Richard's training was now to begin in earnest. His first whipping, and my magnificent orgasm that went with it, were just a bit of self gratification on my part. They had served their purpose, as I was now better focused, but it was time to move on to other things. From now on everything had to be done according to a strict plan. Richard was to be taught to associate pain with intense sexual excitement, so that the pain I gave him would eventually become a source of sexual pleasure, and he would come to crave not just the pleasure, but the pain itself. It would be up to me to make sure that he would learn his lesson in the time we had allotted. But I had done this before to other slaves, and had no doubt that one week would be plenty.
We had entered the dungeon in mid-afternoon, and it was now only 5:00 PM. I informed Richard that for the next 48 hours he would be required to hold a very hard and very steady erection, without any break at all. He might not get much sleep during that time, but even during any nap he took the erection must hold. Any wilting, no matter how slight, would be punished instantly and severely. And of course, he would be forbidden to come during that period. Richard started to complain that he could not possibly hold an erection for so long, but that only earned him another forceful swat with the paddle on his ass, and he quickly shut up.
For the last couple of hours Richard had only felt pain. Now it was time to bring some pleasure into the mix. I took out a bottle of a very nice aloe-based cream which I kept in a small refrigerator in the dungeon, spread a good amount on my hands, and started gently rubbing his ass, lovingly feeling the welts from the whip under my hand. Richard sighed deeply as he felt my caress, and I could feel the tension easing from his limbs, in spite of his still being quite tightly stretched out by the ropes. I then slowly spread the rubbing to the rest of the whipped area, but would frequently let one of my hands go over to his prick or his balls, and play with them ever so gently. Richard was now under the dual influence of the relaxing effect of the rubbing of his back side, and the simultaneously exciting influence of my playing with his cock and balls. He obviously loved it, and his cock again pointed straight up and rock hard.
After about a half-hour of this I wiped my hands and his cock and balls with paper towels, put the eye mask again on him, since I would soon give him a little surprise, and then started to play with his nipples. They were already standing up a little, but increased quickly in size as I first rubbed and pinched them with my fingers, and then worked them with my mouth, licking, sucking and biting, first quite gently and then harder, all the while fondling his prick and his balls with my hands. Richard was no longer complaining, but sighing and groaning and purring like a cat in heat. His erection too was now even harder, his prick standing straight up, the head actually touching his abs. I continued to rub him there with my hands, and occasionally with my own cock, grinding against him while I continued to bite his nipples. I could not see his eyes behind the mask, but there was a huge smile on his face.
Richard was really enjoying himself at this point, and it was time to move on to the next stage. But first there was a little housekeeping to be taken care of. I had a can of shaving cream and a razor handy, and proceeded to quickly shave Richard's pits and his cock and balls. The cock and balls I needed to be hair-free for some of the things I had planned to do there. Besides, shaving a guy's cock always takes a part of his manhood away, makes him feel weaker. I was somewhat ambivalent about shaving the pits, since at a later stage I could have pulled the hairs out with tweezers, which can hurt a lot. But I promptly decided to do them now with the razor, since hairless pits go so well with a hairless cock in making a grown man feel like a helpless little boy. So I went ahead and did everything in a quick and businesslike fashion, maybe even a bit rough, but purposely not making an erotic moment out of it. I then wiped away the few remains of the shaving cream with a wet hot towel, and finally rubbed over all the shaved areas with a good amount of Remy Martin brandy. The brandy stung him just as much as a shaving lotion would have, and left a much better taste there in case I might later want to work over any of the areas with my own mouth. His ass I would shave later, as it would be difficult to do so while he was tightly stretched out with ropes to each limb, and I did not want to take him off the ropes yet.
