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Mistress Caroline part 5 - The Final Chapter

I am accused of escaping and punished accordingly!
For several weeks after the session in the cellar, life was rather quiet and a routine began to be established. Mistress Caroline hadn´t said too much about the incident with Kelly, apart from being a little off and stricter than usual with me. For a while every little thing I did wrong was picked up on, but eventually all had seemed forgotten.

It was quite simple, Kelly would awaken me. I would get Mistress Caroline’s coffee and take it to her. After a few minutes, she would come to the kitchen and I would fix breakfast for her and for myself. Then she would assign the chores she wished me to accomplish that day. At various times, four or five a day usually, she would ring her little bell summoning me to stand before her and summoning ‘her cock’ to rise to attention. She thoroughly enjoyed seeing how well that conditioned response was embedded in my brain. Then, about every other week, she would host a ‘play session’ in the basement. At these, I, and two or three other slaves, would be the playthings. We would get tied up, spanked, buggered with strap-on dildos, ordered to masturbate and see which of us could shoot the farthest, and any other forms of entertainment and humiliation that the ladies could think of, depending on their mood.

During these days, I thought a lot about what was happening. Although there were some nice things to think about. For example, one of the chores Mistress Caroline had me perform two or three times a week was giving her a massage. She enjoyed them and so did I. And at least once a week, after a massage, she as she would describe it, would use ‘her’ cock for what it was designed for. She was always on top on these occasions and she always warned me not to cum until after she did. I found this really difficult, since I wasn’t in control of the action. But after a few times, she learned to read me completely. By watching my breathing and my facial expressions, and by the feel of my body tension, she could keep me at a level of excitement just under orgasm. It was fantastic. Then finally, she would let herself go, slamming down on me and moaning loudly as she reached her climax. When she finally said, “OK, cum for me J,” I didn’t have time to reply. All the muscles in my pelvis would spasm as I would explode inside her. And those ‘play sessions’, I really didn’t want to admit it, but the spankings and the sensations I experienced from the strap-ons really did excite me.

But on the whole, I was being humiliated, demeaned, and embarrassed. My body was a being assaulted, and I was being forced to do menial labour, but what could I do about it? I decided the only way I could stop it would be to find some means to escape from this place, but was I secretly enjoying it. Was I much worse off now than before? I had always fantasied about being under the control of a mature woman, and now it was really happening. Could I go on like this forever, did I really want a normal life back? I had visited dommes before and paid them, just to humiliate and embarrass me, and here was someone doing it for free! Perhaps this was my future, and what I really wanted!

* * *
As usual Kelly was again awakening me, only this time she seemed to be in some kind a a hurry. “Come on J, come on, its time to get up.”

“Why? Does Mistress Caroline want her coffee already?” I asked in a low voice, still struggling to open my eyes.

“No J. She´s already up, and she wants to see you as soon as possible. You’d better not keep her waiting,” Kelly said in a soft but firm voice. “As soon as you’re ready, go to the kitchen. Your Mistress is waiting.”

“Oh god! Not another session in the cellar?” I complained as she turned to leave.

Kelly laughed. “No J. Nothing like that.”

I rolled out of bed and headed for the bathroom. I did what I needed to do, washed my face to wake up, pulled on my thong, which was really the only piece of clothing I had and went directly to the kitchen. Mistress Caroline was sitting at the table drinking coffee with some of the other mistresses, and was dressed in business attire.

“Good morning J,” she said.

I replied with a good morning, and stood waiting for my instructions.

Then Mistress Caroline smiled pleasantly at me and said, “Off with the thong. You’re not going anywhere, so as usual, collar and cuffs is the uniform of the day.”

“Yes mistress,” I said.

I dropped my thong to the floor, picked it up, and hung it on a peg on the wall. No sooner had I done that than she rang her little bell. I hadn’t expected that, and I was surprised, I don’t really know why, at the immediate reaction of my penis. It began to swell and rise. My feeling of embarrassment in front of the ladies made no difference. My body became warm all over as I blushed. The women thought this was hilarious, and their laughter just intensified my humiliation. My cock, however, was proud that it had been summoned and rose to the occasion. Obviously, the conditioned response Mistress Caroline had created was now locked into my brain.”

I’m taking a little trip J. I have to go away on business and I’ll be gone for perhaps a week. While I’m away you will be under the control of Kelly. You are to be as obedient, responsive, and respectful to her as you are me, or, at least as you are expected to be to me. Since you are a newcomer here, I expect you will transgress occasionally. On such occasions Kelly will correct and instruct you, just as I would. If you go too far over the boundaries, then Kelly will report it to any other of the mistresses around, and they will report back to me. Do you have any more questions?”

