Sharleen's Sexual Adventures Ch. 06

Jess approached Harold and took his cock into her mouth, swallowing the whole organ until her lips touched his scrotum. After a few minutes of this she then climbed onto the bed and straddled Harold's hips, then guided his cock into her entrance and sat down hard. The pain as her lips and clit pressed against his groin caused her to grimace, but then she began moving back and forth, arousing both herself and Harold, who began thrusting upwards as much as he was able. It took less than five minutes before Jess was ready to cum.

"Mistress, please may I cum?" she asked desperately.

"Yes, but only after slave Harold cums."

Jess grimaced, but not from pain this time, and continued to move back and forth on Harold until with a final upwards thrust he came hard into Jess's tunnel.

"Ooohhh, he's cumming, Mistress, please may I cum?" Jess asked, even more desperately now.

"Yes, you may cum."

It took only a few seconds before Jess leant forward to support herself and groaned as her orgasm washed over her. I watched her enviously. After a short time, Mistress told her to climb off him and allow him to receive his cane strokes.

Once Jess was off him, I immediately noticed that his shiny cock was flaccid.

"There you are, slave Shar, you may now cane slave Harold. First off, strike across his cock as it lays on his belly. It's soft now so you can cane quite hard without doing any damage. Do five strokes for a start."

I caned his cock five times, spreading the strokes apart. I was fascinated how it twitched with each stroke and then gradually developed parallel red lines across it.

"You'll notice that it moves with each stroke. That's good because it also protects against permanent damage. If you were to place it on a hard surface and cane it you could certainly do some serious harm. Now for his balls, lying so innocently and unsuspecting between his legs. You need to be a little gentler with them but as you cane them their tolerance for pain will increase, so you can gradually make harder strokes. Strike when you're ready, let's make it five on each one. The easiest way to do this is to straddle the guy's head, which, of course, allows him to lick and suck your pussy, except, of course, that you're still closed up. Oh well, there'll be another time I'm certain."

One of my dreams had been to cane a guy's balls; never did I think I would have the opportunity, until now. I straddled Harold's head and felt him reach upwards with his tongue and give my pussy a lick. I vowed to cum like that sometime, imagining being eaten out while caning Ben's balls: the stuff of dreams.

I aimed for Harold's left ball first, striking it firmly but not hard and watching it respond as it was pulled upwards into its sac at the same time as Harold's body jumped beneath me, but he remained silent. Second blow was to the right ball; same response. I alternated the next eight strokes between his balls, noticing that they seemed to swell slightly with each blow.

"Mistress, they're swelling. Am I damaging them?"

"Not at all, that's just his body pushing fluids into the sac for protection. Actually, it means you can probably hit them harder now. Try another five on each."

I did, the dark part of me gaining immense satisfaction from the pain I was inflicting on poor Harold. Once I finished and was standing beside the bed again, looking at his swollen, red balls, I felt very sorry for the pain I'd caused. It seemed the sensitive, caring part of me went into hiding while the dark part took control, but after it was over, the sensitive part resumed control. Is this how people with schizophrenia feel, I wondered, two personalities in the one body, both amazed at the actions of the other?

I untied Harold and helped him sit up, then we discussed the day and I expressed the feelings I had.

"That's quite normal," replied Mistress, "I have those feelings also. It's only time for concern when the sensitive, caring part does not return. Then you're doing things vindictively and if you're a domme it's definitely time to quit. Nobody said this was easy, but some people, myself included, feel a sense of satisfaction for a job well done once a person has been punished at a level they expect. Basically, we're a service industry; we give people what they want, even if they have difficulty verbalizing it. Some people have such deep desires that even they do not know what they really want. That is where skill and experience come in; we need to diagnose what they need and give it to them, but always only with their consent and only with a safe word."

I took that lesson on board and thought about it during supper. Once we retired to our bed we slept; Jess and Ben were sore and I was unavailable for any sexual romps. They would have to wait.

Later that week Harold unstitched my labia.

