WARNING. This story includes graphical descriptions of extreme, forced sexual practices of almost all kinds. If you think something might offend you or are under legal age to read porn stories, please don't go further and delete this file. DISCLAIMER. This story is fiction. The author does not condone, and much less support or suggest, any form of sexual harassment or non-consensual sex. Blackmailed Secretary By Prof. Anacletus Whip Part 1 Roberta's entrapment Roberta woke in a sweat. As soon as she was conscious, her thought ran to his boss. She began feeling nervous again as he had finally asked to talk to her in his office that day. Her night had been troubled and she had tossed and turned as she thought back to that terrible moment when, a few days ago, Mr. Depoulos stepped into the agency with a roll of documents and tossed them on her desk. Roberta had gone blank as she easily recognised the documents. "I don't care why you manipulated those documents, Roberta, all I know is that this is illegal, against the company's interest, and that I will have to take action against you for that". Mr. Depoulos watching her, his little black eyes sharp as knives. Roberta blushing hard and unable to speak. "We will discuss your situation later". Roberta did not cheat on the insurance company for her own interest. She was moved to compassion and had helped a customer. She knew Depoulos too well to even think about discussing her reasons with him. She had rushed home and searched through her books to figure out what could happen to her at worst. The result was that the worst was simply unbearable. Apart from losing her job, she could be prosecuted by law, and get a penalty that would take years to be paid, and ruin her life. After that mistake, also, it would have been very hard for her to find another job, at least in the insurance business, which was all she was experienced in. And, something that made her heart ache, her marriage with her beloved Rod would probably vanish. Rod. She didn't have the guts to tell him. If Depoulos forgave her, Rod would just never know about all this nightmare. If she was forgiven... She just had to be. As she opened her suitcase, she unconsciously chose clothes that would make her look prettiest. She went for a black bra and matching thong, and a grey business suite comprising a short, quite tight skirt, and a jacket that would show a bit of her ample cleavage. Then she opened her pantyhose drawer, hesitated, and closed it. She opened a lower drawer and fetched a pair of silk black hold-ups. She would wore high heels, and fine makeup. She hurried to the bath to prepare herself. Her heart was pounding. She briefly felt guilty about trying to look sexy. Yet that was not meant as an invitation of sorts, she thought that it's simply a fact that good looks can put your interlocutor in a better disposition. She slipped into her thong and began feeling nervous again. She combed her long curly hair and embellished her green eyes with mascara. ------------------------------------------------------------------------------------------ Roberta stepped into Depoulos office. He was a Greek, small and a bit overweight, almost bald, with intense little black inquiring eyes. Roberta would never consider him as an interesting man, and that was not just the appearance. He was also a greedy, cynical and hard to please person. He made a brilliant career in the insurance company mostly thanks to his lack of scruples. Although they knew each other since three years, Roberta and her boss were definitely not friends. She couldn't remember to have seen him smile. She used to think he probably hated or just despised her. Depoulos raised his eyes from his large, shiny desk to her. She greeted and, following his gesture, sat on a chair before him. Her heart was racing and she was already blushing. She felt like she was before the judge... well that was very close to the truth. "I hope that in these few days, Roberta, you got an accurate idea of the consequences of your action," he said coldly. "Yes, sir," she replied in a low voice. Her gaze went to the floor briefly, then she urged herself to raise her face and meet his eyes. "You are aware of the pecuniary penalty, of the fact that you would be banned from insurance and other financial employment," he paused to see her nod, "and maybe even of the fact that I have the power and the will to bring this to the extremes and ruin your whole life. All correct?" Roberta sadly nodded. "Yes sir," she murmured, "but let me..." Depoulos raised his hand to interrupt her. "I'm not interested in what you are willing to offer or say to amend your mistake. And there's an obvious reason, Roberta, because I can take anything I want, independent of what you offer." He grinned. "Or am I wrong?" Roberta weakly shook her head. "No you're not," she