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An Officer, and a Businessman

"Away from his wife, the office empty, his beautiful assistant nearby, Chip was in perfect bliss."

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Mili-Tech Concepts’ Regional Office, London

Head researcher, Charles “Chip” Dane, looked out his office window towards the gray, depressing skies of London and sighed before rotating his office chair back towards his desk. There were several large stacks of papers on it that he still needed to look over and approve before he left for the end of the day. Almost everyone else had already left, save for him and his assistant, and based on how much reading he still had to do, they weren’t going anywhere soon. Looks like another night at the office.

Although Chip normally worked at the company’s main office back in the states, it was routine for him to work out of one of several offices around the globe closer to whatever government or other client they had at a given time, in this case, the Royal Air Force of the United Kingdom. The project he was involved in was developing a new type of stealth material-sensing radar that could possibly detect the new stealth planes being developed by Russia and China. The project started three weeks ago, and he was still living out of a rented condo in the city, although it would have been more accurate to say that he was living out of his office, given how busy he was.

Not that Chip would normally complain, though. He often relished the opportunity to get away from his cheating wife and do a little cheating of his own, usually with some pretty woman younger than himself in an expensive hotel suite in the most expensive part of the city he was working in at the given time. However, thus far he had been so busy with the new radar system he’s been working on, the project specs of which he had been reading that evening, had kept him too late at the office, and too tired afterwards, to actually enjoy being away from his wife. Three weeks with no female companionship was too long for Chip.

Dropping the pen he was holding harshly on his desk, he looked at the mirror hanging on the left side of the office. Despite being a little over forty-one, he still thought that he was looking pretty good. Chip was six’ two” and he had jet-black hair, with no grays, tanned skin with almost no wrinkles (remarkable given the stress he was generally under), a classically handsome face like an old movie star, and since whatever office, condo or other place he was working or living in had a gym, he managed to stay in pretty good shape despite working in an office all the time. He might not have been built like an athlete or a bodybuilder, but he managed to stay in shape and maintain a reasonably muscled physique. God it’s great to be rich, handsome and always working away from the wife, he thought as he let out a small laugh.

It had been two years since he had divorced his first gold-digging wife, only to end up with another one. At least his current wife, Kimberly, had double D breasts, which thankfully she purchased herself before she met him, instead of having him pay for them like his first wife. Kim was pretty damn good looking, and the sex with her was amazing, but she was prone to getting upset if she didn’t get everything she wanted, just like her daughter, his now stepdaughter Becky, which drove Chip and his son, Phil, crazy.

This was especially true when he learned about how his darling wife was fucking her daughter’s boyfriend, Todd. Learning such a thing naturally pissed Chip off, but the issue was settled in the same way that all of their arguments were: when they were both at home, he gave her money to spend, and she gave him sex, a pretty mutually satisfying relationship. In many ways, their marriage was arranged the same way he operated at work: like a business arrangement.

Kimberly was the kind of wife that was good to be with in small doses; it made their time together more passionate and appreciative. This was in contrast to his first wife, which he pretty much saw every day before getting his promotion to head one of his own research teams, which routinely took him out of the States on business. Normally, he would have time at the end of the day, or even the occasional whole day off in order to hit a club, check out some swanky bars, or in times of desperation, call up the most upscale escort service there was in whatever city he was in. Unfortunately, thus far, his trip to London was all work and no play.

Chip tried to get back to work in the hope of salvaging at least a few hours of the evening for entertainment, but he just wasn’t able to concentrate on the research papers and schematics piled on his desk. He did manage to sign off on a few work orders, but after another half an hour, he shoved the papers he was reading back into the folder that they had previously been occupying and decided to take a break to clear his mind, which would hopefully allow him to finish before nightfall.

Just as he managed to slide the last papers into one of the folders, there was a knock on his door, and he already knew who it was, since there was only one person left with him in the office this late: his assistant, Eva.

“Come on in, Eva.”

The door opened and predictably his assistant/liaison to the Royal Air Forces, Sgt. Eva Williams, walked into the office. Seeing as how the project he was working on was both very secretive and very important to the Air Force, they insisted that he not hire his own assistant, and in turn, they would send him an officer to act as one for him. Normally such a stipulation would annoy Chip, seeing as how he usually liked to hire attractive, young women to serve as his assistant so that they could ‘assist’ him more ways than just filing and answering the phone.

