Back Again---and speaking of BACK----let us step through the backdoor----On Being Anal…

This is not a posting about being anal retentive. (For that, if it is problematic you might want to contact a good psychotherapist.)
I had a few requests for a post like this. I have been fortunate enough to be speaking with a woman that has very deeply and successfully been exploring and blogging about her exploration of D/s since her divorce. She has ceased blogging recently but I will add a link if she begins anew. Some of the requests for this post came from people that like anal oriented activities and some from those who have yet to experience much anal. Analingus (oral-anal contact) and Anal Intercourse (anal penetration with the penis) are usually what people think of by Anal. Unless you are lucky enough to be into D/s, in which case those are just the lovely beginning of a creative, erotic, sometimes demanding and always sensual experience.
An interesting observation I have made about analingus—oral to anal contact---it is not the act exactly, but the perception which decides the dynamic. I love a woman’s ass. I love to touch it, kiss it and tongue it, inside and out. She can be lying on her stomach or sitting on my face during love making, or tied down during rough sex, I enjoy doing it and do it when I can. There is nothing the least bit submissive about the act of my tonguing a woman’s asshole. Yet, when my slaves lick and kiss my ass or asshole, whether I command it or they have begged to do it, it is a most submissive act. Slave S, said she found it one of the most submissive things she could and ever did. When we started she was very into kissing and licking feet, but once I demanded a thorough tongue bath and she started to lick my ass, her first time doing this, she found she much preferred it as a much more submissive act! Though M and I never discussed it, she seemed to get excited by the total tongue bath experience, and seemed anxious to serve her Master by kissing and licking my ass. However, when it came to getting her ass licked, it is possible that no one ever enjoyed it more than M!
When it comes to Anal penetration I have noticed similar dynamics. There is an entire sex culture of anal that does not include D/s. And of course, for gay men it is the only form of intercourse available, and not all gay men are into D/s. Just like analingus, since the ass has many nerve endings, and is sensitive, it is an erogenous zone and experiences effects and changes during sexual arousal. Clearly, if we are comfortable allowing it, the ass is made to be a part of the sexual experience. Now, as for it being separate from D/s, I cannot speak to this from experience, because as it happens, every woman I have ended up having anal sex with also ended up submitting to me. This is not a scientific sample because in all but one case, Slave S, I pursued exploring the issue of D/s before a sub and I got much into the physical relationship and therefore did not have anal sex before we explored D/s . I have explored how this sometimes occurred in an earlier posting: http://enteringsub.blogspot.com/2010/04/first-time.html
I think I like and am attracted to anal sex because I definitely seem partial to a woman’s beautiful ass and it seems like a D/s thing to do, at least to me. I have been with a few women and some had large breasts and some were very small, some were tall and trim, some were shorter but all had incredible butts! Obviously, there can also be a pain aspect to anal intercourse. For some, like M, there was a certain amount of pain every time but what made it particularly enjoyable with M was not that there was a certain amount of pain, but that it was one of the activities that made her more excited and her pussy dripping wet than almost anything else. Obviously, I enjoy inflicting a certain amount of sexual punishment, however, I would not enjoy dishing out nonconsensual pain or pain in a way that did not lead to the other goals the submissive and I each had. In other words, if M experienced the same anal pain, but did not get excitement from it, and in fact was turned off by it, even though accepting of the pain, it would not have been enjoyable for me. Just like I would not want a woman to be whipped by me solely because she cared for me, but didn't actually enjoy submitting and get turned on by the acceptance of her punishment. That might, in actuality still be consensual, but for me it would not be D/s.
So, there can be a certain amount of discomfort or pain involved with anal sex, but there does not have to be. It depends on using enough lubricant and it also depends on the combination of the size of the man and woman. While not the thinnest woman I had been with, M was one of the shortest and while not huge, I have been told I have a fairly large sized cock, and the combination seemed to be about as much as M could take. K was a smaller framed though taller woman, and in truth I think her ass felt the tightest, but if there was any discomfort she simply did not betray it. For some, like slave S, there was a little discomfort at times but never any real pain---and usually just pleasure. And as I said, for slaves like K, if there was any pain involved it was so minor that someone with the tolerance she possessed never gave a hint if there was any discomfort. So clearly since I enjoyed it with everyone there is more to it than discomfort. But then, I suppose if you are into dominance and submission you can find a D/s dynamic in almost any act. I'm thinking that what is also dominant about anal sex is that you are pushing your way into an orifice that isn't normally used for this purpose. Therefore I can find oral sex to be a D/s activity too. Yet there are millions of women out there who don't think or feel submissive when they perform a blow job. Certainly there are positions, forcefulness and dialogue that can make any act more or less D/s, so I am sure that is part of it. But if I had to give an opinion I do think anal sex is more overtly D/s than a lot of other acts.
Now nothing really makes anal sex more D/s than expecting the slave to suck your cock when it comes out of their ass. I am sure there are people into D/s activities that would just pull out of a slave’s ass and then push it in their mouth. As I've mentioned many times the real world is not always that convenient so I'm not like that. I like to check that things are clean first. I think people, Doms and just guys that like anal sex, think it is okay to just expect certain things because in most anal sex videos, especially with a D/s storyline, that's exactly what the guy does----takes his cock out of the girls ass and shoves it right in her mouth and tells her to clean it off. The thing is, you only see what the camera allows you to see, you can't be sure where they cut the video, and you don't know what preparations have gone into making sure the actress was ready. Now, as I said I always check, and the vast majority of times things have always been clean. I have not written about the times they haven't been! In general, the body has a good way of keeping things remarkably clean, and during arousal have mechanisms in place to help with this. However, for some people, whether just the way their bodies work, or because of transient issues, they may require some help. Enemas are an area that I have heard are both erotic and obviously very useful if somebody is not naturally usually ready for anal sex. However, I am not into enemas and so far in my experience have not needed any regular additional help to clean out my slaves. So this is not an area I can speak to and if you are interested in these, or you feel you or your slave needs this kind of preparation, you'll have to seek additional information elsewhere. It should be noted that just because a cock, or strap on, may come out clean enough to be licked and sucked afterward, you can never assume it's clean enough to go right back into a vagina. That is not the case!
So, is bending over or getting on your hands and knees and spreading your cheeks and taking a big fat cock up your asshole a submissive act? I think so, but that is only one dominant man's opinion! There are plenty of movies out there where women get fucked up the ass without displaying the slightest bit of discomfort or pain, in fact they are moaning and screaming in pleasure, and then suck the guys cock as soon as it comes out of their asshole, and there isn't the slightest hint of D/s. But are the people watching these films into D/s?
As I mentioned there are changes to the asshole as we become more and more sexually aroused. I'm sure anyone reading this is aware of that but just in case, I will mention it here that under extended arousal the asshole opens up. Therefore, especially when introducing a slave who is new to anal sex you need to proceed slowly. And I don't just mean not to rush through the entire idea of anal sex; I mean not to rush when you're actually doing it. You need to penetrate slowly, especially when you've never done this with the girl before. You need to be adequately lubricated. I have always found that an excited woman provides enough lubrication in her pussy. I never needed to use additional lubrication besides what I got from their pussies with M though sometimes with K because she was so tight I would add lubricant and maybe it would've helped with M. Because of her discomfort I offered her a lubricant on several occasions but she declined, saying she thought it was not necessary because my cock would be so wet from her and the actual penetration was easy. She thought it was more a matter of size and relaxation and that she was prepared for the discomfort while serving me. Interestingly, slave S, a taller, larger framed woman, never appeared to have much discomfort from anal sex but insisted, despite her also being one of the wettest women I have ever known, on using an additional lubricant. She had always heard you were supposed to use lubricant and therefore I believe she just felt it was a requirement. Kayla was one of the least wet women I have ever known and she blamed that on her body's reaction to birth control pills, but she didn't like the idea of lubricant and insisted on only providing her own---naturally. This made for a difficult penetration, one that seemed as painful sometimes for her as for M, though she insisted it was not the case and that she really did not experience discomfort. It was hard to know but as I have mentioned many times in a lot of ways she was a very annoying person so I'm sure if she really didn't like it I would've heard about it! So I think it's safe to say that as a general rule, especially with girls new to anal sex, you should plan on using additional lubricant. Also, even when you're with someone extremely wet and they themselves don't feel you need a lubricant; you should still always have one nearby. The reason is if you need additional lubricant while in the act of fucking her asshole, it would not be prudent or sanitary to expect to be able to re-lubricate your cock in her pussy. You could use your fingers to get some lubrication and bring it to her ass, but it is better to be prepared. There are many good personal lubricants on the market, but make sure your choice will be safe and pleasant for her if you expect her to suck your cock afterwards.