I again began to worry that I might have made a mistake in agreeing to be Will's prisoner for a whole week, when he told me that for the next 48 hours I would be required to hold an absolutely rock-hard erection without any interruption, that any wilting of my cock during that period, even in my sleep, would be severely punished, and that I would also be punished if I came during that time. I have held a fairly hard erection for several hours many times, even after having come a couple of times during the period, but the longest I had held a really rock hard one without any wilting at all was only for three hours, which I had once done in front of the whole football team, on a dare from a high-school classmate. Of course, it helped on that occasion that I was able to turn the dare into a contest that was joined in by several other team members. It was a lot easier for me to hold my own very hard stiffie while I was carefully watching a bunch of naked hot young jocks trying to hold their own woodies. Anyway, I told Will he was crazy thinking I could hold a really maintain a really rock hard erection for 48 hours straight, even when sleeping. For a reward I got another very hard paddle to my ass. It was obvious that Will would not tolerate my contradicting him. The accumulation of pain from the whip and the other paddlings I had already received made my ass even more sensitive, and each swat hurt more than the previous one. I decided the only thing I could do at this point would be to shut up, and try to survive.
That was obviously the right decision, since as soon as I was quiet Will proceeded to rub my whole back side, from my neck to my ankles, with a very nice, cool and sweet smelling cream that greatly soothed the pain from the whipping. He did not neglect my cock and balls either, and fondled them very gently quite often during the whole process, never once squeezing them hard, although I really don't mind a little pressure there once in a while. My cock responded instantly, and pointed straight up and rock hard, beautiful to behold. I could tell Will liked it a lot, from the way he kept looking at it. I was again sure of myself, and knew in my heart that once Will had tasted that cock in his mouth or in his ass, or better yet in both places, he would be so in love with it that he would agree at once to submit to me as my slave.
After this had gone on for a while Will took some paper towels and wiped dry his hands and my cock and balls. My back side he left with the cream on, which was nice, and I was feeling much better. He then again put the mask over my face, so I could not see a thing, although my ears were left uncovered. I did not like being blind, but then he went on to play with my nipples, which I like a lot. Having my nipples played with always drives me crazy with lust, and I could feel them quickly growing hard under Will's touch. At first he used only his fingers, rubbing and pinching, sometimes fairly hard, but then he put his mouth to my nipples, going from one to the other, licking and sucking and then biting, first quite gently and then slowly harder and harder. The pain form the biting was quite intense, but strangely pleasurable at the same time. My whole body was shaking, but this time not from fear but from excitement. Each time he bit one it felt as if a jolt of electric excitement would jump out from his teeth and pass through my nipples over to my whole body. I had often before tortured my own slaves, and enjoyed it a lot, but today my body was encountering real pain for the first time. I was surprised how sexually exciting it could be. My cock was twitching, and not just because Will was also rubbing it with his hand, and occasionally with his body, both our cocks grinding hard against each other. This, I felt, was not going to be so bad. How wrong I was.
Of course, I could not see what Will was doing, as the mask was still covering my eyes, and could only figure what was going on by the feelings in my body. Will had left my nipples free for just a few seconds when I heard the characteristic sound of shaving cream coming out of a can. I then felt Will spreading the cream in my pits and all around my cock and balls. I knew it would be useless to complain, and so kept my mouth shut. I was still quite hard, of course, and did not mind my cock being handled, but Will did everything quickly and even roughly: first the pits, then the cock and the balls, pulling and turning as if he was in a great hurry. The only part I enjoyed was when he wiped everything up with a hot wet towel. He then put on a shaving lotion which stung a lot, though it smelled more like some kind of liquor than a normal lotion would.
