II

Ruby's Fuck Toy

I heard her heels click long before I opened my eyes. I knew what was coming, she played with me almost every day, but I had been here for so long that I started longing for it. Begging, for it. The clicks drew closer until I could smell the rubber of her catsuit and the sweet touches of her perfume.

"Wake up doggy." She said teasingly and ordered. "But no looking at your mistress."

I roused from my lying position at once and prostrated myself in front of her within my cage. Naked as always. Ruby rattled my cage and giggled.

"Good doggy."

Every night I spent inside of this prison until morning, when Mistress Ruby would wake me, as she did today, and use me as her morning exercise.

"Did you sleep well?" She asked enticingly. Mistress Ruby didn't really care if I had slept well or not. She did care though, whether I was and vexed by the chastity device that was snuggly wrapped around my cock. The steel device was a constant reminder, as was the collar around my neck, that I indeed belonged to her.

I whined at her question, implying that yes, I was frustrated into sweat and whimpering by the chastity device and that I need to cum badly.

"Excellent. You have been good for a while now. I just might let you cum today, sissy boy." She giggled. "Lift your head, but you still cannot look at me."

I obeyed.

Mistress Ruby attached a dog leash upon my collar and I heard her sigh in pleasure.

"Now, I will take you out of your cage and play with you until I see fit. But before I do, you will kneel in front of me and beg to cum today. Otherwise, it will only be for my pleasure again." She said devilishly.

Of course, for a long while now, it had not been just for her pleasure. After the first few sessions of my chastity device I noticed that coming to an orgasm was only pleasurable if she allowed it. If she ordered it.

That being obedient and subservient to Mistress Ruby was far more important than feeling any kind of pleasure. Or, rather, that her pleasure was above mine. That anything she allowed me to feel should be a reward.

After those first sessions, I started booking with her more often and, after I time, I don't even remember how it all happened, I just stopped going home. Mistress Ruby did discard her previous and mentioned a few times that she needed a new one. I guess she chose me.

The lock on the cage clicked and, following the tug on my leash, I crawled out. Still on all fours, I stayed prostrated until she ordered me to kneel and beg. I felt the collar tighten over my neck, brandishing my mind as her property.

"Now, doggy, you may beg for your treat." She giggled evilly, sending my caged cock into a painful spasm. I lifted myself, heavily, from the floor and upon my knees. Finally, I opened my eyes, and looked upon my mistress.

She was as gorgeous as ever.

Her pretty feet were neatly placed in crimson heels with, dark, latex stockings running all the way up her leg, to the upper reaches of her thigh. It was like second skin on her and the dark pantyhose she wore beneath only made her legs shine hypnotically.

Upon her torso, Mistress Ruby wore a black bodice that accented her breasts, pushing them up, as the red stripes made her air all the more devilish. Her hands were coated in opera gloves of the same latex as the rest of her outfit. And, upon her lip, she wore her usual sadistic grin.

I love you.

I said somewhere deep within myself, where I was allowed to have my own thoughts but I dared not say it out loud. Dogs and sissy boys, were not allowed to speak unless spoken to. Sometimes, not even then.

"Like what you see my little sissy boy? You may actually speak this time." She said with a chuckle and a curved lip which had shiny red lipstick upon it.

"Yes! Yes Mistress! You look hot as always." I said, though human words seem strange to me. I had been using them so rarely that most of them seemed foreign to me.

"Alright. Start your begging. You may kiss my heels as you do." Mistress Ruby laughed as I bent down upon her shiny heel and started kissing with fervor. The latex of her heel felt divine upon my unworthy lips and the feeling of being beneath my mistress, at the end of her leash... owned, was heavenly.

"Please Mistress Ruby, allow me to cum today. I will remain obedient and subservient, I do not need a life outside of your dungeon. You are all I have and all I need." I whimpered, still somewhat afraid of what I was saying.

"Good boy. And how does my sissy boy want to cum today? Does he want his chastity device removed or... perhaps does he want to cum as he usually does. Like I have been training him all these past months." She giggled, knowing exactly what I will beg for, no matter how much it terrified me.