As may have been evident from previous posts, I enjoyed inserting a great many things into my slaves asses. My tongue and their fingers are the easy ones. Although as I've mentioned, M did not find her fingers very easy as she was embarrassed to play with her asshole. When I first started with D/s, the first things I ever inserted inside a woman's asshole besides my tongue, my fingers, or my cock was a thin, hard, black leather covered, smooth metal studded whip handle. M was the first to experience this. I could tell she really didn't like it. M has never had a problem with me wanting to put my cock in her ass which was much bigger and wider than the whip handle. But while she submitted and tolerated anything I wanted to put up her ass, she has never enjoyed objects. The only time she gets soaking wet when her asshole is stretched is when it is stretched by my cock. I suppose this shows the psychological component of sex. M clearly enjoyed anal stimulation, even painful stimulation, but clearly in her mind it was to be provided by her lover and his body parts. She moaned and writhed by the touch of my fingers, went into ecstasy with my tongue up her ass, but was resistant to touching her ass with her own fingers. She was in pain but got soaking wet when my big cock stretched her asshole, but got little enjoyment by a much thinner whip handle or similar sized butt plug. I say little enjoyment instead of no enjoyment because she did clearly stay in the moment and in the experience, and I believe that was related to her desire and excitement in serving me. The first couple of times I inserted the thinner objects into her asshole she did not seem to respond positively. After that though, since I planned on continuing the practice because I enjoyed it, and since she was willing to submit to it, I would start to talk to her more while I was doing it, about how she was serving her master, or I would stand in front of her and fuck her mouth while I stimulated her asshole. She started to respond much more excitedly once she saw the effect inserting these objects into her asshole had on me and my cock. After a while, if she would displease me, she started to suggest anal punishments as often as any other harsh punishment. Once when we had plans to go to the opening of a movie on a Friday night, she forgot she had made plans with some friends of hers. The friends kept reminding her of their plans, and I did not bother reminding her of ours, as this was not usually a problem, and she ended up standing me up. This almost never happened and she was very upset and apologetic. I was so annoyed I did not take any of her hints that we should settle this in a D/s way. We made plans the next morning for later that day, and when I arrived at her house she answered the door naked, save for her collar and cuffs. She never did this if I did not instruct her to do so. I walked in only commenting “Nice outfit.” She got into her slave position bent over the end of the couch with her hands reaching back spreading her ass cheeks. There was a small wooden folding tray next to her, not something usually there, and on it was a rattan cane, her heavy wooden sorority paddle, 2 Japanese clover nipple clamps, several pounds of weights that we used to hang from those clamps, and this very large (fat and long) rubber cock with ribs and protruding studs. I once brought that dildo to her along with Slave S, and threatened to abuse M’s ass with it if she did not play with her asshole to my liking in front of Slave S (to make up for the fact that previously she had been very resistant to this in front of S, and of course she was punished for this resistance, but I was not going to tolerate her embarrassing me again). “I see you are feeling very guilty.” I said. “I was so angry I was going to leave you to stew in your guilt, but I guess you know me pretty well. Naked and bent over with some of our harshest instruments ready for use makes me think I should settle this your way instead….” I stood behind her and lowered my pants and teased her slightly parted pussy lips with the tip of my rock hard cock. “Besides, you obviously know how to improve my mood!” She moaned as I pulled the tip away from her pussy. “You’ll get my cock back when you have taken your punishment.” I said. Then I picked up the fat studded dildo and brought it near her face. “What do you think I should do with this?” I asked. She stared at it and paused, then spoke very softly. “I think you should…” she paused again, then looked up into my eyes, “fuck my asshole with it Master.” Then she immediately averted her eyes and buried her face in the couch cushion. “I see.” I said. “I think that will be a terrible punishment for you.” I said. Muffled a bit by the cushion I heard M say, “I think so too.” I looked at the table again, “You picked out so many severe punishments that I will end with the cock up your ass and perhaps by then you will find it a welcome change of pace.” I snapped a leash on her collar and pulled her from the couch. She immediately got on her hands and knees and crawled over to the wall where I had a hook in the wall to chain her arms above her head. Here is where I whipped her standing up, facing the wall, but when I bound her with her back against the wall she knew it was for nipple and tit punishment. She raised her hands above her head when I told her to stand, but stood sideways and asked which way she should go. “Your back to the wall slave! You chose the clamps and the weights so it’s your tits that will suffer first.” I hung 3 pounds from each clamp, less than the most weight she’d ever experienced, but extremely painful, and I left them on for 5 minutes, which was not the longest she had stood either. She stood there, tits jutting out, eyes closed, hands above her head, lips tightly pressed together as I announced the end of each minute by giving the clamps a push causing them to swing painfully. When I said 5 minutes I grabbed the clamps and pulled them off quickly. I had never told her it would be a 5 minute limit and she was totally unprepared for the rush of pain that stung her nipples as the clamps were removed and she screamed out most unexpectedly for M.
I snapped her leash back on and instantly she was on her hands and knees as I led her back to the couch. As soon as her leash was removed again she was back into her slave position with her cheeks spread. I attached her ankle cuffs to the legs of the couch then pulled her hands from between her cheeks and pulled them outstretched above her head and used long cotton rope to attach those to the other end of the couch. She was tied down tight and her ass was a lovely, round and firm target. “I like to see your ass with thin red stripes so I will begin with the cane as once I use that paddle your ass will just be so red and bruised that the thin welts won’t show at all!” I said.
“Yes sir. I am sure you’re right, thank you.”
“And what does my bitch think about this punishment now that it has begun? Do you wish you had chosen a few different instruments?”
“I think I am very glad you decided to punish your bitch instead of staying angry with her. I would not have chosen differently because I knew you would only agree if you felt I was serious and sincere about this punishment. A riding crop and butt plug would not have proven anything to you.”
“You know me very well M.” I said as I swished the cane in the air and then walked behind her. I only gave her 15 strokes, but they were firm strokes. M had chosen some pretty severe punishment and I did not want to overdo it. Also, I was anxious to see if her ass could take that rubber cock and just as anxious to end the experience with a good fucking to show her she had more than made up to me for her poor behavior. I then picked up the heavy paddle and rubbed her ass with it. “I almost hate to ruin these lovely red stripes with this heavy thing!” I said. I put the paddle down, picked up the cane and said, “In fact, I am not going to do it. You have offered yourself up to a great deal of punishment tonight and you are getting it for sure, but I think 10 more with the cane will suffice, and will leave your ass looking the way I like while I abuse it with the rubber cock.” I said.
I could hear disappointment in her voice, but could not tell if it was her expectation or for me as she said, “Master, a few strokes won’t ruin the look, will it?” “I suppose not.” I said. I gave her 3 hard strokes with the paddle, one right after the other, then gave her 5 more strokes of the cane, very hard strokes, and then left her tied there while I picked up the rubber cock.”
