Breaking Jen Ch. 01

by real_first_time

story tags: control, blindfold, submission, seduction, revenge, love,
power_struggle, vampire, lesbian, redemption

https://www.literotica.com/s/breaking-jen-ch-01


https://www.literotica.com/s/breaking-jen-ch-01

An Unconventional Love Story.

Page 1 of 6 page(s) (21085 characters)

/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

by real_first_time (UID 1077695)

https://www.literotica.com/s/breaking-jen-ch-01

An Unconventional Love Story.

Page 2 of 6 page(s) (21195 characters)

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

by real_first_time (UID 1077695)

https://www.literotica.com/s/breaking-jen-ch-01

An Unconventional Love Story.

Page 3 of 6 page(s) (21231 characters)

"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.

Breaking Jen Ch. 01

by real_first_time (UID 1077695)

https://www.literotica.com/s/breaking-jen-ch-01

An Unconventional Love Story.

Page 4 of 6 page(s) (21299 characters)

Perhaps more information is required now for the purposes of what I'm
about to tell you.

I am in my thirties. I'm of mostly European descent but there is just a
little mixed family history in me that often makes me appear 'Italian'
or 'Mediterranean' looking to other people. My hair is dark black and
my eyes are a very deep brown. 

What I was wearing that night was extremely conservative compared to
what Tracy wore but we males don't exactly have a lot of options in
that department do we. (Well....not unless you are one of those German
fetish freaks that run around in gimp suits. I can tell you right now
that I am definitely not one of those.)

No. Women definitely get to have all the fun in that department whilst
we males must be content to carry around all our fetishes on the
inside.

As it so happens I had chosen to wear mostly black attire a little like
Tracy had done but I went a different way. I wore an expensive designer
label shirt and pants. I contrasted my mostly black attire with a
'steel grey' coloured tie which gave me an almost fascist appearance. I
guess if you're gonna project an image of control then you go can't go
wrong with black.

The real fun was about to begin and I felt a huge rush as we approached
the room. I motioned for Tracy to enter first and she happily obliged.
I wanted Tracy to be the first thing Jen saw. I wanted her to see this
evil and beautiful vision and to see the look in her eyes as she began
to grasp what was about to happen.

Tracy opened the door and strutted into the room as if she owned the
entire world. I heard a sudden ruffle of sheets as Jen was jolted into
reality and tried to collect herself. I entered the room immediately
after her and closed the door behind me. 

Jen stared with a startled expression at the both of us until she
finally just focussed on Tracy and watched her every move. She seemed
to go into a state of utter panic then. The sheets around her were
tussled from all the writhing about she had done in the last couple of
hours. 

"I think you're ready now" I said calmly as I studied her reaction. I
drank in every little nuance and expression.

Fear, shock and alarm. Her eyes bore into mine in a desperate and
pleading way before they locked back onto Tracy and I heard her whimper
into the ball-gag. 

Tracy seemed to be almost ignoring Jen as she walked to the side of the
bed a placed the bag and the riding crop on the corner table. I could
tell that Tracy was acutely aware of those fearful eyes practically
burning their way into her and I could sense the satisfaction that it
was giving her.

Tracy then walked towards the television and took a quick mental note
of what Jen had been watching before smiling and switching it off. A
frantic submissive girl on-screen had been screaming in ecstasy as two
mistresses double penetrated her thoroughly with toys.

Tracy looked back at Jen and began to speak. "Oh you were enjoying that
weren't you baby-girl." Jen just continued to stare at Tracy. "You were
wishing that was you weren't you. Your little pussy is just aching for
a bad girl like me to give you what you deserve."

I could see that Jen was visibly shaking now and her eyes continued to
travel up and down Tracy's body.

"Let's find out just how badly you want it." Tracy said calmly before
slowly walking towards the bed. Jen shot an alarmed look at me but all
I could do was smile. 

Tracy walked slowly towards the head of the bed. She stretched out a
gloved hand and let her fingers trace a line up Jen's leg as she
walked. Her breathing doubled when she felt Tracy's hand ease up her
inner thigh.

Jen then bucked slightly when Tracy's latex covered palm pressed up
against her crotch and began to grind into her over the top of that
tiny little g-string. She applied firm and deliberate pressure before
withdrawing her hand and examining it.

She smiled once more as she turned her palm to face me and I could see
the beads of moisture covering her glove.

"The little slut is soaking wet. I think she needs it real bad. I'm
gonna start working on her now if that's okay with you." Jen
immediately looked at me and shook her head in protest. I simply
ignored her and nodded to Tracy who wasted no time and began to get
herself into position.

Jen just shook and whimpered as Tracy got onto the bed on her hands and
knees and positioned herself directly above Jen. She stared coldly into
her eyes as she began to speak. 

"This gag is about to come off. You are not permitted to speak. You
will accept my tongue into your mouth and you will let it explore you.
Are we clear?" Jen nodded with what looked like fear in her eyes. 

"That's a good girl. You know how much you deserve to be punished for
what you've done, but things will go a lot easier for you if you behave
for mistress." She seemed to panic as the gag was being removed but Jen
wasn't given much time to think or react after that.

As soon as the gag came off Tracy pulled her head forward off of the
pillow with one hand and locked herself into a deep and passionate kiss
as her tongue invaded Jen's mouth.

Tracy supported herself with her free hand while she straddled Jen's
body with her knees. The freedom of that position gave her the
opportunity to use her body in more inventive ways.

At first she started to grind her own pussy into Jen's body and
practically humped her like a dog humping a chair as they continued to
kiss. A minute or two later she subtly changed position as she drove
one knee high up against Jen's pussy as she continued to grind against
one of her legs. Her movements would repeatedly drive that knee up
against that soaking crotch and it was becoming apparent that Jen was
enjoying every second intensely.