In a dramatic twist of good fortune though, the RAF sent Eva to act as his assistant. The RAF officer who assigned Eva to him told Chip that she was one of their brightest young officers, rising to her current rank of sergeant despite only being twenty-five years old. However, it wasn’t the sergeant’s credentials that he was ultimately concerned with, but rather her amazingly good looks. Eva was almost six feet tall, with long blonde hair, deep blue eyes, and long legs that any man would love to have wrapped around him. Her ass and tits were large, but not porn star large, making Chip wonder why she didn’t go into modeling and make a fortune rather than working for the Air Force.

“Evening, sir, may I come in?”

Eva’s English accent always managed to slightly arouse Chip; accents on beautiful women always did.

“Of course.”

“I know you still have paperwork to go over, but Mr. Harrington just faxed this over and asked for your signature.”

Chip looked over the papers while Eva stood silently with her hands clasped behind her back, very professional looking. The papers were an authorization to begin testing of the new radar system, in this case on an RAF base in Barbados in the Caribbean, likely to get away from any prying eyes that might be spying on the project in the UK. He quickly signed them, not caring where the project was tested, but instead worrying about whether or not he could finish the rest of his paperwork before the test actually happened.

While he was reading the fine print of the document, Eva had leaned forward in order to watch him read the papers she had handed him. While some bosses may have insisted that their assistants step back and not look at such private documents, Chip trusted Eva, but more importantly, as she leaned over, the sergeant's cleavage became more visible through her uniform. While Chip had been with a number of smartly dressed women; executives, socialites, club-goers, and so forth, he still had not been with a woman in uniform, and Eva wore her uniform very well.

The uniform Eva was wearing consisted of a light blue blouse, a darker blue/grey coat, a blue/grey skirt that matched the coat, and a pair of bluish-grey patent leather stiletto heels, the one part of the uniform he didn’t believe women normally wore in the RAF. In addition to the heels, there were a few other articles of clothing that Chip was sure that Eva was not wearing according to RAF standards. For one, her skirt had clearly been hemmed halfway up her thighs, instead of below the knee as it probably should have been, and she also was not wearing that odd tie that women in the armed forces normally wore.

Speaking of the tie, not only was Eva not wearing it, but her shirt was also not buttoned up as it should have been. Had the sergeant been wearing the tie, then she would have had to button up her blouse all the way to the collar. Instead, she had left several buttons undone, giving anyone who looked at her a generous view of her even more generous cleavage. While issues such as the heels she was wearing, how short her skirt was and how she was leaving her cleavage visible would have gotten her in trouble were she still working at the base she was previously assigned to, here, Chip not only didn’t mind the sergeant’s attire, he greatly appreciated it, after all, he always wanted his assistants to dress like that.

Realizing that he was probably staring a bit too much at the woman’s chest, he forced himself to finish reading the document instead of staring at Eva’s tits. Chip quickly finished reading, signed the last page of the papers, and put them in his outbox.

“I’ll hand these to Mr. Harrington tomorrow, I don’t want to send signed papers out by fax to a private residence.”

“Understood sir,” Eva replied with a nod. “So, are we staying in late tonight, sir?”

“There’s no need for you to waste your evening sitting around the office waiting for me to finish reading these papers. Why don’t you take off, enjoy what’s left of day?” Chip recommended.

“It’s no problem at all, sir. I don’t really feel like doing much tonight anyways, so I don’t mind keeping you company.”

If only you knew the kind of company I’d like to keep with you, Sergeant, he thought to himself, driven by his basic male desires given how sex-deprived he had become after three weeks.

“Well, I really appreciate it, Sergeant.”

Eva smiled warmly.

“Please, sir, call me Eva. You’re not a member of the Air Force and I feel that given the amount of time we have worked together I can refer to you by your first name. That is, if it’s alright with you, sir?”

Chip had to laugh a little.

“Of course, Eva, so long as you do away with the sir and call me Chip.”

“Understood, Chip.”

He laughed again before looking back at the paperwork on his desk and letting out a long sigh. Seeing that Chip was frustrated, Eva decided to take a seat at his desk and ask him how he was doing.

“Is everything alright, Chip?”

“Yeah, yeah I suppose. It’s just that it’s getting late and I haven’t had much of an opportunity to relax these past few weeks given all of the paperwork I have had to go through, and I seem to keep dragging you along with me.”

A smile came back to Eva’s face.

“Well, there are far worse people I could be stuck with late at night.”