“If this thing wasn’t so long and fat I think it would still be very difficult to take because of the ribs and bumps all over it.” I said as I reached under M’s chin and held her face and turned her so she was staring at the monstrous cock. I reached over and rubbed the cock between her ass cheeks then pulled it away and leaned it in front of her face on the cushion. “Start licking it. You will want it as wet and slippery as possible.” I said. I walked behind her and slid out of my pants and briefs. My cock was hard and throbbing and I roughly pushed it into her pussy. She was moist and it only took a few thrusts before she was soaking wet. I fucked her hard and fast and reached underneath and rubbed her clit. Soon she was screaming out her orgasm, (M really loved to scream when she came, maybe so everyone would know how many times she could manage in a night). I pulled my wet cock out of her pussy and stuck it right into her asshole. Her ass was about as opened as it ever was, having just had an orgasm and my sticking my cock in there would serve to start lubricating her and to help open her asshole some more for that big rubber cock while I enjoyed myself. That rubber cock, while not the biggest thing I ever shoved up M’s ass, was near to it including the ribs and studs and I had a feeling this was going to be very tough for her. I picked up the rubber cock that she had clearly forgotten to keep licking and I held it in front of her face and started fucking her mouth with it. It was not easy for her, and I pulled it out and the next stop was her pussy. “If I were you I would try to enjoy this because being very wet and very excited will be the only things to help you through this. But when we are done with your punishment we can spend the rest of the night fucking and licking with no more guilt or punishment.” As I continued to fuck her pussy with the big cock I moved around until my cock was near her mouth and I started to fuck her mouth. I knew the feel of my soaking wet cock and the taste of her pussy and ass would only excite her more. The big cock was easily fucking in and out of her pussy. It was wet and slippery and I fingered her asshole and it was as open as ever I found it! I pulled the formidable phallus out of her pussy and started to work the head into her asshole. She wiggled her ass a bit higher and leaned down burying her face in the cushion. I would have used some supplementary lubrication for this scene, but because she did not like it, and we rarely needed it, I did not have any on hand. The head of the cock made its way into her asshole and I slowly proceeded to ease the cock deeper. The first rib started before the cock’s full girth and it made it inside her with a heaving breath and moan into the cushion. I eased the cock a bit farther in and reached the full circumference. As the full size entered her she raised her head from the cushion and gasped then lowered her head into the cushion. We had reached a part with several of the rubber studs and the next rib, both of which made the widest part of the phallus even wider! I stuck my fingers into her pussy which was still wet and collected some of her moisture and spread it on the bumps and ribs and shaft of the rubber cock. I continued to finger her pussy to keep her as excited as possible and then I pushed the first protrusions into her asshole. “Oh that hurts so much!” She cried out as her face left the cushion. I gently eased the shaft out a half inch and she gasped as the studs that had just entered, now exited. I started to slide the cock further out of her ass and she said, “No. Please try again.” She was breathing heavy and buried her face back into the cushion and I could tell she was not looking for a discussion or argument. I collected more juice from her pussy, though it was clearly not as wet as before, rubbed it all over the cock and then began to shove it back up her asshole. With a firm push the studs and next rib slid into her asshole. I was not sure, since it went in easier, if this was a better entry when suddenly she raised her head off the cushion, even from my vantage point behind her I could see tears on her cheeks and she cried out “Oh, Oh!” and was breathing very heavily. I started to ease the cock out. Maybe when I first backed it up she thought I was going to fuck her ass with it by going in and out because she immediately buried her face back in the cushion and cried out into the cushion when the rib and studs exited her ass. But once she saw I kept pulling out she raised her face again, “I’m sorry I can’t take it better. Please don’t stop.” She begged as tears continued to roll down her cheeks.

“Get your face back down slave.” I said, and she did so, adjusting her hips waiting for the next onslaught of that painful cock. Instead she cried out into the cushion as the last rib exited her asshole and the cock slid out. As she raised her head and started talking I sat down on the couch in front of her, leaning off the edge of the cushion because her tied and outstretched arms blocked me from sitting back “Please, Master, I’m sorry, you should not stop, I chose this punishment because I knew it would be severe and it was appropriate.”
“Lovely M, you are an amazing slave, but you have nothing to apologize for. When I originally brought that cock here, it was a threat of severe punishment if you disappointed me, but I have to admit, it is a pretty severe looking punishment for any slave’s ass, not just yours. I did not know then if I would ever actually use it, which is why I have never suggested it in all the time it has been here. I do have to admit, I wondered what it would be like using it on you, and you gave me that experience today. You are my slave, not a machine and you are not expected to take everything. Sure, I try to target things for my slaves so that maybe you can handle everything I choose, but in the real world even well planned scenes go awry. It means a lot to me that you had the guts to offer up your asshole to that terrible looking cock because I know from the look on your face when I first brought it to you that it frightened you. You offered it and you took it as best you could and I appreciate that. What kind of Master would I be if I ignored the level of pain you were experiencing, as well as the potential for physical injury, and continued with that punishment?” I asked rhetorically, then continued,. “Besides my beautiful slave whore, I have to admit every time I stick something up your ass it makes me want to fuck it also. If I kept abusing your asshole with that thing, it would have been way too long before you would have been in shape to accept my cock up your ass again. I decided it was not worth it. You have to understand slave, I enjoy shoving things up your ass and I enjoy punishing you, but what I was seeing now was not exciting, not if it happened to anybody, but certainly not happening to someone I care about. We will go to bed now and find other activities to satisfy us both!”
Now, I would never advocate pushing someone anally, not to try something, and not to go to harsh levels of punishment like I just wrote about. You need to be experienced and well versed in each other’s desires and limits, and be very sensitive to what is going on and be aware of the subs reactions. I knew from early on in our relationship, long before we entered D/s together, that M was anally oriented though we were already into D/s when we started anal intercourse. One of the first times we were alone together when I was roaming my fingers or tongue along her naked body she twisted and contorted herself until her she could get her slightly spread cheeks wherever the action was. Finally, when I tongued her asshole for the very first time while rubbing her pussy, I thought she would scream the glass out of the windows of the apartment I had at the time when she so quickly succumbed to her orgasm! After tonguing her asshole during the first orgasm, I can still remember that evening, so excited and willing was she that I did not want to leave her asshole alone. At this time we had only given hints to each other about her submissiveness and my desire to dominate. As I said, I did not want to leave her asshole unattended, so when I felt like removing my face from between her beautiful cheeks, I brought my hand between them and started fucking her asshole with two fingers. She was sucking on my cock, then I was leaning over and licking her nipples, we were moving all around the bed, but as soon as I pulled my fingers up her asshole, and as I was moving once those fingers came anywhere near her face, she immediately brought her mouth to them and began to lick and suck them. I don't think she was even fully conscious yet of her desire to submit to me, but whenever she licked and sucked anything that was in her pussy or asshole she always became soaking wet, breathing heavily and moaning and writhing. To me this is a very submissive way to be. It could be interpreted other ways I suppose, but having been there and knowing her that seemed to fit best.
So I would say a large portion of how you approach anal activities has to be a very sensitive mix of where your sub is at and where you would like to be. For the inexperienced, anal is new, can be scary, penetration may be painful and even if it isn't that may be the concern and fear ahead of time, or a concern that it could be messy or inconvenient, and may not live up to one or both expectations. Anal intercourse should not be the first stop but more the destination. Tongues, fingers, small butt plugs should all be used to gauge interest, ability and to initiate everyone involved. I have heard from a few people that one partner enjoyed anal penetration and the other didn't, usually the one receiving the cock up their ass did not like it. Over time I have gotten e-mails from dominant women whose lover was also their male slave, and they said how they both fantasized about her strapping one on and giving it to him good, but then when it came right down to it he found it very unpleasant. They seem to have contacted me because they noted in my blogs that when I wrote about anal activities I had slaves like S that enjoyed them and were not particularly uncomfortable, and slaves like M, that enjoyed the activities even though it was very clear it was painful, and they were somehow looking for a magical suggestion of how to make their sub enjoy the activity as much as they both fantasized they would. Sadly, I know of no magic solution. I have noticed that dominants and submissives often have a lot of anal ideas. Most of them that I have talked to have thought about it even if they haven't gotten to do anything yet. What kind of action that will translate to is hard to say, but if there is interest there and certainly if there is no outright refusal there, there is always the opportunity to explore together and find at least certain activities and certain levels of activities that you can both enjoy together. As long as you keep your expectations open hopefully you can find the range of fun anal to occupy your time.
Although I like to vary my punishments, there were some days, and some slaves, when they were due for a particularly harsh punishment that I decided I would focus all my attention on one area. . On these days I even limited how they were going to experience pleasure. To cum, they usually would need some stimulation directly to their pussy as well, but I would limit how they could get this stimulation and what would be happening to them while they got this stimulation, because after all this was punishment!