She began to pull and buck against the ropes and suddenly something
very interesting happened. She let out a quiet moan at first, which
within a few seconds it began to get louder as she responded more and
more to what was happening to her.

Her mouth was still stifled by Tracy's deep kisses, but every time she
felt that knee grind into her pussy she began to let out a whimper that
steadily built into a deep moan. Very soon her cries took on a sensual
rhythm. 

Actually I hate it when stories or accounts like this degenerate into
those pathetic exclamations of "Ahhhhhhhhhhhh!" or
"Ohhhmmmyyygggooood!" It's just so lazy. But ironically the only way I
can describe the noise Jen was making is to say that her cries had
taken on a kind of
"mmmm........ahhhm........ahhhhh........hmmmh........ohhhh........gnahh
h" rhythm.

(Maybe sometimes you have to revert to those sad old clichés to get
the message across. I Promise I will try to keep my 'AHHHHHHHHS' to a
minimum.)

Without warning Tracy abruptly broke off her long kiss and then stepped
away from the bed. 

"She's ready for her first lesson now," she informed me before
continuing...."Maybe now would be the perfect time to spell it out for
her while I get some things ready."

"With pleasure." I replied. 

Tracy exited the room then. I needed to explain things to Jen and Tracy
had her own preparations to make.

"What did she mean by that?" Jen asked as soon as Tracy left "What's
she going to do to me?"

I sat on the bed beside her and then began to explain her situation. My
tone was clear and my delivery was soft. There could be no ambiguity or
mis-understanding in anything that I said. It was vitally important
that she understand the situation clearly. 

"You know why you are here. You know that you need to be punished." Jen
nodded in reply.

"Well then it's important that you listen very carefully."

I was about to give Jen a huge piece of the puzzle and to her credit
she hung on every word.

"Everything that happens to you is entirely in your hands now....do you
understand that?" Again Jen nodded.

"Tracy and I will do our best to make you come nice and hard for us. We
will use everything we know and every dirty little trick in the book to
make you come a total of three times and we have until 8pm tomorrow
night to do it. Do you understand?" Jen nodded but was clearly very
confused by it all.

"But why would it take so long?" came her perfectly understandable
response "God you can make me come right now. I really want to. I got
so close when your friend was kissing me just now."

It occurred to me then that Jen hadn't been formerly introduced to
Tracy yet but I was sure that Tracy would handle that little detail
when the appropriate time came.

"It's important that you understand that your actions have
consequences."

"Yes I understand that." Jen replied sounding eager to please. 

"Well then you must also understand that we're not going to make it
that simple for you. We are going to use every nasty little trick we
know to make you come and you are going to fight us every step of the
way....and we want you to fight us."

"Look you're not making any sense." Jen gasped "You can make me come
right now. God I want you to!".

It was time to make things a little more real for her. She really did
need to understand the situation she was in and I suddenly realised
that I wasn't doing her any favours by trying to take the reasonable
approach.

I slapped her across the face then and I slapped her hard. A look of
shock and anger spread across her face and I could tell that for the
first time she understood the seriousness of her situation.

"Do I have your full attention now?" She nodded, clearly shocked by the
harshness of the slap I had given her. 

"Every nasty little orgasm we give you will have it's own lasting
consequence. In a sense you're actually quite lucky. Many people pay
lots of money for something we are about to give you for free."

I could tell right then that it had all suddenly became very real for
Jen, but unfortunately for her it was now far too late to turn back.
She had been given that opportunity many times.

"Oh fuck...... Look I have changed my mind. Please just untie me and
let me go. This has all been a big mistake." Jen began to plead.

"There's been no mistake" I said coldly "It's important that you keep
your head now. I can't tell you what the consequences will be for each
orgasm yet, but once we've made you come for the first time you will
understand and I will tell you everything."

"God what the fuck are you gonna do to me?" was all Jen could say. 

"The first orgasm will be easier but I know you will fight the next two
hard...... but.... if you can resist the urge to come then there will
be no punishment and no consequence. All you will feel is the pleasure
of having Tracy and I tease and manipulate you for an entire day. Do
you understand better now?" Jen nodded and I for the first time I saw a
faint smile and a defiant spark in her eyes.

"You can tell your friend Tracy to bring it on. She ain't gonna make me
come but I'm gonna enjoy every second of her trying."

I had forgotten how smart Jen really was. She had picked up on my slip
about Tracy's name and all of a sudden she had worked out an angle by
which she could regain some control. Believe it or not that actually
made me very happy. As far as I as concerned it was 'game on'.

"What if I need to use the bathroom?" 

I impressed that Jen had the presence of mind to ask such a mudane
question.

"Then you'll do it under our close supervision." was my brief answer. 

"You will be blindfolded at first while Tracy and I bring you to your
first climax of the night. We'll take it off after that you'll get to
see everything. Oh and feel free to make all the noise you want. We
like that."

I had done enough talking. It was time to get things moving now.

I quickly blindfolded Jen before ushering Tracy back into the room.

"She's ready for her first lesson." I said casually, fully intending
that Jen hear every word.

"Trust me, it won't take long." Tracy replied. Jen began to whimper and
pull against the ropes once more. The defiance she had shown only
moments earlier was beginning to leave her and fear was taking it's
place.

Tracy had not re-entered the room empty handed. She had brought with
her an ice bucket containing a bottle of wine and also one of the
shopping bags she had brought with her from the beauty shop.

Now that Jen was blindfolded Tracy quickly got to work and set up
everything she would need on the bedside table.

