Breaking Jen Ch. 01

"This is going to be one epic night...but I can tell you already that the little slut won't even last three hours." Tracy said looking smug.

"What makes you think that?" I replied with a smile.

"Well, all we have to do is make her have a nasty little orgasm three times right?"

"Yes, three times in twenty-four hours." I said knowing full well what Tracy was about to say.

"Baby you've seen me in action. You know I could make any girl come three times in ten minutes if I wanted her to."

"I know you could." I said carefully stroking Tracy's ego. "But we are going to play the long game on this one. We are going to take our time and do things right. Are we clear?"

"Yessir!" Tracy said as she snapped me an exaggerated fake salute. She was clearly enjoying all this just as much as I was, maybe even more if that was possible.

I'm not a big fan of drawing things out so ill simply say that all the preparations went without a hitch. Things went so well, in fact, that it almost felt like all of this was pre-ordained to happen.

I've given you all plenty of information and you all now know the events that lead to all of this.

So.....grab some popcorn and get yourself comfortable girls and boys, because the build-up is officially over.

The curtain is raising........The feature act is about to begin.

It was 8pm on the dot on that Saturday night when I heard a timid knock on my front door. I opened it to see Jen standing in front of me. She looked nervous and a little scared as she flashed me an uneasy smile and I smiled back (more out habit than anything else.)

That was a huge moment. I actually had to take a few seconds and steel myself then. I had to remind myself why all this needed to happen, because what I now saw standing in front of me was an absolute vision. Jen still had a way, and a presence about her that surely would have tested the resolve of a lesser man.

She was dressed in a red evening dress that stretched tight against her body, almost like it had been painted onto her skin. Everything was red. Her heels, her stockings, it all matched. If she had taken that much trouble with what she wore on the outside then I was dying to see what she had on under that tight little dress.

Her hair was pulled back tight and weaved into a single ponytail that reached to her shoulders. I had never seen her like this before. The dress hugged the contour of her breasts like it had been stitched in place and seeing the faint outline of her nipples pressing up against the fabric was beyond distracting.

I quickly regained my composure, but not before she had seen my reaction to her outfit and she looked pleased. I realised my mistake and almost cursed myself for letting her see that.

'I can't let her see any weakness again,' I thought to myself, and for the rest of that night and the next day, she never saw that again. Sure it was a minor slip, but little things like that can be important.

I re-focussed and then without a word I motioned for her to come in. She closed the door behind her as she followed me into the house.

"Welcome" I said simply and coldly as I walked. She didn't answer.

"Did you sleep well last night?" Jen looked puzzled by my question.

"I'm not sure what you mean."

"It's simple really" I continued. "Did you lay awake wondering about all those dirty little things I'm about to make you do....or....did you sleep like a baby."

"I didn't sleep at all" Jen confessed immediately. "Thinking about tonight just made me all turned on and scared at the same time."

"Did you make yourself come?" I asked casually.

"No. I don't even know why, but I kinda got the idea that you wouldn't have wanted me to do that."

Hearing her say that actually impressed me.

"You have good instincts," I told her and she seemed pleased at my comment.

She continued to follow as I walked into the living room. I took a seat on the leather couch in the center of the room and I watched with some satisfaction as Jen hesitated, not quite knowing what to do next. She decided to sit next to me on the couch.

I let her know immediately that she had made the wrong decision.

She actually jumped a little when I interrupted her and harshly barked out my first instruction of the night.

"NO. You don't get to sit next to me. I want you to stand in the middle of the room and face me while I enjoy the view."

She did as she was told. She looked nervous and on edge. I casually poured a glass of wine from a strategically placed bottle and just sat there enjoying my drink as I looked her up and down and studied her body.

There was some soft 'mood music' playing in the background and I wasted no time in using that little detail to my advantage.

"Move those nasty little hips to the music for me nice and slow. I want to see how you're gonna move for me later." I instructed and she obeyed immediately.

