Taboo! (Jack Stalker and AndNich123)

Henry Carter never really worked late at his office, since he was head of the advertising department at the company he worked for. As such he did not have to work like a slave, as he had others who had to burn the midnight oil and feed him ideas when he was short of a few. Many times he had obeyed the number one rule of advertising, 'To get ahead you will often need a unique idea, and fast.' and its partner in crime, 'The best way to get a unique idea fast, is to steal someone else's'. It was a mantra he had taken to using on occasion, more often than usual lately, as he seemed to be tied up with more and more heated arguments with his wife, Amy, over the upbringing of their daughter, Chloe. He knew he was at the end of his tether with that 'annoying whore' who had spawned his 'young princess'. Amy's infuriating ways and lack of sex drive sent him trawling clubs and bars to kill time and get a few drinks inside him, until he was forced to head home at some late hour, with the excuse that he was working late always on his lips to fuel another test of wills. If it wasn't for his daughter he would have disposed of the sham of a relationship with her mother long ago.

Worse still there was a hot woman working on his floor, another newly joined advertising exec who he had recently assigned to a new minor account. Gillian Anders had caught his eye early and, if she had simply been a secretary, he would likely have fucked her raw and to rags already. As it was he only got to bump into her on occasion or when he engineered it, even though they worked on the same floor, and he had not had a chance to 'corner her' properly and alone. He often wondered if she was into fucking married men, thinking about what it would be like to get hold of her and use her flesh to satiate the frustration that was built up inside him from the need to fuck. She was definitely hot and he knew that if her office had been a few floors down, it was likely she would have a lot more men hovering around her. As it was most of the execs on his floor were women, but none of them caught his eye and fired up his cock like she did. She was beginning to affect his work as he found more and more reasons to call her in to check up on her progress or assign her instructions which might have been easily emailed or sent in a memo.

It had been raining when he got back to the office and when he reached his penthouse office level he had shaken off his trench coat and ditched it on his secretaries chair outside of his office. His own assistant was far too elderly to attract his attentions, and since Gillian was filling his thoughts more and more it was something of a convenience really. The office was empty this late at night, only the security staff downstairs and the cleaners were likely to be about, if at all. He paused to sit on the edge of his secretaries desk, a short distance from his office door, to check his phone before heading inside to collect the papers he had inadvertently left behind. After a few seconds he was surprised to notice that the door to his office was actually still open, he could also hear someone inside. It was an indistinct sound which drew his attention and made him approach immediately, moving up to the door to peer through the gap as he reached for the handle and then stopped.

There she was, Gillian fucking Anders, the woman he thought about day in and day out, the cock teasing whore of his floor who kept him hard and focused all day long, only to have to suppress any urges when he ended up back home with his annoying and frigid wife. He stopped as he was about to open his mouth, watching her and what she was doing as the blood rushed to his cock and a massive erection began to pack out his pants. So many times he had thought about her flesh against his, thought about ripping off her clothes, cutting them off with a knife and just holding her down and fucking her like an animal. She brought out every sick and twisted animalistic urge in his body, hard brutal sex, rough fucking that left her with cum leaking from every abused hole in her body, that was often the only thought on his mind as he waited for the hours of the day to tick by. Now the bitch was in his office, without permission?

He knew right then and there that he was going to make her pay for that, in fact it was essential. He'd been deprived of cunt for far too long, even considering his own daughter at times, now that he had the opportunity, alone in the office with Gillian at his mercy, he was going to ensure that he made the most of it. She was going to have to be fucked and fucked hard, so that by the time he was finished there would be no doubt that she was enslaved to his cock. Nails would scratch her skin, cum would weep from her ravaged holes, strands of tugged hair would smother his fingers and crescent shaped indents would litter her neck from his bites. Her writhing, cum swallowing, cunt juice squirting, ass spanked and defiled flesh was going to be all his. So what if he was married? That made it all the more vile and depraved, cheating on his ignorant whore of a wife with this cock teasing little bitch who thought she could swan around in his office would not only stave off the eventual desecration of his own daughters cunt, but would give him the sinful and sordid buzz that he needed to reignite his inspiration at work. With a twisted and cruel grin he pushed the door open wider and wider, his eyes raping her from head to toe as he watched what shew as doing...

The advertising world can be a scary place. It’s a shark tank of eat or be eaten. It had toughed Gillian up over the years. You have to have thick skin in this line of work. That was the first lesson she had learned. The second was that there was always someone bigger and worse than swimming around in those waters. She had heard how Mr. Carter was just such a shark. A great white to be feared, and if you managed a job with his firm, you were lucky and had best provide results. So she had spent back breaking hours trying to prove she deserved the spot she had already earned there. Rule three was there was always someone younger and hungrier than you coming up behind you, ready to shove you out of their way. So Gillian had to always stay two steps ahead of them.