Eva bit her lip and decided that it wouldn’t be too out of line to propose a relaxing drink, just one or two, to loosen up her boss before he got back to work.

“If you would permit me, sir, err, Chip, I have something that might brighten up your evening a bit.” She got up and started walking towards the door. “I’ll just be a few seconds.”

“Of course, Eva.”

She returned several seconds later, holding a bottle of Glenlivet Eighteen-Year-Old Scotch in one hand and two glass tumblers in the other, a mildly devious smile on her face, causing Chip to grin.

“Eva, you have read half of my mind tonight.”

Eva took a seat in one of the chairs in front of Chip’s desk. She opened the bottle and poured a generous amount of alcohol into each of the two glasses.

“Cheers, Chip.”

“Cheers, Eva.”

The two clinked their glasses together and finished the half-full tumblers in a single draining. While Eva was quite used to this class of alcohol, Chip moaned in appreciation of the quality of the spirits. Eva proceeded to pour another glass for the both of them, this time to sip more appreciatively, and she decided to ask her boss more about how he was feeling.

“I know it must be hard being away from your wife for so long. How are you holding up?” Eva asked as she crossed her legs and sipped her drink.

Chip looked at Eva as he raised his glass to his lips and drank from it. He swallowed and let out a pained moan in anticipation of telling her about his wife. Starting from when they got married, he proceeded to tell her about their mutual infidelities and how the both of them didn’t treat their marriage as anything more than a somewhat mutually beneficial partnership. Both of them were old enough that the concept of dating and remarrying was no longer an appealing prospect. It just made sense that they stay together and act like a couple when they were together while tolerating each other’s trysts when he was away on business.

As he droned on, Chip became aware that the scotch had loosened him up to the point that he had probably said far too much regarding his infidelities against his wife and the lifestyle he liked to lead when he was away from home on business. As he cut himself off, hoping that Eva didn’t feel disgusted by him, he looked over to Eva to find her nodding her head slightly at his last statement, the same gentle smile on her face when they started drinking, as if she wasn’t at all bothered by what he had said.

“I’m so sorry, Eva. You shouldn’t have had to listen to all of that. My marriage situation is my own problem, and I realize that what I have with my wife must seem pretty deplorable, but we just don’t love each other like we used to.” Chip sighed before continuing. “The lifestyle I lead when I’m away from my wife, it’s the only way to escape how shitty things are at home and how stressful it is traveling all over the world for business. I’m really sorry if I’ve made you feel uncomfortable.”

Chip sighed yet again and prepared for the young woman to excuse herself and awkwardly hurry back to her desk outside of his office, but to his surprise, she just took another swig of her drink and smiled at him.

“Don’t worry, Chip. Given the circumstances, I can understand why you like to spend your free time with other women when you’re away from your wife. Hopefully, you don’t mind myself being the other woman that you are spending your evening with.” Eva’s voice had a flirty tone to it that began to arouse Chip, in spite of the dulling effect the scotch had had on him.

“Of course not, Eva, it’s just that normally the time I spend with attractive young women such as yourself is, well how can I put it, more physically active, in nature.” 

Eva’s smile broadened as she finished the remainder of her scotch.

“And why can’t I be one of those women?”

Raising an eyebrow, Chip wondered just what Eva meant; had she simply been making a flirtatious joke due to the alcohol she had been consuming, or did she actually inquire as to why she and him were not having sex yet? As he pondered how to respond to Eva’s question, she uncrossed her legs, stood up, and began to walk around the desk towards him. He stood up and started to walk around his desk in order to meet her halfway, and before he could say or do anything else, she had grabbed two handfuls of his white business shirt and pulled him close to her. She roughly undid his tie as she smiled devilishly at him and stared directly into his eyes with a passion, not unlike an animal looking at a piece of prey that they were about to pounce on.

“Sgt. Williams, are you-”

He never got to finish the question, as Eva pushed her lips into his, silencing him instantly as she grabbed ahold of his shirt again with one hand, while the other one reached behind his head and held against hers. Almost as instantly as she had kissed him, Chip began to lean into the kiss as well, grabbing ahold of the young woman’s hips and pulling her groin into his. He didn’t need to think about what he was doing; he had wanted to fuck Eva ever since he had laid his eyes on the uniformed goddess.

