Will and Richard

After thinking about it for some time, and weighing various alternatives in my own mind, I decided that the next part of Richard's punishment should not include any additional pain. He had gotten quite enough of that for the time being. An excess of pain just dulls a slave's sensibility. Whenever possible I try to use pain in a way that will heighten sexual tension, and for pain to serve that purpose it must be dished out in very careful doses. Often less is more, and more is less. At the same time, there had to be further punishment for Richard, not only because he deserved it, but because I had told him he would get it. The worst thing a master can do is not to deliver on his promise of punishment to a slave. That just carries the message to the slave that he may occasionally try to get away with something, a most dangerous thought. The logical conclusion to my line of reasoning was that the punishment ought somehow to involve not additional pain, but the denial of pleasure. And that is what I resolved to carry out. It was a good thing my dungeon was ready for that too.

I was going crazy trying to figure out what was going to happen to me. My balls were killing me, as were the insides of my legs, not only from the whipping but because they were still stretched out to the sides more than I could bear. But the worst part was just hanging there, without being able to see anything because of the face mask, and not knowing what would come next. I lost all sense of time. I tried to count my heartbeats, but my heart was beating so fast I could not keep track. I was trembling, and it was not from the cold. I had often read about cold sweat, and for the first time I could feel it, as that is what was coming out of my pores right now. I felt myself drenched in sweat, and knew it was from the worst of all fears, the fear of not knowing. I have no idea how long I hung there with my mind spinning, it seemed like hours but was probably much less, and eventually I heard noises again. It was obvious Will was back in the dungeon, though I had no idea what he was doing. I again heard drawers being opened and closed, and that noise I was sure was not foretelling anything pleasurable for me, since I knew what some of those drawers held, and Will had warned me that my punishment was not over.

All of a sudden Will spoke to me. In the state I was in I could not understand anything at first, but after just a few moments I noticed that Will's tone was no longer angry. This had a very calming effect on me, and then I realized Will was telling me I could bring my legs together again. I had not even noticed he had already taken the tension off the ropes that were pulling my ankles apart. It was such a great relief to do as I was told. My hip joints were still hurting, and the pain in my balls, though dull, was quite intense. Even so, I was grateful to Will for not keeping my legs stretched out. It was really good to stand up straight. I was no longer trembling, for I was sure that Will would not do anything to me that I did not deserve, and certainly he would do nothing to me that I could not bear.

My mind made up, I walked down to the dungeon again, as silently as possible. First thing I did was to loosen the ropes on Richard' s ankles, though I think he did not notice this, as he kept his legs exactly where they had been. I did not linger much looking at him, though he did seem to be trembling a bit. I then went looking for the enema bag, which I knew was somewhere in the chest of drawers. I always use a bag when I give an enema to a slave. The enema hose should never be attached directly to a faucet when a slave is getting it.

There is no way to accurately measure the volume of liquid going in, and the slave' s reaction is not a reliable guide. He may complain before there is reason to, and not get enough. Much worse, he may (thinking this will please his master) not complain soon enough, and get too much. It is very easy to do serious damage to the slave this way, and as I said before, a slave (more so one as gorgeous as Richard) is always a valuable possession that you do not want to damage. So I use a two liter bag, which is about the right size for a normal sized adult.

I found the bag soon enough, and not only the bag, but also the magnificent dildo nozzle that went with it. It had been beautifully carved by a former slave back in Madison, from a solid block of mahogany, and shaped very realistically as a seven inch long uncut prick, nicely thick in proportion to its length. The carving was very realistic, with the veins standing out, the foreskin only slightly retracted, the head a little thicker than the shaft. It was stained a deep, dark reddish brown. For some reason most people who see it for the first time think it to be much larger than it actually is. A quarter inch diameter hole had been drilled down its center, with the opening where the piss slit would have been, and with the brass fittings on its base it could be attached to the rubber tube coming out of the enema bag. It was too bad that, because of the face mask, Richard could not see this beauty yet, but his ass would be feeling it pretty soon. I also found the bottle of liquid castille soap that I add to the warm water of the enema bag for the first couple of rinses, as this makes the cleansing much more effective.

After I was ready I went over to Richard. First thing I did was tell him he could bring his legs back together again, as he was still in the stretched out position. He did not seem to understand me at first, and I had to repeat myself a couple of times, but he finally got it. After he was standing in a normal position he let out a huge sigh, apparently one of relief. The trembling seemed to stop after that. I then explained to Richard what the next part of his punishment was going to be. I told him how I had originally planned not to take his ass cherry until the 48 hour period of constant erection had been completed, and that his prize after that would then have been a very, very long (and very gentle and loving) fuck from me, which would culminate in our having a simultaneous orgasm of seismic proportions. As part of his punishment for not being clean, he was now instead going to get a thorough enema, and then would loose his cherry in a very rough fuck, which would only last enough for my own orgasm, and even after that he would not be allowed to come at all for at least two or three more days. Richard had by now apparently learned something, as he heard me in silence and did not even attempt to argue with me.

I then untied both his ankles and his wrists, and took off his face mask, as being able to see the process of the enema would enhance the humiliation. I then led him over to one of several saw horses I had in the basement, this one close to the bathroom. It was just two A frames, firmly bolted to the floor, with a 4" x 4" wood bar (well padded) held horizontally between them. The frames had rings at all the appropriate places, so the slave's wrists and ankles could be tied to it, though I was not going to tie Richard just yet. Again, his not being tied would make the enema more humiliating. I bent him over the bar, and told him to stay there while I fixed the enema. I then went to the bathroom, and filled the bag with barely warm water, to which I added just an ounce of the castille soap. After mixing the solution, I went over to Richard, and for the first time showed him the nozzle I would be using. I let him look at it up close, to his heart's content. This got a reaction!