The late nights at the office and less than ethical ways of getting things had done had taken a toll on her social life. Basically it turned into a barren wasteland. Nothing grew there, and no one ventured there. Still, burning the midnight oil had its perks. The office was usually deserted. Usually. There was always a security guard trolling the halls with a flashlight in one hand and a donut in the other. How he would ever manage to chase down and catch anyone breaking in was a mystery to her. He was close to her own age. Flirting with her, he actually thought he had a chance. Gillian often wondered what she was supposed to be attracted to most with him. His bulging gut hanging over his clearly distressed belt or his scraggly, mountain man bread that often held parts of his dinner. Either way, she was always polite to him but never encouraging. Some nights there was also a stray worker trying to finish up on at the last minute on a proposal that should have been done weeks ago. It was always easy to spot the ones who had a life and those who didn’t think their job was that important.

Another truth that she had learned during her time there was that Mr. Carter may be the great white in the advertising world, but he certainly did not lack in the looks department. She was always excited when he would summon to his office. Inside she felt nervous, like a school girl, but she maintained her composure as more than dirty, unprofessional thoughts raced through her mind. She would always nod and smile. “Yes Mr. Carter.” “Right away Mr. Carter.” Those were the two responses she gave most often to him. Her eyes would always avert from his face. His handsome, chiseled features made her melt between her legs. The way his shirt seemed to kiss his broad shoulders drove her insane, and if she had to inhale his scent for too long, she feared she would have to ask him if she could take a seat as her legs would grow weak. Watching him walk through the offices was also a treat. Slacks that had to be tailored just for his body, his amazing body, hung from his waist, covering the curve of his ass just so. He drew more than a few stares from the women, and Gillian tried to not make it so obvious that she was included in the staring group of women.

As it was on the particular night, she had decided to stay late and keep herself ahead of her younger, eager associates. She found it hard to focus as her thoughts drifted back to Mr. Carter. He had looked even more attractive today than usual. Gillian couldn’t help but be jealous of his wife, knowing she could have him anytime she wanted. In her own way, so could Gillian. Finally deciding she wouldn’t be able to get anything done until she took care of this; she headed up towards his office. It was her little escape really, a way to deal with the urges to have him, knowing she never could. ‘He’s a married man. He wouldn’t cheat on his wife.’ Pushing the door open to his office and nearly closing it behind, she slinked close to his desk. Though he was gone, the office still smelled like him. A wonderful, intoxicating scent that she breathed in. Her fingers glided across the surface of his desk as she made her way to his chair. She stepped from her shoes, and pulled her panties down, before stepping clear of them. She removed her skirt before sitting in his chair. She loved the feel of it against her bare skin. Her relief would come soon as she rubbed her clit until she climaxed. Her cunt was wet, and she delved her fingers into her slick juices. Her arousal heavy in the air, she brought her soaked fingers to her mouth and cleaned her hand before the feelings began to settle. Gillian always felt bad every time she did this. It had occurred to her one night, after making love to him in her mind and cumming hard, that she should punish herself. Standing from his chair, she noticed various things hanging on his wall. One item that always caught her attention was something that had been given to him as a joke from his staff. He was such a slave driver, or so they said, that they had gifted him a rattan cane. Lifting it from the wall she began to strike her own body. At first it was her back, but she progressed to her ass and the back of her legs. Tonight was no different. She rose, and once more took down the cane. Gillian placed it on the desk while she removed the rest of her clothing, never taking her eyes from the cane. Once she was naked, she bent slightly over his desk and began to punish her skin. With each lash, she cried out. “He’s married! You shouldn’t….AH….do this! You shouldn’t….AH….look at him. Don’t….AAHH….make yourself….AAHH….cum thinking….ARGHH….about him!” Strike after strike, the cane sliced through the air attacking her. Gillian never heard the door open as she was too engrossed in her self inflicted beating.

Henry could see Gillian’s panties on the floor as his gaze darted about the scene before him, her skirt nearby, the rest of her clothes discarded haphazardly as she splayed herself over his desk and began to beta herself with the cane he had left hanging on his wall. He could see the way that each strike tarnished her flesh and left a red streak in her skin as she sank into her self abuse with obvious relish. His cock grew stiffer and harder by the second, as he watched the cane streak her ass, batter her flesh, welt her buttocks as she muttered about how she shouldn't do what she was doing. he let a cruel twisted grin spread across his features as he moved up closer to her, looming over her from behind and pausing to simply bear witness to the action as she defiled his office and violated her body with her repeated abuse of it with his cane. He raped her from head to toe with his gaze, letting his stare burn into her, the prefect tone of her flesh, the enticing swell of her cane scarred ass. He listened to her moans as she desecrated her body with bow after blow, trying to apparently push herself towards a climax, attempting to beat an orgasm out of her wretched flesh as she defiled his office with her wicked cunt juice and craven moans.

He watched her for a while longer, then he quietly moved towards the scene of debauchery which was unfolding before him. He wasted no time in grabbing a fistful of her hair with one hand, then grasping her cane wielding wrist with the other. "Well, well, well... this is a surprise Miss Anders. You dirty, filthy little slut..." he growled loudly into her ear as he forced her flat against the desk, wrestling her into position with the fistful of the hair he had taken hold of and giving her no chance to resist or speak in protest before he assaulted her with a barrage of his own words to cancel and drown out the sounds of her own voice. He roughly shoved her down onto the desk, face first, compressing her tits into the hard surface as he slid her forwards across it. Her body was slammed down hard and far enough for her cunt to jam into the edge, then slide onto it as her feet left the floor to splay apart and dangle free of the floor. His other hand slapped away her wrist and snatched up the cane she had been using which dropped from it. Immediately he started swishing it around, then he brought it up between her thighs to push across the lips of her cunt. The thin edge drove through the crease of her gash as it squeezed between desk and quim folds, letting her cunt juice smear along its length as he spoke to her in a lust fuelled tone. He savoured the look of her cunt flaps parting as he slid the cane between them, before slowly withdrawing it to admire its now soaked and slick length.