The pain in my nipples from Will's biting had gone down quite a bit during this process, but the excitement remained while he was shaving me, and I was groaning with pleasure during the whole time. The fact that he was touching me was enough, and the fact that he was acting rough actually only made it better. Suddenly I felt a very sharp pain at the base of my prick. It seemed at first that Will was biting me there, but then I realized that was not possible, since he could not be biting both sides at once. Yet it did feel like there were teeth there. The pain was horrible from the first instant, and kept getting worse, first just on one side of my prick, then on both, and I started to scream again. Will accused me of being a baby, and said he had only put a few alligator clips along the base of my shaft, though I could tell from the tone of his voice that he really enjoyed hearing me scream. But I was not screaming for his pleasure, but because it really did hurt. I couldn't see a thing, but it felt as if there were at least a hundred of those clips torturing the base of my cock. I was now again trembling from fear, and would have trembled a lot more if I had known what was to come. After the first few minutes the pain, while still there, was not quite as sharp, and I tried to regain my composure, breathed deeply, and stopped screaming. That was a mistake. Will took it as a sign that more pain could be applied. I felt him pulling on my foreskin, and then lightning hit. I could tell he was putting more of those damned clips there, and it hurt much more. My foreskin is extremely sensitive, and while I certainly enjoy very gentle bites there when I am getting a blow job, an assault like the one I was now getting was absolute hell, much more than I could possibly take. I was again screaming and babbling. Most of the screams must have been incoherent, but I think I was also asking Will to please let me go, that I could not take so much pain. This earned me a very hard swat with the ass paddle, and even in the midst of the pain I stopped screaming. Will then reminded me that if I wanted out I had safe words at my disposal, both to slow down and to stop, which I had not used, but could if I wanted to. I then surprised myself by making a mental resolve that I would show Will I was stronger than he was, and that no matter what he put me through during the whole week I would not even use the safe slow word. I pressed my lips firmly shut, and signaled a "no" with my head. Will would not break me. I would get through this week, and make him mine the next, no matter what.
Among the many goodies I had prepared for Richard, I had four dozen alligator clips I had bought at an electrical supply store. As their name implies, these are long and narrow clips, shaped like the jaw of an alligator, and have fairly sharp teeth along the inside of the jaws. A spring wrapped around the hinge at the base of the clip holds them tightly shut. I had tried many different stores back in Madison, looking for the strongest clips, and had finally purchased the ones I now use. Their jaws (measured form the hinge) are an inch and a quarter long, their teeth sharp, and their spring fairly strong, so their bite is quite painful. I have tried them not only on most of my slaves, but even on myself on certain occasions, and can say that the pain they cause is quite intense, and just this side of the unbearable. I had all four dozen ready on a nearby tray, and only had to reach over for them. If Richard only knew what was about to hit him, he wouldn't be purring so much. With one hand I grabbed the skin on the base of Richard's prick and pulled it out to the side, while with the other I quickly attached two clips there. Richard was already screaming loudly before I had a chance to repeat the operation, putting another two on the other side of his prick.
If Richard's prick had been very hard all this time, mine was now even harder than his. With my left hand I felt the velvet smoothness of its skin as I moved it slowly back and forth along the steel-like shaft, the foreskin closing over the deep red head, and then opening to reveal it again, my hand moving very, very slowly, as I did not want to come again too soon. All the while Richard was giving me the gift of his loud screams, much sweeter to my ears than any music could ever be. I stepped back a little to better appreciate the gorgeous sight before me. I turned on two spotlights above Richard, one slightly in front and the other slightly in back, leaving the rest of the dungeon in darkness. And there, in the middle of it all, was this gorgeous hunk, this absolutely beautiful piece of hard young meat, perfect smooth skin nicely tanned, his muscles sharply defined as he fought against the pain by pulling on the ropes that held him stretched out, his biceps formed into a tight ball, his chest a beautiful V-shape, going from the very wide lats to the narrow waist, the width of the lats emphasized by the smooth hairless pits, the six pack of his abs standing out sharply as they clenched and unclenched with his ragged breathing and screams, the whole back of his body still showing the ministrations of my whip, his round and nicely muscled bubble ass showing the most welts, and best of all the rock hard cock, pointing straight up in its light pink skin, the thick ropes of the veins standing sharply out in a light blue, the loose flaps of the foreskin lightly covering the angry red head, with the large piss slit clearly visible, oozing pre-cum by the bucket, the whole thing trembling from the pain being provided by the alligator clips, two on each side of the base. I was struck, as always, by the incongruous beauty of a grown man's large, hard and quivering prick surrounded by the smooth, hairless skin of a boy. It was almost too good to be true, so for good measure I put an extra clip on each side of his prick, but I don't think Richard noticed the difference, as his screams continued just as loud.