It was good being able to stand up straight. Although my arms were still tied they were not too tight, and I was able to move them a bit. I could also lift my knees, which eased the pain in my hip joints. The intense throbbing pain in my balls was a constant presence, but I tried not to pay it too much attention. Will then told me what was coming next. He was going to give me a rough fuck! Hell, if that was the worst that was in store for me, I was sure I could take it. I had often enough fantasized during the last few days about being fucked by Will, and in my fantasies it was usually a rough fuck. He also told me that as part of the punishment I would not be allowed to come, not only while he fucked me, but not even for the next several days. That I did not like. No sir, not at all. I usually come several times a day, preferably while fucking some cute jock, or while getting a blow job from one, and by my own hand if nothing better is available. I cannot remember when was the last time I went more that 24 hours without coming at least two or three times, certainly not since I was in fifth grade or so. Not being able to come, and not the rough fuck, would be the real punishment. On top of that, not coming in all that time would surely not help my aching balls, which were loudly begging for release. But I had no choice in the matter, so I said nothing. I knew by now it would be a waste of time to argue with Will, and might even earn me additional punishment.

Will then untied me completely, took off my face mask, and led me over to what looked like a whipping horse. It was awesome, a thick piece of wood (at least it was padded) held horizontally by two A-frames. There were rings all over the frames too, I suppose so one could be firmly tied to it. But Will did not tie me, at least not yet. He did bend me over the horizontal bar, none to gently, and told me to stay there. You can be sure I did as I was told. Will then went over to the bathroom which was just next to the frame, and I could hear a faucet being opened, and water running. It did not take me long to realize Will preparing the enema which I now realized I should have given myself before coming over to his dungeon! I started to tremble again. I had never had an enema, not even when I was little. Will had not mentioned the enema itself would be rough, only the fuck, but I could not make too much out of his silence on the matter. I was only a slave at this point, and he did not have to tell me every detail in advance. But I have to admit I was really worried. So I did the only thing I could do: I just held my position, even though I was a little dizzy from being bent over, and perhaps also from thinking about what was going to happen to me next.

In spite of my forebodings, I was not prepared for what Will had in his hands when he came out of the bathroom. It was an enema bag, connected with a rubber hose to a monstrous dildo. Clearly Will intended to use the dildo as the nozzle for my enema, but there was no way my ass could take that beast. The main problem was not its length, though it seemed to be at least ten inches long. What scared me was its thickness. If the shaft looked thick, the head was even more so, it surely had to be over two inches in diameter. I was certain my virgin ass could never stretch enough to take it. If I was a little dizzy before, I was close to fainting now. I could feel my heartbeat racing again, and my legs began to tremble. If I had not been bent over the horse, I would have fallen down for sure. And damn Will, as soon as he noticed how scared I was he actually started to laugh! He then brought the dildo up close to my face, and I had to admit to myself (though not to him) that it was a real beauty. It seemed to made from wood, stained very dark, which made it all the more menacing. But it was really very well carved, and was very realistic, with thick veins standing out all around, a beautiful foreskin retracted just barely enough to show a small piss slit from which the enema water would surely come out. Will turned it slowly in front of my eyes, letting me feast on it. The effect was strangely hypnotic. I was afraid of the brute, no doubt about it, I was really terrified, but at the same time I was curious to know how it would feel to have it pushed up my tight virgin ass. I was sure it would rip my sphincter, sure that the pain would be terrible, and maybe even do permanent damage, yet there were moments when I seemed not to care. I was panting, I was trembling, my throat was painfully dry, I couldn't speak. I wondered if I was going crazy or what, I did not know what I was thinking or what I wanted.

But the fear won over. I was so scared I started to retch, and I thought I was about to vomit. There was no longer any doubt in my mind: I had to ask Will for mercy. I made a great effort, produced a little saliva in my dry mouth, and after swallowing it was able to croak out a plea of mercy. I knew that the safe word would no apply, but surely Will would respond to my justified fear, and would take pity on me. I asked for permission to speak, and thankfully Will granted it. I then explained to Will that he would surely kill me if he pushed that monster wooden prick up my very tight virgin ass, that there was no way on earth I could stretch enough to take that gigantic two inch thick head. I probably started to repeat myself, but I had to get Will to realize my ass had never been penetrated before, that such a colossal dildo was not meant for a beginner like me, and that it would rip me open. Will, God damn his soul, did not even answer. He just kept showing me the object of my fear, moving it slowly in front of me so I could see it from every side, and all the while he had the biggest smile on his face that I had ever seen. The more I pleaded the more he smiled, until finally he was laughing out loud, my terror serving only to amuse him.

He finally tired of the game, put down the dildo on a table next to the frame, and with his right hand gave my ass two very hard swats, one on each buttock, while telling me to shut up. That really brought me up short. I knew for sure there was nothing I could do to stop the mayhem which was about to overwhelm my ass. The inevitability of what was about to happen did not make me feel any better, but I knew when I was beaten, and that if I continued to argue I would only make things worse for myself, so I resigned myself to my fate and shut up.

I did not dare to rise from the bent over position which I had been holding for a while, but did lift up my head a bit to see what Will was doing. He was standing right in front of me, obviously on purpose so I could see everything. The monster was still on the table, but Will now had a big jar of petroleum jelly on his left hand, and was taking a big glob of it on his right middle finger. He then walked around me, and told me in a very forceful tone to spread my cheeks, using both my hands, and to try to relax, for my own good. Tears were already running down my eyes in anticipation of what was to come, but I complied in fear as well as in silence. I reached out behind me, and spread those cheeks as wide as I could.

Will had promised to be rough, but he started out gently enough. It was obvious he began with only one finger, which entered me quite easily. He moved it around for a while, and I could feel when he took it out, took some more jelly, and then went in with two. I had no trouble accommodating two of his fingers, and actually started to enjoy what he was doing. He moved them slowly in and out, and wiggled them around, pushing in all directions, and going deeper each time. He quickly found my joy spot, and had me grunting with pleasure. After a while it appeared he started using three fingers, and it was not so nice anymore. He was really stretching me now, and when he went in really deep with all three it started to hurt. He was jabbing hard now, trying to go in all the way each time, not caring about my joy spot any more, still making me grunt, though not so much in pleasure now. This went on for a while, surely longer than I would have liked, until Will apparently decided it was time to move to the next stage.

