3 comments/ 54691 views/ 27 favorites Breaking Jen Ch. 01 By: real_first_time Author's Note: People may remember this series of stories. I first posted them on Literotica in 2009. They were a mixture of fiction and fact taken from my life. The 'Breaking Jen' series became pretty popular and each one rated higher and higher as my writing improved. I think by the fourth and final instalment they were getting close to a 4.9 Lit rating. I took them down for a few reasons. I am very fond of them. I am a better writer now and I really did think that I could do, what is actually a very personal story, much more justice. So....after a massive re-write I re-present to you the new first chapter of 'Breaking Jen' (there are four in total). Think of it as a 'director's cut'. The original 'Breaking Jen Chapt 1' was little more than 13,000 words and the new version is now closer to 21,000. There are additions and omissions to the original story. In turn I will be re-writing each of the other three chapters but there is no time table on that. They will appear as time and inspiration allow. Some of this story is fiction and some of it is very real. Considering the subject matter some of you will find it hard to believe that there is genuine emotion and an unconventional love story of sorts going on. I guess not everyone's love story can be like 'The Notebook'. For me I guess the most tender of moments ended up coming from some of the harshest and unexpected circumstances. But....it is a love story none the less, and sometimes, you have to take love where you find it. Peace and love........William. (aka real_first_time) ************************************* I want people to know that I'm not a spiteful person by nature. I don't believe in carrying grudges or holding on to hurt. I remember once hearing a certain quote and it has stayed with me ever since. I honestly don't remember who said it, or even where I heard it anymore, but despite all that, I still remember that quote word for word. 'Holding a grudge is like swallowing poison and then expecting the other person to die'. Those words seemed to resonate with me and I tried every day to live by their sentiments. But, as much as I tried, I wasn't completely successful in living a grudge-free life. There was one exception that I just couldn't shake. Jen. Jen was the girl I was going to marry one day. She was the one. Have you ever been in love with someone so deeply that you would literally step in front of a bus for them? I'm not speaking metaphorically here. I mean you would actually trade your life for theirs if it ever came down to it. I would have given my life to save hers in a heart-beat. It was that kind of love. Perhaps I should have been more careful about whom I gave my heart to, but I think that love tends to trump good judgement. That's been the story of my life. Deep down we all know how a love like that always ends. The truly ironic part of it all is that knowing this still makes no difference at all. You never see the end coming until it's much too late to stop it. We do it to ourselves over and over again, each time thinking 'this time will be different'. But it never is. The world I thought I knew ended for me in a single day. Sometimes there are clues and warnings, but sometimes you just get blind-sided by life. It's hard to explain. Let me put it this way. Imagine you are standing beside a deserted highway surrounded by nothing but barren and lifeless country-side. Out of the corner of your eye you spot a beautiful wild flower growing out of the dirt on the other side. It distracts you, and you think to yourself 'how could something so beautiful grow in this desolate place?' You look right and left and see nothing but empty highway before crossing the road to pick that flower. You never see the huge truck that appeared out of nowhere until it hits you. You were so focussed on that flower that you didn't see the danger until it was far too late. To say it broke my heart when the truth about Jen finally came out doesn't convey the feeling. Words can't express what I felt. That's the dilemma I have in writing this. I'm trying to use words to describe to you something that words cannot express. No. Saying it broke my heart doesn't come close. It would be more accurate to say that it destroyed me. By now maybe you're realising that this is no simple story or work of fiction. While much of what you're about to read is fabrication there is a very high percentage that is drawn from pure fact. Do not doubt that the pain was real. I will blur the lines of reality in some areas, but I think we all do that in our own way. Our own emotions often colour our memories making the truth subjective to our own experience. I have no delusions about myself. I know what I am. I know that I am damaged. I know that my past has made me almost unable to trust or to connect with someone on a truly personal level. That inability caused me to seek other ways to deal with people. It actually saddens me that these new ways have turned out to be infinitely more effective. The kindest of acts are not appreciated fully without first showing cruelty. I wish that were not true, but knowing that was a kind of revelation. It made me into the kind of man I never wanted to be, but also wildly successful at what I do. I remember feeling physically sick when I first discovered the truth about Jen. The realisation that I wasn't the only man in her life, there were many. Knowing that what I had cherished the most in life had been a lie. Knowing I was worthless. Jen had worked for a law firm but she was not a lawyer. She planned events. She organised the conferences and travelled to all the cities where they were held. She was good at it. A true multi-tasker in every sense of the word. She was skilled at manipulating people and situations to her own benefit. I knew that from the outset but in my stupidity I had assumed that I was somehow special, that her manipulations did not extend to me. I believed in my heart that she loved me. A natural flirt who used the attention she got to her own ends. Maybe it was my own stupid male pride that was my undoing. Like having a tiger on a leash, you start to think it's tame until the day it bites you. I had been made a fool of for years. While attending conferences in other cities she had regularly taken her flirtations to the next level. I don't even know how many times that must have happened or how many other guys she had fucked over the two years we were together. I do know that some of them were guys she would see regularly when she was in certain cities, and some of them even knew about me. She had a great thing going. A stunning and gifted liar. I really do have to give her that. Maybe some of you will understand now. You don't bounce back from something like that. It changes you. It changed me. It was as if the experience broke me and then re-made me on an almost daily basis. You go through stages that repeat and recycle over and over again. Each time is just a little less painful than the last. Sometimes you go through those stages many times in one day. You get to experience every negative emotion. Humiliation turns to anger. Shame to depression. Repeat. Repeat. Repeat. The down-ward spiral. I thought about her for years with that mixture of heartbreak, anger and sadness. In time, a profoundly different man emerged on the other side of the