“Yes mistress.”

“Go ahead J. Ask your question.”

“Will Kelly be staying here, or am I to go somewhere else with her?”

“She will be staying in one of the spare rooms. She will show you where it is. You will be staying in your usual room.”

At that point Mistress Claire spoke up, saying, “I think it’s time for us to head for the airport, Caroline.”

“All right J, behave yourself, and serve Kelly,” she said, looking at me. At that point she took me completely by surprise. She walked over to me and kissed me on the cheek. Then she patted my bare ass and said, softly, “Bye, bye.”

As soon as they were gone Kelly said, well ordered, actually, “Get these dishes cleaned up J, and do it quickly. I’ll be back shortly,” and she left the room.

Kelly took on a different identity while Mistress Caroline was away. She tried to be more strict, but I could tell it wasn´t in her nature, but did as I was told anyway. I wanted her to get comfortable, while I looked for a chance to rebel, it was like when you were at school and had a substitute teacher, you always wanted to see how far that you could push them. I would have to watch carefully for an opportunity, and I gave no thought to potential consequences.

Three days had passed since Mistress Caroline left. All was going well, I had not gotten into any trouble with Kelly.

Each evening since Mistress Caroline left, I had persauded Kelly to let me go outside of the facility. At the back there was a large garden, which seemed to go on forever. I had noticed some woods in the distance and although I didn´t know where this led, had always fancied finding out. I saw this as my opportunity to rebel a little.

When we were together, Kelly had only trusted me outside as long as I was naked, except for my collar and cuffs. She would also fasten the leash to my cock and balls for extra security. She had told me tales of slaves trying to escape, and how they were quickly recaptured and punished very severely, by burly security women that patrolled the perimeter. I just took this as her way of trying to frighten me into behaving for her, but it just made me more determined to explore where it led.

Also each evening, Kelly took me to the room where I give Mistress Caroline her massage, and had me do the same for her. Nothing else, but a massage. Even though we were alone, I think Kelly didn´t want to risk the wrath of my mistress, also I think she liked the fact that she could act like Caroline and knew that by not having sex with me, would really torment me.

She had stripped naked and lay on her belly on the table while I rubbed her with fragrant oils and massaged her arms, back, buttocks, and legs. I could feel the tension go out of her body. She became very relaxed and was ready to go to sleep as soon as I had finished. The first two nights, at the conclusion of her massage, she had taken me directly to my room, told me to go to bed, and locked the chain from the head frame to my collar. Then she went to her own room and fell immediately into a deep sleep. The third night was different. As I massaged her, she fell asleep on the table. I was not sure what I should do.

Now was the time I thought. I was alone, unchained, and unobserved by anyone, and it was dark outside. I went to my room and put on my thong and some shoes, then I went to the kitchen and rummaged around in some of the drawers. I quickly found what I was looking for, a flashlight. I left our living quarters and managed to reach the door that led to the outside garden. My luck was definitely in, it was unlocked. I suppose they thought all the slaves would be chained up by now. I crept out the door and bolted towards the woods. I left the light off for now, just in case someone was watching. I was in business.

The woods went on for miles, and I plucked up the courage to switch the light on. Eventually I reached a stretch of water that ran as far as the eye could see. SHIT, I thought, what now? I didn´t fancy wading through the water, it was cold enough as it is, without getting soaked. My adventure had come to a close, and I felt disappointed.

All of a sudden I heard what seemed like a motor running. Then a light shone in my face blinding me and an authoritative female voice barked, “This is security, stay where you are!”

My first thought was to start running, but where to? I had had it. My reply was to do as ordered.

"Lie on your stomach on the floor with your hands behind your back!” came another cry.

Completely shocked, I complied with the orders. As soon as I was on the floor, a figure stepped onto the shore from a boat. It was a large, not fat, but powerful looking woman. She was dressed in all black, trousers, boots and a coat with in big yellow writing the word "security". Kelly had told the truth, there were really women who patrolled the woods, stopping slaves who tried to escape. But I wasn´t trying to escape, I was only being curious!

She strode over to me, and without a word, quickly secured both my wrist and ankle straps, which in my haste to get out, I had not thought to take off. I was going to protest, when I heard a ripping sound and some duct tape was pressed hard across my mouth. Then she shouted, “Take him off!”