Richard's eyes really opened up when he realized what I had ready for him. The look on his face was exquisite. He had that strange combination of fear and curiosity which I have so often noticed on slaves when they are about to get more of something than what they had expected. I had used the enema with this dildo many times on many slaves in Madison, and his reaction was about typical. For a while he just looked at it, mesmerized by its beauty, and probably also by its size, wondering how it would feel as it pushed slowly into his ass. But soon he realized that the feeling would involve pain, and his expression changed. He asked permission to speak, and I granted it, only because I was curious to know how he would try to talk himself out of something he surely must have known he could never avoid. His voice was quite raspy at first, apparently the fear had dried his throat, but soon he started babbling about the dildo (he even called it the monster, the beast) being over ten inches long and over two inches in diameter, asking for my pity, saying over and over that he was a virgin and could never take something that big. He must either have been lying, or more scared than I realized, since the dildo was only seven inches long and just a little over an inch and a half wide at the widest point of the head. I had no doubt that he was indeed a virgin, and for the rest assumed it was just his fear speaking, since it was not uncommon for slaves, seeing the dildo for the first time, to think it was bigger than it actually was. Indeed, even though it had been fashioned using my own prick as a model, it had been carved on purpose somewhat smaller than mine. If I am going to use it on a slave just before I fuck him, I don't want the slave's ass to be stretched out of shape when it's my own prick going in. So I did not even take the trouble to answer Richard, but just laughed in his face as I brought the beauty up close to him, and turned it slowly around, so he could see it from every angle. His pleading, while funny at first, became tiring after a while, so I gave his buttocks two very hard swats with my open hand and told him to shut up, which he quickly did. At least he seemed to be learning proper behaviour.

After that it was up to me to keep the show going, so I got out a jar of petroleum jelly to lubricate Richard's ass. This type of jelly is no good when you are going to use a condom, as it harms the latex, but I was going to fuck Richard bare back, and petroleum jelly makes the best water-tight seal for an enema. So I told Richard to use both hands to spread his cheeks, which he did very quickly. I could not resist inspecting him at that point. He was a jewel to behold. He was bent over the bar of the horse, head deep down, chest panting, muscular legs quivering ever so slightly, his cute pink asshole staring straight at me. His balls still showed the whipping they had recently received, and their sight excited me no end. I could have continued to stare for quite a while, but once a process starts the pace must be maintained, so I started to work the jelly into Richard's ass, first using only one finger, which he seemed to barely notice, and then two. He seemed to enjoy this part, and I decided to prolong it.

I had told him the fuck would be rough, and would be only for my pleasure and not for his, but could not resist wiggling my two fingers deep inside his ass, moving them slowly in and out, turning them around in every direction, and when his grunts let me know I had found his joy spot I rubbed it repeatedly. Richard really liked that. The whole principle of my slave training process is to have them associate pain with pleasure, and this would only help.

Matters changed when I began using three fingers. There was no doubt in my mind (not that there had ever been) that Richard's ass had really never been penetrated. My fingers are not that thick, but apparently when I pushed three of them deep inside his sphincter had trouble adjusting, and the tone of his grunts changed considerably. But he did not complain, which was good for him, for any complaining would just have earned him a spanking. So I kept up working the three fingers in, pushing hard to go deep every time. He might not be enjoying it for the moment, but it was actually for his own good, as it would make the dildo's entrance easier. Every once in a while I could feel the hard turd which had brought the whole process up, but it did not bother me any more. Actually, I now realized it had given me a chance to teach Richard a valuable lesson which he might otherwise not have learned.

When I considered his ass had been sufficiently lubricated, I reached out for the dildo and lubricated that too, leaving only the base so that I could grab it well. The bag was already full of warm and soapy water, so it was time for the next step. Richard was still holding his cheeks spread out with both his hands, and I warned him to hold that position and not move. I then placed myself behind him, dildo in one hand and enema bag in the other. I decided to hang the bag from a rope that hung from the ceiling, as that would leave both my hands free for the dildo. Richard was bending his neck first one way and then the other, trying to see what I was doing, and I did not mind, for when I started to push he would probably close his eyes. So I grabbed the last inch and a half of the dildo (the part which I had not lubricated) and placed the tip gently upon the pink pucker of Richard's ass. He had at some point told me he had fucked many of his own slaves, so he had to know what was coming next, but I warned him that it would be best not to try to close his ass, but on the contrary to relax as much as he could. I even reminded him that the best way to relax the sphincter was by pushing out, as if you were trying to take a shit, but that in this case he would have to be very careful about the pushing, for if he actually pushed a turd out he would regret it the rest of his life.

Pushing a dildo into a tight ass is a rather delicate operation, specially if it is made from a hard substance such as wood, and not from rubber. When you fuck someone with your own prick, the prick head is somewhat sponge-like, and eases rather gently into the ass hole. It is only the prick shaft which is really hard, and since that comes later it makes the penetration somewhat more gradual, and thus gentler. But a dildo made out of solid mahogany is something else, more so if (as was the case now) the head is actually its thickest part. So I had to go in slowly, as I surely did not want to tear Richard's ass. With slaves, causing pain is one thing, doing damage is something else altogether.

I knew for sure what was coming next, but that did not ease my anxiety. My virgin ass had already been stretched quite a bit by Will's fingers, but I knew the dildo would be a lot worse. I had seen it up close, it was made out of wood, which is actually a very hard material, much harder than a prick, or even three fingers. But the problem was not how hard it was sure to be, but how huge it was. When I was alone, and not expecting a visit from any one, I had of course often played with my own ass, pushing a couple of fingers in and wiggling them around, massaging my joy spot while jerking off. But that was just for fun, and what was coming up for me would not be any fun, I could be sure of that. The more I looked at that monstrosity in Will's hands, the more I knew it would tear my ass apart, even with the advance stretching that Will's fingers had provided. Not only that. There was also the matter of Will's warning, that he was going to be rough with me. Even in the gentlest of hands that beast would rip my ass, I was sure. Handled roughly it would kill me. But I dared not move and make matters worse for myself, so I kept to my position bent over the whipping horse, even though my legs were trembling with fear.