With M I enjoyed days when I focused al my attention on her ass, or her breasts, because she could tolerate a lot of punishment and attention shown to either. With Kayla, if a day was to have a specific focus it tended to be on her breasts. With M I probably leaned a little towards focusing on her firm, round ass because M could take an incredible amount of punishment to her butt and abuse of her asshole, but she was also so great at tolerating prolonged nipple punishment that I would really hate to choose which I enjoyed more with her, which is probably why days where I focused on one area were few and far between. They often seemed like a good idea in fantasy but in real life I like to roam around and vary my activities! But since M’s breasts were small it was hard for me to focus my attention on them almost exclusively. With Kayla I could rub my cock between her large tits and fuck them, and then cum on them, but that was a difficult proposition with M’s much smaller tits. So for Kayla I could focus on breast punishment and use because she had very large and firm breasts and could handle a decent amount of nipple torture and was very fond of having her breasts shown constant attention. Slave S also had large firm breasts, but she could not handle the amount of breast punishment or nipple torture that M could and at times not even as much as Kayla. But S was another one with a firm, round ass who could take a pretty harsh whipping! On a day when I chose to focus on her ass, M or S could find themselves tied down bent over a piece of furniture for an hour or more at a time. I might use several different implements, mixing in less intense whips with canes and paddles. I might then go at their asshole with my cock but not with the intent of cumming anytime soon. I would continually stop and hold myself back from cumming so that I could work on their ass as long as a half hour before pulling out and beginning the whipping again. As I said though, when I chose to focus in this way, I altered how the sub would get their pleasure and I limited how I would get mine. For example, for M on a day when I focused on her ass, for her to cum, I would only allow her to use a vibrator on her clit, with another vibrator buzzing inside her pussy, while I fucked her asshole. M was the only sub I personally knew that really didn't like using toys, as I said she had enough trouble just touching herself. With me she had gotten to the point where she could masturbate to orgasm in front of me, but she never enjoyed inserting a toy or touching herself with toys. The problem for M was though she might act like she was willing to forgo the orgasm rather than use toys, she also had a high sexual appetite and was used to cumming five or more times in an afternoon or evening. As much as she might try to fight it eventually she would acquiesce and find herself bent over with a vibrator buzzing in her pussy while she rubbed her clit with another vibrating piece of plastic. All while my cock was buried deep up her ass. Now for Kayla, on a day when I was focusing on her tits, it was much different. Since Kayla enjoyed using vibrators and dildos, that was not going to be a difficult orgasm for her like it was for M. Kayla had quite a personal collection of toys and used them whenever she had the time and inclination. When she had day of focused punishment on her breasts and it was time for her to try to cum, often I would attach her nipple clamps to the wall and have a very powerful vibrator attached to a stick between her legs but a little bit out of reach. Her hands would be tied behind her back and would offer her no ability to pleasure herself. If she wanted to cum she would have to stretch just that little bit extra to touch her pussy to the vibrator, which was also just far enough away to hurt her nipples. Often by the time she was ready to cum she would be groaning from the pain in her nipples and then the screaming from her orgasm would take over! Then I would detach her nipple clamps from the wall and lay her down on her back, those biting clamps still attached, and then I would straddle her chest and hold her tits tightly together and fuck her between her tits. I would make her look down and watch my cock slide in and out between her tits all the time with her mouth open because when I would finally shoot my load it would not be on her breasts, but go straight to her face and I wanted to see her try to catch my cum in her mouth. But Kayla’s breasts are a digression. We are talking anal today and I am trying to keep to the subject just like when I try to have an afternoon or evening of punishment focused on only one area. As you can see, it is as hard for me to stay focused on one area here as it turns out to be when I have a slave kneeling before me for punishment.
There are so many things you can do in D/s and anal that everyone else is missing out on! I have been out at bars and restaurants with a few subs; M, K, and Kayla to name a few where I had them go to the ladies room to remove the butt plug they had been wearing for at least an hour. They had to bring it back to the table (whether they washed it off I cannot say) and then I have commanded the slaves to lick it like a lollipop, as the wait staff and guests could possibly see. Even in a dark restaurant, in an out of the way corner, choosing a place that I knew would not be particularly crowded, these are very humiliating acts and were only possible with the most submissive subs who had a penchant for public acts. However, wearing the butt plug while out to a bar or dinner is always a good way to remind a slave of their position, and keep them stimulated, even without adding the acts of public humiliation. A small vibrator in her pussy at the same time really creates a personal and private experience while out in public. And in fact, I have used vibrating dildos in place of butt plugs when I wanted a stronger effect. I have not used inflatable butt plugs much, as I am uncomfortable not knowing exactly what is going on as I inflate it. You can only go by a slave’s reaction and so I would only use these with an experienced sub.
Just like everyone else, I do not think all submissive girls like anal sex, nor do I think you have to be submissive to enjoy or seek anal sex. I can say that all of the submissive girls I have been with that tried anal enjoyed anal sex (and that was all but one). For M, it often was a painful yet very exciting experience, for K and T it was sometimes uncomfortable and always exciting and for Slaves like S and Kayla, it was just a pleasurable experience. M seemed to find anal a form of submission, maybe because she felt she was submitting to me because it was often a painful act. S enjoyed anal sex before she started exploring D/s with me and the same for Kayla. K was already into anal and D/s when I met her so I do not know. I do find, at least in my limited experience that D/s and anal go hand in hand. At least, I am very into D/s and very attracted to a woman’s butt and everything I can do with it. I think, unless you have an aversion to it, everyone into D/s should at least explore the opportunities of anal. Even if you never get passed licking and fingering. Even if you cannot tolerate even well lubricated penetration with a cock or a butt plug, you can explore anal masturbation. It is very submissive for a sub to have to play with her asshole at her Dom’s command, and for me, a very exciting thing to see. Whatever concerns or fears you have about anal there is always something to try and possibly enjoy. If you have the interest and not the experience, slow and careful and lubrication are the words. If you are experienced, or would like to be, please comment for the rest of our readers!

Playing Together. (A continuation of the exploration of "forced bi".

In the last post I talked about “forced” bi as part of slavery. I'm going to talk about some of the first bi experiences of the women I have known while they were serving me as my slaves. This might seem more suited for Entering Submission, and in fact it was intended for that blog, but by the time I finished the post I realized it was better suited for this blog. I will also recount the next exploit of slave M submitting to a friend of hers who was interested in our lifestyle. The first time she served in this way can be found here: http://enteringsub.blogspot.com/2010/07/when-company-calls.html This is one of my favorite posts because it was an amazing experience. This scene that I will recount will also include another slave I had a few dealings with but have not had occasion to mention before now. On another occasion when M's friend R was coming over and we had decided we would all “play together” again, I decided to bring slaves C also. BUT FIRST, let me recount some other experiences, as we talk about what kind of experiences and progression you might encounter once you and your sub have decided they are going to engage in bi activities in service to their Master.
Whenever I had a slave who finally acquiesced to bi activities (and as you know some of my slaves were already into those activities), I don't know about you but I remember having these visions of hanging out at lesbian bars and some hot lesbian or more preferably bisexual girl was going to strike up a conversation with my slave, express great interest in learning about our lifestyle, be able to establish they were clean and healthy and we were going to run home and have great times together! As we know in real life that almost never happens, and in fact with some of the posts I've been able to relate to you here I have to say I was quite lucky over all with the experiences I was able to manage. But of course initiating slaves is much slower and more complicated than you can relate from a blog where the posts are not necessarily in chronological order and where they can skip over months of preparation or less than exciting experiences. For instance, for quite some time after M offered herself to me completely with the understanding she would do whatever I wanted, including be with another woman, all I got to see was M clothed and kissing a couple of her friends when they were drunk. M's old college friends still liked to party occasionally and M was pretty good at holding her liquor as am I. Once she had accepted that she would do things with other women she started telling me stories of her near girl to girl contact. She implied that when she and her friends were very drunk they kissed and she remembered thinking that one or two of her friends had felt her up when they were kissing while drunk. While she would not say she enjoyed it, she did admit that she did not try to stop it while it was going on. She always attributed this to her drunkenness, but also admitted that she cannot remember a time when she was so drunk that she would've ever let a guy do things with her if she did not want them to. It was one of her college friends that I mentioned in the beginning of the previous post. Because of one of these kissing incidents I was hopeful I could get more out of her but as you read here--- it wasn’t much more. How I came to try to get her to interest R in being with us came from a similar story. For some reason she had no trouble telling me about kissing drunk girls at college, but the tale with R took a lot longer to get out of her. I will recount that story soon, as the beginning of the rest of this post about our next experience with R . But first I'll talk about some of my slaves other initial experiences.
As you know K was bisexual and lived with a girl who was her younger mistress. Before she let me in to that, but after she was submitting to me and I knew she was interested in other women, we would go to bars then the Village, and eventually she would be kissing another girl. We weren't looking to take home strangers so she did this mostly to whet my appetite, so to speak, for when we got home. Interestingly, these were some of my first experiences with a sub trying something with another girl and it matched my imagined fantasies that I mentioned earlier about picking up girls in lesbian bars! That was about all K did until she admitted about her roommate and we started doing those things together.

Kayla was an interesting one because I believe I've mentioned while she had never been with another woman she'd definitely leaned that way and had fantasies about it. Although she didn't do much in high school she said a lot of the girls around her at the private Catholic school she went to tried kissing and other girl -girl activities. She seemed wistful that she didn't try them then. Kayla had a couple of friends she found attractive, they weren't that close friends, but they were long-term. One was a single mother and Kayla told me she would like to try and interest her in our activities. Kayla said this girl always needed money and if we were willing to pay her something we might be able to use that as the beginning. Keeping this in mind we all went out for drinks one night and Kayla turned the talk to her submission to me. She seemed mildly interested but it wasn't going anywhere so I turned the talk to money. We'll call her F for friend. “F, Kayla says you are interested in doing some part-time work for me to get some money. I don't really need any help at the office, but if you would assist me in training Kayla, I could pay you for your time.”