Though, not as much as before and I guess, soon, it won't at all. And I would have it no other way.

"Like a sissy boy." I said and planted more kisses upon her heels. "Like you have been training me. That is how I need to cum. Sissy boys and dogs don't need their chastity removed."

She cackled at my pathetic begging and whimpering pleads for an orgasm only bestowed upon those barely human. I planted more kisses over the tip of her heel, never touching her latex stocking. I wasn't allowed to kiss it, or ordered, so I only kissed the heel. That feeling of following orders that weren't spoken is what made me love my mistress so much. She simply expect things of you and you simply... obeyed.

"What a good you are my little sissy boy. I see I have trained you well. You might even last longer than the last I owned." She giggled menacingly. "Now, remain in that position. I need to get your favorite toy."

I whimpered. She removed her heel and I placed my forehead upon the cold floor of the dungeon. Shivers ran down my spine of pure delight, knowing what toy she was going to get. It was a large rubber strap on that Mistress Ruby used only when she allowed me a sissy boy orgasm. Her heels clicked closer again as she stood above me one more time.

"Ready for you reward, pet?" She asked evilly.

"Of course mistress. Please reward this pet my giving him a sissy boy orgasm." I whispered in anticipation. Mistress Ruby laughed and walked behind me. I felt her cold, latex glove massage and touch my ass cheeks.

"Good sissy boy. Good puppy. But for the remainder of your reward, I want you to only speak like a dog. Human words are strictly forbidden or I will plow you until you faint and not even allow you a sissy boy orgasm." She giggled and I whined. Dog words were better than human words anyway.

Then, with a thrust, her gloved head rammed into my ass, lubing it, readying it for her enormous cock. I sighed in pleasure as I enjoyed the feeling of her cold, latex glove inside and upon my ass. It was like she was clicking buttons of pleasure deep within me and my soul and each edged me into a blissful state of being.

With my sighs and cries of pleasure increasing in desperation my mistress sneered down upon me, lavishing in the way she tortured me. Melted my mind into nothing but goo beneath her heels, before molding me into whatever she saw fit.

"I could make you cum with only my fingers pet. But today, you are learning something new. Are you ready?" She teased.

A whine of pure approval escaped from my throat, for more of whatever Mistress Ruby had in mind.

"Good sissy boy."

WHAM!

I felt a metallic, yet rubbery, crop hit my ass as I cried in pain.

"This, my pet, is your lesson for today. Since I have trained you to cum without me even touching your dick with your sissygasm, now I will train you to cum from spanking alone. Doesn't that sound fun?" She laughed menacingly as my heart sank.

WHAM!

WHAM!

WHAM!

Three more strikes landed upon my ass as I continued to cry in pain... yet even after only a few hits and a couple of touches upon my pleasure buttons by her gloved hand I felt... pleasure.

WHAM!

WHAM!

This time, groans and moans of bliss and relish escaped my lips. Drool left my mouth and slid down my jaw as my eyes started going back inside of my head.

"Oh, you like it already. Don't break now. I need you sane to be of any use to me." Mistress Ruby laughed. "Are you ready for your favorite toy?"

With a sinister laughed she removed her gloved hand.

WHAM!

After another hit with her crop, which sent sizzling sensations throughout my body, I finally felt the tip of her large strap on the edge of my sissy hole.

"Beg for it." She ordered.

I whined with all of my heart, pouring every tear, drop of sweat and drool into my begging. I whimpered and wagged my ass obediently, hoping to please my mistress.

WHAM!

WHAM!

WHAM!

Hit after hit of her crop landed upon my wiggling ass and Mistress Ruby laughed after every hit.

"Oh, I just love training new toys."

WHAM!

WHAM!

WHAM!

"Here we go, my cute little sissy boy." And with sadistic laughter, she penetrate my prostrate. It was like my soul and mind were run over by a truck while every fiber of my being, sizzled with bolts of raw pleasure that threatened to ruin my mind.