hurt. A calculating man devoid of empathy. A predator who pursued and used women in ways that were radically different to anything he had ever done before. There was no alluring mystery to me in the females that I sought out. I saw through the outer image that each projected and instead found the woman underneath the facade. The rose coloured glasses of infatuation had gone. They were replaced by the eyes of a colder man who fed off of dominance and control. I became a dispassionate observer. An emotionally detached man who would analyse the women around him and then act accordingly without feeling or hesitation. I fed off of their emotion and in turn I gave them back the kind of experience no other man had dared to. I made their most desperate feelings real. In a way I became a kind of vampire, but not in that pathetic 'Twilight' sense that has become so popular now. In my own very real way I drew out their dark tendencies and fed off of them. They screamed out to be used and I simply obliged. There are many of you who will accuse me of being a woman hater after what you have just read. I wish it were that simple. If that were true then I would have nothing at all to do with them. I don't expect you to fully understand what I'm about to tell you because I don't understand it myself, but the more detached I became, the more I was fascinated by what I saw. The discovery that women have a power they aren't even aware of. Tragically fickle creatures too hung up on their own self image to know what it is they really have. Conflicting emotions and petty insecurities robbing them of their ability to appreciate their own gifts. Knowing that truth led me to an important question. What would you find underneath it all when you strip away all those barriers? How would that same woman behave when set free from her insecurities. She could do anything. Be anything. Only a fearless and uncompromising man could bring about that end. A man with nothing left to lose. Someone who could stay the distance and trust the process. And most importantly.......What was the most efficient way to achieve this end? That, my friends was my most important discovery. That is what sustained me. In my inability to feel, I had found a way to live vicariously through my conquests. I found a way to fill the void. So you see I was a true vampire of sorts. A seducer of the vulnerable. A devourer of energy, and much like a vampire, I could not go where I was not invited. I found that I had developed a gift. I knew almost instinctively now what a certain kind of woman wanted but was ashamed to admit. The desires that she could not understand let alone ask for. There really is very little mystery to obtaining this gift. For me it was as simple as discovering how not to feel. To observe without letting your own emotions cloud your judgement. Once you stop caring about yourself it is easy to become fearless. There is irony that. I had a power that only a broken man could process. The audacity of someone with nothing left to lose. Empowered with that knowledge I embarked upon what could only be called a 'campaign' of conquest and domination. Debasement and depravity on an impressive scale. I took what appeared to be the sweetest looking girls and then proceeded to thoroughly 'dirty them up'. I soon discovered that the public persona that each of them presented to the world usually bore no resemblance to the desperate and repressed person that hid just under the surface. The filthiest acts always resulted in the most intense climaxes. I had unwittingly tapped into a kind of desperation that people never acknowledge and almost never talk about. Humans are complex creatures. For every noble thought there is also a corresponding base desire. We go through life trying to show all those noble and good tendencies to the world whilst trying to hide away all those dirty and base ones. But those dirty and base thoughts never really go away. A desire suppressed is a desire magnified. The darker side of female desire became the tools of my trade and let me tell you girls and boys, trade was brisk. I did all the things that other men were afraid to do and I did them immediately and without reservation. I would never lie. I detest liars. I would make it clear during the very first conversation that I was different. I didn't play nice and I didn't play fair. Nothing was off limits to me. I would use all of her dirty little secrets against her and make her do things that would make her mother ashamed of her if she were to ever find out. Do you know how many girls walked away upon hearing that? Not one. Tied down and spanked with ball-gags stuffed into their mouths and that was just the first date. I'm even going to share one of my more amusing tricks (one of many) with you right now for all of you playing at home. Next time you have a girl on her hands and knees on your bed try this. (And for all you girls reading this you get double points if you use this one on your best friend. Don't you even try to tell me that thought hasn't crossed your mind.) Insert the two middle fingers of your hand into her mouth and instruct her to make them as wet as possible. Next get her to suck the thumb of that same hand and repeat the process. You'll be rewarded with a deep groan when you insert those two middle fingers into her pussy nice and deep, but that's still not the best part. That's when you casually inform her that you're about to take her 'bowling'. Smart girls will 'get it' right away but believe me it's actually a lot more fun if they are a little slow and need it to be spelled out. Which will go something like this. "Think about it. If I've already got two fingers inside your pussy then where do you think my thumb is about to go?" (I guarantee you'll never look at the 'thumb hole' in a bowling ball the same way ever again). The mental image alone is enough to make them moan and I discovered very quickly that a certain percentage of women will orgasm immediately when they feel that thumb invade their tight little ass. It's an effective way to see how she handles double penetration. Also it introduces them to the concept of being reduced to an object and used accordingly. Ignorant people would call this degrading. Yes, that can be true if you go about it the wrong way. The more intelligent among us know how empowering this trick is. The realisation that you have become someone's mere play thing suddenly takes away all accountability. All guilt and shame is erased. One memorable night I simply watched as I made one girl practically devour her best friend's pussy. They were a cute couple. They had been life-long friends but they had never crossed that barrier with each other or any other girl for that matter. Christ it was just so painfully obvious to me that they were desperate to get the 'girl experience' out of their system. It took very little on my part to convince them that doing it with their best friend really was the best way. The results were more than spectacular. Sweet little Maria buried her face between her best friend's legs and almost wailed as I started to fuck her with force from behind. I pushed her face hard into that soaking pussy with one hand while I used the other to squeeze each nipple mercilessly. As I dug my fingernails in harder, the pain sent her over the edge. They both came very loudly and very messily. So many climaxes that