Breaing Jen

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.