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Mistress Caroline part 4 - My Training Ends!

My training is taken a step further.
I was awakened by someone bending over me and touching my neck. At first I was startled, then I realised she was unlocking the chain attached to my collar. It wasn’t Mistress Caroline. Who was it? Not yet fully awake, I couldn’t think straight. Did I know her? I couldn’t remember. She looked familiar, but…

“Good morning J,” she said, smiling pleasantly. “Do you remember me?”

“G…Good morning,” I stammered. “I…I think I might know you, but…”

“But you’re too sleepy to think right now,” she said, laughing.

“Yes. I…I mean yes ma’am…”

“Just ‘yes’ will do J. I’m a subbie, not a domme. I’m Kelly. I helped give you a shave in the salon. Do you remember now?”

I blinked my eyes. I was beginning to gain my senses. “Oh yes. Now I remember. Hello Kelly. What are you doing here?”

“Waking you up,” she said, laughing again.

I laughed too. “I’m aware of that. I’m not sure I want to be waked up, but I’m aware of it. But why? Why you? Do you work here too?”

“No J, I live next door with some other subs and I’m a friend of Caroline’s. I help her sometimes, particularly with jobs she is not accustomed to doing, like waking up slaves. She’s still in bed. She’s your mistress, and she wants to see you now!!"

I followed Kelly down the long corridor to the master bedroom, or should it be called the mistress bedroom here? She indicated that I should enter and she followed behind me. Mistress Caroline was sitting up in bed, a sheet pulled up to just below her bare breasts.

“Good morning mistress,” I said, looking at them.

“Good morning, my slave,” she said. Then, laughing, she said, “Please look me in the eye when you greet me J.”

“Yes ma’am,” I responded, with a sheepish smile.

“Good morning Kelly. Thank you for getting my new slave up. If I had had to do it myself, it might have made me grumpy,” Mistress said, smiling.

“I was glad to do it Caroline. Since I have to get up earlier than you do, I’ll be glad to do it every day, so long as you feel you need to chain him to the bed at night.”

“Thank you Kelly. He got a bit rebellious the other day, and I’m not sure that is completely over with, so I think the chain at night will be needed for a while.”

I said nothing. In the back of my mind I wasn’t completely sure, either. Besides, Kelly was so pleasant, I wouldn’t mind at all being awakened by her every morning.

Then she looked directly at my crotch. “Look at that J. My cock is hanging there so soft and limp. I like to see it hard. Come stand here next to the bed, close to me,” she ordered.

“Yes ma’am.” I stepped closer.

“Now, put your hands behind your back. I’m going to train my cock to stand up for me whenever I want it to.”

“Yes ma’am.”

Then she opened the drawer of her night stand and found a small bell. She held it up in front of me and rang it gently. I made a pleasant tinkling sound. “Whenever you hear that sound, my slave, you shall stop whatever you are doing and come stand perfectly still in front of me just as you are now. Do you understand?”

“Yes mistress.”

She rang the little bell again, then she lifted my cock and placed it in her mouth. Immediately, I felt her tongue circling the head then caressing the underside of the shaft. It responded instantly, slowly swelling and lengthening. In less than thirty seconds I had a rigid erection. The sensation of her hot mouth was delightful. I closed my eyes, leaned my head back, and moaned softly. Instantly she released my rigid cock and sat back against her pillow.

“Lovely,” she said, smiling and staring at the erection she had created. “Now, I’ll be up in a few minutes. Go to the kitchen and fix me a coffee. I’ll be along shortly.”

I was frustrated, but I tried not to show it. “Yes mistress," I sighed.

Just as I was finishing she came through the door and sat down at the table. Before I could greet her, she rang her little bell.

Remembering my instructions, I went immediately to her side and stood with my hands behind my back.

She lifted my cock with her fingers and said, “Limp again J? You know how much I like my cock to stand at attention for me.”

Again, she rang the bell. She put her tongue under the head and ran it all around the rim, squeezing and relaxing her fingers on the shaft as she did so. The disired response came quickly. Within a half minute it was hard again. This achieved, she stood, walked over to the worktop and picked up her coffee.

