I am Going to Break You

I am going to break you...

One of the first things my Mistress said to me. Kneeling down at her feet, my tongue buried in her pussy, she stared down at the sissy she'd found online. Innocent, inexperienced, yet with an insatiable willingness to submit. To serve. I'll never forget the look on her face when she said it, the confident smile, as if it wasn't a mere statement. It was a promise.

And Mistress Madelline never broke a promise.

Leaving her place after our first session, I felt the confines of my new pink clit with every step. I wasn't a stranger to chastity, it being a forerunner in most of my fantasies. But wearing one, especially one you did not have the keys to, was a completely different experience. Every morning I woke up whimpering, the strain between my legs so intense I could barely think. But I kept reminding myself this was what I wanted, what I had been searching for, what I craved.

I could do this!

However the next weekend Mistress Madelline had me quickly in tears, begging to be released, as her gloved hand gently spanked my aching balls, rubbing and teasing relentlessly. Dressed in some latex sleeved gloves and matching stockings, my poor clit had been dripping before she even laid a finger on it. But she had no interest in unlocking me it seemed, my tormented moans bringing a smile to her face each time.

Once more I left her house in an excited, frustrated state. Once more I spent a week tossing and turning, left to the mercy of my own imagination. When I finally saw her again, shaking with need as she dolled me up for the evening, I pleaded with her to take it off just for a little while, just a short reprieve from my tiny, pink prison.

Mistress simply smiled, kissing my forehead, dismissing my silly pestering with a gentle pat on the head. Staring into my eyes, she gave my clit a few firm, but loving taps, moans easily forced out of me.

"I am going to break you, remember Rory?" She asked, her stern expression holding me in place. "And I'm going to use this to do it." I whimpered, unsure how I was going to get through being caged for her, another week of endless nights filled with frustration. However shortly after I watched her step into the answer, a beautiful cock strapped between her legs. With patience, fingers, plugs, lube, more lube, and aggressive thrusts, I came harder than ever before.

I slept like a baby.

Mistress Madelline's fuckings became a constant thing in my life, one I desperately looked forward to. I still felt the aching between my legs, the constant strain as I squirmed looking down at my cute, pink clit. But, her cock made it much easier to forget, fucking the frustration right out of her poor sissy. Each time she'd praise me, watching the cum erupt and drip from my little clit, smiling as I licked up my own mess. Always made to blush, calling me her cute cumeating sissy.

As I waited on all fours, legs quivering in anticipation of being fucked, Mistress Madelline surprised me with a smack to my poor balls, left exposed between my legs. Whining, I tried to pull away, but she held me in place with her leash, shushing my protest. I felt the leash fall to my side, her hand comfortingly resting on my white corseted back. My ass framed in matching fishnets, their own built-in garter leaving my ass and clit firmly on display.

Another smack, desperately trying to hold in my whimper, the tingling between my legs intensifying. After ten my eyes brimmed with tears, no longer able to stay quiet. Mistress' soothing hand ran up and down my back, a constant call ofthat's my good girl echoing in my ears. Balls aching, she slid the massive cock I had been trained to take inside of me, her little smacks never ceasing, cumming in pain as she fucked me over the edge.

Whimpering and confused, I snuggled into her arms afterwards as she played with my wig, a light kiss on my forehead.

"I'm sorry for hurting you, baby girl. But it is for your own good, I promise." I whined, the pulsing pain between my legs begged to differ, but she continued. "Soon you will need the pain in your clit to cum at all, all part of turning you into my cute, broken, little sissy." I groaned as she moved her hand back down between my legs, gently squeezing with her fingers. "You just keep being my good girl, Rory. I'll focus on the rest."

Mistress Madelline persisted, my caged balls a constant target for her palm, fingers, and crop. With each orgasm, while the pain was always constant, it almost began to feel...welcomed. Needed. Deep down I knew how badly I wanted to belong to her, in every way, and I felt myself slip further under her control with each new torment she introduced to me. I was her toy, her plaything, and happily so.

Many other 'trainings' soon followed, all coming with their own little twists. I learned how to curtsy in the multitude of pretty dresses and skirts Mistress made me wear, each mistake quickly corrected with a cane. She beamed with pride as I showed off to her friends, most of which giggled and laughed, my face burning red while I perfectly presented myself as Mistress Madelline taught me.

I also spent hours tied up in several different positions, her cock punishing my throat, until I could take all of it with ease, however she wished. On my knees, hogtied, upside down, even suspended from the ceiling. Mistress made sure I knew exactly how to take her cock, a smack on my ass always quick to correct me.

This too, she had me show off to her friends, earning myself another endearing nickname from my Mistress: her sissy cocksucker.

With my new humiliating title, I found myself servicing her friends far more often. Real cock or fake, several of them took a liking to using Mistress Madelline's little toy. Almost every time I was over at her place, I had someone to serve, someone to focus the frustration of being constantly caged, brimming with energy that I couldn't release on my own. I eagerly followed any instructions given as if it had come from Mistress herself, falling further down the rabbit hole.