night. There is now a special dimension to their friendship which I believe brought them far closer than before. They are friends in every sense of the word now. I discovered, in fact, that there seemed to be a never ending amount of girls who just wanted to be treated badly. They didn't want romance, they just wanted to be punished and dis-respected and the more I dis-respected them, the sooner they came. I know it still won't make sense to many reading this. I know that's not what all the books on relationships tell you to do. We are supposed to be living in a time when mutual respect between the sexes is considered the ideal. I was discovering the real truth about men and women and it just seemed so counter-intuative in the beginning. The realisation that when it came to sex, the normal rules of society didn't apply. Christ what a true revelation that was. That the rules and standards of common conduct not only didn't make sense between the sheets, they failed miserably. Yes I know it seems so obvious, but it took me a long time to understand that simple truth. At first I was confused by it all, I mean is this really the way it is? After a while I stopped asking questions and got on with giving them what they wanted (in most cases, desperately). As years went by I got more inventive and even more ruthless. I became an expert at teasing and punishing and I discovered how to make the most innocent girls beg for the vilest things to be done to them. Maybe a more recent example will help to explain. Recently one night I met a school teacher at a club. She was 25 and in-experienced in most things. She was one of those people who seem worldly when you first meet them but on closer examination turn out to be a little lost and ill prepared for the world. It's been my experience that these kinds of girls are usually about as repressed as it's humanly possible to be. We spent the first few hours chatting and talking about her aspirations and dreams. I listened attentively. I watched her closely and drank in her essence as I formulated a plan. I sent a quick text message to a very good female friend of mine once I had decided on what needed to happen. The rest feel into place seamlessly. The next 12 hours would turn out to be the most memorable of that cute little teacher's life. A well structured and deliberate seduction. It started out slowly but with each hour, little by little, things became more daring and perverted. By the third hour she was tied to a bed in her lingerie. By the sixth hour her ass cheeks were red and lined with welts from being spanked with a wooden ruler. As the tenth hour passed she was on all fours begging my friend Tracy to fuck her virgin ass with a strap-on while she attempted to deep throat my swollen cock. But I digress. It had been almost 5 years since I had last seen Jen. I had no desire to ever lay eyes on her again but to be honest, it was a minor miracle I hadn't run into her before then. To the best of my knowledge she had moved to another city over four years ago and that was fine by me. I honestly didn't know how I would react if I ever saw her again. The very idea of that seemed to repulse me. Every story like this seems to start with that old cliché, 'It was just an ordinary day', but the truth was that it really was just another ordinary day. I worked in the inner city. I believe my chosen profession is vital. People see me in order to maximise their potential and become the best human being they can. If you think I'm being vague about what I do for a living then you're absolutely right. You will find out much later what it is I do, but right now it's not important to the events I am about to describe. That's the way it works with me. You don't get personal details until I think you need them. I am not a fictional character. What I chose to share about my own life will be done so as the situation demands. On this particular day I had given myself a nice long lunch. I was having what I like to refer to as a 'donut day' (I had lots of clients in the morning and then in the late afternoon but there was a huge gaping hole in the middle of my schedule.) As I was walking back to work I caught a glimpse of something familiar. It was her shape that I noticed first, a silhouette that became a woman as she drew nearer. We were walking in opposite directions and with each passing second it became clearer that it was Jen. As the distance between us decreased it also became obvious that she had seen me too. There was an instant and obvious tension. It was far too late to turn around or just simply pretend we hadn't seen each other. 'This had to happen sooner or later' I told myself as I slowed down and Jen began to do the same. She didn't look at all comfortable and I didn't even try to disguise my own dismay. So began perhaps the most awkward and unwanted conversation I'd ever had in my life. Breaking Jen Ch. 01 Jen looked like she always did, just maybe a little older. No taller than 5'6, sandy blonde hair to her shoulders and pale blue eyes. Usually in accounts like this the author will give you the broad strokes about someone's appearance and then just let the reader fill in the blanks with their own imagination. Normally I would do that also, but in Jen's case I can give you an almost exact reference as to the way she looks. In certain photos and from a certain angle you would swear you were seeing Kirsten Dunst's twin sister. That's not a good thing. During those first years that I tried to forget about Jen, even just seeing Kirsten Dunst on a movie poster or on a magazine cover would make my blood run cold. No offence to Kirsten Dunst, but they looked so much alike that it was just an unwanted reminder for me. (For anyone unclear about the actress I'm referring to then go see a 'Spiderman' movie...any of them except the latest one). Jen was cautious. She avoided eye contact at first before she became more comfortable. When our eyes finally did lock I turned to stone. I was cold and resolute. I gave her nothing. She knew very well the anguish she had put me through 5 years earlier and I guess she half expected me to show anger or hatred, but all I gave her was that man of stone. Even if I did have something to say I wouldn't have had much time to say it anyway. This was all just a passing encounter on the street, nothing more. (And that's probably the way it should have stayed). She didn't affect me anymore and I felt calm. I began to study her, maybe trying to figure out how this seemingly innocent girl (looks can be deceiving) had such an effect on me in the past. Actually I could see why I fell for her. To quote a wise old man who lived long ago (In a galaxy far, far away).....'The force was still strong with her' (not to trivialise matters, but throwing in an old Star Wars quote amuses me). She did all those familiar little things that drew men to her. All those cute little gestures and mannerisms that made you want to sweep her off of her feet and be her knight in shining armour, only this time I didn't feel that way at all. I knew her all too well and what she was capable of. In the end it was a pleasant conversation and business cards were exchanged. We said our good-byes and I wondered if I'd ever see her again. I honestly didn't care either way. If you're wondering why I don't elaborate more on the words we exchanged the truth is that I don't remember them. I had