I could not immediately tell to whom she had spoken, but I quickly found out. Two more female officers, younger looking but dressed in the same manner as the first, came ashore. They quickly grasped me under my armpits, lifted me up, and proceeded to drag me back towards the facility.

Once there, I was then taken to a cell, similar to a police cell and threw in and left to stew.

I remained in the cell for three days, potesting my innocence every time that I was fed, but it fell on deaf ears. Kelly came to see me, but she was told I had to wait for Mistress Caroline’s return, since I was her property.

When Mistress Caroline finally returned and came to see me, she was very angry. She spent very little time talking to me. She told me simply that she had acknowledged that I was, indeed, her slave, and that she had to appear in court with me at nine o’clock the next morning.

When the next morning arrived, my wrist straps were shackled behind my back, and my ankle straps were connected to a short length of chain. I was hustled into an elevator and up to a court room on the floor above. I was taken directly to what was, obviously a prisoners dock, a small cage with vertical bars, that was located to the left of the judge’s bench. Mistresses Caroline and Claire were both there, as was the arresting officer, and a small number of observers. The judge entered and sat down. She was a middle-aged woman of average build. She wore a black robe and a stern look on her face. Without preliminaries, she inquired, “What is this case?”

The security woman stood and responded, “The case of runaway slave J, property of Mistress Caroline Smith.” Then she sat down.

The judge asked, “Is Mistress Caroline Smith in the courtroom?”

Mistress Caroline stood and answered, “I am here, Your Honour.”

“Good,” the judge commented. Then she looked at the burly security woman and said, “I have read the charges. What is your testimony regarding the circumstances officer?”

She simply stood, and stated, “He was apprehended late at night four nights ago, alone in the woods, obviously trying to escape.”

“Did you apprehend him?” the judge inquired.

“Yes your Honour,” she replied.

“Alright then, the slave is hereby found to be guilty of attempted escape. I will pronounce sentence,” the judge declared.

I was shocked. Apparently, I was to have no defence of any kind. I couldn’t help myself. “Is nobody going to speak in my defence?” I asked aloud.

“Shut up, slave! You have no defence!” the judge snarled, otherwise we will have to apply some more duct tape.

It had already been decided, even though I knew that I wasn´t trying to escape.

The sentence is twenty strokes of the cane, to be applied to the buttocks of the convicted slave by the arresting officer on the public canning rack at a time and under circumstances to be declared by her, and if it is the will of the court he will be at the pleasure of any and all Mistresses .

What happened next however took me completely by surprise. She turned towards me and said "You have heard the sentence slave J, but as is the law here, you do have a choice. You can accept the punishment or you have the right to refuse it. This will mean that you will be released immediately from Mistress Caroline´s care and returned to your past life. Mistress Caroline will then take on the punishment. in the form of not being permitted to own another slave for a period to be decided by the court, for causing us all this trouble."

All of a sudden I felt everyone staring at me, and I glanced across at Mistress Caroline. Her head was bowed down, and I thought I noticed a tear running down her cheek. She looked so dejected and hurt, that I took a deep breath and found myself announcing, "I will stay and face the punishment ordered by the court," after all, how bad could it be, and deep down I knew that spanking was getting to become a big turn on for me. Along with the fact that I was a plaything to a good looking mature female, which I had fantasised about all my life. In that moment, I realised that I wanted to remain with her, no matter how she treated me.

"Mistress Caroline, now that your slave has accepted his fate and new life, you shall take him home and see that he is delivered for his punishment, at the time and in the manner directed by the officer. Do you understand?”

“Yes, Your Honour,” Mistress Caroline acknowledged.

“Good! The slave is released in the custody of his mistress, pending presentation for execution of the sentence. Next case.”

I was released immediately to Mistresses Caroline and Claire, and taken home.

A week had gone by since we returned from the so-called trial, and I was surprised that I heard no criticism, or comment of any kind, from Mistress Caroline about my late stroll in the woods. Also, she was not punishing me in any way. Life returned to normal. The usual routine was re-established, including her use of the little bell. She was childish in her gleeful enjoyment of this.

One morning my curiousity got the best of me. When I took Mistress Caroline´s coffee to her bedroom, I said, “Mistress, I have a question.”

“Yes J?”

“Mistress, I know you were very angry at me when you returned from your trip.”

Before I could ask my question she interrupted me. “You’re damn right I was angry! What did you expect? I came home and found you in jail after trying to escape from our lovely paradise!”

I replied instantly, "But mistress, I wasn´t trying to escape. I only wanted to know what was beyond the woods, nothing more."

This bought a smile to her face, and she seemed relieved.