"Slave Shar," began Mistress as she examined my pussy at close range, "I am pleased with your progress. I am also aware of your high libido and how frustrating it must have been without intercourse for these past few days. As a reward, I'm going to allow slave Harold to fuck you. However, there is a condition. You may each cum when you're ready without asking permission. However, if Harold cums before you have cum three times, you will be severely punished; if you cum more than once before Harold cums, then he will be severely punished. If either of you cums within ten minutes of commencement, you will both be severely punished. Is that clear?"

My heart dropped. This was a winners and losers game, there was no happy ending. I couldn't cum more than once before Harold without him being punished, but he couldn't cum before I'd cum three times without me being punished. And if we came early we would both be punished. I felt despair; not because of the impossibility of us both winning, but because the punishments were unspecified. I looked at Harold and noticed he was grinning; what was there to grin about, I wondered. I saw no real way to avoid punishment for one of us.

Harold picked me up and placed me on the bed while Mistress sat in a chair, pulled her gown up and commanded Jess to attend to her needs with her mouth. Harold was, as usual, hard, just as I was, as usual, wet, so he wasted no time in entering me and began slow-fucking me, sexily, teasingly, determined to see out the ten minutes without either of us cumming. I looked at the clock on the table as I felt myself becoming more aroused. I knew that had I wanted I could have cum in a few seconds, I was so horny.

Time seemed to drag and I climbed the slope towards orgasm, holding myself at the brink as I felt that Harold was also on the brink and ready once the time was up. It was not helped at all by Mistress writhing in her chair as she came several times on Jess's tongue. Finally, the ten minutes was up and I came hard beneath Harold, my body writhing in release. A few seconds later I felt his cum fill me as he thrust deeply inside and remained in position as his cock pulsated in my cunt. So, Harold had cum after I'd cum only once, therefore I would be punished.

I looked at Mistress, who was now well on the way to her second orgasm. I encouraged Harold to continue fucking me, intent on cumming at least once more. I felt him pumping me towards number two, closer, closer, then I was there, biting my lip to remain silent as my body shuddered through a second release. As I came down from that one, Harold kissed me and I felt his cock was again fully hard. We moved together once more, each stimulating the other, each aiming for one more. Higher, closer, closer, then I was there and as I came hard I felt him release another flood of cum inside me. We collapsed together, holding each other as we both experienced another ecstatic orgasm.

Once we recovered, Harold climbed off me and I sat up, noticing that Mistress was now sitting on her chair, her skirt in place and Jess kneeling alongside her.

"I hope you both enjoyed yourselves," she said smiling, "I know I certainly did. So, who is to be punished?"

"I am," I said.

"Yes, I thought as much. So, what dastardly punishment do you think I should dream up for you?"

"I - I don't know, Mistress," I replied.

"Well, how would 100 strokes of the cane on your ass sound?"

My heart dropped. Surely not, not after all I'd been through; call red, I thought. But my rational mind wasn't in charge.

"Yes, Mistress, whatever Mistress says," I heard myself reply.

To my utter amazement Mistress began laughing, holding her sides as she rolled around in the chair with laughter. I noticed both Jess and Harold were also laughing. I was about to have my ass cut up, which would take months to heal, and they were laughing. Finally, Mistress gathered her senses.

"Well done, slave Shar, well done. Your training has come through and overridden your rational mind. Excellent. There will be no punishment. This exercise was to show you the power of the unknown. Fear of what could happen, without actually specifying what could happen, is extremely powerful. People like certainty, even if that certainty is very painful. Had I told you what the punishment would be at the start, you would not have been nearly as concerned as you were when you didn't know. So, remember that; never specify the outcome before you need to. Harold and Jess have gone through this training program before, so they knew what was to happen, which is why the laughter and why Harold made no effort to withhold his orgasm until you'd cum three times. Learn the lesson well, slave Shar."

"Yes, Mistress," was all I could say as I knelt on the floor, lesson well learnt.

During the next few weeks I progressed in both ability and confidence. I understood at a deeper level the unspoken needs of the people to whom I administered punishments and learnt a variety of techniques for enhancing painful experiences from a psychological perspective. The most important thing I learnt was the power of the mind, which could conjure up incredibly horrendous outcomes, far worse than those that were actually administered.