said. Depoulos nodded. "The documents proving your unwise conduct are now in a safe place, in a locker", he said. She looked a bit surprised. "A... locker?" "Yes. Simply put, Roberta, until I own those papers I own you. I own you completely. And I care for my properties." He let his gaze down her face to her jacket. "Now Roberta, I would like to inspect my property immediately." As the truth made its way to her mind, Roberta's face blushed crimson and she began to tremble, her heart racing faster and faster. She hoped she was wrong. She tried to act like she had no idea what he was saying. "Excuse me?" she muttered. Depoulos shook his head slowly. "Don't behave like this, Roberta," he said, "I could have you bend over, rip your panties off, and whip your ass for pretending to be more light-headed than you are. What do you think I mean by inspecting my property?" Roberta felt tears in her eyes. "Please..." she sobbed, "please don't..." Depoulos shook his head again. His grin was even more obvious. "This hesitation makes for five strokes on your bare ass. You'll get them before you get out of this office. From now on, each hesitation in answering a question, or obeying an order, will be punished. Do you understand this?" Roberta nodded. "Yes..." she murmured. A big tear ran down her cheek. "Good. Now answer my question. What do I mean by inspecting my property?" Roberta nervously looked down to her stockinged knees, twitching her fingers. "That... you want me to undress, sir". Depoulos nodded. "Correct. Stand up." Roberta stood slowly, her legs were slightly trembling as were her hands. "Raise your skirt, bitch, slowly." The order came cold and sharp as a razor. Roberta reached for the hem of her skirt, almost unconsciously, and lifted it up slowly, revealing her thighs... he looking... then the hem of her stockings... he still looking... then her black thong... Depoulos nodding. "Turn around". Roberta turned on her heels, displaying her firm, round ass to her boss. "Do you always dress as a whore like this, or did you think of me while you were dressing up today, Roberta?" Roberta's heart was rushing, and she couldn't even try to find a less humiliating answer than the truth. "I was thinking of you, sir" she muttered. Depoulos laughed. "Remove your thong, bitch". Roberta tried to lower her hands to the waistband of the thong, but she didn't have the nerve. "Please... Sir..." she sobbed. "Ah, well," said Depoulos. "So we are up to ten strokes on your ass. Your next hesitation adds five on your cunt. Do you understand?" Roberta felt the first big drop fall from her eyes. "Yes sir" she muttered. "I'd better check it. Repeat. What did I say about your next hesitation?" She sobbed. "It will cost me five strokes... on my... cunt sir". She shivered as she said that word. She would have used another one. But was too frightened to displease him. "Good. Now remove that thong and try to use your brains from now on, stupid worthless bitch." Roberta reached for the waistband, tears flowing. The thong slipped down her beautiful legs to the floor, and she stepped out of it. Still she was standing with her back to Depoulos, her shoulders shaking with her weeping. "You have a sexy and spankable ass, Roberta. Now bend over, spreading your legs, and show me your cunt." She moved her feet apart, trembling and crying, and bent down. She put her hands on her knees. Then, without the need for another order, lowered more and reached for her calves with her hands. She was on display in the most humiliating way she ever was. "I'm sure you know how whores display themselves, Roberta. Open your cunt lips quickly." Roberta was now in a nightmare. Her trembling hands went to her sex and she gently parted her sex lips, showing her pink inner skin to Depoulos. He stood, smiling. "Good bitch," he said, reaching for her sex. She felt a shiver down her spine as the fat fingers of her boss touched her exposed sex, and his middle finger slowly slid up inside her. "Who uses this hole, Roberta? Your boyfriend?" Roberta nodded, eyes closed, tears slowly pouring. "Speak loud when I ask you something bitch", he said, punctuating his words with hard slaps on her ass. "Yes... my boyfriend, sir". Depolous smiled again, and began pumping his finger into her hard and fast, adding another one after a few thrusts. "But his small cock isn't enough for a large whore cunt like yours, am I correct Roberta?" The poor girl sobbed. "Y..." her voice dying. "Yes sir". Depoulos spanked her ass again. Being spanked felt so humiliating, the psychological pain much deeper than the physical. And the words he used... "Full sentences from fuckpigs, Roberta" he hissed. "Answer again." His fingers pushed deeper with each thrust. He pushed in deep and held still, impaling her sex on three fat fingers. "His... small cock is not enough for me Sir". "For your