Jen moved and swayed in a slow, hypnotic way and as our eyes made contact I could see her fear begin to transform into something else.

"That's it baby, now slide those hands all over your body for me."

She continued to sway as her hands moved over her hips and belly. I could see a spark of arousal begin to form and then grow in her eyes. Her movements were soft and sensual as her hands roamed across her body, mimicking the soft touch of a gentle lover.

Every minute or so I would issue a new command and she would follow every word without question.

"Now work those breasts for me like a good little girl. I want to see those nipples get nice and hard."

Once more she obeyed and her hands slowly travelled up her belly. Jen closed her eyes momentarily as she began using the palms of her hands to caress her breasts through that tight dress.

"No not like that. I want you to rake at them with your fingernails." I instructed her before elaborating. "Gently scratch at them until those little nipples can't get any harder."

Her long nails began to scratch and tease at my command. Within moments her nipples became erect and clearly very sensitive and a familiar look began to cross her face. It was an expression that was not specific to Jen as such. It was that look you see on the face of a woman who is beginning to surrender to herself and let her desires take over.

All those little tell-tale signs and triggers were beginning to happen. I always love watching all those beautiful little events begin to take place inside a woman. You can see it all happen right before your eyes if you know what to look for.

There is a beautiful kind of 'Domino Effect' that takes place as a woman's body responds to intense pleasure. A kind of 'positive feed-back loop' that occurs as her feeling of arousal floods her with hormones, which in turn trigger her biological responses, which in turn makes her even more aroused to begin with.

It takes an intelligent man to not only know how to maintain that loop but to magnify each cycle until a woman is driven insane by her own arousal. But again I digress. Now is not the place or time to be giving up my secrets.

"I bet you'd let me do just about anything to you right about now wouldn't you?" I said in a very 'matter-of-fact' kind of way.

"Uh-huh" was Jen's slightly nervous and breathless response as she continued to rake at her nipples. Her hips were still swaying gently to the music.

"Then say it." I said sharply.

A hint of a smile crossed Jen's face as she replied. She gave her words a slow sensual drawl as she said them which left me in no doubt that she meant every word.

"You can have me any way you want. I'm gonna be so dirty for you".

"Oh I know you are." I informed her before standing and then walking up behind her. I slowly pulled the zipper on the back of her dress down to her hips and then like a well trained little slut she automatically began to shimmy out of the dress until it slowly slid down her body toward the floor.

As soon as it had fallen I reached around her from behind with my left arm and pulled her in hard against my chest. The sudden jolt took her by surprise and she tensed up for a brief moment before realising what was going on and then let her muscles relax.

I now had her effectively pinned up against me as my right hand reached around and explored her body with complete freedom.

I could almost sense her desperation as I let my hand wander all over her. I could practically feel her melt under my touch.

I focussed on her thighs at first, and then gently teased my hand all the way up her body before pausing at her mouth and lips. I gently circled her lips with my fingers and she accepted them eagerly when I slipped two of them into her mouth. She immediately sucked on them and worked her tongue in slow circles. Her breathing was harder now and she began to grind her cute little ass into me as I stood behind her.

She wore a tight lacy g-string and push up bra which made her tits just sit up as if inviting me to tease them. She now had on nothing but her lingerie, stockings and those spiky red heels. I must admit that she had excelled herself in the presentation department. When I had asked her to come dressed like a slut I had no idea she would be such a natural at it.

I pulled my fingers out of her mouth and slid my hand back down her body with excruciating slowness. I let my fingers wander and dance in teasing circles until they were at last pressing up against the thin lace of the g-string that barely hid her pussy.

Jen's reaction was immediate. Her hips began to grind forward to meet my touch and so I pressed a little harder until I could feel the wetness flowing out of her and begin to soak through the thin lace.

"Tell me why you are here tonight." I whispered softly into her ear.

Jen hesitated for a moment as if unsure of what to say. It took a few seconds before she was able to compose herself and choose the right words.

"I am here to be punished for what I did to you."