"This is the sort of outrageous activity which could finish you with this company, Miss Anders. It could ruin your career if this got out to our clients. This behaviour is so wretched, so wicked, so disgusting that you could not possibly be allowed to continue working here. You enter your bosses office, take his things, abuse your naked body as you confess to your and sick twisted fantasies involving him, when he's a married man no less!" he continued as he looked down at her from behind. He wrenched her head up, forcing her back to arch as he caught her eyes in the glass of the window behind his desk. The reflection of the sordid scene was playing out there in front of them, behind his desk and chair as the city lights glared back from afar. He brought the cane up in front of her face, showing her the drenched tip and length, sodden and soiled with her secretions as he rotated it about. "You have even vandalised a gift from my workers, fouled it in the filthy fuck juice you've been weeping from your evil... little... cunt..." he hissed with amusement. A growling ferocity creeping into his words as he drew the tip of the cane across her cheek.

"Do you honestly think you have what it takes to drag a man away from his wife? Do you think you have what it takes to make a married man give up on his spouse and daughter, simply in order to feel what your tight young cunt would be like wrapped around his cock?" he asked her as he brought the cane around to her ass, stroking the tip across her buttocks. "Is that what you get off on Miss Anders? Teasing yourself and fucking yourself in a married mans office, defiling your tight holes in the hope you can entice him into adultery? Do you flog yourself and cane yourself and soak your fingers in your filthy fuck juice, in the hope that you can get him to use his cock to spread you open and fuck your tight holes instead of his wife’s?" he hissed. "Your sort of brazen behaviour needs to be punished... and I'm afraid that I'm going to have to do that myself, if you are to have any hope of remaining with this firm." he assured her. He placed the cane down on the desk next to her and ran his hand down her back, fingers scratching along her spine until they reached her ass, where he raised his hand and brought it down to smack hard against her ass, leaving a fading palm print against her flesh.

"I'll tell you what I'll do Miss Anders. I came late to this party of yours, so before I can pass judgement on you I'll have to know exactly what it is you've been doing in here. I need to know exactly how much of a depraved, debauched and twisted little cunt you really are." he told her in a stern and commanding voice. He released her hair and walked around his desk to the other side, standing facing her, before sitting down and leaning back in his chair. There was a picture of his wife and daughter set on the desk, his wife Amy wearing some dress which would have likely suited a fifties sitcom, while his daughter was wearing 'rape me' spandex and walking out of a gym. "Let's see if you can get me hard enough to forget about my family, let's see if you can get me hard enough to forget about punishing you for abusing yourself... so I can start punishing you with cock for being an adultery causing whore." he growled.

Each strike was sending her further and further down her path, towards another orgasm that her body so desperately craved. The can would connect with her flesh, sending precise lines of pain through her skin, spreading outward, until it consumed her ass. Burning had settled in, along with a dull ache, and she pushed both to grow in intensity. Each punishing blow was an attempt to make everything she experienced stronger, more powerful, despite knowing her hands could only take this torture, this pleasure, to a certain level. As if her life depended on it, Gillian kept pushing, trying to push the plateau that she always found herself frustrated upon.

Then she felt something new, something different. Her scalp felt the instant sensation of someone pulling her hair, and her wrists stopped in mid air. The strong hand held her in place as the words cut through the air. “Mr. Carter! I….I….No wait! Please! I can explain! I just….” His tone was well defined. He wasn’t going to listen to her. Her words didn’t matter in the slightest. Mr. Carter had come into the room with the goal of taking the situation in hand, and he had done so swiftly. She felt her body pressed into his desk, unable to move, to fight him off, to do anything but rest there and listen to the harsh, heated words coming from his lips. He had slid her across the smooth, lacquered surface with ease. Her nipples pinched as her body weight rested against them. Her skin squealing as he had moved her long was the only sound in the room that could rival his voice. He was manhandling her, clearly. She felt the cane fall from her fingers, and she brought her other hand up near her face where the other one was. Gillian wanted to protest, to try and explain herself, but really what explanation could she give him? The can fell from the wall and landed in my hands as my clothing just happened to fall? The voices in my head told me to spank myself? None of that even remotely made any sense, and in her current situation, it was all that came to mind. The truth was exactly what the scene he had walked in on was. She was a dirty, filthy slut. She didn’t even try to kick her feet. No. Gillian lay there still, listening to what he had to say. It didn’t even occur to her that he had picked up the cane. She was convinced he was disgusted by what he saw, and her days working with his firm were over.