I also explored my darker side, especially with myself, asking for and receiving painful experiences to scope exactly how much pain I could tolerate and why pain was a sexual stimulant for me. I never learnt the answer to that; I guess that some things are simply unknowable. I do know that I developed my pain fetish quite remarkably, enjoying many objects, such as a toilet brush and increasingly hot water in my cunt while also managing to first tolerate and then need my clit squeezed hard. I also found that I enjoyed piercing and usually had several needles in my breasts and labia during the day.

Mistress trained me to become proficient in the use of a wide variety of whips which were first used on me, to refresh my memory of previous training. After that I could practice on Jess and Harold and use them in punishment and other sessions with clients. I also learnt to supervise punishment sessions, suggesting suitable punishments for slaves and supervising the use of the equipment for its administration.

As the end of my training time approached, I wondered whether I would graduate. The feedback Mistress gave me became less frequent and when I asked about this she told me it was important to be able to self-evaluate and to develop the confidence to be able to make decisions based on this self-evaluation.

"You're not going to have me there to praise your work when you run your own Dungeon," she told me one day, "You must be able to make your own decisions and be able to justify those decisions if necessary. Remember also that you are ultimately responsible for the welfare of your clients, so never inflict a punishment which you believe to be more harmful than the client really needs. Let them think it is, but make sure it only has a real danger far less than the perceived danger."

After that she increasingly tested my self-evaluation abilities, asking me to justify decisions I made and guiding me by suggesting other possibilities, pointing out that there was no 'right' or 'wrong' decisions, but only 'best' decisions and these were based on experience and availability of the equipment required and the needs of the client.

A few days before the end of the course I was given a Master who had two slaves, one a male who had impregnated the female slave without permission. The Master told me that both slaves needed to be punished severely in an appropriate manner. Mistress and I, along with slaves Harold and Jess, met them in the Dungeon.

I looked at the two slaves kneeling before me, something that I was still struggling to come to terms with, being more used to doing the kneeling rather than accepting it from others.

"Do you love each other?" I asked.

"Yes," replied slave Tom.

"No," replied slave Maggie.

"Did you know what you were doing was wrong?" I asked.

"Yes," they both replied.

"Slave Tom, if you knew it was wrong, why did you do it?"

"Because I loved her."

"Slave Maggie, you don't love him. Why did you allow him to do it?"

"Because it felt good. I enjoyed it, but that doesn't mean I need to love him."

"So, you're a slut, willing to have sex with anyone for your enjoyment?"

"Yes," she muttered softly.

"Did you take advantage of slave Tom's love for you and allow or encourage him to have sex with you when you knew you could become pregnant?"

"Yes."

"And slave Tom, did you let your love for slave Maggie overrule your common sense by having sex with her while she was fertile?"

"No, I didn't know she was fertile. I love her; I wouldn't do anything to harm her."

"Is that true, slave Maggie? Did slave Tom know you were fertile? Did you tell him to stop?"

"I knew I was fertile but I really wanted sex, so I didn't tell him and no, I did not tell him to stop. Instead I encouraged him," replied slave Maggie, looking at the floor.

"So, you, slave Tom, made love with slave Maggie even though you knew you should not, and you, slave Maggie, encouraged slave Tom to make love to you even though you knew you were fertile, information that you withheld from him. Is that correct?" I asked.

Both slaves agreed that was correct.

"So, slave Tom, for you I will punish your cock and balls for performing a sexual act which you knew was wrong. Do you agree with this punishment?"

"Yes, Mistress."

I felt a warm glow pass through me as he addressed me as mistress. I could get used to this, I thought. I looked towards Mistress and she gave me a small nod of approval, so I continued.

"And you, slave Maggie, will receive a far greater punishment, one that will prevent you from enjoying sex for the remainder of your life. I will tell you what that will be once slave Tom has been punished. Now slave Tom has said he loves you but you do not feel the same way about him, you have told me. Slave Tom has also been instrumental in making you pregnant and causing you to require punishment. Therefore, it is fitting for you to administer the punishment to him. Do you understand?"

"Yes, Mistress."

"Slaves Harold and Jess, please fasten slave Tom to the frame for cock and ball punishment," I instructed.

They quickly attached him to the frame, spreading his legs wide apart as he lay with his shoulders on the floor, knees and lower legs tied to the vertical steel frame. His cock was only semi-erect and lolled to one side while his balls were held tightly in their sac at the bottom of the vee made by his spread legs. They appeared to be eminently punishable.