large fuckpig cunt?" "For... for my... large... fuckpig cunt sir". Roberta was broken. Depoulos resumed fucking her sex with three fingers and, to add to her desperation, she felt on the edge of climax when he withdrew. He sat back in his big comfortable chair. "Stand up and turn, bitch". Roberta finally released her sore sex lips and stood, turning to face Depoulos. He looked at her, clearly wanting to take it slow now, as if he knew... he probably knew... that Roberta was unbearably suffering in the fires of humiliation. "Remove your shoes." She dropped her stiletto heels one by one, raising her calves and pushing them off onto the floor. Depoulos nodded. Knowing she was bare feet, with just stockings, added to his sense of power and her sense of defencelessness. "It looks like a nice set of udders on this fuckpig," said Depoulos. "Show me." Roberta reached with trembling hands to the buttons of her blouse. Her heart was still pounding hard and fast, and her face was purple red, wet with tears. As soon as she undid her last button, Depoulos guided her next step: "pull those balloons from the bra". She sadly obeyed, pulling her large breasts from the enclosing satin bra. Her breast was big, firm, young and healthy. She was proud of it... in normal circumstances. Now for the first time in her life she found herself feeling that she was too big... feeling that she was obscene. Depoulos grinned. "Nice big udders like yours are very good for spanking and torture," he said. "Now, fuckpig, I hope your know what your mouth is for. And I hope you can tell me now, or it's gonna be a hard punishment. Say what you think about your mouth, bitch. What is it for." She knew what he wanted to hear. She did not even try to find a less crude way to say it, unsure if he would be pleased at all with the words she could find. "M... my mouth..." she sobbed "is for sucking cock... sir." He nodded. "Yes. And do whores like you suck on their knees Roberta?" She hesitated. "Yes... sir" she muttered. "Good, then you may kneel, as I am going to give you the honour of sucking a bigger cock than you are used to, Roberta". "Yes sir", she muttered again, kneeling promptly. Roberta was a few steps away from her boss. "Crawl to me, on all fours like a wanton doggie bitch", he commanded. Roberta fell on all fours and moved across the carpeted floor. Depoulos watched, enjoying the sight of this beautiful young girl crawling almost naked, her big tits gently swaying with her movement, and shapely ass in the air, her firm legs on display in those sexy stockings. She crawled to her boss' feet and rested, eyes lowered in shame. "Do you like to drink cum, bitch?" he asked. Roberta sobbed softly. She didn't. But knew better than tell the truth now. "Yes... sir" she submissively replied. "Good," said Depoulos. "From now on, you will drink my cum at least three times a week, otherwise you get a tough punishment. Do you understand it bitch? "Yes sir." "At times, you will have to beg for my cum, and I'll accept your request only if you prove to be willing to humiliate and degrade yourself for it. Your main duty from now on in this office is forgetting any self respect you have. If anything you do or say makes me think you consider yourself anything more than a filthy cum drinking cheap whore you will be punished. If you don't put all of yourself into pleasing me you will be punished. Does the bitch understand?" "Y... yes sir." He slapped her face, suddendly, hard. A cry escaped her lips. "FULL sentences from fuckpigs, roberta. Does the bitch UNDERSTAND?". "Yes sir... this bitch understands sir." Roberta eyes cast to the floor. His eyes cutting her dignity like knives. "I hope so. Now unzip my pants." Roberta closed her eyes as her hands slowly moved to the man's crotch. "Look at me bitch" he said. She opened her beautiful green eyes and looked up through the tears while her trembling hands fought with his button, and undid it. Her lips had a tremor as she pulled the zipper down, forcing herself to stare into his cruel eyes. "Take it out." Her right hand moving into the opened pants, finding his very hard cock. She pulled it out gently, carefully. Her eyes briefly moved to his rod, then she raised them again to meet his gaze. "Feel it nice and slowly, Roberta, I know you like it, whores like big cocks. Does this whore like big cock?". She reluctantly wrapped her fingers around the big shaft, and began to pump and caress it slowly. "Yes.... Sir... this whore likes big cocks". "Did you ever drink sperm from a bigger cock, bitch?" he asked. Roberta shook her head no, fighting back the tears. "No... sir". That was true. Depoulos kept looking at her, waiting. Full sentences. "I... never drank sperm from a bigger cock sir..." she muttered. "So, either your boyfriend has a poor small prick or you never drank his cum, or both. What." Her