Will had taken his fingers out of my ass, and for the moment that made me feel strangely empty. But he soon moved over to the table and picked up the dildo, which he thoroughly covered with the same jelly he had used on my ass. He then grabbed the bag, and moved behind me. I was scared to try to see what he was doing, but could not resist the curiosity, so I twisted my head around, while keeping my position bent over the horse. From what I could see Will tied the bag from a rope which was hanging from one of the ceiling hooks, and then stood directly behind me. In spite of my awkward position I could see him clearly, and he was, as always, magnificent. Bent over as I was I could not see his chest very clearly, but I could surely see his balls and the underside of his gorgeous prick, which swung from side to side each time Will moved. His erection had, if anything, gotten even bigger. It was obvious that working my ass with his fingers had made him even hotter than he was before, and all I could think of was that as soon as the enema was over that very prick would be going in and out of my ass, and that I was actually looking forward to being raped. This was so strange, since I had never felt like this before. I had always been a very aggressive top, and here I was, bent over a whipping horse, patiently waiting for an enema, and wanting to be fucked by Will's huge prick. How was it possible for me to have changed so much in such a short time?

But I had no more time to think about my strange situation, as Will had finished tying the bag to the rope, and the tip of the monster dildo was already touching my ass. Will was kind enough to remind me to relax, which I was not sure I would be able to do. He put one hand on my lower back, the part that was just over the horizontal bar of the horse, which calmed me somewhat, but then he started to push. The dildo, of course, had a very blunt shape, and as soon as it started to go into my ass it also started to push my hole wide open. But in spite of his warning about being rough, Will was actually being quite gentle. I think he had pushed it in no more than a half inch when he slowly pulled it out again. I could also feel sort of a twisting motion in my ass, as Will worked the dildo in and out very slowly. This process was repeated several times, with very small penetrations, and I was beginning to enjoy it when the real thing began, and Will started to push in earnest. He was still working the beast in and out each time, but when he pushed in now he pushed hard. He was not being gentle any more, that was for sure. Each time the beast went in deeper, and each time the penetration hurt more, until it was quite unbearable. Will was encouraging me all the way, reminding me to relax, but it is hard to relax when your ass is being torn apart, when your flesh is about to be ripped open. I tried pushing out, as I had been reminded to do, and it helped a bit, but the pain of the penetration was still more than I could take. Each time Will pulled the monster out just a bit I pleaded with him not to continue, but each time he pushed it in again, just a little bit harder, just a little bit deeper, and each time I could only scream, and scream again, while the ever increasing pain in my ass dominated my whole existence. Will was no longer saying anything, just grunting slightly each time he forced the dildo in, stretching my ass hole more and more.

When I thought my ass was about to rip open, when I thought I would die in this damned dungeon, the strangest thing happened. After a particularly hard push from Will the dildo's head finally made it past my sphincter. The pain was extremely sharp as it went through, and I screamed loudly again, but it did not last long, and after a few moments I felt a little better. It was the shaft, of course, that was now holding my sphincter open, and since it was slightly narrower than the head the pain level had gone down from impossible to manageable. Will must have noticed too, as he made some comment about the worst part being over. I could feel the dildo now being slowly pushed all the way in, and in a strange sort of way it actually felt quite exciting. Very soon Will was making short jabs with it, pushing it in and out maybe an inch each time. It felt like he was also twisting it around, and the non-stop friction on my ass was very erotic. After a while Will found my joy spot, and hit it again and again, which made me moan with pleasure. But letting him know I was enjoying the process was a big mistake, as he then moved on to the next part. He told me that with the dildo now being firmly in place, the enema water would start to flow into me. I was also warned, in no uncertain terms, that I would be in big trouble if I let any of the water drip out, and that I had better clamp my ass tight around the dildo. In spite of the pain I was still feeling I did as I was told, which did not make the pain any easier. The bag was already hanging from the ceiling, although there must have been some sort of clip on the hose, as no water had come out yet. But no sooner had I thought of this than I could feel the liquid flowing into me. This went on for a couple of minutes, and I was starting to feel uncomfortably full, when Will told me the bag was now empty, and he was disconnecting it and just leaving the dildo in. I was again reminded about letting any water drip out, so I made sure my ass was still clamped quite tightly around the dildo, which to my surprise I now found a quite enjoyable feeling, at least for the moment. Although Will did not mention it, it was obvious there was a clip somewhere on the hose, as the bag was now disconnected from the dildo, yet I was sure there was no liquid flowing out through it. At first the whole situation of having my intestines full of water was more unpleasant than it was painful, but I was still bent over the horse, not a comfortable position, and after a while I could feel my guts starting to churn, and the liquid wanting to come out. I could only wish that Will would not make me hold it too long.

I held my position as best I could, as I had no doubt that any complaining would only bring me more trouble. After what seemed like an eternity, but was probably only a few minutes, and when I thought I was going to have to run to the toilet, Will or no Will, he finally told me that I could get up from the horse, go to the toilet, take the dildo out, and let the enema flow. He also warned me that if any of the water leaked out before I got to the toilet, or if any splashed out after I got there, I would have to clean the floor with my tongue. So I reached behind me, and with one hand I grabbed the part of the dildo that was still sticking out of my ass, to make sure it did not come out ahead of time. I then straightened up slowly, and tip-toed over to the bathroom. Will was watching me all the while, naked, his gorgeous prick still sticking straight out, looking hotter than ever, and I felt really humiliated, having to cross over to the bathroom in front of him, while holding on to a huge dildo sticking out of my ass. But I had no choice, so I did as I had been told.