The only reason he had never acted on his instincts sooner actually came down to her uniform, ironically one of the things about her that aroused him so much. The truth was that Eva was not just some administrative assistant from within the company looking for an easy promotion, she was a member of the Royal Air Force, the people bankrolling the project he was spearheading. If he had tried to make a move on her and she reported him, he wouldn’t be able to shrug it off so easily, especially if it resulted in him costing his company the contract with the RAF. However, luckily for him, Eva was the one who had initiated the sexual encounter.

Eva broke the kiss and slowly backed away from Chip, smiling seductively as she did so. After stepping back three or four feet, she removed her jacket and undid all of the buttons on her shirt that weren’t already undone to reveal a dark blue bra. It wasn’t until Eva had finally opened her shirt to Chip that he finally realized just how large her breasts were, despite all of the cleavage that she regularly showed off to him; they had to be C’s, at least, more likely smaller D’s.

“Do you like what you see, sir?”

He loved that she called him sir, it made him feel powerful, but he still wanted to acknowledge that she was a uniformed officer of the air force, as her position and her uniform excited him in particular.

“Yes, I do, sergeant. Please, continue.”

“Of course, sir.”

With her boss’ approval, Eva let her shirt fall behind her onto the floor and walked forward to kiss him once again. Although he thought he may have been imagining it, Chip swore that Eva’s lips had a sweet taste to them, like the subtle sweetness of strawberries, as cliched as it may have sounded. He didn’t have much time to ponder the taste of the woman’s lips, as she slid her tongue into his mouth and began to play with his while she slid his jacket off and began to unbutton his shirt before giving up and just ripping it open. She paused their kiss briefly to exhale sharply in excitement at the sight of the toned body that was hidden behind the now ruined shirt.

The pair’s kissing started again, slowly, passionately, at first, but the two adults had been so stressed out, so sex deprived over the past several weeks that their kissing and groping quickly grew a lot more aggressive. Eva began to roughly rub Chip’s cock through his pants, while his own hands pawed and squeezed at the sergeant’s large breasts and ass cheeks. Luckily for the both of them, neither minded the other’s overly forward approach.

“Oh, Chip. I like it when a man gets a little aggressive.”

“And I like it when a woman is a little aggressive as well.” He was glad that she approved of how contentious and fast he was; he had started to worry that Eva might be feel threatened by how grabby he had become in his lustful state.

As Chip’s hands made their way to her desperate, aching pussy, Eva cried out as he touched her and stumbled backwards, grabbing onto his desk to steady herself as his finger’s started to aggressively massage her pussy through her thin panties. Just as she thought that she was able to get ahold of herself, Chip’s finger’s slid underneath the fabric and began to rub the inner folds of her pussy, sending new shocks of pleasure through her body and causing her to grip the desk tighter, partly due to the intensity of the pleasure, and partly so she didn’t collapse to the floor.

Seeing the woman struggle to maintain her composure at the simple touch of his fingertips, Chip helped Eva up onto his desk and spread her legs as he sat down on one of the guest chairs in front of it. Since she still had her skirt and panties on, Eva assisted by pulling her dark blue panties, the same color of her bra, aside so that her boss could more easily access her pussy. Chip admired the shaved pussy of his assistant and the nice little tuft of blonde hair just above it. Not wanting to keep Eva waiting, he started to gently rub his fingers over her wet lips, much to her delight, as she moaned, both out of pleasure and as a way to further tease Chip.

“Mmm, nice hands, Chip.”

Convinced that he had done enough foreplay, Chip moved his fingers to her clit and started to rub little circles around it

“Oh, oh Chip, please don’t tease me anymore; you know what I need.”

He did indeed know what she needed, as well as part of what he needed, so Chip leaned forward and stuck his tongue into the woman’s pussy and licked around its outer lips briefly before diving in deeper. Not wanting to neglect one of the most important parts of pleasuring a woman, he continued to use his fingers to pleasure Eva’s clit, occasionally switching to his tongue and then going back to licking her inner folds while furiously fingering her clit. The feeling of his tongue and fingers made Eva squirm as she struggled to maintain her composure, while her breathing had become fast and ragged.

“Ah, ah, oh Chip, oh, oh, my God,” she uttered in pieces between deep breaths.

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The mix of deep moans, loud breaths, and all of Eva’s squirming told Chip that he was doing a good job in pleasing the young woman. He continued to alternate between using his tongue to flick at Eva’s clit while shoving his fingers in and out of her pussy as if they were a surrogate penis, and then changing to using his fingers to vigorously rub her clit while his tongue slid up and down the puffy outer lips of her pussy to lap up the mix of pre-cum and his own saliva that dripped between her legs and onto his desk. By alternating his tactics, it kept Eva’s body from getting used to any one type of stimulus.

