Breaking Jen Ch. 01

"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.