often wondered how I'd react or feel when I saw Jen again. The reality was that I felt nothing. It had no meaning to me. Maybe we talked about the weather or maybe we had discussed the possible cure for cancer, It's not important. What happened not long after however, was important. Two days later I received a pleasant e-mail from Jen saying how much she enjoyed meeting me again. That seemed a little odd to me. I didn't recall any sign of enjoyment or even a smile from her when we had met. The next part was even more surprising and to be honest, slightly disturbing for me. Jen wanted to meet again. She wanted arrange a coffee date and an 'official' catch up. Thinking back on our past it did seem to be in keeping with the way I remember Jen operating. It's also worth mentioning that for all she knew I was probably the same man she had known five years ago. She had no way of knowing what I had become. If she had known that, then I am certain she never would have sent me that e-mail. When I thought about it that way, the idea of meeting for coffee suddenly became a very interesting prospect to me. What would I see with my new, un-feeling eyes? What discoveries would I make about the person who had inflicted so much pain on me in the past? I sent back my reply and informed her of a certain cafe and a time I would be there. I was even going to take it easy this time. This was purely an intelligence gathering exercise and I would be a complete gentleman...unless. There was one huge caveat to my good behaviour, something that Jen did not know. Here is where it is important for you to fully understand me. Even the worst of people get a second chance from me. That is extremely important for you to know that. If I could change as radically as I had, then there was every chance Jen could have changed too. She would be given every opportunity to prove that she was a better person now. But.....If she even tried to pull her old tricks or flirt her way into my good books then the gloves would come off and a lesson would need to be given. In all honestly I hoped she would pass my test, for my sake just as much as hers. I hoped for that very much (which was uncharacteristic of me). She emailed her reply shortly after and the date was set. I arrived at the cafe very early and found a table I liked. I chose a seat in the corner with my back to the wall, that way I could observe everyone coming in or out of the cafe. It was a position of control and when I felt satisfied with the arrangement I ordered a cup of coffee. Fifteen minutes later I saw her arrive and I watched quietly as she nervously scanned the cafe for a familiar face. I let her search a little while longer before I put my hand up and waved her over. Just like our first meeting, the conversation was tense at first, but to my surprise even I soon loosened up and the conversation flowed freely. There was much shared experience between us even if a lot of it in the past had been bad. She began with an apology for the things she had done to me in the past which was a good start I guess. Actually that did go a long way toward smoothing out the conversation, and I have to admit that the signs looked good. Perhaps Jen had decided to join the human race after-all. I always tend to lose track of time when engrossed in conversation, but I became conscious at some point of wanting our coffee date to end. This was not because I was having a bad time, but because I'm a firm believer in quitting while you're ahead. This had been a good start so I was anxious to put an end to it before something happened to take the shine off of the meeting. (In my experience something unfortunate will always happen if given enough time). My instincts turned out to be correct. I had never in my life wished to be proven wrong more than at that moment, but that's not how life works it seems. It was about 40 minutes into our conversation when she nervously leaned forward and said quietly, "I know I was terrible to you, but do you know what? I really miss all those dirty things you used to do to me. Nobody has ever done half of those things since you. I think about it a lot." I felt her leg brush up against mine under the table as she said it. The disappointment I felt at that moment could not be underestimated. To most people what she did and what she said might have been dismissed as harmless, but to me it spoke volumes. The old Jen was clearly alive and well and up to her old tricks all over again. This was her modus operendi. This was how she manipulated people and how it always started. All of her kind words suddenly meant nothing to me. Sadly, there was now only one way this could go. The change inside me was rapid and automatic as I began to run through my standard scripts and structures. Up until a few seconds ago I had no intention of using them on her, but it was out of my hands now, she had chosen this, not me. I know what I just said might confuse a lot of people so perhaps some explanation is necessary. I have what I do down to a fine art. I can say that without a word of a lie. When it comes to a certain type of female (roughly 65% fit that psychological profile), I have merely to run through certain verbal structures containing triggering subjects and key phrases. Body language and intonation are also key. The result is a foregone conclusion. There is nothing 'hit and miss' about any of this. I can identify more or less straight away if any given female fits that profile. Jen most certainly did. (Note: Before any of you even think it, I do not use any form of hypnosis or NLP. This is not the 1980's people. The assumption that I control someone or take away their will power is a false one. Why try to control someone when all you need to do is guide them in the right direction and then let human nature take It's course? You can leave all those 'self help' notions to those tacky Anthony Robbins clones. In my book they are no better than used car salesmen.) This notion may be hard for some people to grasp or believe. I'm fine with that. They don't have to believe in it for it to work on them. Chances are they won't even realise they are being manipulated, it will all just seem like it's their idea. If you ever meet someone like me you won't even know it, I only hope that when you do, you are both on friendly terms. But I have said too much already. Also I'm sure that many of you will be curious as to what Jen was talking about when she referred to all those 'dirty' things I used to do to her. Well it wasn't in the same league as the things I do now but it was still pretty interesting. I would tie her up, maybe blindfold her. A good hard spanking used to set her off pretty spectacularly and as soon as it was over she would waste no time in straddling me and riding me good and hard until she came very loudly. It's fair to say she had an untapped freaky side. She would often tell me she had fantasies of me tying her to a chair and then being made to watch me fuck another girl as a way of punishing her. Like an idiot I was too in love with her to do it back then. I looked Jen squarely in the eyes, and then, knowing full well what I was doing, began the process. "A lot has changed since you were around." I said calmly before continuing. "I can tell right now that you're not suitable for what I do." "Getting a little ahead of ourselves aren't we?" Jen replied with a smile and went on. "I