Sharleen's Sexual Adventures Ch. 06

Sharleen learns to administer erotic punishments

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Author's notes:

1. This is a work of fiction. The activities and practices described in this story are not necessarily either condoned or recommended. If you choose to do anything described in real life with real people you do so at your own risk.

2. All characters are fictional and any likeness to any living person is purely coincidental. The story is purely imaginary and, to the author's knowledge, bears no relationship to any factual occurrence.

3. This story follows on from Ch. 1 to 5 of Sharleen's Sexual Adventures. While this is a stand-alone story, if you haven't already read those stories I would advise you to do so first.

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The few weeks break before the last session passed quickly. Shar and Ben spent every night together, making love, cumming on his beautiful cock as he filled her to overflowing with his potent cum. He admired her beautiful breasts with their matching gold rings, symbols of the learning she had undertaken to gain the skills of love making that they both enjoyed so much. Then the final week arrived and Dale insisted they have a farewell party before Shar returned to Master Simon or Mistress Elizabeth.

The date for the party was set two days before I was due to leave and Jude, Mark, Joe, Trevor, Ben and Dale prepared for what appeared to be designed as a farewell orgy. I had no idea when or if I would be permitted to cum during the next session, knowing only that it was designed to teach me to inflict sexual pain on others. Perhaps, I thought desperately, there would be no sex permitted; I realized that this was probably unlikely, but certainly being prohibited from cumming was a distinct possibility. I also realized that graduation from this session would be accompanied by the insertion of a clit hood ring, which may put me out of action sexually for several weeks while it healed. So, I resolved to make the most of this party, although they were very close lipped about what they had planned.

It turned out to be no big deal, mainly, I guess, because by now I had experienced so much that most things were no big deal. Probably the highlight of the evening was when I was given a round robin of double penetration, with two cocks or strap-ons being used on me for nearly an hour as each man came inside my vagina while Dale and Jude took turns lying on their backs, their strap-on in my ass, their legs and arms holding me widespread as I was fucked mercilessly by each of the men. Needless to say, during this process I was not permitted to cum, although I desperately needed to. I was very grateful for this practice after several weeks of cumming at will with Ben.

Once that was finished, Jude wheeled in a Sybian machine. I have no idea where she obtained it, perhaps you can hire them, I don't know and didn't ask. However, they inserted a dildo in my ass, I lowered myself onto the ten-inch dildo affixed to the machine, and they turned it on. Then Ben sat beside me, whispering in my ear, ordering me to cum every two minutes. The first time I came hard because I was so frustrated from not having cum while being continually fucked, then the next three times I really enjoyed also, but after that it becomes a blur. I know my body responded to each command but each orgasm seemed to become more exhausting until I was functioning like a robot after twenty minutes. Soon after that, I was later told, I became unconscious and they turned off the machine and lay me on a mattress to recuperate. I have no memory of these events after about the fifth orgasm, so I only know what I was later told. All in all, I've definitely been to better parties and as I snuggled up to Ben in bed later that night I began to look forward to my next training session in which I would administer the punishment as well as receive it.

The following morning, I was again miraculously horny for Ben, as he was for me. I aroused him then continued playing with his balls, moving them in their sac, pushing them into the sockets against his pubic bone, then holding his sac tightly in one hand while I pressed down on his trapped balls, squeezing them against the hard bone. Ben told me they were quite sore, but after repeated gentle presses they seemed to lose their sensitivity and I found I could press harder and harder without causing him more than discomfort. I then straddled him and rode his hard cock to heaven, cumming several times before he finally spurted his semen deep inside me. For the first time I found myself wishing I could just live with him, go off my birth control and have babies together. I caught myself in these thoughts and wondered what was happening to me.