"And you want that badly don't you." I whispered again.

"Yes." She replied softly before adding. "I want to be dirty for you. I want to make things right."

My next few words to Jen were important ones. I was about to give her yet another opportunity to pull out. (Even though I already knew what her answer was going to be.)

"You need to know that you are about to experience the most filthy acts and have the most extreme orgasms of your life. If you have any doubts at all about atoning for your sins then you had best walk away right now."

Jen's response was a simple one. She broke from my grasp and turned to face me. She then gave me the most frantic and deep kiss that she had ever given me before pulling back and whispering.

"What if I don't want to walk away?"

That was all I needed to hear. I took her by the hand then and led her to the master bedroom.

She started to shake as pushed her down onto the bed, but it wasn't until I began tying her down that I could see the fear spread across her face.

Each wrist and ankle was tied to a corner post of my queen sized bed until she was spread like a starfish. Despite her fear I was amazed at how willing she took to it all. It seemed to me that the more helpless I made her, the more turned on she became.

"I wish I could tell you about the things I'm going to do to you on this bed tonight but I really don't want to ruin the surprise." I said calmly.

"Oh god I can't stop shaking." Jen was clearly getting more excited by the second.

"I wouldn't get too worried just yet." I reassured her before continuing "Because the first thing I'm going to do is give you is a lesson in patience."

"I don't understand." She replied.

Jen's little lesson in patience was actually just a convenient cover for something very important I needed to do. Believe it or not I actually had to pick up Tracy from her work. Once we got back she would change into something more appropriate for Jen's punishment and together we would set to work on giving Jen the most memorable night of her life.

I propped Jen's head up with some pillows so she was comfortable and had a good view of the room. I then began to tell her about what was about to happen.

"I'm leaving you like this for a couple of hours. It'll give you time to think about your past sins and how you're going to pay for them. When I get back things are going to get interesting for you. Do you understand?"

I could see the confusion and disappointment in her face as she began to speak.

"You're gonna leave me here like this for two hours?..........Alone?"

"Yes."

"No please don't do that....You can do whatever you want to me right now. I'm ready. I want you to!"

"You don't get a choice, and I'll be the judge of when you're ready." I said firmly.

I quickly made sure Jen's bonds were secure and then gave her some quick instructions before leaving.

"I've arranged some wholesome, family entertainment for you while I'm away," I said as I switched on the 42 inch flat screen TV at the end of the room. Suddenly a porn video of a girl getting fucked in the ass by a famous porn star lit up the screen in high definition.

"Oh I almost forgot," I said as I opened a draw and removed the red ball-gag that was inside. "You can't be serious!" was the last thing Jen was able to say before I gagged her and shut her up.

I took one last look at my handiwork and was very satisfied. There she was, tied up and spread wide. She looked like a total slut in her heels and nasty red lingerie. I turned the volume up on the TV until the room was filled with the sounds of grunting and moaning.

Before I left I turned to give her one last piece of advice. "I wouldn't let yourself get too comfortable.......because in two hours your punishment really begins."

She nodded meekly and I closed the door behind me as I left the room.

Making Jen watch porn while I was away was actually Tracy's suggestion, but I had also thrown in a few details of my own that I felt added a little value to the situation.

I had set up the porn that she was now forced to watch to start with nice, almost conventional sex acts, but by the time I got back with Tracy she would be watching some pretty hard-core lesbian bondage. This wasn't done just for kicks.

I had a pretty strong hunch (form something she said to me years ago) that the very thought of being punished and fucked by a mistress was something that had featured in her fantasies for years. If it worked like I almost certainly knew it would, then Jen would be frantic and soaking wet by the time Tracy and I even entered the room again.

I had tied her down securely so there was no way she could touch herself let alone get free. I had always known about Jen's filthy little bondage fantasies, and I also knew that she had probably never acted upon them. I was going to use everything I knew about her to full effect tonight.