After I got to the bathroom I realized that taking the dildo out would not be easy, as the thick head would have to pass my sphincter again. And I would have no privacy either, as Will had moved over and was standing just outside the door-less bathroom, looking in and smirking. But either I took the monster out now or my intestines would burst out on their own, so I decided the sooner the whole thing was over the better it would be, and grabbed the dildo firmly and started pulling on it very slowly. Things went very well for a short while, but when the thick head reached the sphincter I came to a quick stop. It was clear this part would again hurt like hell, and (what was worse) I would have to inflict the pain on myself. I was already carefully squatting over the toilet, but did not know what would be better, to take it out slowly or to do it fast, and without much thinking decided on the last. Well, that was a huge mistake. I gave the dildo a hard quick pull, and almost killed myself. I screamed as the dildo tore out of my hole, followed immediately after by a big, fat, hard turd, probably the one that Will had fingered earlier, and a large amount of what seemed to be soapy water, with several smaller turds following. It did not smell nice either, which only embarrassed me more. By some sort of miracle none of the water fell outside the toilet. I then sat down, feeling like some kind of an idiot holding the dildo on my right hand, and let the rest of the water flow out, trying not to think about the pain in my ass, while Will still kept watch over me, a huge grin on his face.

At this point I felt quite sure of myself, and very cool and in control, which is essential when you are going to push a hard dildo into a slave's virgin ass. Richard had been prepared as much as it was possible to prepare him. His ass was very well lubricated, and the preliminary stretching with my fingers, even if slightly painful for him, had been for his benefit, as it would make it easier to insert the dildo. Hell, it was really for my enjoyment, I had a great time fingering him, but he would get some benefit from it too. And he was going to need it. A wood dildo is not easy to take by a novice. The one in my hand in particular was quite blunt, which meant that by pushing it in only a short distance it would open Richard's ass hole quite a bit almost at once, and there would be less chance for him to adjust. And of course, mahogany is quite hard, so the pressure on his ass would be unyielding. Unlike a human prick, the dildo does not adjust, does not accommodate itself, but pushes out with brutal pressure. On top of that, Richard seemed to be very scared, and even though the dildo was not as big as he seemed to think it was, his imagination might take over his senses, and make him feel it really big. At any rate, Richard would have to take everything I was going to give him. I was not going to make any concessions to his lack of experience, or to his nerves. My plan was well thought out, and I was going to carry it out with precision. I was going to be rough at the appropriate moments, totally merciless if necessary, and Richard would feel the pain, no doubt about it, but I would also be gentle whenever gentleness was required. It was going to be a fun trip, certainly great fun for me, but for Richard also, even though he would probably not think so, at least part of the time.

It was now time to push. I did so very gently at first, the dildo just barely entering Richard's ass, and as I had expected he started to complain right from the start. I realized this was more out of fear than from any real pain, so I pulled out and then pushed in again a short distance, very lightly, very slowly, taking it in and out several times, to get him slowly used to the idea that his ass was going to be royally fucked. At this point I was only opening Richard's ass maybe a quarter of the full diameter of the dildo's head, and surely less than it had been opened when I had three of my own fingers deep in him, but Richard continued to complain, and actually started letting out little screams each time. Well, I realized being too gentle can be a mistake, and slaves often don't appreciate it when you go soft. So I started to push for real now, not going all the way in yet, still pushing in and then out, always very slowly, but now pushing a little harder each time, and opening Richard's ass more and more with each inward jab. The dildo's head was still not going all the way in, but his ass was now stretching to about 80% of the maximum diameter of the dildo's head. Richard was now screaming really hard with each jab, and his screams were the sweetest music to my ears. He was also complaining and arguing, asking me to stop, saying he could not bear the pain, but I wasn't really listening to his words. He wasn't using the correct safe word, and even if he had used it, it did not apply during punishment. I only had ears for his screaming. Life was good.

But all things must come to an end, and after one particularly high pitched scream from Richard I jabbed with full strength, and pushed the head of the dildo all the way in, plus about a couple inches of shaft. Of course he did not disappoint me, but screamed very loudly again. This time I did not pull out, but for a while just left the dildo motionless inside Richard's ass. Actually, it was not really motionless, as his legs were trembling, and therefore so was his ass, and therefore so was the dildo. The hose, which was still attached to the enema bag hanging from the ceiling, oscillated back and forth from the trembling, which I found quite amusing. But Richard seemed to calm down considerably after this. He quickly realized the pain in his ass was no longer as sharp, that the dildo's head must now be deep in his ass, and that the worst part was over. He breathed deeply a couple of times, always a good sign, and seemed to relax more.

Even if Richard was undergoing punishment I considered it wise to give him some pleasure at this point, to reinforce the association of pain with pleasure. This is the most important part of a slave's training, and when done properly culminates in the slave actually deriving pleasure from pain. So I now moved the dildo very slowly in and out, just a couple of inches each time, rotating it a little as it moved back and forth, letting the head lie safely inside Richard's sphincter, but using the shaft to gently massage the inside of his ass. I knew he would find the friction of the shaft on his tight sphincter very erotic, and even more so as soon as I could find his joy spot and hit it with the dildo's blunt head. After just a few tries Richard's intense moans were a clear indication to me that the spot had been found, and I jabbed and then gently rubbed it several times, until he was purring like a kitten. What a guy! He was bent over a whipping horse, had just had his virgin ass brutally raped by a big wooden dildo, and yet he was having the greatest time of his life, the very same dildo now giving him the most intense pleasure. His training was coming along just fine. But this was punishment, so his pleasure had to be brief. We had to move on.