It was an interesting list of items.

A set of piercing needles and a selection of rings and studs. A riding
crop and a decent range of dildos (regular, double ended and strapons).

An impressive array of other accessories such as vibrators, plugs, and
lubes were also lined up.

Tracy and I had planned all of this days earlier but now that it was
actually happening we both felt an evil rush and we couldn't wait to
finally tell Jen what was really going to happen. 

This is the part of my account where I'm probably going to lose many of
you but I make no apologies for what I did.

Jen needed to understand that her actions had consequences. As I said
much earlier, I was about to give her a lesson in causality and
consequence.

Her first climax would probably come easy because she didn't know what
the consequences were yet. But after that first time, she would know
everything and she would be faced with some very real choices. Assuming
she was even able to control herself she would have to decide if her
orgasm was worth the price.

Maybe you have guessed already but I'm gonna spell it all out for you
anyway. 

We were about to tease and caress and bring Jen to a series of three
crashing orgasms. But...... there would be a price for each time she
came. If you read the first part of this account you already know that
Tracy performs body piercings (amongst other things) for a living. 

At the height of each orgasm she will receive an instant piercing
through an intimate area of her body and a nice little piece of
jewellery to adorn it. Her nipples will be pierced first.

After the second nipple is done, Tracy and I will work patiently and
methodically to achieve that final climax. As you might have guessed,
if Jen comes for the third and final time she will have the hood of her
clitoris pierced with a small barbell stud. After that, the lesson will
be over and she will be free to go.

If at the end of all this Jen actually has both nipples and her clit
pierced, then she will only have herself to blame. Those three little
piercings will be a reminder to her of how much of a slut she really
is.

"It's time." Tracy announced loudly so Jen could hear every word "I'm
gonna heat up this little bitch and then cool her down with an ice cube
or two. Did you hear all that slut? Answer when I speak to you!" 

"Yes" Jen replied quietly. "Yes, what!" Tracy corrected her. 

Jen paused for a few moments, not sure what to say at first before
replying "Yes Mistress." 

"Good girl" I replied. She was learning fast.

Tracy began to work on Jen. She picked up the riding crop and ran the
tip of it up and down Jens body. I popped the bottle of wine and drank
as I watched the show.

As you will discover, the ice cubes inside that ice bucket were much
more important than the bottle of wine they chilled.

Tracy spent 15 whole minutes caressing Jen's body with the crop and
making her twitch and squirm. She couldn't see a thing with that
blindfold on so all those little signals coming from her body were
being magnified to compensate for that lack of vision. 

"Oh god please just tell me what's gonna happen.....I really do wanna
come now....I really want to let it happen but I'm so scared." After
there was no reply she tried a different tactic and started speaking to
me instead.

"Please, I know you're watching. I want you to fuck me hard while she
punishes me. I'll come so hard if you do that." 

"That's enough talk out of you bitch!" Tracy snarled as she began to
whip Jen hard with the crop and set her skin on fire with every little
sting of leather. 

I watched in awe as she spent 5 minutes turning Jens belly and thighs
red. Jen's moaning and pleading became constant and frantic. 

Jen let out a loud tortured scream when Tracy finally focussed the crop
on her pussy and began to whip it hard through the now soaking
g-string. The pace was blistering and all Jen could do was pant like a
dog as the stinging blows rained down. 

"God I don't care any more. Please just fuck me. Fuck me till I come."
Jen practically shouted in my direction.

"Your mistress has control of you for now." I informed her "It's her
you should be begging."

Tracy waited a few moments before slamming the crop much harder once,
and then twice into Jen's pussy which produced an instant reaction. 

"FUCK ME MISTRESS!.... FUCK ME!" 

Tracy suddenly changed her technique then. She sped up the pace of the
riding crop even more but the blows were much lighter and focussed now.
Each little stinging slap landed on the same exact little spot on Jen's
g-string. Every blow was landing on Jen's clit now.

"No no no no no no." Jen began to recite over and over. We had brought
her to the very edge of coming and I have no doubt it would have
happened in mere seconds, but Tracy and I both had something a little
more dramatic planned for her first orgasm of the night.

The situation required that I act quickly now.

I grabbed the ice bucket and placed it on the bedside table. Tracy
immediately took a pair of scissors from her bag and then snipped the
shoulder bands of Jens lace bra exposing her full breasts to the cool
air.

Her nipples already looked rigid and excited and wasting no time, Tracy
began to rain stinging blows from the riding crop down onto Jen's
exposed breasts and nipples.

Poor, unsuspecting, blindfolded Jen. We had brought her to the very
edge of a crashing orgasm only to have it snatched away from her and
her nipples then set on fire by stinging blow after blow.

"Oh god....please just let me come.....please let me!" Jen began to
beg.

Tracy now focussed her blows on the right nipple and Jen began to
scream louder. The moment was approaching fast and Tracy handed me the
crop. I resumed those sharp little blows on Jens clit that had brought
her so close to the edge before and Tracy grabbed an ice cube from the
bucket and set to work. 

Jen's body arched upwards to meet the touch as she felt Tracy begin to
slide the cube of ice over her right nipple.

"No no no....oh god no," Jen began to babble once more. It really was
very curious how conflicted Jen seemed to be about what was happening
to her.

Tracy quickly grabbed a small, thin piercing needle from the bedside
table. She positioned it right beside the nipple ready to strike. She
was now straddling Jens body to keep her still and everything was
ready.

Jen was so close to her first orgasm that It would only take the
smallest of acts to send her over that edge now. I had that little
detail well under control.