The sound from the cane alerted her to his possession of it, and it also was the reason she began to fear something more. ‘He wouldn’t,’ she thought. She had displayed the audacity to come into his office, strip down naked, and use something on his walls, in his office, to spank her naked flesh with, and she actually thought he wouldn’t do something like spank her. She knew he had every right to, and had it been the other way around, she would have spanked him. She winced, her ass tightening, at the feel of the cane as it touched between her thighs. She was more convinced now than ever that he was going to strike her with it. The cane spread her slightly as he began to delve into her wet sex. Gillian paused a moment, holding her breath, unable to believe what he was doing. A simple thought couldn’t even form in her mind as she drank the feeling. She panted, releasing her breath slowly, her entire body twitching with each jagged release of air from her.

He moved, the cane absent from her cunt, and Gillian released the rest of her breath. His words rang true. ‘He’s disgusted! He’s right! I did this because of my lust for a married man! I’m so ashamed!’ Her cheeks flushed red, and she wanted to cry. Just as her tears were about to flow, he brought her head up. Gillian took in the sight of her body on his desk and his hand in her hair. As much as she hated it, what she saw only excited her more. Her fingernail gripped his desk as she glanced over in the glass searching for his face. The cane caught her attention before she look in the view of his features. She could smell her cunt cream all over the surface. A surge raced through her body. She wanted to lick it, to suckle it clean, but he had other plans as he touched it to her cheek. No matter. It was the contact really that drove her wild. He moved the cane once more, and as she felt it touch her ass, her body braced for impact. ‘No. I know I don’t have what it takes to take a married away from his wife. It’s why I have my secret fantasy in here. I want to tell you so much, but you wouldn’t give me a second look.’ Gillian knew not to answer him. ‘Punish me yourself?’ Her mouth slowly opened in shock, wanting to beg him to do so, but Mr. Carter was always one step ahead. His fingers touched her skin, and she felt a jolt. It was electrifying. Sparks danced down her spine as he teased his way down. His hand connected with a smack, and she moaned.

He moved before her, issuing what seemed like a challenge after he sat down. Gillian swallowed hard, feeling her head tingle from his grip on her hair. ‘He wants to know. Fine. I’ll tell him.’ She didn’t move. Her eyes were locked with his. It was so much easier to think she would tell him. It was another entirely to open up her mouth and speak the words, laying out every sordid detail for him to hear. She would hear them as well, in her own voice. While she had done these things, yes, it was also another thing to explain them, to hear them, to admit to them verbally. She cleared her throat slightly. “Alright Mr. Carter.” She felt a moment where she wanted to apologize, but it was the intensity behind his eyes that stopped her. Whether it was really there or not, she felt it. He had already shown her he was a man of action. Apologies were weak in a situation like this. He didn’t want her to apologize, or so she thought. He wanted details. “I come in here whenever the thought of you becomes too much. You see, I watch you every day, walking around here in your expensive suits, your slacks hanging from your waist, covering your ass, your shirts clinging to your body, and I become aroused. I know you’re married, and I would never ask you to cheat on your wife. I would never ask you to fuck me until we both cum just so I could feel one moment of satisfaction. So I sneak into your office when my thoughts, my feeling, the stirring between my legs becomes too much to handle. I sit, half naked in your chair, the very one you’re in now, and I make myself cum. I take some pleasure in knowing the next day you will sit in my dried slut juices. It’s as close as I’ll ever get to you I tell myself. Of course I feel bad after I do such an act. So I strip naked and take down your cane. I punish myself for bad, evil, wicked thoughts. I try to make myself cum again. Sometimes I even lay the picture of your wife down and imagine I’m being caned while laying over her body. I imagine her naked flesh pressed against my own. I think of what it must feel like to have your cock sink into my tight cunt. I’ve never even seen it, but way your slacks fit your body, I can only dream about it’s size.” She closes her eyes, clearly reveling in the thoughts dancing through her head. “I want you to push me down and drive your cock deep in all my holes, fucking me until you fill me, leaving me a cum dripping mess moaning your name now addicted to your cock, but I know you’re married. Even knowing that, Mr. Carter, I still don’t care. I still want all of you inside me. I fucking dream about it. I rub my clit in the bathroom sometimes and smear my cunt cream on your papers before I give them to you,” she hisses. “I want you to fucking defile me. I don’t care if you think about your wife. Hell bring her along,” she smirks. “I just want your cock stuffed inside my body. Just once Mr. Carter, and if I’m not addicted to you, I’ll leave you alone. No more secret cum sessions. No more cum smeared papers. No more pens left on your desk that have been inside my cunt, but if I’m addicted to you, then I’ll do whatever you want just for the satisfaction you can give me. That’s what I want. You’re married? You have a family? I don’t care. All I care about is that member between your legs and how it can make me feel between mine.”