hands still massaging his cock as she humiliated herself: "my boyfriend has a poor... small prick sir..." Depoulos nodded. "Lick it and say you can't wait to have it in your cunt, whore". Roberta felt a new rush of tears filling up her eyes. She could hardly see Depoulos through them. She couldn't go down this way. "Please... sir" she muttered. "Ok, bitch, that makes five strokes on your cunt. Or, if you so prefer, you can get out now and face what expects you". Depoulos smiled as he saw two big tears running down her cheeks and falling onto her big naked breasts. "Be quick to decide." Roberta found herself considering her situation all over again. But for all she could think, there was no way out of this nightmare. "I'm... sorry" she murmured. She bent forward slowly, kissed it, stuck her tongue out a little, began to let it slide along the shaft. "I'm sorry sir... I can't wait to have it in my cunt sir". "Be careful, you'll get physical punishments for misbehaviour only until you become too boring. After that, I will stop all that and just fire and ruin you. There's not gonna always be a second chance. Do you understand me cocksucker" He slapped her left tit, suddenly and hard. The loud smack seemed to awaken her to his painful nightmare. Her full heavy tit bounced against the other. "Yes sir I understand sir" she murmured, still licking at his shaft. "Now suck as the cumdrinking fuckpig you are, Roberta, and be careful not to disappoint me". Roberta wiped her tears from her face and gently let his cock slip between her closed lips into her mouth. Closing her eyes, she began to suck as sweetly as she could. Her lips began moving along the shaft slowly as she caressed it with her tongue and softly sucked. Depoulos watched the beautiful kneeling girl and grinned. "Look at me while you suck bitch". Roberta raised her eyes to meet his as her wet mouth pleased his cock. She tried to be as careful as she would be with her boyfriend in a most passionate moment. She realised she had probably never been *that* good for Rod. Depoulos seized her hair and began to pump her mouth obscenely on his cock. "Don't blow me like a good mannered teenager, bitch. You are a whore. Let me hear you." Roberta fought herself to keep her eyes on him as she sucked harder, making washing sounds with her mouth. "That's better," he said, "now finger your clit and pinch your nipples bitch." Her hands reluctantly moved to her body. Her right hand went between her thighs, as she began to rub her clit. Much to her shame, she found it erect. Her mouth was still pumping on that huge cock, obscenely filled with it, as it pushed deeper and deeper against her throat. Her left hand went to her ample breast, and she began rubbing and pulling at her nipples, alternating between them. Oh god, she thought. She felt dirty as a porn actress, kneeling there with all her body on display, in holdups, sucking cock and masturbating like a wanton slut. "You will be masturbating a lot from now on, bitch, and I'll make sure you will most often have some toy stuffed into your holes and teasing you... but you will not cum unless I tell you to. Do you understand bitch?" He pushed her face off his cock. "Yes... sir I understand sir" she muttered again. "Your cunt is my property, isn't it. Say it bitch while you lick." "My... cunt... is your property sir" she murmured again, mesmerized by his steel cold voice, as her pink tongue gave him more submissive pleasure. He nodded. "Good bitch. Do you want to drink my cum now." She looked at him, desperation and a silent plea in her eyes. "Y... yes sir" her voice replied. "Beg for it while you masturbate." Roberta briefly closed her eyes, then looked again into Depoulos small cruel black eyes. "Pl... please sir..." she murmured. Depoulos was now holding his own cock, rubbing it slowly against her cheeks. Waiting for more. "Pl... please let me..." His cock against her nose, onto her eyes, getting wet with her tears. "Please let me drink your cum sir..." Depoulos grinned as he rubbed his huge sex on her pretty small face. Then he opened a drawer and fetched a small camera, placing it on his desktop, pointing at her. "I'll have souvenirs from time to time Roberta. You'll get used to perform before a camera." Roberta blushed. "I know what you're thinking bitch. That I might use this to blackmail you". That was true. "In fact you think about it just because you are stupid. I already have all I need to blackmail you til the day you die. Correct?" Roberta sadly nodded. "Yes... sir" Depoulos switched the camera on. "Now bitch make it worth the cost of the tape." "Yes... sir" she muttered again. "Wrap your little sexy hand around my cock and pump it... let it point to your face... keep looking at me... and keep begging me to cum on your face... and I mean beg. Humiliate yourself, stupid fat