Without the slightest warning I grabbed one of the ice cubes from the
bucket and then yanked Jen's g-string to one side. I pushed the cold
hard ice cube deep into her hot pussy in one firm push and she
screamed. A few seconds later she sucked in a sharp breath of air
through her clenched teeth before babbling a few final words.

"NO.....OH FUCK NO!" She practically shouted this time and I knew right
then that my next action would be the one that would finish her off.

I leaned in, closed my lips around her throbbing pussy and then
suddenly and without mercy attacked her clit with my tongue.

Her body tensed. A massive and desperate orgasm tore through her then
and just as it reached It's peak, Tracy struck with efficiency and
pierced the right nipple in a movement that took only milliseconds.

I'm not sure how to describe what happened next. Jen paused for a split
second as her body went rigid. A few moments later her screaming
sounded more like a wild animal and her body convulsed as the pain and
shock seemed to multiply her orgasm ten-fold.

Breaking Jen Ch. 01

by real_first_time (UID 1077695)

https://www.literotica.com/s/breaking-jen-ch-01

An Unconventional Love Story.

Page 5 of 6 page(s) (21582 characters)

"Oh shit..oh shit ..awwwwww fuck!" was all Jen could get out as Tracy
quickly slid a nipple ring into the piercing and fastened it tight. Jen
was still shuddering and had started to pant like a dog once more.

"Oh God, what the fuck was that......WHAT THE FUCK WAS THAT!" Jen
repeated as her body continued to shudder from the post orgasm high she
was still experiencing. 

I removed her blindfold then and instructed her to take a look for
herself.

For the first time Jen saw her brand new, freshly pierced nipple with a
very tasteful silver ring adorning it. Unfortunately she didn't seem to
be at all happy about her new look.

"FUCK" Seemed to be the only word she could think of for quite a few
seconds until she began to regain her wits and suddenly get more
articulate in her responses.

"Oh you fucking cunt. Don't you fucking come near me you fucking whore,
I swear I'll make you pay I swear......." Jen was stopped in mid
sentence by a sudden slap across the face from Tracy.

"Listen to me you little cunt you came here to be punished so don't you
dare speak to me like that ever again or you will really suffer, you
got that?" Jen nodded. She seemed startled and scared now. 

"We already told you that all you have to do is not come," Tracy
continued to speak. "But next time you come for us we will pierce the
other nipple."

"Oh fuck please stop...please....I change my mind. I just want to go
home now." Jen began to practically sob.

"But you haven't even heard the best part," Tracy continued to torment
her captive. "If you still feel like coming again after all that, then
we are gonna finish by putting a nice little stud in that pretty clit
of yours. It's gonna look so beautiful." 

"Please stop her," Jen now pleaded directly to me. "Don't let her do
it. Oh god please just stop this."

"That's entirely in your hands now," I instructed her further.
"Remember all you have to do is not come. If you can do that then
you'll have the best day of your life."

Jen calmed down then and once more I saw her resolve return. That spark
of defiance once more shone in her eyes and I could see her mentally
begin to prepare for what was to come.

When I said before that the first orgasm would be easy compared to the
next two I was not exaggerating.

Jen had full knowledge now of our plan now and also the consequences of
her actions. The only real advantage Tracy and I had left was that Jen
didn't know about our methods yet. 

Knowing that, we both threw ourselves at that challenge.

Every subtle trick and every brash move was used.

For that reason, if I was to go into every detail of what Tracy and I
did over the next two hours it would take an entire novel to cover it.
You can, however, be content in the knowledge that the seduction and
violation of Jen was legendary. 

At first we tore off her soaking g-string and shoved it into her mouth
to shut her up. She became our personal 'fuck toy' as I rammed my hard
dick all the way into her pussy in one stroke while Tracy straddled her
face. I have no idea if Jen had any experience with girls in the past.
She hadn't when I knew her, but Tracy was giving our new little whore a
through lesbian workout.

We were both conscious of the fact that Jen was in fact enjoying all of
this treatment immensely now. She was engaging vigorously and
responding strongly. She would allow herself to feel intense pleasure
up to a certain point and then work hard mentally to shut herself down
if she felt she was letting herself get out of hand.

A new approach was called for.

We both took a short break and admired the view. Jen was still tied and
spread for easy access. The bra and g-string were now gone and she lay
there spread for us in heels and stockings. Jen had clearly opted for
the 'full brazilian' approach to grooming and her crotch was smooth and
hairless. I approved.

Tracy peeled off her g-string and we discussed our plans, making sure
Jen heard every word. "Make sure you're ready to do her other nipple,
I've got a feeling this may get loud." I instructed Tracy. She placed a
needle and nipple ring on the bedside table ready to go and we got
ourselves into position.

It became very interesting reading Jens reactions to everything. She
was clearly trying to calm herself down and control her body. 

Tracy and I were undiscouraged by this. We had both seen little signs
and reactions starting to creep in that told us that Jen was starting
to lose that control little by little.

Her pussy had stayed in a constant, 'dripping wet' state and even the
nipple we hadn't pierced yet had remained rigid and extremely
sensitive.

Tracy leaned in and began to lick and bite the un-pierced nipple. For
the first time she then reached over and lightly tugged on the new,
sensitive nipple ring as she did it. 

Jen grunted. There were clearly strong, new sensations coming from that
freshly pierced nipple that she wasn't used to. That new sensation was
going to be our doorway to her next orgasm.

Every time Tracy tugged on the ring, newly awakened nerve endings were
shooting pleasure messages to Jen's brain and for the first time since
we pierced her, she let out a small moan.

"Oh that's so hot baby," Tracy whispered. "I'm gonna make your other
nipple feel even better!" Jen's control seem to be slipping more now.
She was aware of that but she was still holding on bravely. Tracy
continued to lick and bite Jen's left nipple while she lightly tugged
on the nipple ring on the right with her fingers.