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I was met by Mistress Elizabeth and Master Simon at the door of the mansion where I would be taught during the next few weeks. I had followed their instructions to the letter, wearing only a thin white gown with a halter neck, bare back to just above my ass, narrow straps that barely covered my aureoles and reached to the top of the skirt, leaving my abdomen almost naked, and a skirt that consisted of multiple strips of fabric, each about an inch wide with no overlap, that stretched from my hips to half way down my thighs. On my feet were silver shoes with five-inch heels. Unlike previous arrivals, my journey today was by public transport and required changing buses twice during the trip, followed by a walk of several hundred yards down a public street through a throng of people. On many occasions during my lengthy trip I felt hands touching me, reaching between the skirt strips and beneath the halter neck straps to feel my breasts, ass and pussy. I was amazed that instead of feeling these touches to be intrusive, they caused me to become increasingly hot and horny so that by the time I arrived at the mansion all I wanted was to be fucked. However, my training cut in as soon as I saw Master and Mistress. I knelt before them, looking downward.

"Did you enjoy your journey here today, slave Shar?" asked Master Simon.

"Yes, Master."

"And do you feel sexually aroused from your journey?" asked Mistress.

"Yes, Mistress."

"That is good," she continued, "And remember that you may only cum with permission, understand?"

"Yes, Mistress."

I was told to stand and that I was permitted to look at them, so I raised my eyes and smiled at them both, feeling genuinely pleased to see them again.

"We have some other slaves for you to meet," said Master Simon. "They will be assisting in your training. As you are no doubt aware, you are here to learn how to inflict sexual pain on others this time. Within certain restrictions, you will experience this pain yourself before inflicting it on others. Those restrictions are due to your gender; you cannot, of course, feel how it feels to have pain inflicted on male sexual parts. That is what slave Harold is here for. Both he and slave Jess will be your test subjects and will provide accurate feedback on the effects of the pain you inflict upon them. Both will, at times, also inflict pain on you so you can gain an even greater perspective of the pain you inflict on females.

"Towards the end of the course you will preside over a Dungeon and will be responsible for providing the pain for many people simultaneously, instructing slaves in what you wish to be done to clients. Here we operate a working Dungeon and as well as training slaves, it is also used for recreational punishment and for correcting slaves owned by Masters and Mistresses who do not themselves own a Dungeon. So, during your time here you will gain much experience in many aspects of sexual punishment and torture of both males and females. Do you have any questions?"

"No, Master, Mistress," I replied.

"Good." Master clapped his hands and a male and a female slave appeared from an adjoining room. Both stood in attitudes of submission before Master and Mistress. I noted that each had gold nipple rings and that both were naked except for leather bondage around her breasts and pussy and around his cock and balls.

"You may look up and relax," Master told them.

They looked up and relaxed, looking at me with interest, noting my slutty clothing and barely managing to suppress their smirks.

"This is slave Harold and slave Jess," introduced Master, "Slaves, this is slave Shar. You will have no doubt heard the information I have just given her. So that it is clear, I regard you all as equals as none of you have completed this course. By the end of this course slave Shar will outrank you both but will be short on experience. It is your responsibility to teach her as much of your experience as you can. Unless you are told otherwise, you may indulge in sexual activities together whenever you have free time, which will mainly be during the night. To assist in this, you will all sleep in the one bed, so can you both please escort slave Shar to your bedroom and ensure she is dressed in the customary manner."

"Yes, Master," both slaves replied in unison.

They escorted me away silently until out of earshot, then they both greeted me with hugs. It felt strange being with others who recognized me as their equal. The room they took me to was plain and consisted of a dresser on one wall and a large king size bed in the center of the floor.

"I hope you like sex," said Jess, "Because Harold wears me out. It'll be great to have someone to share the burden."

"Oh yes, I like sex alright," I grinned, relieved that I wasn't going to be sexually deprived as I'd feared.

"That's good," said Harold, "I like breaking in a new filly every now and then." He grinned evilly at Jess as she stripped me out of my dress.

"Do you want to do the honors of dressing her?" she asked Harold.