"Oh J, why didn´t you tell me this before?

“I´m sorry mistress, I suppose I should have spoken up sooner, but the court case happened so quickly”

“Oh well J, your punishment is out of my hands now. It has been prescribed by the court, and, if I may say so, you will find it more severe than any punishment I could have given you. Also, you redeemed yourself somewhat in my eyes by accepting your punishment. If you had left, it would have been the ultimate embarrassment for a mistress, to be banned from owning another slave. The other mistresses would never let me forget it."

“Oh. I see,” was all the response I could come up with.

The very next morning, when I took Mistress her coffee, she said, “With regard to your punishment J, I have some news for you.”

“Yes ma’am? What is it?”

“I have heard from the officer, and I am to have you on the green round the back at fifteen minutes before noon today. I’m afraid you’re going to leave there with a very sore ass.”

I breathed a sigh of apprehension. “Yes mistress,” was all I could muster.

* * *

Mistress Caroline and Mistress Claire took me to the green. In the centre of the green was a structure like I had never seen. It was a wooden rack that sloped upward to a point that was waist high, then at a sharper angle, about forty-five degrees for another three feet or so. Above it was a sign, which said simply, “Runaway Slave.” The officer was standing beside the rack holding a length of cane about four feet long and a quarter inch in diameter.

As soon as we arrived, in an authoritative voice, she instructed them, “Strip him naked and strap him to the rack.”

Without saying a word, they set about to do as they were told. They both had very serious expressions on their faces. They bent me over the rack, bound my arms tightly above my head, and spreading my feet apart about two feet, strapped my legs firmly to the rack.

It was between ten and five minutes before the hour of noon. No one was saying anything. All were just standing around. A number of people were beginning to gather and stare at me on the rack. Most of them were women with their slaves, slaves like me it appeared, on leashes. The slaves were kneeling in front of their mistresses facing me, and the women were talking softly to each other and nodding in my direction. I was embarrassed and humiliated to be seen like this. I closed my eyes and began to think about what was going to happen. I’m sure this won’t be too bad, I thought. I have been beaten pretty hard by Mistress Caroline often enough. I’m sure this won’t be any worse than that, and it will all be over in no more than five minutes. I was convinced I could get through it and I was determined to avoid further embarrassment by remaining silent, by not crying out, I wasn´t going to give her that satisfaction. Or so I thought.

A couple minutes before noon, the security officer stepped in front of the rack and faced the onlookers. “Your attention, please!” she called out. “You are about to witness the punishment of runaway slave J, property of Mistress Caroline Smith, as prescribed by the court. The court has decreed that he shall suffer twenty strokes of the cane.”

Some in the crowd gasped. The officer continued, “I shall administer the required strokes in groups of five, starting exactly on the first tone of the clock on the building, above. Between each group of five strokes of the cane there will be a rest period."

I heard muffled cries of surprise from both Mistress Caroline and Mistress Claire. I could hear the sound of the cane as she warmed up, slashing it through the air—whooop, whooop, whooop. The crowd was deathly silent.

At exactly the instant of the first chime of the clock, the first blow came, BONG, WHAAACK.

“AAAAAHHHHH,” I screamed. My back arched and my head flew back, eyes wide. I had never felt anything so painful.

The second blow came before I could suck in a breath. It coincided with the second tone of the clock, BONG, WHAAACK.

“AAAAAHHHHHH.”

The next three blows were timed exactly with the next three clock tones, and each one bought a louder cry of pain from my mouth.

After a short break, and without anyone speaking to me, the officer stepped up again to administer five more whacks.

My ass was still stinging from the first five, so I gritted my teeth and prepared myself for more pain. She began my caning and my screams were broken only by the necessity to suck in the next lung full of air to scream again.

This continued until my twenty strokes were completed, the security woman was merciless, as she dished out the remaining strokes. I thought I heard her give out a laugh at one point, but wasn´t sure, as I was too engrossed in trying to snuff out the pain from my bright red and very sore ass. Even though I was finding it very painful, one of the ladies watching noticed that my cock was standing at full erection, which seemed to amuse the crowd. Mistress Caroline caught my eye, and was standing there with a massive proud grin on her face, as if to say "that´s my slave."

I was expecting that to be it, and to be released and taken inside, but was I wrong!

The security woman, who I now had grew to really hate, stepped before the excited crowd.

"As further punishment, and is the norm on these occasions, we will be leaving the escapee fastened up for a few more hours, for him to think about what he has done. While he is thinking about his wrongdoing, any mistress who wishes to try out his ass for their own pleasure may do so."