I could have continued to enjoy this for a very long time, but after a while Richard took a deep breath, evidently trying to collect himself, and stopped screaming. It was now time to up the ante, so I grabbed a hold of his cock, pulled it out towards me, again admiring the bulging, dark red head inside the foreskin, with the large open piss slit clearly visible in the center, dried off the excess pre-cum which made it slippery and awkward to handle, and as quickly as I could put three alligator clips to the center of the foreskin, on top, fairly close to each other but not touching, one jaw of each clip going inside the foreskin and the other one outside. I know from personal experience that the clips hurt a lot more there than they do along the base of the shaft, and Will's reaction confirmed this. The screams resumed. They could hardly have been louder, as he had been screaming at the top of his lungs from the beginning, but now the pitch was much higher, and the screams sounded almost girlish. I could see tears coming out below the eye mask, which excited me even more. I was enjoying this more than I could have anticipated. The weight of the clips was pulling the foreskin partly down, and they jiggled back and forth as Will swayed and fought against the ropes holding him, revealing more of the dark red prickhead than was visible at first. After a while the screams began to form into words, and Richard again started to complain about how he could not take so much pain, and could I please let him go. I listened without paying attention to the words, but after a while I got tired and decided to put a stop to that, took the middle weight paddle, and gave Richard's ass a very hard swat. This proved perfectly effective. His body jerked forward against the ropes, not going very far since he was still tightly bound, and before it had time to swing back the screams had stopped. I then reminded Richard that he had safe words available which he could use. I asked him if he remembered them, and he nodded yes. I asked if he wanted to use them. After a slight pause he closed his lips firmly and signaled "no" with his head. I smiled, though he could not see me because of the mask. This was going very well. He was setting himself up as the strong macho type, which would make his inevitable fall later on even more dramatic. But it was now time to again add some pleasure to the pain, mixing the two so they would in time be unmistakable to him: pleasure would be pain and pain would be pleasure.
Will then went back to my nipples. They were still hard and at attention, and as he closed in on them with his mouth I once more swooned with pleasure. The pain on the shaft of my cock, and even more on my foreskin, was still a throbbing presence, but it eventually moved to the background. Will was very gentle now, licking and sucking and even pulling with his teeth, but not biting hard. He also reached around and fondled my ass, digging his fingers deep into the muscles of my buttocks. He then went on to do the same to my shoulders and then to the rest of my back, but all the time maintaining an almost constant attention to my nipples. After a while the pain on my prick was almost forgotten, and I was audibly groaning and sighing with pleasure. This was another big mistake on my part. Will then wrapped his arms around me, holding me tightly to him, and started to grind his whole body against mine, particularly grinding our pricks against each other. This would have been heaven under other circumstances, but was unbearably painful now, as the pressure from his prick made the teeth of the alligator clips bite harder, both on the base of my cock and on its foreskin. As I started to yell again Will kissed me deeply, his tongue inside my mouth pushing forcefully against mine. This stopped the yelling, but not the pain. For some reason I remembered the name of an old movie I had seen a long time ago, The Agony and the Ecstasy. It described my situation perfectly. And it was not that the two were separate from each other, but that they blended into one, the pleasure and the pain unified in a single, impossible sensation. I was sure I was going to go crazy.
After a good while Will stopped, took off my eye mask, and told me he was going to take the clips off. He warned me that this would hurt even more than when he put them on, and that it would make no sense to use the safe word, since there was no way to stop that pain until it went down by itself. He suggested I watch as he took them off. Of course, it was Will himself I wanted to watch, as he was still naked, and I had a hard time taking my eyes off his beautiful body and even more beautiful prick. But I had been warned, and braced myself for what was to come. When I looked down I realized there were only nine clips on my cock, three on each side of the base of the shaft and three more on the foreskin, and not the twenty or more I had imagined. I was also amazed at the strange look of my hairless prick, but had no time to dwell on that as Will grabbed my cock with one hand and with the other first dried all the precum with a paper towel, and then quickly yet gently took off the three clips on the left side of my shaft. As the mouth of each clip opened a sharp pang of pain shot through, each successive one adding intensity to the pain of the ones before. And a few seconds later it got worse, as the blood started to flow back to the whole area where the skin had been pinched, though I was not sure it was really worse than at the beginning, when the clips had been put on. In spite of the fiery pain I kept my resolution not to scream, though I did groan a lot through my clenched teeth. After a while I managed to take a look at Will and he was smiling at me. I somehow sensed that he was proud of me for making an effort not to yell any more, and this made me feel very proud of myself. It came as something of a surprise to me that I really wanted to please Will, and that his approval meant so much to me. After the pain had eased a bit Will took off the three pins on the other side of the shaft. Knowing what was to come this time made it no easier than the first side. I was squirming against the ropes holding me as the intense pain form my cock shaft radiated out again, consuming me.