“What would I have to do exactly?” F asked.
“Whatever you would be willing and nothing that would make you too uncomfortable. Order her to do things, punish her, and if you would, use her.”
“Well I'm sure Kayla told you I use to fool around with girls in high school but I have to tell you I'm not real into that anymore. I don't know that I really want do anything to her and I'm not sure that I want her to do anything to me.”
“That's fine. If you're interested I'll tell you all the different things I would like and you pick and choose what you do.”
F agreed and primarily the only physical contact was that she would let Kayla massage her feet and lick them clean with her tongue, and she would, while fully clothed, put on a big strap- on and fuck Kayla in the pussy and ass. Other than that she would just punish Kayla and usually not hard enough despite my prompting and demonstrations, and order her to do things like clean around the house. It was pretty good but far lacking in everything I would've liked to have had to go on.

That was most of the experiences along that line that I can recall right now. Now back to M and R. Before I relate the experience I want to, I will tell you about that first experience when I was not around between M and R. It was after college, R did not go to school with and M, and they met at a bar on a Friday night after work. After they drank a bit, R asked M if she'd ever kissed a girl. R said many of the girls where she worked talked about all kinds of things they did with other girls back in college or even high school. R said she felt left out. M admitted what went on in college when she was drunk a few times. R nervously asked, “are you that drunk now?” M just smiled and said, “no”. R jumped up and called for the waitress and ordered more drinks. M said she remembered being nervous and a little uncomfortable, but she also admitted that she accepted the drinks with the unspoken understanding that after drinking some more she would kiss R. When she felt she’d had enough she still told R this wasn't college and this wasn't a college bar, and she was not going to kiss a girl in public. She said R suggested they go to one of their cars even though they were clearly not ready to drive and she accepted R’s suggestion. M doesn't remember whose car they got into, but she remembers saying, “just one good kiss”. However, she admitted they kissed for several minutes, with all the eagerness they would've shown a boyfriend, but she insisted their hands did no roaming! That was about the best M had to offer, but it was also the reason I thought we should pursue R. I asked her why she chose to do this with R when she had already had her experiences kissing other girls and said she wasn't interested in women. She said she wasn't sure. She had been drinking already, and said she felt a little bad for R; that she felt left out. Since she'd already kissed girls she knew there was nothing bad about it, she simply had no desire to take it anywhere further, so for her it was more like helping a friend out and sharing an experience that she was privy to that her friend was not.
Now, we move to after my first experience with M and R that I gave you the link for, for those of you who missed the post So R was coming to visit M on the weekend, and R asked M if she could talk to me. M told her she could call my cell, and when M told me R would be calling, I asked her if she had any idea why. “She didn't say, but I can guess.” M said. “Then guess, I would like to hear.” I asked. “I've seen M for dinner a few times and she hasn't brought up what went on between us all. But since we decided she would come and maybe stay the week, all of a sudden whenever we talk, she asks about you and if we still do all the things you like to do.”
“And what do you tell her?” I asked.
“You know what I tell her.” She said, “That nothing has changed.”
“So, again, what do you think she wants?” I asked.
“Well, at the very least, I'm guessing she wants to punish me and then have me eat her pussy.” She said stoically.
“And how do you feel about that?” I asked
“You know that too. I wouldn’t look for that, but I will do it with you and for you.”
“I see. And if that's what she asks what do you think I'm going to do?” I asked.
“Oh, I know what you're going to do. You will agree and then enjoy it immensely as I spend the weekend with my butt caned mercilessly by my friend, with my ass rammed by my friend wearing a big fat strap-on, and with my face buried between my friend’s butt cheeks and thighs, my mouth soaking wet! That's what I think.”
“You do know me well don't you?” I laughed.
So when I received the call from R I was not surprised when she turned the conversation to her weekend with M. I was a bit surprised how difficult it was for her and how embarrassed she seemed however. The conversation was going nowhere, but since I was all for this I decided to help out. “R, you seem to be having difficulty getting to a point. I assume you would like to play mistress once again to my slave?”
“Yes!” She gasped relieved.
“That would be great. But I would like to introduce something into the weekend that M is not expecting and that I think you will enjoy. When M and I were apart, before M asked to try again giving herself completely to me, I had met this girl named C. C likes pain. Like K that I've told you about, C can take an incredible amount of whipping and severe nipple punishment. At least as much as M. And C, like M, would do whatever I say. But for C, she gets something out of this on many levels, not just sexual, and not necessarily primarily sexual. She also has some other issues. We don’t look for her to get fucked up the ass; she will serve anybody with her mouth, but does not particularly care if she gets fucked or has an orgasm. However, I prefer to see that she does, but often the only way for her to orgasm is also what's most embarrassing for her, which is have to masturbate in front of everybody until she comes. Anyway, as you know, while M will service you for hours, she knows that I will be fucking her at some point and that I will make sure she cums many times. For M sexual gratification is a very big part of slavery; both my gratification and hers. For C it seems a little different. Also, she's been with women, with and without me. She says she's really not interested in women but she lived with one. She said she was just looking for someone who would make her, her bitch, and this woman came along at the right time. However, I've seen pictures and that woman was beautiful, and C is also very beautiful. I am quite sure many guys must've been hitting on her at the same time. None of this matters to me, or really should to you except for her limits of course, I'm just letting you know what she is like. What should be important to you is that she is very pretty, very willing, and very able to take any punishment you want, but you just can't fuck her up the ass.”
“That's okay.” R said, “because I don't actually get as much from strapping on a big fat rubber cock and fucking a slave up the ass as you do from watching. It's fine as a form of punishment but it's not my most preferable.”
“Great. You see, if I let M dominate another woman, she wants to fuck her up the ass, because even though M get’s soaking wet from it when she is used that way, it still hurts her a lot, and she wants to inflict that on other women who have the nerve to be with me in any way! What she doesn't understand because it isn't her personal experience is that it's not a painful punishment for some other women. She particularly likes to punish S when they are together, and she always likes to grab a big strap on and fuck S up the ass, so much so that I ask S to play along and act like it's painful, though I never used S much anally, certainly not as much as I used M, because while S enjoyed it, it neither hurt her at all like it did M, nor made her nearly as excited as it did M, so it was much more occasional when I did it with S. You should know that quite some time ago M was with C once. C had asked for my help with some stuff at work and I ended up having to do a great deal more of the work than I expected. I saved her ass so to speak, and then she stated that she should owe me hers in return! I agreed and picked a weekend when I had been particularly hard on M that week, and decided M could use a rest from punishment and service. I brought in C and informed them both that C would be slave to a slave. Interestingly, I enjoyed the weekend and I believe C got what she enjoyed, but I don't think M got much out of it. As I've mentioned M really likes to be the ultimate submissive because she knows that's the role I desire most from my slaves. When she does have to dominate another woman she likes to fuck them up the ass as I've mentioned because she considers that a particularly painful, harsh and humiliating punishment, but as I mentioned C doesn't get fucked anally. And I had C service M all weekend but she doesn't particularly want to have another woman licking her pussy or her asshole even though she clearly came a couple of times. So of all of us M probably got the least out of the weekend. Therefore, M will serve right alongside C, and even though C can take and appreciate the harsh punishment even more than M, we should both probably use and punish M a little bit more. At some point we should tell M she's a slave to the slave because of how well C is taking her punishments, and we should make M take a harsh punishment from C, you and myself, before sexually servicing all of us. This should give M a much better experience and then when it's time for C to come we can just have her play with herself in front of all of us until she cums.
“I can’t wait!.” R said.
“The important thing is that I would very much like to see one slave kneeling in front of you eating your pussy while another slave kneels behind you, her face buried between your cheeks, tonguing your asshole. I am quite sure you will enjoy it as much as I want to see it.”
“I am so wet right now. I'm so glad we had this talk!” R said.
“Me too!” I said. “If you were with us now I would make sure M took care of that beautiful wet pussy of yours! " I said.
“Would your cock be hard while she did it?” She asked.
“What do you think?!” I said.
“I told you more about the fantasies I wanted to experience last time. Of course we needed to proceed slowly and once we got started everything sort of unfolded on its own, with you as the Master and the guide. If I wanted to try some other things, you told me last time M would accept anything, but is that still true? Did she have any problems with the fact I sucked your cock right alongside her? That you punished me? Would she let me submit to you even more?”
“There were no regrets, why?”