wasn't offering and I wasn't suggesting we jump in the sack, and besides that, I remember very well what you do and it'll take a lot more than that to scare me!" This was all very familiar territory. Once upon a time I even enjoyed all that power-play banter we used to share, but that was a long time ago. "You may remember what I did five years ago, but you have no idea who I am now and what I get up to in the privacy of my own home." "Elighten me." Jen replied, clearly fascinated and drawn in. "You really want the truth?" I was having fun with this now. It was all just so easy. "Of course. Tell me the truth, if you dare." "Fine." I took a long pause and drew out the moment before beginning. "I take dirty girls like you and I punish them. I spank them till they sob uncontrollably and then tease them until they beg for me to make them come. They come for me in filthy and degrading ways and they do it over and over again until it drives them insane." My tone was unwavering and my eyes never left hers. Nothing about my demeanour suggested that I was being anything but deadly serious. "Fuck!.........You had me at 'I take dirty girls'!" Jen replied, clearly stunned by what she had heard. "I think we're done here." I said bringing the coffee date to an abrupt end. The timing of this was deliberate and intentional as you have probably already guessed. "Christ you really know how to make an exit!" Jen interrupted as I got up to leave. My sudden decision to end our meeting had taken her by surprise. "Thank-you for the conversation Jen. It was nice to see you again. Best of luck with whatever it is you chose to do." I shook her hand. I left immediately. I didn't look back. Like clockwork, two days later I received a follow-up e-mail from her. Two days is the magic number for this kind of contact. One day seems too eager but three days seems too complacent. She thanked me for the coffee and then went on to say... "I can't get the last part of our conversation out of my mind. I'm very distracted by it. I'm dying to know what you meant when you said you made all those girls come in filthy ways. You weren't exactly clear about that. Would it be so wrong if I asked you to show me what you mean?" And there it is girls and boys. It's almost disappointing how easy it really is isn't it. In truth this was far easier than most similar situations, but in this case I had the benefit of knowing Jen and what made her tick. While I haven't shared with you all that I said to her during our coffee date I have given you enough information for you to get a very firm grasp on the situation. I'm not a monster. I don't get off on just hurting people. There has to be intense pleasure for the female in everything I do. It's giving pleasure that drives this whole process for me and I've never seen a girl come harder than when she is pushing her boundaries and living out her dirtiest fantasies. Sometimes a little pain and adrenaline turns a great experience into something they will remember for the rest of their lives. Long before I ran into Jen on the street I had already come up with what I considered to be the perfect lesson. It was the most beautiful and the most intense session and it was only to be used on either the bravest, or in this case, the worst of women. An attitude adjustment and a sexual experience unrivalled by any other. As luck and fate would have it, it would now be Jen who would turn out to be it's first lucky recipient. It was clear to me that she had already chosen that fate anyway. I even felt that this experience could be the making of her. This could be the key to her transformation into being a good and decent human being. There would be intense and almost unbearable pleasure in what I had planned for her....but let's not forget that she had hurt me very badly in the past. If I was to give her what she wanted then there would have to be some cruelty involved to fulfil my own sense of justice. There had to be some kind of payback for what she had done and it wasn't going to be as simple as a spanking. It would be a real experience that would result in a constant reminder that all her actions had consequences. It would be an intense sexual experience containing both punishment and reward. It would be a lesson in both causality and consequence. Her session would be structured and deliberate. Her fate would be placed entirely in her own hands at all times. If Jen was able to keep her head and control her desires, then she would receive nothing but pure pleasure. But.....for every lapse in control there would be a price to pay and a reminder of her weakness. Every climax would come with its own consequence. A lesson she should have learned all those years ago but apparently never did. Back then it was her pleasure that brought me suffering, but very soon she would bear all the responsibility for her own actions. Even at that point I gave Jen a way out. When you get right down to it I really did give her so many chances to save herself. I even e-mailed her back with a warning. 'Jen. I think you mis-understood my intentions. You and I have history. There are many unresolved issues and to be honest I've never forgiven you for the things that you did. If you are suggesting that I simply overlook all you have done and engage in some simple mutual act of gratification then you do not understand the situation. However, if you desire to atone for your sins then that is another matter entirely. The price for your atonement will be your full sexual submission over a period of my choosing. Your punishment will be intense but the pleasure will be unlike anything you have ever experienced. You may consider this as both a promise and a warning.' Interestingly Jen's reply took an entire week to arrive. It was a process that I was familiar with. No doubt she would have dismissed my e-mail at first glance but it would have almost surely crept under her skin. Within a couple of days it would have become a source of great distraction for her. In her confusion she probably would have changed her mind many times before she finally sent the inevitable e-mail that would start the ball rolling. Here's part of the reply e-mail she sent. '......and I know I'm probably going to regret this, but god I have to know....I think about what you said all the time. I know you will make me pay for being such a bitch to you...god...I think that thought is turning me on even more. I don't even know what you're gonna do to me...and that just makes me want it even more...please just tell me what to do and I'll do it.' And so it began. I told her to keep the weekend free and I also made it clear to her that for a period of twenty four hours her body would become my property. She would fulfil my every whim and obey my every word until I chose to set her free. If you think that she might have had an issue with any of that or was perhaps defiant in some way then my simple response is this. Once you take charge and clearly instruct a certain type of woman about what you want and expect, then she will just do it. I'm not a misogynist. I'm telling you this because that has been my experience. Many women just crave a strong male to take charge, but it has to be someone they respect and trust. This does not lessen the role of women, it's just a simple truth that people don't talk about for fear of being labelled a 'sexist'. Like I said earlier, humans are