Richard's nipples were from the first a joy to behold, and would be much more so after I worked them over. I took them in my mouth, alternating from one to the other, at first just licking and sucking very gently, but after a while I couldn't resist biting them, lightly at first and then progressively harder, though never hard enough to draw blood. I also pulled them out with my teeth, to see how far they would stretch. Not too much, I found, since his skin was quite firm. But the nipples did grow in size, becoming hard and erect, like tiny pricks. I knew Richard was in pain from the clips on the base of his cock and even more from those on his foreskin, and thus the action on his nipples would distract him. He was now groaning, but I could tell they were groans of pleasure. He even seemed to enjoy the biting. To add to his delight I reached around with my hands and started to massage his buttocks, kneading them deeply with my fingers, and then extended this to his shoulders and eventually the rest of his back. And of course, my mouth would constantly return to his nipples, working them over carefully. Even though Richard's eyes were still covered with the mask, I could see the rest of his face, and it showed a huge smile. He was obviously enjoying himself a great deal, in spite of the pain I was sure he still had in his prick. This is precisely what I wanted: pain and pleasure had to become a constant association for him, until one would be completely undistinguishable from the other. I proceeded to reinforce this by hugging him tightly with my arms and grinding my whole body against his, taking extra care to grind his cock against mine. Now the very place where his pain was sharpest would also be the very place where the pleasure was greatest. Perhaps I went too fast, or pushed too tightly, but Richard let out a loud yelp at this point. The moment I saw his open mouth I kissed him hard, pushing my tongue deeply inside, feeling around all over. Richard's yelp was immediately drowned, and his groans of pleasure soon returned. It was a long, hard kiss, and Richard's tongue was soon playing with mine. I was now more sure than ever that Richard would belong to me forever.
Like all good things, the grinding and the kissing had to end. I like to change the action frequently, and never let my slaves grow bored. I decided to start taking the clips off. Anyway, if they stay on too long the skin becomes essentially numb, and the pain disappears, which destroys their whole purpose. I first took off Richard's eye mask, as I wanted him to watch what was going to happen know. I was still naked, of course, and very hard, and the spotlights were still on, and from the moment his mask went off Richard had a hard time keeping his eyes off me. This was good. A slave should be in love with his Master's body, and even more with his Master's prick. Richard would, of course, become intimately and deeply acquainted with my prick that same day, but that would have to wait a while still. Everything must come in due time.
I then told Richard that I was going to take off the clips. His cock was by now covered with precum from top to bottom, filling the loose flaps of the foreskin, sliding down the shaft, covering his balls, and dripping to the floor, where it had formed a small puddle. The wetness made the whole thing shine brightly under the spotlight. It was really a lovely sight. But the precum was also quite slippery, so I first dried things off a bit with a paper towel. Then I grabbed Richard's prick firmly with one hand, and with the other quickly took of the three clips on one side of the shaft. I knew that as the blood started to flow back to the skin that had been pinched by the clips the pain would be intense, but even though Richard was grimacing he kept his mouth tightly shut, and did not cry out. After a while I took off the clips on the other side of the shaft, and again Richard held on. I smiled at him, and when he noticed he smiled back. This was going on very well. We had quickly reached the point where my approval was important to him. I again looked him over carefully, enjoying the sight of his beautiful body, entirely at my disposal. The three clips on the foreskin were still there, but they had been the last to go on, and could still stay a while more before being taken off. There was something else I wanted to do first with Richard's balls, which had not received enough attention yet.