“Because while we were talking I just imagined that I would serve your cock with more than my mouth while our slave bitch M would play with slave C in front of us for your entertainment, and then maybe they would both get behind you and lick your asshole while you fuck whichever of my holes you would like. I just wondered if that would go over well. “,
“When they wear their collars they will do whatever I command. C contacts me from time to time, and she knows M and I are emotionally tied, but she misses what we used to do to together, and she offered herself in whatever capacity M and I might choose to use her. She was well aware I could give her to M, and she might spend the weekend in pain and sexually deprived while she watched M and I fuck all weekend. Both M and C are particularly well skilled in submission. M would watch me do things with C if I decided, even if you were not around. For M and me, you are all props for our D/s relationship. As long as you can remember and remain within that guideline we can do whatever we want. The only time we run into a problem is when a slave thinks I will leave M behind for them…”
“I really can’t wait until we are all together…” R moaned.
“Then don’t. Play with your pussy while we continue to talk about how the two of them will serve you and how the three of you will serve me.” While we spoke on the phone R masturbated until she came. We set the date and time. Later on I called M and gave her, her instructions. I did not mention anything about C (whom I would be bringing with me), but I informed her that R would already be at her house with her when she prepared for my arrival. I knew M would find it particularly embarrassing to have to get into position naked, after putting on her cuffs and collar, when it was just R and her in the house.
At the appointed time when C and I arrived, I rang the bell and R let us in. The way the rooms are set up we could see ahead M from the side, bent over the end of the couch, reaching back and spreading her cheeks exposing herself. As soon as we walked in, C knowing her place, immediately stripped naked. She was already wearing a collar and cuffs, and she got down on the floor on her hands and knees.
“This is your slave C.” I said to R loud enough for M to hear. M and R will both be our bitches for the weekend. You will use and punish them as hard as I do, or you'll be used and punished yourself just as severely.
“I understand… Master.” R smiled as she responded.
“Get into position slave.” I barked at C, and she crawled into the living room, stood up and then bent over the end of the couch right next to M, spread her legs as much as she could which put her ass and legs right up against M, then reached back and spread her cheeks.
R and I walked in and stood behind them both. “Is there a hotter sight, then two beautiful slaves ready to submit?” I asked.
“Judging from how wet I am right now I don't think so!?” R whispered into my ear.
“Say that out loud I want our bitches to hear it!” After R repeated it, I got close to our slaves and pulled both their heads up a little by their hair.
“Slaves, what do we think about our mistresses soaking wet pussy?” They both responded, M basically saying she should do whatever her mistress wants to make her pussy feel good, while C essentially said, she should eat her mistress’ pussy until she cums, then she can lick all her juices up and mistress can start again.” I let their hair go and they put their heads down again. I motioned R to go sit on the other couch. “Kick off your shoes and relax.” I said to R, then, “Slaves, over to your Mistress and kneel at her feet.” They turned and M immediately got to her hands and knees and began to crawl. C started walking, realized what M was doing and then immediately dropped to her knees and began to crawl too.
“Out of practice, little whore? Don’t even remember your place without help from the other bitch? You must miss being punished also to have earned it so quickly!” I could see C’s expression did not change but M looked angry and dismayed. Already the momentum of submission was going in C’s direction and I was quite sure M was not looking for a repeat of their last time together.
When they were both kneeling before R, I sat down next to her and looked down at my two slaves. “You never greeted each other properly.” I said. They turned to each other, neither looking the other in the eyes, then moved in close and began kissing. “You have not seen each other in a while so get to know each other better!” I commanded. Their hands started roaming over each other’s bodies. They pulled each other close and tightly embraced, then after feeling each other’s asses they started to work their hands between their entwined bodies and then between their legs. As they started to touch each other’s pussies I told them, “That’s enough. You were doing what I wanted, but you have other things to focus on first.” M looked disappointed. I think when I stopped them she was hoping I was going to tell her she was doing something wrong and needed to be punished.
“Attend to your mistress’ feet while we figure what to do with our lovely whores.” I demanded. Each slave immediately bent to the foot closes to them and began to kiss it. Moments later R’s feet were each in a slaves hands being massaged while their mouths cleaned and sucked her toes and licked the soles.
I turned to R, “I know your pussy is soaked but I want you to wait a while before you cum. I myself would love to have my cock inside my little hot bitch M right about now, but before that, C has earned punishment, and truthfully I have been thinking all week about how I was going to make my beautiful M suffer BEFORE I fuck her.” I looked at M and saw her smile a little. I was glad this made her feel better because I was not anxious to have her screw up all day just to earn more punishment than C.
“I’ll wait Master. I want to do everything just the way you want.” R responded. I could see from R’s attitude that was going to make sure she was not going to allow M and C to be the only girls to serve me, and I suspected she planned to serve me far more intimately than just using her mouth which was her only opportunity last time.
“So, R, you have had a few months after your first experience to think about how you would like to punish and use your slaves next. How shall we punish C, and then, since I would like to punish M, though I have my own ideas, I would like to hear your thoughts on that as well?” I asked. Before Rcould answer I said, “M, take C and gather up every instrument of punishment we have here and lay them all out so R will find it easier to decide. Just the punishment, not all the collars, cuffs or outfits.” M and C turned from kneeling at R’s feet and crawled off into the bedroom.
“Any questions or concerns while they are in the other room?” I asked.
“I don’t think so. I understand C’s very few limits and I understand that she can take incredible amounts of punishment, and I was already impressed by what M could take, so really anything I can come up with will be acceptable. Since we will not be fucking C anally I feel I should not do it to M either.” R said.
“Really? I have a different take. I think it would be particularly effective and humiliating if I have C strap one on and fuck M up the ass with a particularly nasty rubber cock. Or if I have you or I fuck her up the ass while we make her eat C’s pussy or lick her asshole, maybe after making her beg to do it, again, while being fucked anally.”
“You have a deliciously devious streak.” R remarked.
“The hallmark of a good and creative Master, I think.”
“Why did you have them go gather up everything?” R asked.
“I know what we have and where it is. You don’t. You know we have nipple clamps, but not that we have several types, all with different methods of stimulating and punishing. We have some new whips, a new dressage whip, a couple of nice lunge whips, new canes, a thick leather signal whip. You need to see what we have, and I meant to have M put all that out earlier because I like to have it all accessible. Usually I don’t need everything because how much can I use with one slave, but we have 2 and I suspect I will have 3 slaves to use and punish before the weekend is out.” I answered.
“I hope you will make that happen, sir, about the 3 slaves.” R said. “If you do, I welcome you trying every instrument you can on me.”
“Really? You were not punished too severely last time and unless you have been punished a lot since, I think you should be careful what you wish for.”
“You are right Master that I have not been punished, except in my fantasies, almost every night. I am ready to try more, to take it as best I can, and even if I do not take it well, tie me down and make me accept whatever punishment you see fit.”
“For a new sub you have certainly become comfortable with punishment..”
“Perhaps it is because I have learned from my friend who I have come to consider, though I admittedly have limited experience, she is one of the best slaves a girl can be.” R answered.
“You are right about that, M is a unique and incredible slave.” I answered.
At that moment the slaves came crawling back into the room, each dragging 2 large bags. Those 4 bags were divided by type of punishment implement. The large duffle carried all the whips, canes and paddles. It was a large and long duffle because some of the firm shaft whips were 3-4 feet long. The next bag was much smaller and comprised nipple clamps, clothespins and weights and chains to attach to the clamps along with a host of leashes to attach to the collars.
The third bag contained strap-ons, butt plugs, dildos, vibrators, not straight punishment items—it depended how you used them and what size you! The 4th bag had miscellaneous items such as candles; fat stubby ones for collecting hot wax to long tapered elegant ones to be inserted anywhere I thought would make a good candle holder, to dog bowls, along with paper towels, tissues and condoms, which I placed over certain items before insertion, such as the candles because I was always afraid the wax would melt inside a slave and be difficult to remove. In this bag, and not with the nipple clamps, were the pins, wooden boards and tap hammers I used for more severe nipple torture, extra tacks for the seat of the punishment chair, tweezers, and any other assorted items I decided would be interesting to try on a slave. The slaves each emptied one bag on the floor, then started to arrange the items on the bag that had just contained them. Then they did the same with their other bags. Then they just stayed still and silent, kneeling next to all the instruments of their punishment.
“M, I do not see the punishment panties (the leather thong panties with 2 detachable dildos, which are only a form of punishment because I insert the bigger dildo in the ass), I don’t see the dildo handled duster, face sponge or other cleaning items. Do you not think humiliation is punishment because I thought you have gone through enough semi-public and private humiliation to see that it is!”