complex creatures. Jen's instructions were simple, but for me it was all the things that she didn't know about yet that were complex. There were many preparations to be made. She was instructed to arrive at my place on Saturday evening at the prescribed time. What she wore also indicated what her role and status would be over that weekend. She would become a good little slut for me...she would wear the tightest dress, the highest heels and the nastiest lingerie she could find...and she would do it all for my pleasure and enjoyment. The fun was just beginning. I immediately made an important call to a very close friend of mine called Tracy (Yes, I'm referring to the very same 'Tracy' I mentioned earlier. The Tracy that fucked that sweet little school teacher with a strap-on). She was almost beside herself as we discussed my ideas for Jen's punishment. She was flattered and excited to be given such a pivotal role in the re-education of Jen and she even added a few touches of her own which turned out to be pure genius. I really should tell you a little about Tracy because she will factor heavily in what you are about to read. She was a nurse once upon a time, but I suspect that the role of a nurse required a person to have a little more empathy than Tracy possessed. Sympathy is not one of her strong points either. For that reason alone she was the perfect partner in crime during many of my conquests. She now calls herself a 'Body Modification Specialist', which just means she does body piercings and hair removal at the local beauty shop. You could say that pain and discomfort are a minor by-product of a job well done for her. Her hair always seems to be dyed jet black and if I was forced to put her into a category (which I am loathe to do but it may help matters) I would describe her as a sort of slutty emo/goth chick. I'm sure you know the type, short skirts and fishnet stockings with boots. She wore those clothes as if they were some kind of uniform practically every day. There's no denying that Tracy has that dark quality that seems to attract both males and females in equal amounts and seeing as Tracy has an equal opportunity policy with both males and females it all makes for a very successful combination. Tracy and I met up in person for a final discussion on the night before it was all due to go down. She would be bringing her full bag of tricks with her on that fateful night. Her skills and expertise were to play a key role. I told her to spare no expense and that I would be covering all the costs involved. She just needed to be ready to step up and play her part when the time came. Breaking Jen Ch. 01 "This is going to be one epic night...but I can tell you already that the little slut won't even last three hours." Tracy said looking smug. "What makes you think that?" I replied with a smile. "Well, all we have to do is make her have a nasty little orgasm three times right?" "Yes, three times in twenty-four hours." I said knowing full well what Tracy was about to say. "Baby you've seen me in action. You know I could make any girl come three times in ten minutes if I wanted her to." "I know you could." I said carefully stroking Tracy's ego. "But we are going to play the long game on this one. We are going to take our time and do things right. Are we clear?" "Yessir!" Tracy said as she snapped me an exaggerated fake salute. She was clearly enjoying all this just as much as I was, maybe even more if that was possible. I'm not a big fan of drawing things out so ill simply say that all the preparations went without a hitch. Things went so well, in fact, that it almost felt like all of this was pre-ordained to happen. I've given you all plenty of information and you all now know the events that lead to all of this. So.....grab some popcorn and get yourself comfortable girls and boys, because the build-up is officially over. The curtain is raising........The feature act is about to begin. It was 8pm on the dot on that Saturday night when I heard a timid knock on my front door. I opened it to see Jen standing in front of me. She looked nervous and a little scared as she flashed me an uneasy smile and I smiled back (more out habit than anything else.) That was a huge moment. I actually had to take a few seconds and steel myself then. I had to remind myself why all this needed to happen, because what I now saw standing in front of me was an absolute vision. Jen still had a way, and a presence about her that surely would have tested the resolve of a lesser man. She was dressed in a red evening dress that stretched tight against her body, almost like it had been painted onto her skin. Everything was red. Her heels, her stockings, it all matched. If she had taken that much trouble with what she wore on the outside then I was dying to see what she had on under that tight little dress. Her hair was pulled back tight and weaved into a single ponytail that reached to her shoulders. I had never seen her like this before. The dress hugged the contour of her breasts like it had been stitched in place and seeing the faint outline of her nipples pressing up against the fabric was beyond distracting. I quickly regained my composure, but not before she had seen my reaction to her outfit and she looked pleased. I realised my mistake and almost cursed myself for letting her see that. 'I can't let her see any weakness again,' I thought to myself, and for the rest of that night and the next day, she never saw that again. Sure it was a minor slip, but little things like that can be important. I re-focussed and then without a word I motioned for her to come in. She closed the door behind her as she followed me into the house. "Welcome" I said simply and coldly as I walked. She didn't answer. "Did you sleep well last night?" Jen looked puzzled by my question. "I'm not sure what you mean." "It's simple really" I continued. "Did you lay awake wondering about all those dirty little things I'm about to make you do....or....did you sleep like a baby." "I didn't sleep at all" Jen confessed immediately. "Thinking about tonight just made me all turned on and scared at the same time." "Did you make yourself come?" I asked casually. "No. I don't even know why, but I kinda got the idea that you wouldn't have wanted me to do that." Hearing her say that actually impressed me. "You have good instincts," I told her and she seemed pleased at my comment. She continued to follow as I walked into the living room. I took a seat on the leather couch in the center of the room and I watched with some satisfaction as Jen hesitated, not quite knowing what to do next. She decided to sit next to me on the couch. I let her know immediately that she had made the wrong decision. She actually jumped a little when I interrupted her and harshly barked out my first instruction of the night. "NO. You don't get to sit next to me. I want you to stand in the middle of the room and face me while I enjoy the view." She did as she was told. She looked nervous and on edge. I casually poured a glass of wine from a strategically placed bottle and just sat there enjoying my drink as I looked her up and down and studied her body. There was some soft 'mood music' playing in the background and I wasted no time in using that little detail to my advantage. "Move those nasty little hips to the music for me nice and slow. I want to see how you're gonna move for me later." I