My ass was sore as hell. It also felt strangely empty. It was not just because the dildo was now out, although that was a big part of it. I also felt the emptiness in my bowels, after letting out that big turd and the small ones, plus all the enema water. I was in a daze, and just sat there on the toilet, the dildo in my right hand, not knowing what to do. Will seemed to loose his interest in me at this point, told me to clean up (both myself and the toilet bowl) and walked over to another part of the dungeon, where I could not see him from the bathroom. I looked around then, and although the toilet bowl was a real mess, I felt thankful that the floor was perfectly clean. Will had not been specific as to how I should do the cleaning, so after very gently wiping my ass with toilet paper I flushed the toilet twice, wiped the inside of the bowl with more toilet paper and flushed it again, then went over to the shower, where I first washed the dildo thoroughly, using plenty of soap to remove the small amount of shit that had attached to the petroleum jelly, and then took a quick shower myself. I did all this as quickly as I could, as I did not know how patient Will was going to be, but I really needed the shower. I stank like hell, both from the perspiration and from the shit, and a warm shower was really what I needed. You can be sure I washed my ass very carefully too, and very gingerly. I probed it lightly with a finger, and it felt puffed out, and as I pushed a finger into the hole it seemed less tight than usual. I considered that was to be expected, and did not give it another thought. I then dried the dildo very carefully, and then dried myself. Although I was trying to do everything fast, I was able to inspect the dildo up close, and to my surprise it did not seem to be so big anymore. This just confused me, as the message I was getting from my ass was quite different. But I dared not linger to think about it, and so went out to look for Will, the dildo as a sort of trophy still held in my right hand.

Will was standing next to the whipping horse, and told me to bend over it again. I complied quickly, and he took the dildo from my hand just as I was bending over. I was sure he was going to fuck me now, and felt quite excited about it, but the next thing I heard was the faucet being opened again. Damn, Will was filling the enema bag once more. I was going to get the monster one more time. Knowing in advance what was coming did not make things any easier. In fact, it was worse. I knew my ass was going to get ripped again, and now I knew for sure how painful that would be. It did not take Will long to come back with the full bag, to tie it again to the rope from the ceiling, and to connect it to the hose and the dildo. I managed this time to see the clip on the hose, which was closed. Once more Will took the jar of petroleum jelly, and put a big glob on his finger. This time he did not start the process with just one finger. It seemed to me he was pushing three fingers into my sore ass from the start, and going deep very quickly. It was hard to tell whether this was now worse than the first time or not. My ass was now stretched quite a bit, so Will did not have to push as hard to get his fingers in, and that was better. But at the same time my ass was quite sore, and this was piling pain on top of pain. The worst part was that Will was being very rough now, as if he was in a big hurry. If he kept this up with the dildo I was going to be in deep pain.

At any rate, the whole process took a lot less time than before. Before I know it Will had taken his fingers out on my ass, had used the same fingers to apply some jelly to the monster, and was pushing it up my ass once more. And just as I had feared he would, he started pushing very hard right away. I had no doubt at all, this was much worse than before. My ass had already been stretched, and that had to make it at least a little easier, but it was also very sore. Worse still, Will was now wasting no time in being gentle. He pushed hard maybe four or five times and then jabbed it all the way in. He did not even give me time to complain, as I was too busy screaming. And I was screaming really hard, specially when the monster's head broke past my sphincter once more. I think Will was doing things this way on purpose, as I now realized he probably loved to hear me scream.

Even though I was feeling awful, and was even a little dizzy from the pain, and from being bent over, I forced myself to think. I remembered how I had promised myself that I would show Will how strong I was, and would try not to complain nor to scream. I felt ashamed at not having kept that promise, and resolve to do better from this point on. While I was going through this mental process I noticed that my intestines were filling up one more. Will had not even bothered to warn me this time when he opened the clip on the hose. After a while I started to feel quite full, and by bending me head I little I could see when Will closed the clip on the hose and disconnected the bag, which was now obviously empty. Like the first time he told me to hold the dildo so it would not come out, and warned me about losing any water, but I already had my hand in place and my ass tightly clamped around the dildo. It hurt like hell when I did that, but I had been warned, and I certainly was not going to lick the floor clean, even if it was water out of my own shit hole. This time Will kept me bent over a lot longer, and he had evidently added something to the enema, as I was getting a strong message from my guts that they wanted the water out, and fast. I told Will very insistently that I had to go, and his only reply was a very hard swat on my left buttock with a paddle, which I had not noticed he had in his hand. He could not hit me on the right, as the arm holding the dildo was in the way, but the single swat made my gasp in pain.

I don't know how I managed, but I held on, and on, and on. After what seemed like an eternity Will told me I could get myself over to the toilet and do what was necessary. I then tried to get up from the horse, but couldn't. I was so cramped up that I couldn't move at all. Will had to help my to straighten out, and hold me while I walked over to the toilet. But I did not let a single drop of water escape the whole time. When I was over the toilet bowl I ripped the dildo out of my ass, pain be damned, as I could wait no longer. The pain was terrible, worse than the first time, but at the same time felt sort of distant, as if I was floating above it. I let the water flow out, which again smelled pretty bad, but could not feel any other turd come out with it.

From this point on I really lost track of what was happening. I know I got at least three more enemas, and the last one felt very cold. Indeed, before the last one I think that Will actually pushed several ice cubes up my ass. I was now feeling very faint. I had no idea how long it had been since I had last had any food, and either from lack of food or an excess of enemas, or more likely from a combination of both, I felt weak with hunger. I was definitely dizzy, and after letting out the cold water of the last enema, which no longer smelled bad, I almost fell down when I tried to get up from the toilet, and needed to lean on the wall to avoid falling. I did not even take the trouble to wipe my own ass this time, much less clean the toilet bowl, but just stood there, leaning on the wall. My ass now was now radiating pain so bad I could not walk. Will had definitely gone too far with me.

It was now time to start the actual enema. But before I opened the clip which would let the soapy water begin to flow I warned Richard about not letting any of the water drip out of his ass, either at this stage or later when it would come out in the toilet. To be sure that he would be extra careful I added that any drippings would be cleaned with his own tongue. I then opened the clip, and the water flowed down easily, with no more pressure than that provided by gravity. As soon as the bag was empty I disconnected it, leaving the dildo with only a short piece of hose, with the clip now closed. Richard was told to hold the water until he was allowed to go to the toilet. You have to hold the slave in place for a while at this stage, so the water will go a little deeper into the intestines, and get all the filth out. The bent-over position on the whipping horse helps a lot, even if it is not very comfortable. But the whole purpose of the apparatus was not to be comfortable for the slave, but to be effective. Thus far I had been watching the dildo, to be sure it was not coming out, although the thick head would probably hold it safely in place, but I now warned Richard that keeping the dildo from coming out would be his own responsibility, and he quickly reached over with his right hand and grabbed firmly onto the small part still sticking out of his ass. I really loved to watch him in this degrading position, his beautiful naked body bent over the whipping horse, his ass in full display, obedient to my every command.