whore. Roberta held his cock timidly, and began to pump it. She looked into his eyes and weakly began pleading... it was terrible to hear her own voice... knowing it was being recorded... "please sir cum on my face... cum on this whore's face... i am just a fat low whore Sir, please give this whore the cum she needs..." Her left hand was still onto her clit and rubbing it... well she could have pretended, Depoulos couldn't see what her hand was really doing... nor could the camera... but she rubbed herself because of the desperate heat that was growing between her legs. She had to. It was relieving. She pumped this huge cock and rubbed herself and her voice was moaning now: "please cum on this fuckpig sir..." She felt his huge cock throb in her hand and the first thick shot hit her lips. She involuntarily closed her eyes, then opened them again. Depoulos was still staring right into her eyes as he shot her pretty face. She felt big drops of her boss' sperm slip down her cheek and nose to her breasts. Depoulos held his cock in his right hand and used it like a paintbrush to smear his cum onto her face, staring into her eyes with a wicked grin. "Ooooh yesss... whores like the smell and taste of cum, don't you Roberta?" "Yes... sir... I do like the smell and taste of your cum sir..." Depoulos grinned again and slapped her face with his still almost completely erect, huge rod. "You need not waste the cum that fell on your tits Roberta, I think they are large enough for you to reach to lick them". Roberta nodded and murmured "yes sir" as she unwillingly lifted her breasts to lick his cum. Depoulos grabbed her hair and polished his tool with it, looking at Roberta as she licked his warm cum from her big round boobs. "Now put what you used back in place" he ordered, alluding at his cock. Roberta quickly reached for his cock and put it back into his pants, zipping them close gently. Depoulos nodded. "I hope you like what you will be feeding on in the future, bitch." "Yes... sir". Depoulos was satisfied for now and switched the camera off. He then pointed at the chair before his desk. "Now sit, we have a few more things to discuss." Roberta stood and lowered her skirt, but Depoulos shook his head. "Did I allow you to cover your cunt and ass, bitch." Roberta looked up with a hint of fear in her eyes, as her hands quickly moved to raise her skirt again. "no, sir, I'm sorry sir" she replied. Depoulos shook his head. "You are behaving like a silly brat. Sit down." Roberta sat before her boss, skirt still raised to her waist. "Because you have been bad, and forgot again to answer in full sentences, you will get a full punishment now." He walked towards her and kicked her shoes near her chair. "Put these back on". Roberta obeyed, putting her shoes back on her stockinged feet. Depoulos took a heavy wooden ruler from the desktop. "Now raise your knees and hold them as high as you can. Your asscheeks must be in view." Roberta suddendly noticed that Depoulos had fetched two pieces of rope. He knotted the rope around her left knee, then forced her right hand behind her head and knotted the other extreme of the rope to her wrist. Next came the binding of her right knee to her left wrist. Roberta was crying. She had never experienced bondage, not even in this light form. Her legs were parted by the bondage, her pussy was on display, and, to add to her mortification, it was patently wet. She was dimly aware that he had her put her shoes on to have her look more sexy as she was receiving punishment, and that caused a strange feeling deep inside her... and, strangely, some form of obscure, fetish arousal at the thought of her own looks, bound like that in stockings and heels. Depolous looked at her in silence for a little while. "Now, bitch, here are some rules for you to begin with. You will receive daily an e-mail with instructions about your dressing for the next day. You will follow those instructions very carefully. You will always call me Sir. If you are guessing about limits, well, it is rather simple: there are *no* limits to what this whore will be forced to do. Although, nothing you will do will leave any mark that would reveal your submission and enslavement to you wimp boyfriend. Apart from that, you are about to do the most humiliating and disgusting and painful things you can imagine, and surely many you wouldn't imagine, too. Either accept it from the outset or call yourself out and get a very good lawyer. Is that clear whore?" Roberta nodded. "Yes... sir it is clear". Depoulos grinned. "Now, I promised you some strokes. Where are you gonna get them whore?" "On... my ass..." she began, in a muttering low voice. "Speak aloud bitch". "On my ass and pussy" she said. "No!" he said, hitting with the ruler very hard on the back her thighs. She let out a high cry... god that ruler was so painful. "Ladies