Chip turned out to be so good at what he was doing that it only took a few minutes to make Eva cum as a final wave of pleasure cascaded over her and drove her to orgasm. A loud ‘Ahhhhhh!’ was all that she was able to utter in response, as the level of gratification kept her from composing a coherent warning/message of praise for what Chip was doing to her

Chip lapped up as much of the sergeant's juices as he possibly could, but the young woman was just so wet that it proved to be an impossible task. He didn’t know if it was down to his wife’s age, or simply the fact that she was not as turned on by him as she was when they first met, but she didn’t release anywhere near as much juice as Eva just did. Well, at least I know that I haven’t lost my touch when it comes to pleasing a woman, he opined to himself.

After a few more licks, Chip stood up to kiss her, and she didn't hesitate to kiss him back, despite the fact that his lips were covered in her own juices after having just been buried in her cunt. Both moaned into each other's mouths, Eva because of the pleasure that her boss had just given her, and Chip out of anticipation of what she was likely to give him next. Not one to disappoint, she slid herself off of Chip’s desk and slid her hands down his sides as she began to lower herself in front of him.

“I think it's time for me to serve you, sir.”

Eva’s accent was driving him wild, and he was sure that she knew it as well, especially given the large bulge that was desperately trying to free itself from his pants. She smiled at Chip as she paused to slide his ruined dress shirt off before continuing her journey to her knees. Upon making it to the floor, she proceeded to undo the man’s belt and button, slide down his zipper, and pull out his cock, which by then was so stiff from everything that had been going on that evening that he was almost in pain. Eva smiled again, this time not as a means to tease Chip, but for herself, as she was looking forward to having her boss’ approximately eight-inch cock inside of her, and in more ways than one.

Starting off simple, Eva took Chip's cock into her right hand and began to gently stroke it while he maneuvered himself towards his desk, his cock never leaving her hand as he leaned against the desk. After a few more pumps, Eva proceeded to undo her bra and drop it on the floor before grabbing her breasts and wrapping them around his cock. Once they were in place, she began to slide her soft, natural tits up and down the hard shaft of Chip’s cock.

The feeling of the soft flesh wrapped around him made Chip moan loudly, moans that practically came out as grunts in response to how good Eva’s breasts felt as they massaged his cock. His wife had occasionally done the same thing for him as well, but her breast implants felt odd as they pushed against him and mashed with the natural parts of her breasts. It was clear to him though that Eva was an all-natural girl, and that made all the difference to him as she jerked him off with her tits.

“You have no idea how good that feels compared to my wife, Eva.”

Eva smiled up at him.

“Well, I’m happy that you approve, sir.”

The pleasure kept building for Chip as Eva continued to slide her breasts up and down his cock, threatening to bring him to a climax before he was anywhere near ready to do so. Apparently, his focus on trying not to cum was really obvious, because he noticed that Eva was looking up at him with an amused look on her face and she slowed her momentum to fully grab his attention.

“What is it, Eva?”

“Are you trying to hold back, Chip?"

“I’m not ready to cum just yet, this feels way too good.”

“Well, you’re going to have to cum eventually.”

“True, but there’s no reason for me not to try and stretch this out for as long as possible. Besides, it will only make the final outcome all the more impressive.”

After giving him a quick smile in response, Eva looked back down at her handiwork and started to move her breasts up and down at her previous pace, speeding up gradually over time. Eventually, she started to lick the tip of his cock, teasing him with the possibility that she was about to put the whole thing into her mouth but instead continuing to simply stroke him with her breasts, which Chip certainly had no objections to.

“Yes, like that, Eva. Just… like… ohhh...” he trailed off, unable to finish a coherent sentence in a manner similar to Eva when he had been pleasuring her.

After another minute, Eva decided that it was time to go all-in, that is it was time for all of Chip’s cock to go into her mouth. She removed him from in between her breasts and proceeded to lick his cock from its base to its tip, eliciting another deep moan from her boss. Once she finished licking it, she opened her mouth as wide as she could and swallowed it whole, having learned to loosen up her gag reflex quite some time ago from her abundant experience with orally pleasuring men. The tip of Chip’s cock slid into her throat and she swallowed, causing her throat to squeeze the head of his cock, soliciting the biggest moan that he had given that evening.