As I looked down at my cock a few minutes later, after the pain on my shaft had eased somewhat, I noticed with alarm that it was no longer quite as hard as before, and that instead of the head touching my abs the whole thing was now only about 45 degrees above the horizontal, maybe just a little bit better. I mean, I was still hard, but not absolutely rock hard as Will wanted. The three clips on my foreskin were still there, of course, and still hurting a great deal, and their weight (though not that much) was perhaps helping to bring the cock down. I was afraid that if Will noticed he would punish me. But apparently he didn't care, as he proceeded to squat in front of me and started sucking on my balls, first one and then the other, alternating slowly back and forth between them. This brought my prick back up almost instantly. I was really enjoying this, and as far as I was concerned it could have gone on forever. Surprisingly, the fact that I was tied and helpless, and totally at Will's mercy, made everything even more exciting. I was even starting to enjoy the pain in my foreskin, which was no longer as sharp as at the beginning, but still a constant, throbbing presence. After a while I realized I was groaning loudly with pleasure. But then I noticed Will was trying to get both of my balls in his mouth at once. Now, I must mention that I have very large balls, and they do not fit easily into a normal mouth. But Will had the left one already inside his, and was sucking on the right one very forcefully, while at the same time pushing it in hard with his fingers. Eventually it popped inside, joining its twin brother, and I could not help yelping loudly at the pain I felt as it went between Will's teeth. I was worried that Will might choke on them, but as I looked down he was looking up at me, smiling broadly, and seemed much pleased with himself. I was not so pleased with what came next.
Will then started to chew on my balls, forcing them to each side by pressing between them with his tongue, and then squeezing them with his molars. He had a very strong tongue, as I already knew from the experience of his french kiss a bit earlier, and he now put it to good use by separating my balls and forcing them sideways, thus keeping them between his molars. He then set up an impossible to predict sequence of squeezes on my poor balls, sometimes closing his jaws very, very slowly and increasing the pressure steadily until I thought they would explode. When that happened I could not avoid letting out a long, loud and high-pitched scream. At other times he would give them a series of very rapid squeezes, perhaps not as hard as the long, slow ones but also quite painful. But he would also mix the chewing with very gentle sucking, and often his tongue, instead of forcing my balls to the sides of his mouth, would move them slowly around in a very gentle caress, making me moan with exquisite pleasure. Again, the agony and the ecstasy, the pain and the pleasure becoming an undistinguishable whole. This went on for quite a while. I was sure my balls would be so swollen by then that Will would have trouble letting go of them. I also started to worry about Will, thinking that he must be tired from the position he was in, although he was no longer squatting, but kneeling. The very idea of that powerful hunk kneeling in front of me excited me tremendously.
And then, as though he had been reading my mind, and at the end of a particularly hard and painful slow squeeze, Will released the pressure of his tongue so my balls could move more to the center of his mouth, closed his jaws enough so that the balls would not be able to exit between his teeth, and started pulling on my ball sack, stretching it out, not biting on the skin but squeezing my balls, not between his molars but between the back of his teeth and the stretched skin of the ball sack itself. I thought he was going to rip them out. I was really scared, not just because of the pain which engulfed both the balls and the ball sack, although there was a lot of that, but even more because he kept steadily pulling harder and harder, and I really thought something was bound to tear. When I thought the limit had been reached Will just pulled harder, and then harder still. My heart was pounding from the pain and the fear, and still Will kept on pulling. I looked down and could see the pale and impossibly stretched skin of my ball sack coming out of Will's mouth. I was sure it was going to rip. Then all of a sudden Will opened his mouth just a tiny bit more, pushed very hard against my balls with his powerful tongue, and my balls very slowly oozed out between his partly clenched teeth, both coming out together, gaining speed and making a loud pop at the very end. The pain at that point was so bad I thought I was about to vomit. I wanted to scream but the scream would not come out. I tried to breathe in and my stomach muscles were so cramped that I couldn't. It seemed I was also going blind, as I couldn't see anything clearly, only dark spots moving wildly in front of my eyes. I think I actually fainted, and came to, trembling, only when Will threw a bucket of very cold water on me.
[To be continued. Comments will be appreciated by the author: rob8mann@hotmail.com.]