"Of course," he said, collecting some leather straps from a dresser drawer. He approached me and placed loops of leather around my breasts, one strap going around the outside of both breasts, the other going around the inside of each breast and being held in a sleeve with the first strap at the top and bottom of each breast. I had been dressed in such a breast compressing bra before, I realized. He then fastened the loose ends together at the back and pulled them tight, compressing the bases of my breasts and causing the nipples to stand out prominently. He pulled the breasts through the loops further so they were larger and firmer, then tightened it a little more at the back.

Next, he took the broad belt and fastened it tightly around my waist, cinching it in until my belly was quite compressed and I had a distinctly hourglass figure. He then attached a thin leather strap to the front of the belt and attached an eight-inch dildo to it by feeding the strap through a hole in the base. He then attached a thinner four-inch dildo to the strap in a similar manner. He lubed my vagina and asshole then fed the eight-inch into my vagina and the four-inch into my asshole before taking the end of the leather strap to the rear, pulling it tight and fastening it to the belt. I remembered I'd been in a similar piece of 'clothing' before but without the dildos.

They both stepped back to admire me in my new outfit.

"How long do I keep the dildos in me?" I asked.

"Probably most of today. It's so you can experience what it's like, right from the start. Often you'll have these in you for the morning and they'll be removed for the afternoon, which is why I don't have any at present. I did have this morning. They will be increased in both length and diameter during your course. I usually wear an eleven-inch dildo that's about seven inches around in my cunt, smaller in my ass of course."

"So, what do you wear?" I asked Harold.

"I have my cock fitted with a tube and a dildo up my ass. I also have my balls banded, not tightly, but enough to remind me that it's there. Can't be too tight or I could become a eunuch, which is the ultimate punishment for some slaves and a preference for others. Funny how the world works, eh. The tube becomes real torture if I'm aroused because it's too short and too small a diameter to allow my cock to reach its normal erect size."

"So, remember that first thing each day it's enema time," continued Jess. "If you forget and need to shit it can be really painful waiting till midday. Now, we need to get you back to the Dungeon or they'll wonder where we are."

We walked to the Dungeon, past many closed doors, and found Master and Mistress waiting for us, sitting chatting to each other. We immediately lowered ourselves to our knees and waited with eyes looking to the floor. After a few minutes, they finished their conversation and looked at us.

"Are you all settled in, slave Shar?" asked Mistress.

"Yes, Mistress."

"Good, and have you been told about the wearing of dildos each morning?"

"Yes Mistress."

"Slave Jess, what size dildo has slave Shar at present?"

"Eight inch in her cunt, four inch in her ass, Mistress."

"That's good. Increase them by an inch each day for the next four days, then keep them at that for the rest of her stay."

I did mental calculations. That meant I would spend some mornings with a twelve-inch dildo in my pussy and an eight-inch in my ass. They were huge! I'd never feel Ben inside me after ten weeks of this. I felt panic rising and exercised strong control to ignore it and to remain exactly where I was right now. Everything is fine right now, so relax, I told myself, after all, a vagina can have a baby's head pass through and still feel great when fucked by a normal sized cock.

"Slave Shar, today we'll do some learning about clamps, clips and torturing pussy lips. Please all stand and you can look up or wherever, as you may in most teaching sessions. Also, you can remove your dildos and other clothing during these sessions so we have free access to your whole body."

We all stood and 'undressed', then followed Master and Mistress to a set of drawers where Mistress opened one and removed a number of items ranging from normal spring clothespins, through paper clips to clover clamps. I recognized most of them and knew that they could be used on nipples, clits and other places to cause a great deal of pain, and also enhance arousal, depending on location and the pressure exerted.

"Slave Shar, lie on the table with your legs wide apart."

I lay down and spread my legs as widely as possible. Mistress then pointed out my outer and inner labia, then clipped a spring clip to each of my outer labia. I felt the sting of the pain then a dull throbbing, but quickly became used to it. She handed Jess two clips and she clipped those alongside the first two, then Harold clipped two more in place.

"How does that feel?" asked Mistress.

"That's not too bad, Mistress, bearable."

"Good. Get used to it because it is one of the most basic pussy tortures. We will go far beyond that today. Now, you can come off the table and fit some to Jess."