After five minutes (carefully measured by a clock with a big digital display, about which clock I will have more to say later) I told Richard he could now go to the toilet and let the water flow out, but he would have to take the dildo out by himself. This part I knew I would enjoy in many ways. Slaves usually dislike having to take the dildo out themselves, for it means they are cooperating in their own humiliation. It the master is watching, and I intended to watch, the slaves hate it even more. In this case I expected extra enjoyment because Richard's ass apparently did not stretch very easily, and pulling the dildo out past the thick head would probably not be easy for him. The bathroom in the dungeon had been purposely left without a door of any kind, so it would be easy for me to watch the whole process. When Richard reached the toilet he just stood there for a while, apparently trying to make up his mind about what to do. He was squatting slightly, trying to aim his ass towards the toilet bowl, still holding on to the short piece of dildo sticking out of his ass. But he finally made a decision, and pulled the dildo out in one fast movement, and almost simultaneously sat on the toilet. He must have had his sphincter clamped on quite tightly, remembering my warning about spilling any water outside the toilet, because none was spilled. But precisely because of that the pain on his ass as the thick head came out must have been something awful, because as he was sitting down he let out a very loud scream. The sound of the soapy water coming out of his ass was quite audible for a while, and then stopped, but I told him to stay put and make sure he pushed every last drop out. The smell was pretty bad, even from where I was standing, and I knew this would just add to Richard's humiliation. But I did not enjoy the smell, and after telling Richard to clean everything up, including himself, I went to get things ready for the next stage.

Richard took a while in the bathroom, and I could hear him showering, but eventually he came out, looking for me. He had the dildo in one hand, now quite clean, and a really silly look on his face. It was clear he was not enjoying his punishment, which was fine with me. He still looked very sexy in spite of everything, the dildo in one hand and his own prick sticking out, quite as hard as it had been all day. I told him to bend down over the horse once more, and took the dildo from him as he was bending down. I then reconnected the dildo to the enema bag, and went over to the faucet to fill it up with lukewarm water once more. This time I added a larger amount of the liquid castille soap. This would be more effective in getting all the shit out of Richard's bowels. It knew this would also make it more irritating, and harder for him to hold it in, but that would be his problem and not mine. After the bag was ready I again tied it to the rope hanging from the ceiling, and once more proceeded to lubricate Richard's ass with the petroleum jelly. This time I did not linger, but started right away with three fingers, pushed in deep from the start. Richard's ass had already been stretched enough by the dildo, and there was no need to waste any more time. Besides, he had enjoyed the fingering too much the first time, and this was supposed to be punishment. After he had enough jelly in him I used the same fingers to lubricate the dildo proper, and proceeded to ram it in place, again wasting no time. As was to be expected Richard complained, quite loudly, even more so on the last push when the head went in, all of which was great fun for me.

As soon as this was done I opened the clip on the enema hose, and once more the bag quickly emptied into Richard's bowels. I decided that this time he would have to hold the water in for ten minutes, as I wanted to be sure his insides were quite clean when I rammed my prick into him. I knew that with the extra soap it would be hard for Richard to hold the water all that time, but watching him squirm would be fun too. As soon as the bag was empty I closed the clip on the hose and disconnected the bag. I reminded Richard about the dildo not coming out, and he quickly grabbed onto it. I now watched him closely, and soon enough he started to complain that he could not hold the water in. I had a small paddle ready for this, and although one side of his ass was covered with the arm holding onto the dildo, I gave the other side a sharp swat with the paddle. This not only shut him up, but brought back a nice rosy glow to his ass cheek. which I found quite attractive.

I waited the full ten minutes before telling Richard he could get up, and he grunted and grimaced the whole time, making a big show which I enjoyed a lot. When I finally told him he could proceed to the toilet he had apparently cramped, and I had to help him to straighten up. As soon as he reached the toilet Richard squatted over it and ripped the dildo out without any hesitation, sitting down very quickly after, almost in a single motion. I guess he had really meant it when he said he was having trouble holding the water in. Once more I heard the water gush out of his ass, and once more I could smell it. Again I told Richard to clean up, and this time he came out much faster. From experience I knew that two warm soapy enemas should be followed by at least two with clear water, to get all the soap out. So Richard was told one more time to assume the position over the horse. He was now strangely quiet, as if resigned to his fate. But either way he was going to get what I decided and not what he wanted. I now filled up the enema bag with water straight out of the cold water faucet, which was quite cool if not actually cold, and the whole process was repeated from start to finish. This time there was very little smell when the water came out, but I took a look at it before Richard was given orders to clean up, and it still had a slight color of shit, so it was obvious that more rinsing was necessary. This time Richard bent over the horse without even being told to do so, and he seemed really passive, even a little morose, but I did not feel too concerned. He was a strong and healthy young man, and I felt confident he could take what I was giving him. So he got the fourth enema, and on this one the water came out almost completely clean.

But of course, almost is never enough. I decided he would need a fifth. This time I was pretty sure it would be the last, so I added an extra twist. When I fuck one of my slaves I sometimes find it quite exciting if their ass hole is rather cold, so I can then warm it up with my fucking. Also, if the ass hole is in some way inflamed, as Richard's now quite clearly was, cooling it will bring the inflamation down. I had some ice cubes ready for this, made in a special tray that forms them as cylinders, two inches long and only a half inch in diameter, to make them easy to insert. So this time, before sticking the dildo into Richard's ass, I inserted a half dozen of those cylinders into him. To my surprise Richard made no comment, although he must have felt the intense cold as they were going in. So to make sure I added a half dozen more to the bag. They would not fit through the hose, but would at least make the water very cold too. I then let the water flow. Again Richard made no comment. I did not want to let the cold water and the ice inside him too long, as it could bring his body temperature down, so after only three minutes I told Richard he could get up. He did not respond, and I had to help him get up form the horse and over to the toilet. He did take the dildo out himself when I told him to, and sat on the toilet, but the water did not come out right away, but only after a few minutes. He did push out hard when I told him to do so, and when I was sure all the water was out and told him he could get up, he did so but appeared to be dizzy, and just stood there, leaning against a wall. He had not even cleaned himself. I also noticed that he had lost his erection. I thought if he should be now punished for this, but decided to overlook it, as there were more urgent matters to attend to. I did make a mental note, however, since it would give me a good excuse to punish him later in the week if I felt like doing so.