Slowly, Eva slid the wet shaft out of her mouth and let the head exit with a small ‘pop.’ After a quick giggle-filled smile that showed off her flawless white teeth, she swallowed Chip’s cock once again, this time not letting the head leave her mouth as she slid the rest of the shaft in and out of her mouth. She deepthroated him repeatedly, occasionally switching to using a hand to jerk the base of his cock so that she was able to pleasure all of him while managing to give her throat a break from time to time. All the while she was working on his cock, her left hand was underneath her panties rubbing her clit, keeping herself fully aroused until the cock that she was sucking ended up in her pussy.

Despite spending most of Eva’s blowjob leaning back on his desk with eyes closed, Chip did manage to keep from totally getting lost in pleasure. He reached down with a hand to stroke the young lady’s hair and caress her angelic face. Eva would look up and lock eyes with him as she continued to suck him off, something that he found incredibly erotic. Once again the thought of his wife interrupted his enjoyment of the evening, as he thought about how his wife would hardly ever look at him while they had sex. Looking into the eyes of the person he was fucking always brought an intensity to the situation that further aroused Chip, and his wife seemed to try and avoid it whenever she could.

As much as he wanted to continue, Chip felt that sensation a man feels right before having an orgasm and his mind goes blank for a second. He barely managed to utter a warning to Eva before he came.

“Eva, I’m gonna, aarrgh.”

The sergeant wasn’t able to remove Chip’s cock in time, and with a loud grunt, he shot off his first load straight through Eva’s mouth and into her throat, causing her to gag at the unexpected discharge. As she choked slightly and removed his dick from her mouth, his second batch of cum hit her right cheek. Chip held on as much as possible before letting go of his last load, causing the built-up tension to propel his final batch under Eva’s chin and onto her throat.

Despite the surprise of his cum sliding directly into her throat and choking her a bit, Eva was not at all bothered by it and began to happily collect as much of the spilled cum from Chip’s second and third barrages and lick them off of her fingers. She closed her eyes and moaned as she slowly slid her fingers out of her mouth, the cum that was formerly on them now gone. Chip enjoyed the show, and much to Eva’s delight, he had already begun to get hard again, an impressive feat given that he had just cum seconds earlier; that kind of vitality in a man was hard to come by.

After she finished cleaning the cum off of her face, Eva allowed herself to be guided by Chip back to the edge of her desk. Knowing that it was time for the final act of the night, she slid her panties to the floor and stepped out of them. Just as she began to slide off her skirt, Chip gently placed a hand on her arm and stopped her.

“No, sergeant. Please, keep the skirt and high-heels on,” he directed her with a voice that contained a mix of both a boss’ authority and the mischief of a man about to do something highly sexual. He loved the fact that Eva was a woman in uniform, and he wanted her to retain at least a bit of hers. Besides, he also loved to have sex with his assistants while they wore their skirts and high-heels, a visible reminder that the woman he was having sex with was a woman who worked for him and shouldn’t be engaging in illicit activity with him.

Eva sat on Chip’s desk and spread her legs, offering herself to her boss, who wasted no time getting in front of her and raising her right leg over his shoulder and resting it there, imitating a classic position he had seen in many pornographic films. He positioned his cock at the opening between her legs and looked for a simple nod of approval to proceed, which Eva provided. Without any foreplay, of which he couldn’t stand to spare anymore, he pushed his cock into her pussy quickly instead of slowly teasing his way in. The two had already slowly pleasured each other orally, and both needed to move onto something fast and intense to keep raising the pleasure.

Instead of a shriek of pain, Eva, who was by no means still a virgin, let out an ‘Ooh’ at the feeling of Chip’s cock shoving past her pussy’s lips and penetrating deep into her vaginal canal.

“Ooh, oh, Chip.”

As soon as he reached the back of her pussy, he pulled himself back, but slower than when he entered her, causing Eva to moan out loud as she felt the wide tip of his cock slide along the warm, wet walls of her pussy. The head was thick enough, and her canal small enough, that the tip caused a great deal of pleasure to her as it slowly slid along the inside of her, a sensation that she did not get often with other men. As soon as the head was about to pop out of her, Chip slammed it back in, this time even faster than his initial thrust, making Eva cry out in a mix of both pleasure, and a little pain thanks to the size the head, something she desperately missed since the first few times she had had sex after initially losing her virginity.

“YES! Oh my God, Chip, that was amazing. Fuck me faster,” Eva begged through ragged breaths brought on by the sudden surge in pleasure.