"Use the big one in the bag." Tracy instructed me and I took the
largest vibrator from the shopping bag. It had a large head that was
almost the size of a tennis ball. It was not designed for penetration
but was large enough to vibrate her entire pussy and clit. 

"That's not fair!" Jen protested as she stared at the huge vibrator and
for the first time in a while she looked worried.

"Who told you any of this was going to be fair?" I said smiling
broadly.

Jen made a fearful noise that almost sounded like the squeak of a mouse
when she felt the head of the vibrator ease up against her pussy. I
just ground it in slow circles at first without even turning it on. I
was really just trying to get the head of it slick and wet more than
anything else but even that sensation still made her moan. 

Tracy's little 'nipple tease' act was working. Once more we were
breaking down Jen's defences and I was about to make things even harder
for her. 

Tracy gave her a long sensuous kiss before resuming her 'nipple
treatment'.

"She's ready. I think it's gonna happen again real soon." Tracey
announced.

"Oh no it isn't!" Jen tried to protest breathlessly.

The moment I switched on that vibrator Jen instantly knew she was in
real trouble. 

"OH SHIT!" She suddenly blurted out. I saw her make an attempt at
shutting her body down and then promptly watched her fail when I
switched the vibrating head onto 'high' setting.

"NO...STOP IT...PLEASE JUST FUCKING STOP....I DON'T WANT
TO.............."

Jen watched in almost horror as Tracy poised the needle beside that
left nipple. Her eyes closed tightly when she felt an ice cube slide
over it. 

"CALM DOWN.....DON'T LET IT........"

Jen was in mid sentence when her body instantly became tense and her
pussy began to contract involuntarily.

She came suddenly and violently just as Tracy performed the piercing.

Something else very important happened then. This time around Tracy had
decided to strike just as Jen was hovering on the edge and about to
come.

This time it was that sharp feeling in her left nipple that had been
the trigger for her orgasm and we all saw it.

Tracy immediately attached the new nipple ring as Jen continued to
shudder for at least a minute. When she finally looked down she saw
that both her nipples now matched. 

She panted like an animal once more and she looked angry and turned on
all at the same time.

Now I'd like to point out that I really do consider myself to be one of
those guys who's seen just about everything. I don't really get
surprised by people or situations a lot any more. I had been in many
situations like this one.

It's true that those other situations weren't as intense or perhaps
even as risky as the events of that night but I do actually feel that
I've witnessed just about every reaction that it's possible for a woman
to have.

I had somehow forgotten in all of this commotion that Jen however, was
not an ordinary woman. I had also forgotten that most of the success
she had attained in life so far had been due to her ability to control
and manipulate others.

Jen did something very brave then. She took a risk. Sadly for her the
risk completely backfired on her but her audacity earned my respect all
the same.

I think she had realised what she was up against. She had decided that
trying to hold out and win things her way probably wasn't going to
work. She had already come twice for us and the clock hadn't even hit
1am yet.

From out of nowhere Jen began to yell and even bark orders at us. She
began to spit insults and act as if she was the one in control and we
were simply there to give her pleasure.

"It took me a while, but I think I've finally figured you out you dirty
little cunt!" Jen said trying her best to insult Tracy.

"Oh this should be good" Tracy replied with a smile. "Tell me then.
Please share this big revelation with us."

I couldn't quite believe what I was hearing. This was turning out to be
better than I could have hoped for.

"I bet you dreamed about having someone like me back in high-school
huh!" Jen continued to rail at Tracy.

"You've probably been wetting yourself for years just thinking about
doing all that sick lesbian shit to a girl like me. It's really sad
that the only way you could do it was to have me tied down."

"Oh I prefer it when they are tied down." Tracy continued "We can't
have you running off when you're only moments away from getting fucked
in ways you've never even imagined."

"Well then what are you waiting for you sad little bitch, just shut-up
and start fucking me like a good little whore." Jen looked almost
triumphant when she said that.

I was actually rather glad that she had left me out of her tirade of
insults. I wasn't sure why I had escaped her acid tongue, but as I said
earlier, it was a brave move and a decent attempt at getting Tracy to
untie her. 

Unfortunately for Jen, Tracy was no ordinary girl either. She didn't
react. She didn't get angry. The end result of Jen's act of defiance
was that she had unknowingly convinced Tracy to go much farther than
she had intended.

"You know what?" Tracy said with an evil smile. "I'm going to give you
exactly what you want."

She left the room for a moment then and returned with the other
shopping bag.

"You know I had no idea how anxious you were to really get fucked by a
girl. I thought you were just one of those inexperienced little girls
with lesbian fantasies. But I can see now that I was wrong."

Jen actually looked scared as soon as Tracy said that. All of a sudden
it began to dawn on her far too late that she had tried to fuck with
the wrong girl.

"I never dreamed I'd be using this little toy on you today. I'm told
that the last girl I used it on was never quite the same again."

Jen was officially petrified after she heard that comment and she
hadn't even seen what the toy was yet. 

Her eyes widened in horror when she finally saw Tracy pull that toy out
of the shopping bag.

It was a huge and grossly over-sized strap-on dildo that mimicked the
human penis in almost every detail apart from it's obscene size. The
thing was as thick as a man's forearm and approximately 14 inches in
length. 

Everything about Jen suddenly changed then. All the bravado and
defiance disappeared in an instant. I have to choose my words very
carefully here because her reaction is extremely difficult to put into
words.

Try and imagine the look on someone's face when they suddenly get a gun
pulled on them. At first they can't quite believe what they are seeing
or that this is really happening to them. They begin to stare
transfixed at the muzzle of the gun with a morbid fear.