I then went over to the toilet and this time the water was quite clean. The pieces of ice that had come out of Richard's ass were floating in the bowl, though much reduced in size. He was still leaning on the wall, his eyes closed, not saying anything. I closed the lid on the toilet, sat on it, reached over to where Richard was, and bent him over my lap. His ass was thankfully quite clean, and I just had to dry it a little. Richard was not feeling well, that was clear, but by now I could wait no longer. I helped him over to the horse, and bent him over it. He still had on the leather cuffs both on his ankles and on his wrists, so this time I tied him securely on the horse on all four points.

I was going to fuck him rough and did not want him to fall down, so I added a belt around each knee and each elbow, holding him quite securely to the legs of the horse. And the horse itself was bolted to the cement floor, so he was not going to move any. All this time Richard was totally silent. I now took some water based jelly, which is a better lubricant for fucking than the petroleum kind, and very throughly lubricated Richard's ass, which in spite of the ice was still quite puffy, and also my own prick, which was now hard as steel. I made sure the lubrication was plenty, as I intended to skewer Richard all the way and all at once with a single, hard, merciless and uninterrupted thrust. I did not know if he was ready or not for what was coming, but I certainly was.

I took only a couple of seconds to contemplate Richard's beautiful, muscular body bent over the horse, the pink and puffy pucker of his ass hole staring at me, put the tip of my prick right over that pucker and my hands on Richard's bent over back, grabbed on to him, and thrust my hips forward with all my strength. As planned, I penetrated him fully, going all the way in that first lightning push, my pubes coming at once to rest against his ass cheeks. At last, Richard reacted. He let out a loud yelp, sounding as if he had just come out of a dream. If I needed any other signal that I could go on, this was it. I commenced at once to long dick him vigorously, coming almost all the way out each time and then slamming hard all the way in, holding my prick deep inside for just a few seconds before hitting him again with the same movement. At first, and as was to be expected, his insides felt quite cold. This did not last long. Either because of the heat generated by the friction of my prick on his ass, or because of the increased blood flow stimulated by the fucking, he warmed up very quickly. This only added to my own excitement. I was now no longer waiting between one jab and the next, but added speed to the deep fucking, going in and out without pause or respite.

In spite of the apparent frenzy of my behaviour my senses were quite sharp, and I was acutely aware of everything that was going on. I was conscious of the feeling on every fraction of an inch on my prick as it went in and out of Richard's hole, could feel the foreskin as it closed over the head when the prick was pulled almost all the way out, and as it opened again when it was pushed in. I could feel my balls banging against Richard's legs on each forward thrust. I was as hard and as hot as I had ever been. After a while I realized if I kept up the speed I would come too quickly, and this fuck was so delicious it had to be made to last. So now I slowed down considerably, but still continued the long dicking, going all the way in and then pausing for a good while before coming almost completely out, leaving perhaps only half an inch of dickhead inside Richard before going in deep again.

This had been going on for quite a while when I noticed that Richard, who had been completely passive at first, was now responding. He could move very little, the way he was tied to the horse, but he was lifting his hips to meet each of my thrusts, as if wanting to take me even deeper each time. He was now also moaning, and they were moans of pleasure, not of pain. Well, if he liked it rough so much the better. I was giving him strictly what I wanted to give him, thinking only of my own pleasure and not of his, but I was not going to complain if he enjoyed it also. At least he had enough presence of mind to warn me, after this had been going on for longer than I would have thought possible, that if I kept fucking him like this much longer he was going to come, while his orders had been that he was not supposed to. This time I dismounted him completely, and bent down a bit to have a good look. His prick was below the horizontal bar of the horse, and he had regained his erection for sure. It seems he had been humping the bar, as his foreskin was fully retracted, and he was dripping precum by the bucket. I had to do something, and do it fast, since I was not about to stop the fucking. I had a look at my own prick, and it was as gorgeous as I had ever seen it, bright red from the exercise it had been getting, slick with the lubricant, and actually felt quite hot to the touch.

My prick surely would not allow any delays. So I bent over a bit more, formed a tight fist with my right hand, and struck a swift and hard uppercut direct to Richard's balls. He screamed again, only once, but not his usual high pitched scream, but more of a guttural deep throated one. He also seemed to stop breathing for maybe fifteen seconds. But the remedy had been effective. A quick look showed his erection had deflated considerably. I figured it was now safe to continue fucking him, and did so at once. My erection had not gone down at all in the meantime. If anything, I was harder than ever. So I mounted Richard again, but this time instead of long dicking him I went in very deep in a single hard thrust, and then kept it deep all the way, making very short but very rapid in and out jabs, maybe a half-inch each time, but always keeping my prick all the way deep inside his still very hot ass. It did not take very long before I felt my balls begin to feel ready to explode. This just made me go even faster, and in no time at all I felt the beginning of a deep, body shaking orgasm that went on and on, longer than any one before. My legs were trembling from the effort, but I continued to jab, my prick always very deep inside Richard, feeling the cum spurting out of my prick and deep inside Richard's guts, the pleasure sensations on my prick so intense they were almost painful, and the more I jabbed the more intense they became, and the more intense they became the more I jabbed, until I could continue no longer, and had to lie down over Richard's back in a state of almost total exhaustion, my prick still inside his ass, feeling the beat of my own heart, and just below it the beat of Richard's. Life was good.

[To be continued. Send comments to rob8mann@hotmail.com.]