and tongue her cum-filled asshole. Licking out as much cream as she could manage, even though she was otherwise busy she still bodily pushed Victor forwards to the couch where he found Director Donaldson gasping as her sensitive and raw ass was tongued deeply. Looking up at him, she opened her mouth suggestively. Not needing any extra encouragement Victor placed his cum-covered dick within her mouth. Clearly not bothered by where it had been, she licked and sucked every last drop.

As they both finished, both directors grinned happily at each other.

"I hope you enjoyed yourself Victor," Director Donaldson spoke professionally, ignoring her nudity and the fluid leaking out of her stretched asshole, "we'd like to think that you've had a good experience with us, and we look forward to seeing how you do in the future."

"She means the work," Director Manning explained, wiping her mouth with a hand, "not the fucking, but that was fun too."

"Thank you Directors," he replied, unable to stop himself from grinning like the cat who'd supplied the cream for the other cat to lick up, "even though I imagine I'll be busy in London, if you ever have need of me out of hours you're always welcome to call."

"Careful," Director Manning grinned, "Valerie here might take you up on that."

"Davina!" She hissed, "he is too young!"

"He's been old enough for the last three years," she teased, "I reckon he could manage a few booty calls."

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

At five o'clock later that day, Victor left the office for the final time. He'd thanked both of them one final time.

Director Donaldson, or Valerie as he'd finally learnt, had been unusually taciturn with him, so he'd made sure to 'accidentally' leave his phone number about her office. Age was but a number after all.

Davina had given him a present, saying his new boss would insist upon it but not to open until his first day, which was only a few days away. Of course, he opened the box the moment he left the building, to find another box and a picture with some writing on of Director Manning completely nude bent over a familiar couch.

'Something to help you wait.'

Looking at the beach, Victor decided to skip the bus today, choosing instead to walk along the beach. It was a warm day and, being summer, the beach remained busy, so he spent his walk admiring the bikinis on show. He'd spent the last three years ignoring a partner or even a fuck buddy due to his daily wanks over both of his bosses. Perhaps, now he had one night to himself before the cycle started again on Monday, as he would be spending the next two days moving into his new flat. So why shouldn't he go to the pub and see if he met anyone? His confidence had improved immensely in the past few years, boosted by his bosses, and if he only had a few hours of freedom, well, why not make the most of it?

Feeling confident, he headed into the nearest beachfront pub, choosing the one with the most bikini-clad bodies in the beer garden. Whatever happened, come Monday he knew that, tonight at least, he was going to have a damn good time.