Everything changes then.

Jen just stared at that obscene toy with that same kind of cold fear.

"No." Jen almost whispered to herself at first before finally finding a
few more words.

"JESUS CHRIST NO!......"

Tracy was unmoved. If anything she seemed to be enjoying herself much
more now.

Jen turned her attention toward me then. It was all beyond real for her
now. 

"Please stop her......Don't let her hurt me....Please you have to stop
it!"

I had real doubts then. I knew Tracy well and I trusted her, but maybe
she was about to go too far. Jen wasn't a big girl. She had a curvy
body but a petite little frame. As I fucked her earlier I had even
remarked on how tight and snug her vagina felt.

I had to ask Tracy a very important question then.

"Are you sure you know what you're doing?"

"Trust is a beautiful thing," Tracy began to explain. We both talked in
hushed tones so that Jen couldn't over-hear but it was obvious that I
was worried.

"You aren't too smart are you!" Tracy said. To be honest that comment
just pissed me off, and sensing that, she began to explain.

"Oh the little cunt is scared alright but she's not as innocent as you
think. It takes another girl to see that."

"Then you had better spell it out for me then," I replied.

"You heard what she said earlier. When she accused me wetting myself
for years just thinking about all this 'sick lesbian shit' do you
really think for a second that she was actually talking about me?"

The truth of what Tracy had just said hit me like a ton of bricks.

"And I also suppose you haven't noticed that for some unexplainable
reason the stupid girl actually seems to be in love with you?"

Ironically, out of everything I had seen and heard so far, it was that
comment that shocked me the most.

"Oh Christ. For an exceptional guy you really are just a typical dumb
male underneath it all aren't you."

I didn't really have a good reply to Tracy's comment. The notion that
Jen actually had feelings for me, or actually might have even been
genuinely sorry for what she had done hadn't even been a consideration.

Had I been so jaded and clouded by my own lust for revenge that I had
missed what was really happening?

Tracy almost seemed to read my thoughts then. She saw how disturbed I
had become and she immediately cut to the heart of the matter without
the slightest hesitation.

"Shit you've only just figured it out haven't you. You're still in love
with her. You tried to make yourself forget it by killing your emotions
but you never even stopped did you!"

"Please don't say any more," I replied. I could feel old emotions
beginning to re-awaken and for the first time I doubted my ability to
control them.

"Listen to me," Tracy said as she looked me squarely in the eyes.
"Before you start getting all misty-eyed you had better realise that
this isn't some romantic movie scene from 'The Notebook', this is real
life."

Tracy always had a way of putting things into perspective for me.

"I'm still going to give that little whore a fucking of biblical
proportions, but you need to stay focussed and finish this right. Do
that, and she'll be your obedient little lap-dog for life."

For the time being it seemed to be Tracy's show now and I was fine with
that. I had a little too much to process at that point so letting her
take the lead for a while was perfect for me.

"You better make sure she's thoroughly prepared." Tracy said as she
handed me a very large tube of lubricant.

I approached Jen on the bed then. She was whimpering and pulling at the
ropes and I saw real fear in those deep blue eyes. A curious thing
happened. I gave myself away. I didn't mean to. She saw something in my
eyes and she calmed down.

I kissed her on the forehead and gently ran my fingers through her hair
as I spoke.

"I want you to be a brave girl for me. Can you do that?"

She smiled faintly then. She let out a small moan as she felt the cold
lubricant being smeared all over her pussy and her back arched in
response when she felt my slippery fingers enter her and attempt to
lubricate her as thoroughly as possible.

I prepared her as best I could. I pushed four fingers deep inside her
and started to stretch and push and she understood right away what I
was trying to do. She was extremely tight. She would feel every inch of
that black, shiny phallus intensely when the time came.

Jen's eyes nervously scanned Tracy's every move now. She watched her
slide the heavy duty leather harness up her legs and then firmly buckle
the rubber phallus in place.

Jen was hyperventilating now. She started to shake uncontrollably and
the ropes binding her wrists and ankles were now under a constant
tension.

I find myself at yet another point in my account where I'm struggling
to find words. I am honestly wracking my brain to try and find the
right way to convey both the visual image and the emotion of that
moment. If I was simply just making this all up I'm sure it would be
easy. I will try my best to describe the indescribable.

There was nothing natural about the sight that greeted me. Although
Tracy had discarded her g-string long ago she still wore the boots, the
fishnets, that tight corset and those tight black latex gloves. She had
already looked imposing to begin with but now she was in another
category.

That shiny black strap-on penis protruded from her crotch for about 8
inches and then bent under It's own weight as the rest was dragged
down. It appeared to be rigid and yet flexible.

"Oh god...oh god," Jen began to babble when Tracy began to walk towards
the bed. 

She stopped briefly then and made sure Jen was watching her closely as
she picked up the tube of lubricant and began to smear the tip and the
shaft of the strap-on until it was slick and glistening. 

Every movement was slow and deliberate. Every second was drawn out for
maximum effect as if she was performing some sacred ritual. She was
torturing Jen with her every move and she was loving every moment of
it.

Jen's eyes grew wide as Tracy crawled up onto the bed on all fours and
stalked towards her prey until she was nestled up between her legs.

The strap-on was so ridiculously long that Tracy was able to partially
kneel as she nestled the tip of the thing against Jen's tiny little
pussy.

As soon as I saw the tip of that thing nestled up against that tiny
hole I realised what a gross mis-match in size this whole exercise
really was.

The moment Jen looked down she realised it too.