“I’m sorry Master, I do know humiliation is a very effective punishment. I'm sorry, I just happen to keep those items with my various slave outfits that you specified I did not need to retrieve. Of course I still should have gathered those items. I can get them now, Sir, while you think up a suitable punishment.”
“No need to get them slave. We have enough here to occupy our time, but you shall indeed be punished for this.”
“Yes Master. “ M responded.
“R, look over everything and decide what you want to use to start by punishing C. if you have any questions feel free to ask.” R stopped at the nipple clamps, picked up a pair, then walked back to me and started to whisper into my ear. I stopped her. “There's no need to whisper. They can hear whatever you have to ask so don't be shy.”
R looked uneasy, but continued. “These clamps,” she said softly but loud enough as she held up a particularly vicious pair of adjustable alligator clamps, “are very interesting to me, and I plan to watch C’s expression as I tighten them. But I'm concerned that if I make them too tight, they will hurt terribly and perhaps even draw blood.”
I walked over to where the slaves were kneeling; they were looking ahead but when I got next to C she looked down at the floor. I grabbed her hair and pulled her head face up looking into my eyes. “Do you have an answer for your mistress?” I asked. I let her hair go. She looked in the direction of R but did not look her in the eye. “You do not have to worry mistress. I should be punished as severely as you choose. Blood can sometimes be a risk of that particular clamp. I know them well. Master has made me put them on my own nipples and tighten them myself until I felt like I would scream.”
“Slaves, stand up.” They both did. “M, clip C’s wrist cuffs together behind her back. Then lick and suck her nipples to make them nice and hard.” M did as she was told. She attached C's cuffs behind her back and then came around in front of her and brought her mouth to her nipples. She licked them, kissed them, sucked on them, blew on them and massaged them until they were rock hard and jutting out. I handed M a tissue and told her to “dry off C's nipples so that the clamps don't slip off.” While she was drying her nipples I brought over a chair. “C, when M is done sit down on this chair. By the way, how did M make your nipples feel?”
“Wonderful Sir. She has a talented mouth. I felt each stroke of her tongue as if she were licking my pussy.”
“Excellent.” I responded. “She does indeed have an amazing mouth and talented tongue and inviting throat, though none of you will really appreciate her throat having only strap-ons to fuck it with! I look forward to her demonstrating her capabilities on all of us a little later.”
“Now R, punish your slave.” R approached C sitting down as instructed with her hands chained behind her back. R looked at the clamps and I hands and then looked over at me hesitantly, but I just motioned for her to continue. She pressed open one of the clamps and snapped it shut on C's right nipple. C let out a loud gasp.
“I take it they are adjusted a bit tight from the last time I use them with M?”
“Yes master. I guess M was a bad girl that day.”C said through gritted teeth.
“I guess I shouldn't make them tighter?” R asked me shaking her head as if she already anticipated my telling her that it was tight enough. But before I could answer C intervened,
“it hurts mistress, but clearly M was not as disobedient as I was careless today. I am sure our master thinks I deserve more severe punishment. I suggest you hurt me more than this, lest you find yourself on the other end of these terrible clamps, before you may have anticipated.” I could see R was weighing her options, perhaps considering what it might feel like if I punish her with those clamps, and then it seems she thought better of attempting such severe punishment this early in her own submissive training, and decided instead to pursue a dominant training at this moment. She clasped the clamp in her fingers and was about to begin to tighten when I stopped her and said; “she should have something in her mouth. “Whore,” I said to M , “Take a ball gag and rub your pussy with it. When it is nice and wet stick it in C's mouth and buckle it. At least she will have the pleasure of tasting your lovely pussy while she suffers.” C ran the tip of her tongue suggestively over the moist ball gag as M brought it to her mouth, making the effort to taste M’s pussy, not just be forced to taste it once the gag was pushed into her mouth. If she did this to show M she wanted to eat her pussy, she was barking up the wrong tree because M did not react at all, and despite everything she did with me up to this point and afterwards, M never betrayed even the slightest interest in women beyond what she did with me, or those few modest instances of playing around and kissing her friends. Once the gag was secure M dropped to her hands and knees and crawled a few feet away from C and knelt there. I gave R a nudge towards C. R had left one clamp on C’s right nipple and had left the other clamp hanging. She reached down and squeezed open the clamp on her nipple and C moaned through her gag as she pulled it off. Then R put the other clamp on C’s left nipple. C grunted through her gag and R pulled on the clamp and twisted it. C groaned and screwed her eyes tightly shut. Then R said, “Naughty slaves like you get punished. Maybe this will make you a better slave?” C could not speak through the gag, but she looked into R’s eyes and nodded her head. Then R began to tighten the clamp. The pain was evident in C’s eyes moments before she started to moan and groan through her gag. R stopped as her moans grew louder, then grabbed the hanging second clamp and snapped it back onto C’s sore right nipple. C cried out through her gag, and then R started tightening that clamp! The sounds C made now were much louder though she was not screaming through her gag, it was close. Then R grabbed both clamps and twisted. C ‘s moans of pain were very loud and a lone tear streamed down her left cheek. R stopped and let the clamps go. “I think that is enough nipple torture for this slut today.” R observed.
“Really?” I asked and walked over and removed C’s gag, Now any slave that knows me, that has been with me, trained by me and has wanted to spend any amount of time with me knows what I like to hear and that I like a slave to participate in her punishment, and if it is humiliating---all the better. So it did not surprise me that when I removed the gag and asked do you really think that was enough punishment? C said, “No Master, I should be hurt more than that.”
So, what do you say, slave?” I asked.
C paused a moment, took a deep breath, and then said, “Please Mistress, tighten the clamps more.”
R looked at me, and I said, “You heard her. How can you ignore such a sincere request? I did not replace the gag C, so try not to scream so loud you hurt our ears, and if you really feel you must, you may beg for mercy.” I stepped back and looked at R and said, “You may proceed.” I knew C could take a lot of pain, and when she felt she deserved it, even found it preferable, but her nipples had to be in agony. R had already faltered and I wondered who would give in first in this round. It was rare for C to give in and beg for mercy and she particularly appreciated nipple punishment. There were occasions where she said her nipples hurt, rubbing against her bra or shirts, for for over a week after a severe session!
“What did you ask for slave?” R asked.
“Please Mistress, tighten the clamps more and make your slave bitch suffer!” C begged and R grasped the clamp on her left nipple and gave the adjustment a half turn. C cried out then regained her composure. “Thank you Mistress.” She gasped. Then R grabbed the other clamp and tightened it by half a turn. C gasped again, then took a few deep breaths and spoke …very slowly. “Thank you Mistress.” R grabbed the clamps and started twisting them back and forth forcefully. C cried out, her eyes tightly shut, tears began to run down her cheeks. I suspected R twisted the clamps to hurt C without having to tighten the clamps anymore because I think she was afraid to make them any tighter! Finally, R opened the clamps and pulled them off C’s tits and C screamed out again. “I think this bitch has had enough punishment…to her nipples anyway….” R said.
“I agree that she has not had enough punishment, and that her nipples have had enough.” I walked over to C and unhooked the clip in the back releasing her wrists and grabbed her elbow ushering her to stand. “I am thinking we shall give this bitch a break while we begin M’s punishment…just then C interrupted. “I don’t need a break Master. If you think I deserve more punishment I should get it.” I quickly reached out and grabbed one of C’s abused nipples and pinched it between 2 fingers and twisted. “Don’t interrupt my saying I am giving you a break to say you don’t need one slave. I decide what happens to my slave’s.”
“I’m sorry Master.”
“Perhaps if I snap those clamps back on your nipples for another 15 minutes it would help to remind you who is in charge?” C looked terribly nervous at that, and she bit her lip and considered before she spoke; “Whatever you think is appropriate Master”, and she put her hands under her breasts to push them up and offer them to me. I could see a little fear in her eyes. Those nipples must already be in terrible pain. The thought of those clamps snapping shut on them again must have been scary indeed. “Consider this your only warning slave. Anymore disobedience and as pained as your nipples are now, you will learn that there is so much more that can be done to them.”
“Yes sir, I understand.”