instructed and she obeyed immediately. Jen moved and swayed in a slow, hypnotic way and as our eyes made contact I could see her fear begin to transform into something else. "That's it baby, now slide those hands all over your body for me." She continued to sway as her hands moved over her hips and belly. I could see a spark of arousal begin to form and then grow in her eyes. Her movements were soft and sensual as her hands roamed across her body, mimicking the soft touch of a gentle lover. Every minute or so I would issue a new command and she would follow every word without question. "Now work those breasts for me like a good little girl. I want to see those nipples get nice and hard." Once more she obeyed and her hands slowly travelled up her belly. Jen closed her eyes momentarily as she began using the palms of her hands to caress her breasts through that tight dress. "No not like that. I want you to rake at them with your fingernails." I instructed her before elaborating. "Gently scratch at them until those little nipples can't get any harder." Her long nails began to scratch and tease at my command. Within moments her nipples became erect and clearly very sensitive and a familiar look began to cross her face. It was an expression that was not specific to Jen as such. It was that look you see on the face of a woman who is beginning to surrender to herself and let her desires take over. All those little tell-tale signs and triggers were beginning to happen. I always love watching all those beautiful little events begin to take place inside a woman. You can see it all happen right before your eyes if you know what to look for. There is a beautiful kind of 'Domino Effect' that takes place as a woman's body responds to intense pleasure. A kind of 'positive feed-back loop' that occurs as her feeling of arousal floods her with hormones, which in turn trigger her biological responses, which in turn makes her even more aroused to begin with. It takes an intelligent man to not only know how to maintain that loop but to magnify each cycle until a woman is driven insane by her own arousal. But again I digress. Now is not the place or time to be giving up my secrets. "I bet you'd let me do just about anything to you right about now wouldn't you?" I said in a very 'matter-of-fact' kind of way. "Uh-huh" was Jen's slightly nervous and breathless response as she continued to rake at her nipples. Her hips were still swaying gently to the music. "Then say it." I said sharply. A hint of a smile crossed Jen's face as she replied. She gave her words a slow sensual drawl as she said them which left me in no doubt that she meant every word. "You can have me any way you want. I'm gonna be so dirty for you". "Oh I know you are." I informed her before standing and then walking up behind her. I slowly pulled the zipper on the back of her dress down to her hips and then like a well trained little slut she automatically began to shimmy out of the dress until it slowly slid down her body toward the floor. As soon as it had fallen I reached around her from behind with my left arm and pulled her in hard against my chest. The sudden jolt took her by surprise and she tensed up for a brief moment before realising what was going on and then let her muscles relax. I now had her effectively pinned up against me as my right hand reached around and explored her body with complete freedom. I could almost sense her desperation as I let my hand wander all over her. I could practically feel her melt under my touch. I focussed on her thighs at first, and then gently teased my hand all the way up her body before pausing at her mouth and lips. I gently circled her lips with my fingers and she accepted them eagerly when I slipped two of them into her mouth. She immediately sucked on them and worked her tongue in slow circles. Her breathing was harder now and she began to grind her cute little ass into me as I stood behind her. She wore a tight lacy g-string and push up bra which made her tits just sit up as if inviting me to tease them. She now had on nothing but her lingerie, stockings and those spiky red heels. I must admit that she had excelled herself in the presentation department. When I had asked her to come dressed like a slut I had no idea she would be such a natural at it. I pulled my fingers out of her mouth and slid my hand back down her body with excruciating slowness. I let my fingers wander and dance in teasing circles until they were at last pressing up against the thin lace of the g-string that barely hid her pussy. Jen's reaction was immediate. Her hips began to grind forward to meet my touch and so I pressed a little harder until I could feel the wetness flowing out of her and begin to soak through the thin lace. "Tell me why you are here tonight." I whispered softly into her ear. Jen hesitated for a moment as if unsure of what to say. It took a few seconds before she was able to compose herself and choose the right words. "I am here to be punished for what I did to you." "And you want that badly don't you." I whispered again. "Yes." She replied softly before adding. "I want to be dirty for you. I want to make things right." My next few words to Jen were important ones. I was about to give her yet another opportunity to pull out. (Even though I already knew what her answer was going to be.) "You need to know that you are about to experience the most filthy acts and have the most extreme orgasms of your life. If you have any doubts at all about atoning for your sins then you had best walk away right now." Jen's response was a simple one. She broke from my grasp and turned to face me. She then gave me the most frantic and deep kiss that she had ever given me before pulling back and whispering. "What if I don't want to walk away?" That was all I needed to hear. I took her by the hand then and led her to the master bedroom. She started to shake as pushed her down onto the bed, but it wasn't until I began tying her down that I could see the fear spread across her face. Each wrist and ankle was tied to a corner post of my queen sized bed until she was spread like a starfish. Despite her fear I was amazed at how willing she took to it all. It seemed to me that the more helpless I made her, the more turned on she became. "I wish I could tell you about the things I'm going to do to you on this bed tonight but I really don't want to ruin the surprise." I said calmly. "Oh god I can't stop shaking." Jen was clearly getting more excited by the second. "I wouldn't get too worried just yet." I reassured her before continuing "Because the first thing I'm going to do is give you is a lesson in patience." "I don't understand." She replied. Jen's little lesson in patience was actually just a convenient cover for something very important I needed to do. Believe it or not I actually had to pick up Tracy from her work. Once we got back she would change into something more appropriate for Jen's punishment and together we would set to work on giving Jen the most memorable night of her life. I propped Jen's head up with some pillows so she was comfortable and had a good view of the room. I then began to tell her about what was about to happen. "I'm leaving you like this for a couple of hours. It'll give you time to think about your past sins and how you're going to pay for them. When I get back things are going to get interesting for you. Do