In an instant, one or two of the mistresses present walked over toward me and reaching into their bags, took out a variety of strap on dildos in all shapes and sizes. It seems my punishment was not over!

I was going to protest, when the security officer came over to me and placed some duct tape across my mouth, and pressed it on hard. So this is what was meant by "and if it is the will of the court he will be at the pleasure of any and all Mistresses."

"This will keep the noise down whilst the mistresses have their fun. After all, some of us have work to do and don´t want your moaning disturbing us," she added.

Mistress Caroline came over and told me that she couldn´t stay to watch, as it would be too painful for her to see me being fucked by other woman. Too painful for her I thought, that´s a laugh, what about me!!

A few of the watching ladies left, along with their slaves, leaving half a dozen behind. My ass was still sore from the canings, so I wasn´t looking forward to receiving extra punishment from a group of ladies wearing strap ons.

All of a sudden I felt a pair of hands on the cheeks of my ass, forcing them apart. I grimaced, as their fingers dug into my marked areas, and this was followed by a couple of fingers inserted inside me. The fingers seemed to contain something, which I assumed was lube, which felt cold, but helped them slip in easily. Seconds later, I could feel the familar feeling of a latex cock being placed at my entrance, before gradually sliding slowly in. I tried to cry out, but the tape limited my screams. Whoever was behind me wasn´t being very thoughtful to my condition, as her cock started pounding away quickly. A few of the other women came around to the front to see the expression on my face and to see if I was still hard, which I was. This drew a few giggles amongst them.

I could feel the lube dribbling down my ass cheeks, which was starting to feel quite nice, and relieving my pain somewhat. This took my mind off the pain and I was starting to enjoy the sensation, as she continued to fuck me. After she had had her way with me, a few of the others took their turn. Each one adding more lube, easing my pain. Now my mind was off the pain, I could feel my cock stirring, and found myself getting close to orgasm. I wanted to reach down and stroke my rock hard cock, but couldn´t, adding further to my frustration. However, I didn´t have to touch myself, as I came on a number of occasions, adding to their delight and my embarrassment.

This went on all afternoon, as my ass was used by up to a dozen ladies in their prized dildos.

As the night started to draw in, I found myself alone. I was cold, my ass was sore, and my legs were covered in my own cum.

Then, I heard some familar voices, and looked up to see Mistress Caroline and Kelly. They released the straps that bound me, and helped me back inside. Kelly took me to the shower and thoroughly washed all the cum of and cleaned me up.

Afterwards she took me to my bed and applied some lotion to my red ass. It felt soothing, and I couldn´t help but get an erection again.

Mistress Caroline was standing at the door grinning. "Come on Kelly, I think he´s had enough excitement for today, don´t you?"

With that, my collar was locked to the bedframe and they retreated from my room. I took a while to get comfy, with my ass still stinging, but eventually tiredness got the better of me and I dropped off to sleep.

* * *

That was five years ago. Since then I have tried to escape on a number of occasions. My punishment is always the same, a public caning, although the number of strokes differ. Then afterwards my ass is abused by some of the other mistresses, and every now and then, one of their slaves is ordered to insert his cock into me, which after all this time now, even that doesn´t bother me. Although the canings still hurt like hell, the thrill I get as I walk out to receive them and then knowing my ass will soon be full of latex cocks is too strong a urge to fight. I still leave the green, covered in my own cum and a very sore ass, but really deep down, love it. Pain seems to be my ultimate turn on!

I am still Mistress Caroline’s slave, a very dutiful one, if I may say so. Our relationship sometimes feels like we are husband and wife, not the usual husband and wife relationship, you must understand. I am completely subservient, and I do her bidding without question. Even yet, every now and then, she offers me as the entertainment at the monthly sessions we have in her dungeon in the basement. She still likes to assault my ass with her strap-on every week, and I must be honest, have grown to enjoy them. She organises ejaculation competitions, with the other mistresses, involving a number of slaves. They take various forms, how far the slaves can shoot, or how high, or how much, what ever they dream up. In fact, I don’t find any of this objectionable, and nudity no longer humiliates me, actually I rather enjoy the feel of my collar, tightly fastened around my neck. Mistress Caroline still loves to get a rise out of me with her little bell, and to use ‘her cock’, “for what it was designed for,” and I except that this is my new life, and wouldn´t change it for the world!!

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com with this note attached, it has been posted without my permission.


Continue reading Mistress Caroline part 4 - My Training Ends!

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