It should have been a thirty minute drive to Tracy's work, but in my excitement, I did it in twenty. She was beyond excited when I picked her up from outside the beauty shop. She was dressed in her work clothes, but even then she still wore a tight black outfit that showed off just about everything.

She had brought two full shopping bags with her. I could see clothes and lingerie in one bag, but the other contained a bunch of mysterious items that I couldn't quite make out. I told her how I had prepared Jen and had left her there waiting for us and I could tell that Tracy was very anxious and very ready to get things started.

"Fuck this is all so hot. I'm gonna have your nasty little slut Ex purring like a kitten. She's gonna come so hard she won't even know what's happening."

Tracy was a special kind of girl. She liked a little pain with her pleasure. Her make-up was dark and her lipstick was black today. She had two piercings through her lower lip and one nose piercing and as you have probably already guessed, she has her more private areas pierced too. She was curvy and voluptuous a lot like Jen was, only Tracy was the darker nastier version of Jen and I loved that about her.

Jen had been tied down in that room for almost an hour before Tracy and I arrived back at my place. We had made our arrival as quietly as possible so that Jen wouldn't realise that I had returned.

The frantic sounds of flesh being whipped and spanked was mingled with the rapturous cries of willing females as the porn continued to play loudly on the flat screen in my bedroom. By now Jen would be watching some truly impressive things being done to bound and helpless women as they climaxed over and over again.

Tracy quietly walked up to the bedroom door and listened closely before returning to me. "Oh my god I can hear that little slut thrashing about on that bed of yours. She must be practically wetting herself by now!"

I couldn't resist and I listened at the door too. I could her Jen squirming and rubbing against the sheets. She was breathing hard through her nose because of the ball-gag in her mouth and it was clear that she was exerting herself in some way. There was just no way for her to get herself off, I had made sure of that. She was tied, facing up, and spread-eagled to each post of the bed. All she was going to do was make herself more frustrated.

Jen clearly hadn't heard us arrive or she would have stopped moving. For all she knew it was still just me she was waiting for anyway. She had no idea of course that Tracy was here and I couldn't wait to see the look on her face when she made that little discovery.

Tracy wrapped her arms around me gave me a deep kiss. I could feel her tongue stud tease and dance about my mouth before she pulled away and informed me she was going to change into something more uncomfortable. She grabbed the bags she had brought with her and then promptly disappeared into the bathroom to change.

It was almost 30 minutes before Tracy emerged from that bathroom and when she did my jaw dropped in wonder. She was dressed all in black (did she ever wear any other colour?).

She wore shiny black high-heeled boots that laced tightly all the way up to her knees and underneath those boots she wore a pair of thigh-high fishnet stockings. A tiny little g-string barely covered her crotch and she completed the outfit with a tightly laced corset that squeezed her body into an almost perfect 'hour-glass' shape.

The corset pushed up her breasts in the most amazing way. I also have to make special mention of the tight black latex gloves that hugged her hands and arms all the way up to her elbows. They set off her 'evil dominatrix' look perfectly, but there was also something very sterile and almost surgical about them.

Her black hair had been pulled back into a pony-tail so tightly that it stretched the skin on her face and made her cheek bones sharp and prominent.

God when Jen saw Tracy she was either going to come on the spot or faint with fear.

Tracy held small a black leather case in one hand and it actually looked a lot like something a doctor would carry. In the other hand she held an impressive black riding crop. Somehow I doubted that riding crop had ever been used on an actual horse.

"Time to go to work," Tracy said unable hide her excitement.

I didn't even try to hide my own stunned reaction as I just stared at her for the longest time.

"My god Tracy you look........."

"I know." She replied with satisfaction as she cut me off in mid sentence.

I know that up until now I haven't given you, the reader, much information about myself. It's not that I'm being overly secretive it's just that in a way I don't even feel like any of this is particularly about me.

I know that might sound a little odd seeing as I have driven all this and made it happen. Perhaps it's a personal thing. I don't think I have a huge ego. Often I will prefer to control things whilst staying out of the lime light.