have a pussy, Roberta, dogs like you have a cunt." "Y... yes sorry Sir on my ass and cunt Sir". "It was ten on your ass and five on your cunt a few moments ago. But I remember you hesitated for a few orders and right now chose the wrong word. So I'm gonna add something. Now count each stroke out loud bitch." Roberta thought this was a nightmare... it was like those movies about sadistic school teachers or college nuns... it was all in *that* style, and nevertheless how real it was now... how humiliating... how frightening to be in that situation. "Yes Sir" she mormoured. Depoulos gave her the first stroke on her ass. "One" muttered the girl. "Two..." "Three..." Ten strokes came down. And then Depoulos placing his hands onto her knees, spreading her legs. "Please... please Sir don't... i beg you. This whore begs you..." Big tears falling from her eyes as her pussy was exposed. Prepared for punishment. "Keep counting whore". The heavy ruler landing hard onto her gaping pussy, with a loud smack. She cried, and then counted out: "eleven..." "twelve..." The strokes reached fifteen. But Depoulos didn't stop. It reached twenty... He didn't stop. All her body was trembling and she was melting into tears. He stopped at twentyfive. Her cunt was sore, red, swollen. He untied her left wrist. "Masturbate now" he ordered. She couldn't resist. Her hand moved, she began to rub her aching sex. He parted her arms, pinched her nipples til they were erect. "Keep counting" he said harshly, rubbing the ruler on her erect nipples. "Twenty-six" was right on her right nipple. Pain ran through her spine. He inflicted five on each nipple, alternating between the two. And she kept masturbating. And got very near to climax. Then he grabbed her hand and pulled it off her sex. "Do you need to cum bitch" he hissed. Roberta hesitated, breathing hard. Her face was on fire. She couldn't think, yet she knew what was wanted of her. "Yes sir..." she mormoured. "I need... this whore needs to cum sir". Depoulos looked at her gaping sex, shiny with her juice. "It's a horny hole", he said, his voice conveying more despise than Roberta had ever perceived. He leaned towards her sex and spitted on it, a big hot spit. The sensation, the act, the unexpectedness sent a shiver through her whole system. "You don't cum today whore" he sentenced. "Yes sir..." she replied, feeling that shiver again. He untied the ropes that bound her right wrist to her left ankle. "Knees on the arm's chair bitch." She obeyed, putting her knees onto the chair's arms and opening herself completely. "I will have to get a towel to use for our face to face talk, your dripping cunt is staining my chair." "I'm sorry... sir" was her feeble reply. He looked at her in silence, savouring the stunning sexy shape of his enslaved secretary. God she was beautiful. And God, such a beauty would be so good to humiliate... humiliate to extremes. The poor sobbing girl kept her eyes cast down, knowing he was looking at her open cunt and bare tits. "Did you boyfriend ever humiliate you to get off?" he coldly asked. "Share or expose you to others, call you names, piss in your mouth... did he ever?" "N... no sir" she muttered. He nodded. "He would envy me so much then. He would be green." He lit a cigarette. "LOOK AT ME while I'm speaking to you bitch." She raised her tear-filled eyes. "Sorry sir" she murmured. His gaze went to her pussy, then locked on hers again. "You will shave your hole for me tonight. From now on, you are not allowed pubic hair unless I tell you otherwise." She went pale. "What... will I say to my boyfriend... sir" she timidly asked. He kept silent, staring at her with cold eyes. She suddendly began to feel stupid to have asked. Even a vague fear descended upon her as she tried to bare his gaze. He probably knew, let her savour those feelings. Then he spoke. "Never try again to submit a problem of yours to me, bitch." "Yes sir... sorry sir I will never do that again sir. "Now put your clothes back on, except for your sluttish thong. Then go to the grocery store at the corner and buy a banana. You have ten minutes to come back with the banana in your cunt and get back to work. Does the whore understand?" "Yes sir... this whore understands" she said. "The banana must be in your cunt *before* you enter the building. I don't care where you do it, but if I meet you stepping in without the banana in your cunt, you're done with. Do you understand this as well?" "Yes, sir I understand" she murmored again. "Go now." Roberta quickly stood, gathered her clothes, feeling confused, ashamed, desperate. Trying to dry out her tears quickly as she redid the buttons of her blouse. Hoping she would be able to forget this quickly. Get the banana, do what He wanted, work with it stuffed up her cunt... She opened the door and walked out to face her new life. end part 1