you understand?" I could see the confusion and disappointment in her face as she began to speak. "You're gonna leave me here like this for two hours?..........Alone?" "Yes." "No please don't do that....You can do whatever you want to me right now. I'm ready. I want you to!" "You don't get a choice, and I'll be the judge of when you're ready." I said firmly. I quickly made sure Jen's bonds were secure and then gave her some quick instructions before leaving. "I've arranged some wholesome, family entertainment for you while I'm away," I said as I switched on the 42 inch flat screen TV at the end of the room. Suddenly a porn video of a girl getting fucked in the ass by a famous porn star lit up the screen in high definition. "Oh I almost forgot," I said as I opened a draw and removed the red ball-gag that was inside. "You can't be serious!" was the last thing Jen was able to say before I gagged her and shut her up. I took one last look at my handiwork and was very satisfied. There she was, tied up and spread wide. She looked like a total slut in her heels and nasty red lingerie. I turned the volume up on the TV until the room was filled with the sounds of grunting and moaning. Before I left I turned to give her one last piece of advice. "I wouldn't let yourself get too comfortable.......because in two hours your punishment really begins." She nodded meekly and I closed the door behind me as I left the room. Making Jen watch porn while I was away was actually Tracy's suggestion, but I had also thrown in a few details of my own that I felt added a little value to the situation. I had set up the porn that she was now forced to watch to start with nice, almost conventional sex acts, but by the time I got back with Tracy she would be watching some pretty hard-core lesbian bondage. This wasn't done just for kicks. I had a pretty strong hunch (form something she said to me years ago) that the very thought of being punished and fucked by a mistress was something that had featured in her fantasies for years. If it worked like I almost certainly knew it would, then Jen would be frantic and soaking wet by the time Tracy and I even entered the room again. I had tied her down securely so there was no way she could touch herself let alone get free. I had always known about Jen's filthy little bondage fantasies, and I also knew that she had probably never acted upon them. I was going to use everything I knew about her to full effect tonight. It should have been a thirty minute drive to Tracy's work, but in my excitement, I did it in twenty. She was beyond excited when I picked her up from outside the beauty shop. She was dressed in her work clothes, but even then she still wore a tight black outfit that showed off just about everything. She had brought two full shopping bags with her. I could see clothes and lingerie in one bag, but the other contained a bunch of mysterious items that I couldn't quite make out. I told her how I had prepared Jen and had left her there waiting for us and I could tell that Tracy was very anxious and very ready to get things started. "Fuck this is all so hot. I'm gonna have your nasty little slut Ex purring like a kitten. She's gonna come so hard she won't even know what's happening." Tracy was a special kind of girl. She liked a little pain with her pleasure. Her make-up was dark and her lipstick was black today. She had two piercings through her lower lip and one nose piercing and as you have probably already guessed, she has her more private areas pierced too. She was curvy and voluptuous a lot like Jen was, only Tracy was the darker nastier version of Jen and I loved that about her. Jen had been tied down in that room for almost an hour before Tracy and I arrived back at my place. We had made our arrival as quietly as possible so that Jen wouldn't realise that I had returned. The frantic sounds of flesh being whipped and spanked was mingled with the rapturous cries of willing females as the porn continued to play loudly on the flat screen in my bedroom. By now Jen would be watching some truly impressive things being done to bound and helpless women as they climaxed over and over again. Tracy quietly walked up to the bedroom door and listened closely before returning to me. "Oh my god I can hear that little slut thrashing about on that bed of yours. She must be practically wetting herself by now!" I couldn't resist and I listened at the door too. I could her Jen squirming and rubbing against the sheets. She was breathing hard through her nose because of the ball-gag in her mouth and it was clear that she was exerting herself in some way. There was just no way for her to get herself off, I had made sure of that. She was tied, facing up, and spread-eagled to each post of the bed. All she was going to do was make herself more frustrated. Jen clearly hadn't heard us arrive or she would have stopped moving. For all she knew it was still just me she was waiting for anyway. She had no idea of course that Tracy was here and I couldn't wait to see the look on her face when she made that little discovery. Tracy wrapped her arms around me gave me a deep kiss. I could feel her tongue stud tease and dance about my mouth before she pulled away and informed me she was going to change into something more uncomfortable. She grabbed the bags she had brought with her and then promptly disappeared into the bathroom to change. It was almost 30 minutes before Tracy emerged from that bathroom and when she did my jaw dropped in wonder. She was dressed all in black (did she ever wear any other colour?). She wore shiny black high-heeled boots that laced tightly all the way up to her knees and underneath those boots she wore a pair of thigh-high fishnet stockings. A tiny little g-string barely covered her crotch and she completed the outfit with a tightly laced corset that squeezed her body into an almost perfect 'hour-glass' shape. The corset pushed up her breasts in the most amazing way. I also have to make special mention of the tight black latex gloves that hugged her hands and arms all the way up to her elbows. They set off her 'evil dominatrix' look perfectly, but there was also something very sterile and almost surgical about them. Her black hair had been pulled back into a pony-tail so tightly that it stretched the skin on her face and made her cheek bones sharp and prominent. God when Jen saw Tracy she was either going to come on the spot or faint with fear. Tracy held small a black leather case in one hand and it actually looked a lot like something a doctor would carry. In the other hand she held an impressive black riding crop. Somehow I doubted that riding crop had ever been used on an actual horse. "Time to go to work," Tracy said unable hide her excitement. I didn't even try to hide my own stunned reaction as I just stared at her for the longest time. "My god Tracy you look........." "I know." She replied with satisfaction as she cut me off in mid sentence. I know that up until now I haven't given you, the reader, much information about myself. It's not that I'm being overly secretive it's just that in a way I don't even feel like any of this is particularly about me. I know that might sound a little odd seeing as I have driven all this and made it happen. Perhaps it's a personal thing. I don't think I have a huge ego. Often I will prefer to control things whilst staying out of the lime light.