Henry watched Gillian as she lay sprawled over his desk. He slowly unzipped his pants and exposed his cock, watching for a moment as its thick rigid shaft immediately speared up in front of him. The bulging length was streaked with pulsing veins and the bulbous helm was already glistening with pre cum, as he bore a gaze into her eyes, before allowing his stare to dip and roam almost abusively across her flesh. "You sound like you are every bit the filthy little slut that I thought you were when I walked in here Miss Anders." he began, taking hold of his massive erection and giving it a stroke, making sure that she could see it as it swelled up, as it stiffened even further and forced his fingers apart as it stretched out and jutted upwards like a steel hard pillar of flesh. It was clearly expanding because of her, his casual masturbation of his manhood smearing the juice leaking from the slit of his knob down its length as he looked at her as though she were a piece of meat placed there for his pleasure. "You are a sick twisted little fuck, aren't you Gillian? I am shocked by your list of confessions, shocked at the actions you have taken while supposedly working as a loyal and normal employee, instead of some wanton and craven harlot whose mind is filled with depravity and wretchedness." he smirked. "You are a sick little whore, aren't you Miss Anders? Fortunately for you I have a weakness for those who are sick and twisted." he hissed, leaning forwards a little he reached out and grasped a fistful of her hair, dragging her forwards over the desk, bring ing her head closer to his groin.

"I don't want to think about my frigid whore of a wife, even with you laying naked across her flesh. My daughter, on the other hand, well, daddy's little princess could do with a seeing to, luckily you have engaged me before things got so desperate that I would consider defiling my own flesh and blood. I've long looked at you, Miss Anders, thinking about how far you would go to seal your position here, thinking about what I would like to do to your body. Working on the new advertising account for the erotic toys company hasn't helped, in fact every toy I've seen I've imagined being driven into your holes or beaten against your flesh." he admitted with a growl as he fisted his grip in her hair even tighter. "But enough about me, it's your sin and depravity which needs to be accounted for, all the evil and debauched things that you have been doing in here without my permission, under my nose even. Did you think you would get away with it forever, or were you hoping that one day someone would catch you? That I would catch you?" he grunted, starting to stroke his cock more and more energetically, his fist travelling from balls to tip as its stiff surface ran slick and jerked about violently beneath his attentions. "Regardless of my thoughts and your wicked actions, I'm a family man, with a wife, a daughter and a reputation to maintain outside of work. Do you really think I 'd risk all that simply to ram my hard cock into one of your tiny little holes?" he continued, leaning in closer to her.

He stood up, releasing his cock in order to slap his now free hand across her face, the impact smearing her cheek with cock juice and leaving it red, the force causing her head to tug viciously at his hair grasping hand. SLAP! He caught her other cheek with a wicked grin, admiring her new flushed cheeks, before releasing her hair. "You, Gillian, are a nasty little whore who gets off on fucking married men. I know your sort, you just want a good hard fucking and you think that some guy in a messed up marriage will jump at the chance to fuck you open and abuse your flesh. Well, you picked the right guy you little whore. I want a piece of you, but you're going to have to earn it. Telling me how you want to come on my wife's face while I spank an orgasm out of you, well, swap out my darling but annoying princess of a daughter and I might get hard. I'm far more interested in fucking you though, right now you little slut." he hissed, "First let's get you properly attired though. From now on I want to see you in 'fuck me' heels every damn day. Starting now. Put your heels back on and get back over here." he shoved her back off the desk and looked towards where she had abandoned her shoes. "And you can forget about wearing pants from now on. Skirts and dresses only. Thin panties that can be torn off. Deep red lipstick that will stain my entire cock red when I force it down your throat, the kind that will make my cock look like it just robbed you of your virginity." he seethed with lust as he spoke to her.

"Right now, though, you need to be punished... and you seem to enjoy doing that yourself, don't you Gillian? So show me what a depraved little slut you are, I don't want to just listen to your twisted fantasies, I want to see what a nasty filthy little fuck slut you can be when you have permission to punish and abuse your flesh, right in front of me. Bend over the desk and show me how you abuse and violate your cunt and ass in order to squeeze out an orgasm and stain my office in your foul secretions." he commanded. "Show me how much you can take in order to get me hard enough to forget about my family and sink huge fucking cock into your yielding and willing cunt. Show me what a fuck hungry little whore will do to keep her job and make a married man desecrate his holy vows and plunder her cunt, simply to satisfy his wicked needs." he growled impatiently. All the while his cock grew harder and his hand stroked up and down its length, his eyes ravaging every inch of her as he waited to see what she would do.

Gillian found she confused and aroused. Confused by her words in the sense that he spoke with such a distain for those who would seek to tear a married away from his family, and yet, he was clearly aroused, wanting her, his cock out before her eyes to feast upon. Did he desire her, or was he simply disgusted? Aroused by his bulging cock make her weep between her legs. Her cunt already oozing as she lay pressed against his desk, clearly leaving a puddle marking where her pussy had been. She watched his hand stroke his manhood, and she had to swallow. Thoughts of what it would be like to have his rock shaft wedged in her throat, drinking down his cum, filled her mind. There was a lump in her throat, and her only regret at that moment was simply that it wasn’t his cock she was feeling and swallowing down.

