Breaking Jen Ch. 01

"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."