John Smith sat at his deck with a sly grin on his face. As the work day grew to a close, the 50-year-old VP of Sales could hardly wait for five o'clock. He had worked hard to get to where he was, putting in countless hours of overtime over the years, often at the expense of time with his family, but nowadays, the extra hours he spent in the office were less to do with his career advancement, and more for his own personal fulfillment.
Through their twenty plus years of marriage, John had become a fairly wealthy man and he, his wife Kathy and their two children were able to enjoy the finer things in life as a result. And no one enjoyed such a lifestyle more than his wife. With two independent teenage kids and the money to pay for a live-in housekeeper, Kathy had become very much a lady of leisure, filling her days with tennis lessons, trips to the spa, shopping, afternoon cocktail receptions and such. Her husband was more than willing to put up with her spending habits and relaxing lifestyle, they certainly could afford it, and he reasoned that since they had married when he was just starting out and she had supported his career and raised their children, she deserved it. And she was still a very beautiful woman, when she wanted to be. Kathy kept herself in great shape, particularly for a mother of two, and at over 40-years-old. Her slim and toned body revealed the many hours she put in at the gym and playing tennis, while high priced facials and weekly trips to the salon kept a deceiving youthful glow on her face and her blonde hair perfectly styled. Though he did not begrudge his wife the benefits of his successful career and hard work, in recent years John had begun to feel that he too should take the time to enjoy certain perks accustomed to a man in his position.
The first time he cheated on his wife was on one of his business trips, with a prostitute, a young black girl with a nose ring and big firm fake tits, who reminded him of Janet Jackson. He was a bit hesitant at first, but after getting over his initial bashfulness, John vigorously fucked her several times, enjoying the opportunity to try things his wife would never allow, experiment with different positions, role playing and name calling. More hookers on the road followed, always younger women, and each time he found himself enjoying more and more the feeling of empowerment that having the girls follow his every instruction brought to him.
Eventually, he began having affairs with local woman as well, sometimes women he met through a work function, or someone he would pick up in a bar and take to a hotel. As his adulterous campaign continued, two things became obvious to John. First, he harboured virtually no guilt about cheating on his wife, due in part to both his ego telling him he was owed these pleasures as payment for his years of sacrifice and hard work, and to his belief that his high society wife had most likely had her share of lovers over the years while he was away on long business trips. Secondly, he realized that his appetite for sex was seemingly impossible to satisfy, and he found himself lusting after almost every woman he met.
His latest object of desire was his new personal assistant Hayley. When his long-time secretary Margaret retired three months ago, John immediately decided that in support of his new found love of all persons young, hot and female, he would most definitely be filling the job with a candidate more appropriately fitting his personal requirements. As soon as she had walked into his office for the interview, he knew she was the one. He had barely been able to keep his eyes off her big, supple tits, and as she responded to his questioning, her basically ignored her words, instead fantasizing about the things he could do with her wonderful breasts. It was all he could do to not offer her the job right then and there, but he managed to keep up the appearance of due diligence, telling her they would let her know as he escorted her out, making sure to linger a few steps behind her so he could watch her sexy ass sashay through the door as he thought about how great it would feel bouncing up and down on his hard cock.
Now on this particular day, shortly after five o'clock, there was a knock on John's office door. "Yes, come in," he responded as Hayley entered, looking fantastic as always. Her permed brown hair fell onto her shoulders, as always looking a bit untamed and tousled like she had been running her hands through it all day. She was dressed in a black skirt with white pinstripes that came to just above the knees, obviously half of a suit. She had on black stockings and conservative black heels, while a white blouse - one of fairly sheer material that allowed for a pretty good view of the lacy white bra she wore underneath, barely containing her overflowing breasts - completed the outfit. John was pleased to see that in addition to the thin fabric of her top, she had also left the shirt unbuttoned fairly low, allowing her to show off some truly incredible looking cleavage.
"Need anything else Mr. Smith?" she asked, ever the good employee.
"As a matter of fact yes." John replied, the mischievous smile returning to his face as he pictured the many things he fantasized about doing with his busty assistant. He gave Hayley a list of things he wanted her to do before she left for the day, a bunch of minor tasks that would take her about an hour, likely leaving them all alone in the office by then.
Sure enough, just over an hour later, they were the only two left in the office and his dutiful assistant was on the last of her tasks set out by her boss. This final assignment had Hayley in his personal office, sorting and filing a variety of documents in one of the large oak cabinets that lined the wall beneath a large bay window. As she diligently worked at completing the task at hand, John quietly made his way to his office door and silently pulled it shut, locking it behind him, just in case his assumption regarding their privacy was wrong.
Watching his gorgeous secretary bending over the file drawer, her short skirt riding up her legs, he softly crept up behind her and pressed his body tight against hers, forcing his pelvis into her ass. Startled, Hayley bolted straight up and let out a quick yelp, "Mr. Smith, what are you..." Before she could even finish her question, John had his arms around her, one wrapping her waist while the other reached up and placed a hand on her bountiful chest, all the while continuing to press his hardening cock against her ass, gyrating his hips slowly.
Pressing his nose into the bed of messy curls behind her ear, he whispered softly, "Just working a little overtime my dear, same as you." Before she could even begin to respond, his lips found her neck and began assaulting her flesh. At the same time his lower hand had slipped from her waist, over her skirt and was now exploring underneath it, grabbing at her pussy through her lace thong.
"Oh, my God Mr. Smith!" she cried out. "Stop! Please.." she struggled against him, but to no avail, as she was virtually pinned between her boss and the filing drawers. "Let me go!" she pleaded. "I'll scream!"
"Go ahead," he replied coldly, "no one will hear you." John was now alternating between kissing her neck and nuzzling into her hair, while his busy hands attacked her tits and teased around her cunt. "Besides," he whispered in her ear between kisses, "we can either play nice and enjoy ourselves or we can play rough and risk having to fire you. Now we don't want that do we?"
Hayley was in shock, hearing her respected boss threaten her job if she did not cooperate with his sexual advances. Her mind raced, wondering if anyone would believe her side of the story if she refused. She certainly did not want to lose her job, and she knew it would be hard to find another that paid as well as this one, especially without a reference from her boss. Still, she had to find a way out of this situation, "Please let me go, Mr. Smith. I don't want you to rape me and I don't want you to fire me." she was nearly crying now, "If you let me go I won't tell anybody."
"Rape?" he laughed heartlessly. "Who said anything about rape? No, we're just gonna have a little fun together." His left hand was now roughly rubbing against her thin panties, viciously massaging her quickly swelling clit. "And I know you'll like it Hayley, but if you want to play rough, I can rape you, and then tomorrow I can fire you." He was brimming with confidence now, certain she would relent for fear of losing her job, a certainty supported by the dampness he was feeling against his fingers as her pussy became more and more aroused from his forceful attention.
She thought about all her possibilities - really only two. Fighting back was pretty much out of the question, useless wanted to be raped and fired, while if she let her boss have his way with her she would keep her job. And as his hand worked inside her panties, it might not be that bad she thought.
Tired of waiting for her response, John suddenly pulled his hands off of her tits and dampening pussy and roughly spun her around to face him, drawing her in close. "Listen Hayley, either you become my little office slut or you're finished." he said as he forced himself against her, forcing her back against the filing drawers and pressing his growing erection against her. His hands started roughly grabbing her breasts through her blouse, squeezing them hard enough to make her cry out in pain. "What's your answer Hayley?" he demanded as she tried to squirm away from his hands.