She groaned as he took her hair, her eyes never leaving his. There was a yelp from her lips as her body slide across the smooth surface of his desk. The next sound from her mouth was her confirming what he already knew. “Yes Mr. Carter. I am a sick, twisted whore. I’m everything you think and so much more. As she spoke, she could smell the musk radiating from him. His hand traveled his length as he spoke, and Gillian found it difficult to focus on what he was saying. She settled for only grasping the jist of the conversation, as the sight of him stroking his cock was far more interesting. Even when his grip tightened, it did nothing to deter her growing excitement. Pain was her friend. Pain had helped her come ever so close to so many orgasms. She had long wanted pain to push her over the edge, to force her pussy to flood as she cried out, her body, her mind confused by the overwhelming sensations that would be gripping her. That had elated her. Even with her late night sessions of pleasure and punishment in his office, she had not been able to cum from simply spanking herself. No. She was always so close, just out of reach of what she sought.

His hand connected across her face, and the impact, coupled with the strong smell from his cock, drew a moan from her. Her scalp ached, each strand of hair pulling tighter. Another slap, and her hair was freed. The pain still remained, quickly diminishing though. She listened as he spoke once more. Mr. Carter was a man of many words, but he made his words count. She knew what he wanted. Her body moved from his desk, and Gillian reached for her shoes. She didn’t speak. There was no need to. The shoes slid over her heels, hugging her feet snuggly. Softly she padded her way over to him. Mr. Carter wasted no time in putting her back in her place across his desk. Gillian smiled, enjoying the treatment. So far he was proving to as good as she had always dreamed he would be. “Yes Sir,” she replied. “What if I simply don’t wear panties at all?” The question almost sounded sarcastic, but in truth she wanted to be as slutty as she could be for him.

Then she heard it. Permission..no..a command to punish herself. He wanted her to keep going. Her trembling hand reached for the cane, and she lifted it as high as she could. Her eyes locked to him. “Just for you Sir,” she stated, calmly, before bringing the cane down across her already abused skin. Once, twice, three, four, five times she brought it down with incredible force. The cane sliced through the air. A clear sound heard every time followed by a simple wince on her face. “I want to keep going. I want to keep going until I’m bruised, until I can’t take anymore, until my tears streak down my face, but I can’t cum Sir. Oh I try every time I do this to my pussy explode from the pain, but I can’t do it. My fingers rub my clit until I cum, but I want this to be the cause.” Her hand constantly landing harsh blows upon her skin. Red streaks, welts, begin to form. Lines marking her flesh, showing where the cane had been. Tears began to prick her eyes. “I can’t..cum..Sir. I want to..so badly..but I can’t. Not from..this.” Her breathing raged as the pain had spread across her ass and was now moving slightly down her legs and up her back. “Please Sir. Help me. I wanna cum. I need to. I want..your cock. I want..you..Sir.”

Henry was so fucking hard right now that he could scarcely believe it. The upside was that the whore who masqueraded as an office employee was likely to think that the massive cock protruding from his pants was a regular sight, a normal state for his manhood to be in. The truth was he hadn't been this hard since he'd fucked away his wife's virginity, back when she was capable of fucking that is, that and when he had realized for the first time that his feelings towards his daughter were more than fatherly on her eighteenth birthday. Now both of those events paled into insignificance as he strained and struggled to prevent himself from coming hard, at the mere sight of Gillian Anders parading about his office. His cock throbbed as he watched her move about, naked but for the pair of heels he had commanded her to slip back onto her delicate feet. He shook his head as he listened to her as she returned to the desk, looking at her impatiently as he stroked his rock hard member and thought about how it would feel stretching her cunt, defiling her ass or choking off her air as he throat fucked her. The slit of his cock head wept pre cum out onto the bulbous helm, a slick juice which his fingers began to smear down his length as the veins pulsed and the shaft throbbed with a hunger for cunt.

"I want you to wear your panties Anders... because I want to tear them off you when I get aroused. I want you to wear flimsy, delicate panties, because my wife doesn't. I want you to wear them because when I rip them off you and use them to gag you, or tie up your wrists, or choke off your air, then I'll know that you are getting the treatment that you deserve for being a cock teasing little whore... one who has enticed a decent hard working man away from his family. You'll know that it's your wicked flesh that has ruined his loyalty, that's it's your dripping cunt and tight ass that have goaded him into action and made him into an adulterous bastard. You'll know that his only concern is how loud he can make you scream, when he gets around to fucking you open and stretching very hole in your fragile body." he hissed aggressively as he raped her with his eyes. He watched her grasp hold of the cane again and shift it around to where she could bring it to bear against her own flesh. He burned a gaze into her flesh, leaving his cock momentarily to take hold of the edge of the desk as he watched her. Had he locked the door? he couldn't recall and could care less, if anyone entered it would be the cock teasing harlot who had stripped naked to entice and torment him, not the upstanding boss and family man, laid to ruin by her wanton and craven actions.

The sight of her slashing the cane across her flesh and raising the welts almost made him cum. He stood up rapidly, listening to her debase herself and confess to the wretched level of depravity and sin, which had taken hold of her and now dominated her thoughts and actions. He leaned forwards, one hand grasping her wrist, the one which held the cane, the other fisting in her hair and dragging her forwards over the desk. She lay sprawled on it now, her legs jutting out from it as her face was brought up next to his groin. He manhandled her, fingers clawing at her hair, until his cock was inches from her mouth. "It's not cheating if you just fuck some whore in the mouth, is it Miss Anders? I'm not really cheating on my wife if I fuck your sweet mouth while punishing you for being such a fucking slut." he growled, gripping her wrist he forced her to begin caning her own ass, WHACK! stroke after stroke, each one combining with the thrusts which he began by forcing his cock-head between her lips and watching as her lipstick began to streak his cock as he fucked it into her mouth. He alternated, laying a red line across her buttocks, then forcing his massive shaft between her lips as his cock head fought to invade her throat and choke off her air by bulging out her neck. One stroke into her gullet, the other across her ass cheeks, pausing occasionally to wet the tip of the cane with the liquid sin beading and dripping from her soaking cunt.