I rolled off and Jess took my place, then Mistress, Harold and I each fitted two clips to Jess. She accepted the pain, probably because it was far from the first time she'd had this done to her.

"Now," continued Mistress, "You'll see that Jess has quite a large clit and that it's been freed from its hood. That's something you may want to have done, Shar. That means it's quite easy to place a clip on her clit. Watch while I do that."

Mistress pressed her fingers alongside Jess' clit and pushed inwards, causing her hood to retract and forcing her clit to stick out even further. She placed a clip on it and Jess let out a shrill squeal, attracting a glare from Mistress.

"Sorry, Mistress," she said.

"I should think so. Get off the table now, and Shar, you can take her place."

Mistress then took a glass tube attached to some thin, flexible plastic tubing and what I recognized as a suction pump. She plugged the pump in, rubbed some lube around the tube and then pushed the tube onto my clit. Immediately I felt my clit being sucked upwards and watched as it expanded to half fill the tube. It wasn't really painful, but more a strange feeling. Once it was expanded to her satisfaction, she closed a valve, removed the tubing and turned off the pump.

"Off the table now."

I again rolled off the table, feeling the clips and tube between my legs.

"Right, Harold's turn. There should be another twenty or so clips there; Harold, spread your legs and let these lovely ladies clip them onto your cock and balls."

Harold did and Jess and I clipped them onto him as directed. He showed little sign of pain and soon his scrotum was covered in clips, with several more fitted to the shaft of his erect cock.

"Well done," said Mistress once we had finished. She then took several more paper clips from a drawer. "These are stronger than the ones you've used and I want Harold to clip them onto your breasts and nipples. Just take care, Harold, due to the nipple rings already in place."

Jess and I stood there as Harold clipped the clips one at a time around our aureoles and finally onto our nipples. These clips caused a great deal of pain as they were fitted, then the pain subsided, only to increase again with the next clip. Finally, they were all placed.

"That looks wonderful," said Mistress, "Now for the grand finale."

She ordered me onto the table once again and removed the suction tube off my clit. Even without the tube my clit was now large and upstanding. Mistress then took a large paper clip, opened it fully and placed it over my clit and hood.

"When I let this go, it will hurt terribly," she warned. "I don't want to hear a sound from you. Just suck up the pain. Understand?"

"Yes, Mistress."

I had expected her to slowly allow the clip to close but she did not; she simply opened her fingers and let it grip hard, suddenly. The pain was excruciating, radiating from my most sensitive organ through my body, causing sensations of pins and needles in my fingers and feet. I gasped for breath, determined not to scream. My breathing became rapid and panting, my body convulsing slightly due to the tense muscles as they tried in vain to deal with the incredible pain. I remained silent and remembered that I should relax. I did, and immediately my perception of the pain became different, more distant, more bearable. Over the next few minutes It continued to decrease and once she thought it tolerable, Mistress ordered me off the table.

"Well done, Shar, you accepted that pain silently. Now we shall replace the clips on your nipples with clover clamps. When these are fitted they can have weights added and the more weight there is, the tighter the clamps hold on making them impossible to remove simply by pulling without doing severe permanent damage, which we don't want to do, at least, not just yet."

Mistress took two clamps from a drawer and approached Jess, removing her nipple clips and fitting the clover clamps in their place. Jess accepted these without a sound, but they were painful, judging by the contortions of her face. Then it was my turn and I felt the pain, once again remaining silent. The first pain was from the brief time during which circulation could return to my nipples after the clips were released, followed by the much greater pain as the clover clamps were fitted. Once they were in place I found myself biting my lip and forced myself to relax as much as possible to deal with the pain.

"Now that you're both fitted with these clamps, I could add weights to them and see who could stand the most weight without screaming. Instead of that, a small competition is in order I feel."

Mistress took two lengths of cord and tied one end of each to my clamps then led me to a post and passed the cords around opposite sides of the post. She then called Jess over and tied the other end of each cord to each of her clamps. This left us both about two feet from the post.