While Chip was initially more than willing to do whatever he could to please his assistant, he decided that he didn’t want to give her exactly what she wanted when she asked for it. It was more fun to play with her for a bit, not to mention it gave him the chance to delay his orgasm for a while and extend his, as well as her, pleasure.

“Ah, ah, ah, Sgt. Williams. You should know that it is ill advised to rush while carrying out such an important task for your boss.” Chip smiled as he relished the fact that he remained somewhat in control of what was happening, despite the fact that it was Eva who had initiated it in the first place. “Don’t worry though, I promise that we will both get what we need from this, but at my pace, understood, sergeant?”

Eva nodded modestly at her boss’ response. She knew the game that Chip was playing, and she was willing to play along with his desire to remain the authority figure in their boss-assistant relationship, despite its recent sexual evolution; she just wanted to make sure that he didn’t get too wrapped out in prolonging his own orgasm that he denied her the fast and rough fucking that she desperately needed after working such long nights aside him.

“I understand. Please-” She gasped deeply. “Forgive me, sir.”

Chip smiled devilishly.

“That depends on how well you perform the rest of your tasks this evening, sergeant.”

Despite hinting at not going as fast as possible as a means of chastising Eva for her request, Chip had no intention, nor the self-control, to take things slow and steady. His hips moved faster and faster with each thrust, driving his cock deeper into Eva until she had loosened up enough to allow the head of his cock slam into the back of her pussy freely. The results were easy to see, as Eva steadily cried out a series of ‘Ahhhs’ with her head laid back against the desk and her eyes squeezed close as her brain focused on turning Chip’s somewhat painful thrusts into bursts of intense pleasure.

After staying in the position with Eva’s leg propped on his shoulder for a while, Chip slowed down and asked her to bend over her desk. The sergeant did what she was asked, placing her hands on the desk and leaning over it as she pushed her ass out towards Chip’s cock. He grabbed the woman’s hips and pushed his cock back into her pussy and started fucking her once again, enjoying the view of her perfectly rounded ass bounce as he fucked her. Although he wasn’t the kind of man that liked to smack women on the ass during sex, he still greatly appreciated a nice ass, which he did with Eva by moving his hands from her hips to her ass and squeezing them hard enough that it allowed him to pull and push her back and forth faster over his cock just like when he was holding her hips.

“Your pussy is amazing, Eva. I was wondering though if I could try another spot, however, since you are already in this position.”

She knew what he meant, and was slightly hesitant to agree, as she hadn’t done anal that much, and with a cock the size of Chip’s, it might prove a little painful. Not wanting to disappoint her boss and put a damper on the evening though, she agreed to let him fuck her in her ass.

“Of course, sir. You know I’m here to serve you in any way I can.”

With her approval, Chip removed his cock from Eva’s pussy and probed her fairly tight asshole with the head of his cock. A tentative push that didn’t even manage to get the fat head of his cock into her ass caused Eva to exhale sharply at the feeling of something that big trying to push it’s way into a hole that did not regularly get much use. Desperate to maintain the same momentum as he had with her pussy, Chip decided against gently pushing his way into her and instead removed the tip of his cock and shoved the whole thing into her with one lightning fast stroke.

“AAAAAHHHHH!” Eva cried out in one long scream, this time more from pain than from pleasure. She didn’t receive a chance to get used to the new feeling of having something as large as Chip’s cock in her, as he started ramming it in and out of her right after bottoming out in her with his initial surprise attack. The loudest ‘Ah, ah, ah, ah, ahs’ of the evening filled the empty office space and tears slowly trickled down Eva’s face as she tried to adjust to the new sensation in her asshole.

Luckily for Eva, she managed to adjust to the new intense sensation rather quickly, and all of her moans of ‘Ah’ began to be interrupted with her pleas for more.

“Fuck, fuck, FUCK.” Moaning. “Fuck my ass, Chip, fuck it, please,” she begged him. Gone was the initial control that she had exercised over the evening, as was Chip’s reminder not to try and dictate how he fucked her, not that he cared anymore.

Both Chip and Eva had effectively reached an almost animalistic state in which all they cared about was fucking and getting fucked. Chip’s thrusting even became so forceful that Eva had to brace herself on the desk better by swinging one leg onto the desk while reaching over it with both hands and holding the edges in a death grip to keep herself from getting pushed over the edge by his thrusting. Thankfully, her boss had dedicated one of his hands to reach around her waist to her front and rub her clit for her while she held onto his desk, and thanks to the stimulation being given to both her clit and her asshole, she came again, twice, actually, nearly in rapid succession.