Fuck yes...." he hissed,m watching his cock vanish into her mouth, streaked as red as her ass with the stain of her lips as he fucked her face. "It's not cheating on your wife if you just fuck some whore's face, now is it? It's not cheating if she's a family member either... is it?" he grunted. "Call me daddy you little bitch. Tell your daddy how you want to suck his cock, how you want him to fuck your throat until his wicked seed fills your belly and burns you up inside." he gasped, his eyes wild with depravity as he let the edge of the cane bite into the slit of her cunt for a stroke, before returning it to her ass. He released her hair to take hold of his cock and slap it against her face, smearing her cheek with pre cum, before bringing it back to her lips. "Take it, draw it in, suck on it, spit on it, choke on it you little whore, make your daddy come down your throat. Tasting it is going to make you come like a whore, believe me." he almost bellowed, turning the cane around he fucked the thick handle into her cunt a while, before twisting it about. He tossed it to the side, running his rough powerful hand over her ass as he leaned over her, SMACK! his hand reddening her already cane battered flesh. "Saw it. Do it. Do what your daddy wants. See if you can cum by swallowing all your daddy's thick fucking cum you little bitch. Play my game and I'll make you squirm and quiver and shake from pouring your cunt juice out of that fuck deprived slit." he gasped, drilling his shaft into her gullet in between long moments of cock slapping her cheeks and tormenting her ass with his hand.

As he stood, Gillian wasn’t sure what his actions would be. To be honest, she didn’t care. Any touch from him was welcomed. As it was, he grabbed her, firmly, powerfully, and slid her body across the unforgiving surface of his slick desk. Her wet cunt no doubt leaving proof of her current state along the smooth desk. She gasped, nearly yelping, as his grip in her hair was strong. She could feel the strands pulling at her scalp, threatening to be torn away, and she liked it. A sick smile melted across her face as she reveled in the pain. She could smell his musk. It was intoxicating to her. Breathing in deeply, she held the scent deep in her nose as she held her breath, before releasing her warm breath to his cock. “No Sir,” she replied. “It’s not cheating if you fuck some whore in the mouth.” Her gaze rested on the impressive meat before her. She loved everything about it. The way the skin looked, the smell, the veins, even the tip oozing seemed to call to her. “Please. Let me be that whore,” she whispered her plea to him.

His hand guided her, helping her punish her own flesh for the depraved acts she had committed in his office. ‘I deserve this,’ she thought. Gillian was on the verge of voicing her thoughts when he pushed his cock into her mouth. Precum smeared her lips before the head of his enormous length filled her mouth. Gillian felt a surge, a rush of excitement and lust, down to her clit as he began to fuck her mouth. Each stroke seemed harder to her ass, and his cock seemed to be pushing down her throat. She didn’t know which one to focus on more. Both were delicious experiences, and Gillian didn’t want either to end. ‘Cum in my mouth! Fill me up! Beat my ass! Make me want to cry! Leave stripes across my skin! Welt! Come on! Punish me!’ She could feel her body thrusting towards her climax, more and more, ever closer on the ledge of pleasure. The cane delved into her most private of parts, and she groaned. It was a tease really, but Gillian hoped, she wanted it to push her further. Her orgasm was closer, but it still seemed just out of reach. Frustration began to grown even more so. Her face reddened as his manhood claimed her throat. Lifting her head slightly, she brought her free hand to her throat, feeling the bulge. His appendage was even more intimidating now as she could barely take in a breath.

His words were hot, intense, burning into her. He let go of her hair and pulled his cock from her mouth. For a moment, Gillian was afraid he had changed his mind and was finished with her, but those thoughts soon vanished as he slapped his meat against the side of her face. His scent grew stronger as his precum painted her face. Gillian smiled looking up at him. “I want to suck your cock daddy. I want to drain your balls of every drop of your cum. I want it deep in my throat as you unleash your load into me. Please daddy. Let me suck your dick until you can’t hold back. I want to pull the cum from your body with my mouth.” She wrapped her lips around the tip of his cock, forming a tight seal, and began to draw him in with her suction. Her eyes never left his face. She groaned as he tortured her ass. His hands were so strong, and his punishment of her was unyielding. ‘I deserve this,’ she thought again. ‘I want this.’ Her groans nearly turned to cries as she felt the handle of the cane shoved inside her. She tried to push her body back against it, wanting to fuck it. Again she was conflicting. The burning, stinging ache from his hands as he spanked her, or his shaft plunging down her throat. She couldn’t decide which she thought felt the best. Either way, both were possessing her, making her his. All she wanted to do was to please him and cum. Gillian pushed her face forward, shoving his dick deeper into her throat, until she couldn’t breathe. She could hear her own heart beating in her ears as her body became more sensitive, feeling his intense, strong slaps to her ass. Gillian began to experience everything on a heightened level. What felt tantalizing before now took her body to a new plateau of ecstasy. The painful now became even more excruciating. Still Gillian wanted more. It was sensory overload, and though she needed to back off his cock and take a breath, she found she couldn’t. With every passing second, everything only seemed to be amplified. Her body’s need for air became too much though, and Gillian dislodged his member from her throat and mouth. “Please fill my mouth. Cum deep down my throat so I can have your seed in my belly. Most of all, daddy, make me scream.” Gillian didn’t wait for an answer before impaling her throat back on his length. Her pleading eyes looking up to his face once more.