She instructed me to shower and meet her in the living room. I had just finished when I heard her ring her little bell again. I hurried to the living room and found her sitting. “Yes mistress?” I inquired.

“You know what you are required to do,” she said, smiling and pointing to a place on the floor directly in front of her.

“Yes ma’am,” I replied as I walked to the place she had indicated and stood with my hands behind my back.

Looking directly at my crotch, she rang the bell again. Immediately, I could feel a warm sensation in my cock. She took it gently in the fingers of one hand and began rubbing its head with one finger of the other. She stroked the little opening at its tip, then ran her finger around the rim. It began to swell and stiffen.

She smiled, and began to slide her hand back and forth on the shaft. Again, it was less than a minute before she had it stiff as a rod. She rang the little bell again, then she kissed the head lightly and released it. Looking up at me and smiling.

Afterwards she had me doing chores all around the house. Each time I finished a task, she would ring her little bell and I would, dutifully, present myself in front of her. As soon as I was standing with my hands behind me, she would ring it again and, in one way or another, bring ‘her’ cock to an erection. By the time she had done this three or four more times, it would begin to get hard the moment I was standing before her and she rang the bell. Eventually, she did not need to touch it at all. As soon as I stood in position and she rang the bell, my cock would swell and stiffen, pointing directly at her. She was delighted. “You are so trainable J,” she said, chuckling. “You are giving me a great deal of enjoyment.”

“Thank you ma’am,” I replied, very frustrated but trying not to show it.

At the end of the day, I was returned to my bed and Mistress Caroline picked up the chain and locked it to my collar.

“You did very well today.” she said, then bent down and kissed me on the head, and left the room.

Kelly awakened me again next morning, but this time she seemed different.

“Good morning Kelly,” I mumbled.

Instead of responding to my greeting, she said, “Get up J, quickly, It’s time to go.”

“What’s the hurry?” I asked as I sat up and swung my feet to the floor.

I’m afraid you’re in for a bit of a surprise today. Caroline sent me here to get you prepared.”

“What kind of a surprise?” I asked.

“I’m not permitted to discuss it with you. Sorry, I wish I could. But right now you need to head for the toilet. We need to get you ready.”

“Get me ready? What do you mean?”

She kissed me on the cheek and replied in a very soft voice, “I’m sorry J. I just can’t talk to you about it. I must carry out Caroline’s instructions. Come on now.”

She took my hand and led me to the bathroom.

“Before we start you’d better use the toilet,” she said.

I thought about being stubborn and refusing to co-operate with her until I got some better explanation. What could she do? She isn’t a domme. But she was being so sweet and treating me so considerately that I decided against that. When I finished my morning toilet ritual Kelly said, almost apologetically, “Now, I have to give you an enema. It will be best if you get down on your knees and lower your head to the floor.”

I hesitated for a moment, then shrugged and did as she asked. Before she was finished she had given me three enemas. When she was satisfied I was cleaned out inside, she removed her toga and gave me a thorough bathing in the shower, which made me forget about asking more questions.

“Now we’re ready,” she finally declared.

“Ready for what Kelly?” I asked insistently, hoping to get some kind of explanation.

“You’ll get your answer to that soon enough,” she said, smiling at me.

She donned her toga and picked up a leash, which I expected her to attach to my collar. Again I was taken by surprise when she snapped the leash on my cock and ball ring. “Here we go,” she said as she lead me away.

Kelly led me directly to the cellar door, opened it, and took me down the stairs. We proceeded to the cellar stairs and went down. When I reached the bottom of the stairs, I was startled at what I saw. It looked like an ancient torture chamber. There were all sorts of contraptions, all were fitted with straps, ropes and chains. On the walls hung whips, floggers, belts and more ropes and chains. I could not help but wonder what experiences were in store for me.

“Good morning J” Mistress Caroline said. “I’m sure you are wondering what we are doing this morning.”

“Yes mistress.”

"yesterday, I started to train your cock to respond to me. Well today, it´s the turn of your ass to be mine".

Kelly immediately handed her the leash, which she jerked on hard. At first I thought she was trying to tear off my cock and balls. Without saying another word, she yanked me towards a bench. I was roughly bent over it, and Kelly was told to fasten my wrists and ankles tightly to it.