"OH FUCK NO....IT'S TOO BIG....PLEASE CAN'T YOU SEE IT'S TOO BIG!"

"Hush now Baby-girl. I know it looks big right now but trust mistress.
It's gonna violate your pretty little hole in ways you never dreamed
and touch you in places you never even knew you had."

Tracy was calm and completely fearless. She really was born to do this.
Words do not do justice to what I was seeing.

"Fear can be such a delicious feeling when it's the right kind. And you
are so very afraid right now aren't you baby?"

"You don't know how much." Jen almost stammered.

"You and I both know that's not all you're feeling is it?"

Jen didn't reply.

"You've been thinking about this moment for years haven't you. Dreaming
about the moment when an evil little slut like me violated you."

Again Jen was silent.

"It's important that you're honest with your mistress." Tracy urged.

"I.....I might have." Jen finally admitted.

Tracy reacted quickly. She pushed her pelvis forward in a sharp thrust
and the tip of that massive phallus pushed and stretched at Jen's tiny
little hole.

"Oh god..oh god...oh god...oh god." Jen suddenly shrieked.

The tip of that thing didn't even come close to penetrating her, but it
was a good indication of what it would really take to achieve
penetration.

Breaking Jen Ch. 01

by real_first_time (UID 1077695)

https://www.literotica.com/s/breaking-jen-ch-01

An Unconventional Love Story.

Page 6 of 6 page(s) (12508 characters)

"I think we both know that it's gonna take a lot more effort than that
to get the tip of that nasty cock inside you don't we." Tracy
continued. 

"So unless you want me to just shove that thing all the way inside you
right now, you had better start being honest with yourself and
me.....Understood?"

"Yes mistress." was her shaky reply.

"Let's try that again shall we?" Tracy paused.

"Tell me when those thoughts began. Tell me how old you were when you
started dreaming about all this 'sick lesbian shit'?"

There was another long pause.

"I.....I think I was fourteen."

"And what did sweet, innocent little fourteen year-old Jenny fantasise
about?" Tracy questioned further.

"Miss Mathews.....my..........my english teacher."

Tracy looked very pleased with herself then. I didn't know if she was
reading Jen like a book or maybe just tapping into some kind of
universal female fantasy, but she was getting spectacular results. 

I didn't know about any of the things Jen was confessing. I'm guessing
that they were things she hadn't told another soul in her life before
now. 

"And what did that nasty Miss Mathews do in that dirty little mind of
yours?"

"She was always mad at me." It all began to pour out of Jen then. "She
told me I was a very bad girl. She said that I dressed like a slut."

"Go on" Tracy encouraged.

"She kept me back after class. She bent me over her knee or sometimes
her desk. She always pulled up my skirt and spanked me until I would
cry and promise to be good."

"Oh baby I bet that thought made you soak your little panties and want
to touch yourself didn't it." Tracy replied.

"I made myself come that way all the time until I discovered boys." Jen
finally confessed.

"You're being such a good girl for me now" Tracy said with real warmth
in her voice.

Tracy paused then. She actually turned to me and gave me a sly wink
before looking back at Jen and saying something I did not expect.

"I believe in rewarding good behaviour, so I'm going to allow you to
make the most important decision of your life.................. Right
now."

That got my attention straight away. We hadn't discussed this part. I
didn't know why Tracy was going off the script at this late stage but I
hoped and trusted that she knew what she was doing. 

Hell up until now it seemed that Tracy had a better understanding of
the situation than anyone else in the room anyway.

"But.........before you make that decision you must be totally honest
with me about something very important. Do you understand?"

"Yes mistress." Jen replied obediently.

"I've been watching everything you do and everything you say. I've seen
the look in your eyes when you speak to him," Tracy motioned towards
me.

"When exactly did you plan on telling him that you were in love with
him?"

There was a long pause then as Jen glanced over toward me and I almost
froze. I don't know where it came from but seemingly out of nowhere I
found the perfect response to the situation.

"Your mistress asked you a question and I would very much like to hear
the answer."

"I didn't know how to tell him," Jen said as tears began to form. "But
I wanted to show him. I came here to make it right."

Tracy looked very pleased with herself.

"Well I'm giving you that opportunity right now."

A long silence followed.

"So guess what. You're free to go. It's all over." Tracy said suddenly.

"I don't understand." Jen replied.

"Just what I said. No more teasing, no more fucking, no more
coming....the ride is over." 

I couldn't believe what I was hearing. We didn't discuss this. She was
going to let Jen off the hook just like that and let her go! Perhaps I
should have had a little more faith in Tracy because the next part was
pure genius.

"You may however choose to stay of your own free will. I will torture
your little pussy with this huge cock all for his amusement. I will
make you come like a whore and then give your clit some nice little
jewelery too.

We will be cruel and disrespectful.........And after I'm done then
maybe...just maybe, you will have earned his forgiveness and respect."

I got it right away and I was beyond amazed at the depth of Tracy's
genius at this.

I reacted immediately and began to release each rope that held Jen's
wrists and ankles.

Tracy was still kneeling above Jen with the strap-on still nuzzling her
pussy. There was nothing holding her down now but she didn't move an
inch. 

Jen just smiled in a mischievous almost evil way before looking up at
Tracy and saying. "Well.....I guess you better start fucking me with
that thing."

Both girls smiled at each other for the first time then.

Jen turned her gaze on me then and said something astounding.

"I want you to enjoy watching her fuck me. I want you to know I'll
never lie to you ever again."

"You know what? I think I believe you" I said with a warm smile as I
settled back and watched the fireworks begin.

Tracy leaned in and whispered something to Jen then. A sort of hushed
conversation took place and I was aware that it was not for my ears.
It's only after the fact and after talking to both of them that I found
out what was said.