“Oh, Chip. Oh, Chip, you’re gonna make me cum again, I’m gonna cum,” she roared, feeling exhilarated, not only at receiving yet another orgasm, but in feeling such extraordinary new sensations in her previously underutilized asshole, a new kind of experience that she became grateful to her boss for opening up to her in her future experiences with men.

The tightness of the hole in question made it impossible for Chip to hold back his second orgasm and he tensed up briefly before grunting and cumming inside of Eva’s ass. The sensation of the warm goo in her ass felt a bit awkward at first, but after a second or two it felt really good to Eva, who gave out a final, long moan that tapered off in volume as Chip slowed his thrusting to nothing and let himself go a bit limp before pulling out of Eva. The intense anal experience took a lot out of her and she simply let herself go limp on his desk, not realizing just how tensed up and turned on she was until it was over.

As for Chip, he felt completely reinvigorated, like he was back to his usual self when he was away from his wife. For brief moments such as those, he wasn’t a family man with a slutty wife and two kids at home, nor was he a boring researcher for some mid-level defense contractor; he was a man who got to enjoy the simple pleasures of the company of an extremely attractive young woman. He looked at Eva and decided to help her up. As he helped her off of his desk, his eyes locked with hers and he saw the look of bliss in them at what they had just done and they shared a long kiss.

The two finally decided to sit down and sat on Chip’s plush leather office chair, with Eva sitting on his lap. She was now completely naked after removing her skirt and high-heels and Chip’s semi-hard dick pressed between her ass cheeks. She ran her hands along his body and turned her head to kiss him as he held her in his arms.

“Mmm, feeling better, Chip?”

Chip responded by smiling and giving her a peck on the lips.

“Much better, Eva. If only we had started doing this sooner, I would have enjoyed the past few weeks a lot more.”

“I feel the same way, but I thought that it was best to try and gauge your interest in such a relationship. For all I knew, you may have been loyal to a fault to your wife, or you may have preferred women who are dumb and easy.” She kissed him, longer this time, before making a little proposal to him. “Seeing as how we are in such a relationship now, I have a proposition for you.”

He was instantly intrigued.

“Which is?"

“I know that the project you’re working on is going to be tested soon in Barbados, and that you will likely be called upon to oversee it in person. I’m sure that you could impress upon both mine and your superiors the importance of having the woman who was your assistant throughout the project accompany you to the testing.”

Eva’s face took on a semi-serious, yet still cheerful tone.

“I know that our time together won’t last too much longer, I’m not naive as to think that this is the start of a long-term relationship, nor do I have any interest in it becoming one. I simply figured that it would be beneficial to have a woman accompany you on your work that you are familiar with,” she paused for a moment. “Intimately, familiar with, I should say.”

God, hearing those words in her accent is so fucking hot, Chip thought as his cock began to stiffen yet again.

Eva laughed lightheartedly before finishing her proposal.

“Besides, I haven’t had a vacation in a long time, and I think a little sun, a few glasses of rum, and this body in a bikini...” She ran her hands along her body from her shoulder down her arm, over her belly before coming to rest on the little patch of blonde hair above her otherwise shaved pussy. “Would be good for both of us. That is, if you don't mind me remaining your assistant for a little while longer, do you, Chip?"

He smiled and replied in an official sounding voice within a second, not needing to think about it at all.

“Why, of course Sgt. Williams. It only makes sense that the dedicated assistant who worked with me during the planning phase of the project accompany me to the testing phase as well. I will put in a formal request with your superiors tomorrow.” Chip’s voice returned to normal and he continued, “I feel energized, surprisingly. I think I will finish up my remaining paperwork and sleep in the office tonight. You can go home, Eva. I’ll see you in the morning.”

“Thank you, Chip. I’ll see you tomorrow.” She smiled deviously at him. “I’m looking forward to it.”

Eva picked up her articles of clothing and started to leave Chip’s office. Before she exited, she turned her head and winked at him just before she left and closed his office door. Chip remained on the couch for a minute and thought about his remarkably good turn in fortune. Now that he was having an affair with someone from the office, it would be far more convenient than having to go out to places like bars and clubs to snag women, and this woman also looked amazing in a uniform. Yes, it was a remarkably good change in fortune for Chip.

 

Published 
Written by NobleStallion
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