Out of the corner of my eye I saw Mistress Caroline reach into a draw and proceed to fasten something around her waist.

I wasn´t prepared for what I saw next. She spun around and was wearing a massive black strap on dildo. It must have been at least 8 inches long and very thick. She approached the bench, and forcefully kicked my legs wider apart.

"I´m sorry J, but this has to be done. I can´t put it off any longer."

"But mistress" I started to say.

"QUIET J," she shouted, as she worked some lube between her fingers.

"This is going to happen, whether you like it or not. All slaves have to feel their mistresses cock in their ass at some point, it is the ultimate submission. Just feel honoured that I have deemed you ready so soon."

With that, I felt a wet finger insert slowly into my waiting ass. I grimaced, and gave out a small moan.

"If that finger makes you moan, I don´t know what you will make of my cock deep inside you."

Gradually, more fingers were worked inside me, making me moan louder and my eyes water. As thet were worked in and out, the initial pain started to ease. Eventually their was no pain at all, and my mistress deemed my ass ready.

I felt her cock, as it approached the entrance of my ass, and I readied myself for my ordeal. The cock was lubed up, but it still hurt as it begin to enter me.

“Does that hurt J?” Mistress Caroline asked sarcastically.

“Yes,” I replied.

“WHAT DID YOU SAY?” she shouted.

“I said ‘yes mistress’,” I answered.

"You will address me respectfully every time you speak to me, do you understand that?” she snarled.

“Yes ma’am,” I replied in as respectful a tone as I could muster, considering the circumstances.

Then suddenly, she pushed forward hard, and her cock slid deep between my ass cheeks.

"AARRGGHH..." I cried out.

"Quiet J, or I´ll have to use the gag on you," she said, as I felt her cock going further and further in, with every inch.

I muffled my displeasure, and looked up at Kelly pleadingly, who was standing silent in the corner. She stared back with a sorry look on her face, but I knew that she couldn´t help me.

Mistress Caroline withdrew slowly, then when I was least expecting it, rammed it back in hard.

I tried not to cry out at the pain, but found myself giving out a low moaning sound, and kept it down to a minimum, so as not to be gagged.

Her strap on was now going in and out of my tight ass at full force. Now and again she would pause, and let the end rest at the opening, giving me hope that she was finished. Alas no, she was just lulling me into a false sense of security. She was like a woman possessed, a side I hadn´t seen yet, as she continued to pound my ass. After a while I got used to the pain and just closed my eyes, waiting for my ordeal to end.

It was probably only minutes, yet seemed like hours, before she grinded to a halt. My ass was well and truly used, it belonged to her, the same as my cock. My ultimate humiliation was finally over.

Without a word to me, she withdrew her cock and walked out of the room, leaving Kelly to untie me and help me up. I could hardly walk as she helped me up the stairs and into my bed, and locked my collar up. She began tenderly stroking my stinging ass, as I lay there. The smoothness of her touch felt nice. In fact so nice, that for a brief moment I forgot my ass and noticed that my cock was standing to full attention.

Kelly too noticed, and let her hand wander around to the base. Her hand then proceeded to stroke my throbbing hardness. I looked at her, and then toward the door, wandering what Mistress Caroline would do if she was to enter.

Kelly put her finger to her lips, and whispered softly "Sssh, Caroline is in the shower, I can hear it running. This can be our little secret," as she carried on sliding her hand up and down.

I was by now passed caring what Mistress Caroline would say. My cock was nearing bursting point as her hand worked its magic, as her finger circled the tip. Her strokes increased as I approached orgasm, and it was all I could do to keep silent as my cum shot out all over her hand.

All of a sudden a cough came from the doorway, and in it stood a very angry mistress. Kelly jumped up and exited the room in a flash, leaving me to face the music.

"Get some sleep J," a fuming mistress said.

"I will speak to you about this tomorrow," and turned and left the room.

I heard raised voices coming from the living room, and it sounded like Kelly was getting a real dressing down. I heard a door slam and it all went quiet. I lay there for a while, not knowing what to expect, however nothing happened that night and I eventually drifted off to sleep, again wondering what fate awaited me the following day..

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 3 - My Training Continues.

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