Thrust after thrust she fucked my asshole without mercy as my drool now ran like a river upon the dungeon floor. Though my eyes were open, I saw nothing and felt nothing but the ravaging pleasure she was bestowing upon me. My mouth open in a soundless scream.

"What's wrong pet? Hm? Too much for you?" She giggled.

WHAM!

WHAM!

WHAM!

Though my body was still learning to love the crop, the hits that came now, with her monster of a strap on inside of me, were revoltingly pleasurable. All the fear I might have felt before or reservations that I had... all were shattered by her cock and crop.

I whined, trying to answer, but almost no sound came out.

"Oh, am I breaking your mind?" Mistress Ruby asked enticingly. "I ordered you not to break. If you do, the same fate will happen to you as it did to my former . I have no use for broken toys."

But trying to hold on to anything resembling sanity was impossible for me now. Every time her cock hammered the same buttons she pressed with her glove I felt a part of me disappear and break. The worst part? Or maybe, the best?

I loved it.

The more I lost myself the more I loved her. The more she hit me with her crop the more I yearned for more, the more her large strap on plowed at my ass the more I wanted to scream my eternal submission to her. But I wasn't allowed to speak like a human and I could not even whine anymore.

I was stuck in an endless loop of edged pleasure and Mistress Ruby knew exactly what buttons to press for me not to cum.

"Sissy boy, you are getting what you begged for, are you happy?" She laughed and started hitting me again, knowing full well that I would not be able to answer with my whimpers.

WHAM!

WHAM!

WHAM!

WHAM!

WHAM!!!!!

The only answer I could give was spasm after spasm of my waist that was still hanging in the air. It wasn't a question if I would break anymore, but when.

"Well, I can't lie to you anymore . I knew exactly what would happen if I did this to you. I simply wanted to break you." She laughed menacingly. "I won't discard you I just wanted you to lose yourself, your ego, your mind and everything you held dear and turn it into undying love for me. And now, with this sissygasm, my wish will come true."

Her laughter echoed as she continued ramming her strap on. But it was different now. She was hitting different buttons and with a rush I never felt before, I saw myself coming closer to an orgasm.

"With this, you will never cum from your cock again, you will never think again and you will never be anything but my again. Now, cum your brains out and scream my name! That will be the last time you use human words again, sissy boy."

WHAM!

WHAM!

WHAM!

With a tidal wave of pleasure, pain and humiliation, I felt something break and snap inside of my mind and soul. My past life dissipated into mush beneath her cock and crop while my ego shattered like broken glass.

"MISTRESS RUBY!! MISTRESS RUBY!!!!!!! MISTRESSSSSS RUBYYYYYY!!!!!"

I screamed from the top of my lungs, from the deepest parts of my soul and I... finally... broke.

Mistress Ruby removed her leviathan cock from my ass and walked in front of me as I my ass swayed for a moment and then fell to the side. I saw her heels as she towered over me, placing them not an inch from my lip.

"Kiss them as my true for the first time, sissy boy." She ordered casually. My mind didn't really register her order but my body obeyed none the less. Even the tip of her red, latex heel felt different than before. Endless... orgasmic...sadistic.

"Good sissy boy. Now, it is time to return you to your cage." She giggled and lifted my leash. Obediently, wordlessly, I crawled after her, staring at her heels. Broken.

She locked the cage behind me and sat herself atop of it.

"Head down puppy." Mistress Ruby ordered and I obeyed. She crossed her legs, I knew because I heard her latex stockings squeal and echo in the dungeon.

"I might start collecting toys only to break them and keep them. Who knows, maybe throwing you slaves out once I am done with you was a mistake. I could look upon dozens of you that I plan to collect and enjoy your shattered minds. Who knows sissy boy, who knows."

Mistress Ruby's cackle echoed as my head grew foggy, my shattered mind, dim, and then I fell asleep. My last thought, was simple.

I love you, Mistress Ruby.

---

All characters in the story are over 18 years of age and are not owned by me, but by their respetive owners

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