Henry slapped his hand down firmly on Gillian's ass. He could feel the firm taut flesh submit to his palm, his hand leaving a reddening print of his power and domination stinging her ass cheeks as he spanked her buttocks and sent rippling shockwaves through her flesh to leave her quivering and shuddering at the impacts. His hard cock stiffened as it was driven down her throat and his spanks increased on pace as he noticed her cunt sliming a wretched trail of liquid sin across his desk as he dragged her forwards, her soaking quim staining the wood as he abused and violated her throat. His cock had never felt so hard, his balls heavy with the need to unload and his hands pawing and manhandling her as they tanned her ass and grasped unforgivingly at her hair. He jammed his cock deep into her face, "No, that's right. It's not cheating. It's perfectly all right to fuck a whore in the mouth. You'll be that whore Miss Anders. My whore. You're going to me filthy fuck addicted little whore, who is going to be punished and made to pay for all the nasty thins she's been doing without my permission." he hissed, plans already formulating in his head as his cock got a long overdue taste of a woman's flesh as it squeezed into her throat and expanded her neck with its thick pulsing veins and mercilessly brutal thrusting.

Nails scratched at her ass, fingers covered the thin streaks of welted skin and his hand slapped against her shivering ass cheeks with a ferocious vigor as he face fucked her without pause now. There was no reason to hold back against the increasing pleading and begging which tumbled from between her lips as he delivered thrust after thrust to her, his balls starting to slap against her chin as he fucked her. the way she called him daddy and the firm seal of her whore slips around the rim of his bulbous helm made him want to flood her wicked throat immediately. he managed to hold himself back, stay in control, his cock fighting to hold onto the strings of hot searing cum that were waiting to be disgorged into her. He grabbed her hair tighter, increased the spanks to her ass as she spoke her wicked words, his cock twitching and throbbing across her tongue as it defiled her throat with its mere presence.

He moved both hands to either side of her head, holding it still as he moved his hips back and forth and sent powerful stroke after powerful stroke driving into her throat. His massive shaft bulged her neck and the vicious tightness of her flesh massaged his length from the tip all the way to the root of his shaft as he burrowed it into her mouth. Finally he groaned, reaching down to grasp his cock as he pulled it all the way back until only the throbbing purplish knob remained between her lips. His body spasmed and bucked as he unleashed his seed into her mouth, long strings of boiling cum were blasted down her throat as he came hard, filling her gullet and jetting streams of sperm into her guts. He wrestled his cock free of her lips, its slit still spitting out strands of spunk as he battered her face with it, making sure that his milky fluids splattered across her cheeks and chin, some loose globules spluttering into her hair as he disgorged his load across her face. Gasps and grunts echoed about the room as he rode out his orgasm, and he moved to thrust his cock back into her mouth, fucking it until he was satisfied that the last dregs of his ejaculation were coating the inside of her mouth and drowning her tongue. It was clear that he was still hard, his cock rearing up and drenched with cum and spit as it twitched and throbbed in front of her cum splattered lips and face.

He leaned down, wiping his fingers across her face and chin he gathered up some of his cum, smearing some into her skin and features, while the rest was scooped and coaxed into her mouth on the ends of his digits and strung between them. He forced open her lips, using her mouth to clean his fingers of the spunk that had been scraped from her cheeks and lips. "Not bad you wicked little whore. My wicked little whore. You made your daddy come hard. That's good... but Daddy's not finished." he hissed. he stood up and walked around her, standing behind her he slapped her ass with his stiffening cock, splattering droplets of saliva and cum across her welted flesh. "Start spanking yourself, you filthy little slut. You need to be punished a little more. When daddy sees that you've made yourself cum from abusing your own flesh, then daddy is going to give you the cock. Daddy will finish with this foreplay and fill one of your filthy whore holes. That's what you want, isn't it Gillian..." he paused after saying her name. "That's what you want, isn't it? To make me cheat on my wife? Fucking your mouth isn't cheating... but driving my fuck stained rod into your tight ass or dripping cunt would be, wouldn't it? Let's see if you can make me, by pouring liquid sin out of wretched fuck sheath just by spanking yourself." he growled at her. He grabbed her hair and pulled back her head. "Do it... and every time I want to hear you say Fuck me daddy, until your weeping cunt has flooded your thighs. His free hand dropped between her legs and began to crudely molest her cunt, rough fingers drilling into her while his thumb assaulted her clit.