"You know that the idiot never stopped loving you don't you." Tracy
whispered.

"He said that?"

"Can't you tell? Honestly you two are so fucking stupid that you were
practically made for each other."

I remember Jen looking over at me then as I was oblivious to what was
being said. Considering what was about to happen to her, I couldn't
figure out why she looked so happy.

She said something to Tracy then. The look on her face changed and she
suddenly got very serious.

"Fuck me with that thing. I'll do whatever it takes."

God where do I start in describing this? I remember Jen's face taking
on a frantic and aggressive look as she wrapped her legs around Tracy's
hips and Tracy patiently but firmly pounded the head of that thing up
against Jen's pussy over and over again.

"Just be patient and don't try to force it too much baby." Tracy
continued to speak "Oh god it so Hot. I can see you're little hole open
up just a little each time."

That comment only seemed to enflame Jen even more. She began to grimace
and grunt with every thrust as the pain of her pussy stretching to
accommodate that huge toy was offset by the wild lust she was clearly
in the throes of.

"Remember to pace yourself baby-girl," Tracy said trying to calm Jen
down. " At this rate If you're not careful you'll come as soon as you
feel that thing inside you."

Before we knew it we had gone through 30 minutes of pushing and
stretching and the two girls showed no signs of giving up. If you had
seen the size of the thing then you would realise why it was taking so
long and so much effort.

Sometimes either Jen or Tracy would lose their patience and mount a
vigorous assault on that strap-on only for Jen to wail and then back
the pace down. Despite that however, they were not discouraged.

"Don't you dare fuckin stop...don't you dare!" Jen cried out as the
35th minute passed.

"Oh fuck it's so close baby-girl. It's so fuckin close!" Tracy gasped
back.

"Oh it hurts so fuckin bad but I feel so fuckin good!" was the frantic
reply through clenched teeth.

We were 40 minutes into the ordeal when Jen's vocal patterns suddenly
changed.

She practically screamed out in a high pitch. "OH FUCK....OH FUCK....OH
FUCK....OH FUCK." and then punctuated that sentence with a single
tortured "FFUUUUUUCK!"

Tracy started squealing with excitement then. "OH GOD BABY-GIRL IT'S
IN...IT'S REALLY IN!" 

I immediately got closer to take a look and saw that the tip of that
huge black phallus was buried about three inches deep inside Jen's
pussy now. It almost looked like an optical illusion.

To see her small frame and her tiny pussy accept a toy that was clearly
larger than any human male penis could anatomically be.

"Oh god please don't move. Please don't move. Just let me get used to
it" Jen pleaded.

As soon as she looked down her eyes filled with a mixture of pain and
elation.

"Oh fuck. I can't believe I actually did it."

I think that both Tracy and I wanted to give Jen at least a couple of
minutes to adjust to the size of that huge toy inside her but Jen had
other ideas it seemed.

She turned to me and asked for something very surprising then.

"Please just kiss me and tease me while she fucks me. Please...I want
you with me when it happens."

That was a request I was happy to fulfil. I gave her the deepest of
kisses and felt her tongue frantically search mine out as Tracy invaded
her pussy for maybe four inches and then suddenly sink in to about
eight.

She screamed with what seemed to be equal amounts of intense pain and
extreme pleasure as Tracy began to slowly piston that huge toy in and
out of her. She was careful not to impale Jen all the way and I would
guess that Tracy got to about eleven inches during the deepest part of
the fucking.

I continued to kiss Jen deeply and play with her freshly pierced
nipples as that insane fucking continued. It only took maybe ten
minutes before Jen began to pant those words at me.

"Baby....gonna come. Gonna come so bad."

It happened only moments later and she screamed as her body went rigid.

I don't know how it was even possible with all things considered, but
her orgasm was so intense that she even managed to spray the bed and
Tracy with moisture as the contractions wracked her body.

When Tracy slowly eased out of Jen about two minutes later Jen's red
and stretched little pussy gaped open for a few moments before
attempting to close.

Unlike the first two piercings it was a much more tender and gentle
affair when Tracy gave the hood of Jen's clit a nice little barbell
stud. 

This may be hard to believe for some of you but that final piercing had
taken on the status of a reward rather than a punishment now. It was
proof of what she had been through. It was a badge of honor.

Jen just lay back against my body as I kneeled on the bed. I held her
as Tracy performed the final act. Jen didn't flinch. She didn't even
make a noise. She just kind of melted into me when it was done and then
we all drifted off to sleep in that bed moments later. 

I vividly remember waking up later that morning at about 9am. I must
have only gotten about two hours sleep.

I looked over my shoulder to see two naked girls blissfully sleeping
beside me. Their limbs were entwined in a kind of rapturous slumber. I
pulled back the top sheet and the blonde stirred for one moment before
drifting back into the arms of her dark haired partner.

It was such a beautiful vision.

I stared at the blonde for a long time then. Her body was curvy but her
frame was small. Both her nipples were pierced with delicate silver
rings. 

As my eyes travelled further down her body I saw the faint glint of
silver and then saw the small silver barbell that pierced the hood of
her clit.

Her perfectly shaved little vagina looked hot and red and seemed to be
gaping open just a little bit, but it was clear that this little angel
was feeling no pain, for her face wore an almost beatific smile.

Her eyes slowly began to open then take in the new scene that
surrounded her.

"I had the most wonderful dream last night." She said as she slid
across the bed and fell into my arms.

"That's a coincidence," I said smiling. "I think I had the same one." 

Story Tags: control; blindfold; submission; seduction; revenge; love;
power%20struggle; vampire; lesbian; redemption

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