After six months of being caged for Mistress Madelline, I knew I had become addicted to being her sissy. The torments, teasings, punishments, and fuckings now a normal in my life. I needed them. I needed her. Being in her controlling presence, even surrounded by others, gave me such a sense of soothing relief.

One session, staring up at her, crying as she stared into my eyes, spanking my poor clit, I finally gave Mistress something she had wanted for some time. Quivering, in a confusing state of pain and arousal, I came hard as she smacked my poor balls, my clit exploding all over her hand. Shocked and surprised, Mistress squealed with delight, so happy with her sissy. Sniffling, I smiled as I licked her clean, drinking in the praise she laid over me.

To celebrate, Mistress Madelline threw a party for every kinky person she knew. With the help of some friends, she wrapped rope strategically around my body, snugly squishing my limbs together, softly whimpering around the beautiful red ball gag stuffed into my mouth. I squeaked as they picked me up, even more so when I realised I was hanging off the wall! Quite literally placed on display, I watched the pride spread over Mistress' face. With a playful smack of my clit, and a departing wink, she left me to the mercy of the party patrons.

Three hours (intermitten with breaks for my poor blood flow) later, I was completely covered in my own sweat, tears, and cum. Striped marks were present on every part of my body, moaning with appreciation as Mistress gently rubbed soothing lotion all over me. Sometimes, it was hard to be a good girl for her and her friends, being put through quite a lot. But, knowing she was there at the end to take care of me, to nurse me back to health, made it all worth it.

I no longer remembered what cumming felt like outside of my cage. No longer remembered what an erection felt like. And I no longer cared. Having a cock down my throat, staring up at the person currently using me, being fucked vigorously as I shook with excited energy, feeling the sting of a crop against my skin, or the aching pain in my clit as it was repeatedly struck. Each of these sensations were worth a thousand 'normal' orgasms, and I didn't want it any other way.

Walking around Mistress Madelline's apartment, a strappy pink harness sitting snuggly against my body. Pink nylon stockings, and a cute heart collar finished the outfit she had dressed me in, smiling as I went about the chores I normally did for her. As I was folding some clothes, I moaned as her body pressed up against mine, her hands playfully pushing on the plug secured in my ass.

"Do you know what today is, my little sissy?" I whimpered, shaking my head as I rested it on her shoulder, slowly losing myself in her little touches. "Mmmmmmm, I thought not. Today, it is one year since I caged that cute little clit of yours."

My eyes shot open, a soft little whine escaping my lips, amased that so much time had passed under her control. Turning me around, her commanding eyes holding my every attention, Mistress gently cupped my clit, looking down at the tiny pink cage.

"A full year of my control." A finger placed under my chin kept me staring into her eyes, moaning as I easily fell into her control. "Look at how far you've come in just a year." Mistress placed her lips right on my ear, sending shivers through my body as she softly whispered, "and think of how far you still have to go in the years to come, Rory."

My legs shook, threatening to collapse, moaning from the surge of submissiveness coursing through me. Seeing this, Mistress Madelline smiled, displaying something I had not seen in a very, very long time.

My key.

There it was. Such a simple piece of metal, much smaller than I remembered. I panicked as she brought it down to my cage, protesting. But Mistress quieted me with a look, whimpering as the built-in lock was removed slowly, carefully, the familiar pressure I had become accustomed to suddenly dissipating. Never taking my eyes off her, terrified, I felt her hand gently teased my exposed clit for the first time. Ever.

I thought I was going to explode, that all the past year would be revoked, that my Mistress would lose interest in her sissy if I wasn't a good girl. All these emotions sprung to the surface, glistening in my eyes, frozen in fear as to what would happen next.

But nothing did.

Smiling, Mistress continued her efforts, stroking and teasing. But my clit would simply not respond. Confusion replaced my fear, looking down at a cock I had not seen in a long while, so tiny and squished.

"I told you, my little sissy, that I would break you." Grinning, satisfied with her work, Mistress Madelline patted my cheek, removing any tension I had been holding onto. Gently, she replaced my cage, once again that familiar, comfortable feeling hung between my legs. A firm hold of my hair, Mistress brought me down to her level, wiping away the tears running down my cheek.

"You are all mine, Rory."

As if this point needed to be made, or reinforced. Yet, Mistress did so with her cock, holding both of my arms behind me, vigorously thrusting in and out of her sissy, listening to her moans and cries, watching as she fucked every single drop of cum out of my body. Shoving me into the bed, Mistress continued her fucking aggressively on my ass, her hands punishing my clit as she did so, my muffled moans dissolving into the pillow, as I submitted to her passionate, commanding display of dominance.

Afterwards, both exhausted, lying in each others arms, I held onto my Mistress for dear life, so happy she chose me one year ago. I was her perfect, obedient, little toy, a sense of pride that she shared with the world.

Mistress Madelline had made me a promise. A promise that she was going to break me. A promise that she had fulfilled.

What she didn't say, was how much I would enjoy it.