I selected a cane and a riding crop, both reasonably rigid instruments that could inflict a great deal of pain on a man's unprotected genitals and offered them to slave Maggie.

"You are to inflict the number of strokes that you believe slave Tom deserves using one or both of these instruments," I instructed her. "You will continue to strike slave Tom's cock and balls until you believe he has received his punishment or until I tell you to stop, and it is also your choice how hard you strike him. The punishment will stop if blood is drawn. Do you understand?"

"Yes, Mistress," replied slave Maggie, with far greater enthusiasm in her voice than previously.

Slave Maggie took the riding crop first and felt its slight bendiness, then swished it through the air and took a stance behind slave Tom before looking at me.

"You may proceed."

It was very obvious that she had no love for slave Tom, probably from years of having to submit to his desire for sex whenever he wanted while maintaining a neutral disposition to her fellow slave. She struck him hard right on his balls, causing him to yelp in pain initially then writhe as the dull pain radiated from his balls through his body. He was still processing that when the second blow fell, causing a surge in his writhing as he gave a low moan despite himself. Slave Maggie struck regularly and carefully at a rate of a blow every 15 seconds or so, causing slave Tom to suffer continuous pain from his red and swelling balls.

After ten strokes she began changing her position each stroke, alternating between her first position, from which she would strike his red, swollen balls, to a closer position which allowed her to strike his now-rigid cock that lay against his belly with the head pointing towards the floor. As his cock felt the strokes, it quickly became inflamed and swollen even more than its erect condition would have caused. I doubted very much that slave Tom would be of much use sexually for several days after this.

I was counting the strokes, pleased that slave Maggie was carrying out the punishment so well due to her lack of love for the victim and also that she was able to work her anger out so that it would not have to be held in to cause her problems at a later date. After 30 strokes, I asked slave Maggie to change instruments and handed her the cane, taking the crop from her. She continued using the cane on his balls and cock, each stroke now leaving a red welt on his tender organs. His balls were at least twice the size of when she began and his cock was now red and throbbing. I noticed that it was not being caned as it lay on any hard surface but instead was able to move with each stroke, hopefully minimizing any internal damage.

I didn't quite know how many strokes to allow and was reassured that my Mistress was observing closely and made no move to bring the punishment to an end. I also noticed that the Master who had brought the slaves was taking great interest in his slaves' activities and that he was clearly aroused by the bulge in his trousers. I wondered if slave Maggie would be in for a session once they returned home.

I decided that 60 strokes would be a good number, unless the cane drew blood before that. As I watched, slave Maggie must have sensed that the session was nearing a close and she increased the strength of her strokes after 55. Two strokes later the cane cut the scrotum and drew blood. I signalled for slave Maggie to wait and checked the injury, decided that it would be foolish to continue as the laceration would most likely expand, so told slave Maggie it was over. She handed me the cane and I signalled for slaves Harold and Jess to untie slave Tom's shuddering body.

They did, and assisted him to a chair where slave Jess applied some antiseptic cream to the cut on his swollen balls. His cock was no longer hard but was still very large and very red from the beating it had taken.

"Now, slave Maggie, what do you think your punishment should be?" I asked, prolonging the time of uncertainty, which Mistress had shown me was mental torture in itself.

"I don't know, Mistress" replied slave Maggie, kneeling in front of me once again, "Perhaps having a baby is a lifetime of punishment in itself," she added hopefully.

I chuckled. "No, it will be far worse than that. You will still become aroused, still feel those wonderful sexy feelings that you have in the past, but you will be less able to relieve those feelings. Your punishment will be threefold. Firstly, I shall fit clips to your labia and pull them wide apart so that your trench and clit are completely exposed. Secondly, I shall administer a series of cane and riding crop strokes to your clit so you can experience to some extent what you have just administered to slave Tom, then thirdly, I shall inject your clit with a caustic chemical that kills nerve endings so from today onwards your clit will have no sensitivity. No longer will you be able to easily cum during sex. It will now require greater effort in order to create vaginal orgasms, if these are even possible. Slaves Harold and Jess, tie slave Maggie in the frame like slave Tom was."