“Fine. I'll need the end of the couch for M's punishment, so you may just get on the floor and get into position.” C kneeled, then bent forward until her forehead rested on the carpet, then she reached back and spread the cheeks of her ass exposing her asshole and pussy. M was kneeling on the floor. “Crawl to the couch and get into position.” I commanded. M got into position and as soon as she reached back and spread her cheeks I kneeled behind her and started to lick her asshole, working it deep in before moving to her soaking wet pussy. I know the dominant thing to do would've been to have C, or even R do it while I watched, but I love licking a beautiful slave's ass or pussy. M clearly did not expect me to use my mouth on her when she expected to be punished. She jumped a little at first when she first felt my tongue, since she expected to be punished. At first she may have thought I was just lightly moistening her ass so that I could plunge my cock in, but as soon as she realized what I was doing I could feel her asshole open up as she became even more excited . Besides enjoying oral sex, M loves it when I tongue her asshole, so her already wet pussy became a river. I so wanted to fuck her right then and there, and when I was getting close to cumming, pull out of her pussy and ram my cock deep up her asshole where I would shoot my load. Then I would have C lick my cock clean and then lick my Cum as it dripped out of M's asshole. However, I made R wait for her gratification so I decided I should do the same, but my cock was straining against my jeans and there was only so long I could wait! I pulled my mouth reluctantly from that beautiful, warm and inviting place and stood up. I turned to R and said, “Get me a signal whip, a rattan cane with a loop on the end, and a harness with a large strap-on rubber cock. C, tie M down tightly.” C got up and did what she was told but I could see R was having a hard time. She had a cane with a loop on the end and she picked up a harness that already had a large dildo on it, but she was fondling the various whips without choosing one. “Do you know what a signal whip is R?”
“No Sir, I’mI afraid I don't.”
“Then why wouldn't you ask? Why would you waste our time?”
“I'm sorry Sir.” R responded.
“I can see you need to be trained as a slave as well as a mistress. You have earned your own punishment today and you will receive it soon enough.” I said.
“Yes master. Thank you master.”
“A signal whip is a short thick leather whip. It looks like a mini bullwhip that that appears to have been made just to handle one ass at the time. It can be quite harsh. But it’s short length gives you a lot of control and ensures only where you want to whip gets whipped.” Moments later R found the appropriate whip and handed all three implements to me. I held the dildo harness separately and asked, “Does this look like something I'm going to use?”
“No master. Should I have kept it?”
“Originally I had planned it that way, but now that you are to be punished as well….” I threw the harness down in front of C, “Put that on C. Your punishment will continue after these two bitches have started their punishment.” Then I turned to R. “Get undressed.” I commanded. I turned and went into the bedroom. I returned with collar and cuffs for R. I saw C was done putting on her harness. “C help R put those on.” I stood in front of all three of them and said: “For the remainder of today R will be treated as a slave. I still expect her to help me punish the two of you so I guess today you will both be slaves of a slave.”
I walked over to the tied down M and stuck two fingers in her ass. I fucked her ass with them until I saw R was ready in cuffs and collar. “Kneel next to me R.” I demanded. When she was kneeling next to me, naked and submissive, I pulled my fingers and of M's ass and presented them to R, “Clean my fingers slave.” R did not hesitate to start licking and sucking my fingers. Then I said, “I was so delayed dealing with getting you ready for punishment that I believe M’s ass has dried and I am sure her pussy got bored. Start licking her asshole in and then eat her pussy. I expect both to be soaking wet as well as your face. Now move quickly.” R knelt behind M and stuck her face between her cheeks. She was eagerly working her tongue in and around M's asshole. I had to tell her to move on to her pussy. She was doing an amazing job and I couldn't wait until later when I could have them in a different position giving R easier access to M's pussy. “That's enough.” I said. “Go kneel next to C.” I retrieved a pair of Japanese Clover clamps. They would be tight but not very tight, and I could adjust them by tugging on the chain. I went over to R and put them on her nipples. Then I got behind M with the signal whip.
“M, I've been thinking about whipping your beautiful ass all week. Now that you've earned some punishment as well, I am going to be much harder on you. You don't need to count because I'm going to go far too fast and hard for you to do so. C, go sit on the couch and turn towards M and make sure that she's doing okay and breathing well during the whipping and caning. M you may scream if you like, but if you get uncomfortably loud I may choose to shove a big fat ball gag in your mouth. R, pay careful attention to this whip and cane because you and C are going to feel them today as well. ” Of course, I didn't plan on beating R as hard as I was going to do M or C because of her inexperience and still to be identified limits. But she didn't need to know that as I figured it would heighten her sense of anticipation and fear to imagine the worst.
I took the signal whip and got behind M. I raised it and brought it down a couple times slowly just to get my aim correct. Then I grabbed a handful of M's hair from behind and pulled her head up a bit and leaned in and whispered in her ear, “You going to take your punishment well for your master?”
“Yes master, I'll take anything for you.”
I stood back up behind her and raised the whip and brought it down very hard. I raised it again and I saw M bury her face into the couch cushion below. I brought the whip down hard and raised it brought it down again hard and raised it brought it down again hard, over and over, 10 times hard and fast. By the 10th M was crying out into the cushion, though not that loud and clearly not screaming. I knew M could take much more than this, and though I was doing it pretty hard, it wasn't as hard as I could and I knew, while very painful and with the capability of doing some damage if used thoughtlessly and carelessly, the signal whip wasn't the most vicious implement. Nevertheless, I knew she was suffering quite a bit for me. I let her rest a couple of minutes while I rubbed her ass occasionally pushing my fingers between her cheeks or bringing my hand down between her legs. I started to rub her pussy lightly and then worked a couple of fingers inside. She was not nearly as wet she was before; the painful whipping took care of that, but she was still nice and wet, being tied down, taking the whipping and serving her master took care of that as well! While rubbing her pussy I leaned down again and whispered in her ear, “How many times is my slave whore going to cum for me tonight?” “As many as my Master wants me to,” she whispered, and then she asked, “And how many times will my Master cum inside his slave tonight?”
“I would like to cum at least three times inside my bitch tonight. I'm going to cum in your asshole and these other slaves are going to lick my Cum out! I am going to come in your pussy and they are going to both eat my cum out of your pussy as well, and then I will cum in your mouth so that you can taste it too!” I said, then she whispered, “Is beating my ass so hard making your cock throb?”, to which I replied, “You know it is, it always does.” And then I leaned against her butt so she could feel my erection through my pants. “Then please punish your slave much more, until you cannot stand it anymore Master!” She begged. I gave her a little kiss and then stood up and raised the whip behind her again. I looked over to the C sitting on the couch watching M, and R kneeling on the floor, and then I brought the whip down hard. Waited a few seconds then raised it again and brought it down very hard. Waited a few seconds and raised it and brought it down hard and raised it brought it down hard and raised it brought it down hard another 10 times very quickly. She had her face buried in the couch cushion but this time I didn’t hear M cry out at all and C was watching and she looked at me more with wonder than concern. I grabbed M’s hair and pulled her head up, “I was afraid you fell asleep. You are enjoying this aren’t you slave?”
“Yes master, I had my face down so I would not scream too loud, but found I could take the punishment without screaming at all. I am ready for whatever further punishment you have in store for me. Please punish your bitch.”
“Excellent,” I began, “I think it is time to move on to the looped cane, which I suspect could be even more painful than the signal whip, but only you can be the judge of that. You make sure to tell the other slaves how painful it is because they going to feel it in a little while themselves and I want them looking forward to it.” I positioned myself behind M and to the side then raised the cane over her now red and welted ass, and brought down the loop end of the cane across her left cheek quite firmly. She cried out. I immediately raised the cane and brought it down even harder on her right cheek. She had buried her face back in the couch cushion in between strokes and now her cry came out quite muffled. Quickly I brought the cane down hard on her left cheek then her right, then again on her left cheek and then her right. She was shaking her ass and breathing heavy but she was not screaming into the cushion nor begging for mercy. “Tell the other slaves your impression, whore.” I demanded.
“Slaves, the loop ended cane hurts a lot. I don’t know if it hurts more than the signal whip but it is a different pain. It lands in a smaller spot and does not spread across both cheeks like the whip. It is very intense.” M finished and I raised the whip again and brought it down hard in quick succession; one cheek then the next, then again, and again. She hadn’t the chance to bury her face in the cushion before the first blow and she gasped but did not cry out. By the next blow she had buried her face again. I pulled her face up by pulling her hair again. I placed another cushion on top of the one she was leaning on and told her to put her chin down on it and keep her face up and facing ahead. I told R to sit next to C on the couch facing M. “I want them to see your face as each stroke lands, understand slave?”
“Yes Master.” M said sounding a little dismayed. From my vantage point behind M, I could see her beautiful and ever more reddening ass, and I could look into the faces of R and C watching M’s face. I brought down the cane extra hard. I saw both C and R grimace as they watched M’s face. M barely let out a sound though. I brought it down hard again, and again, and again. M cried out and R and C looked at her face and I could see admiration in R’s face and C---it was hard to tell whether she was impressed, or jealous, or a little of both.
“C, untie M and then tie R down in M’s place.” Soon M was free and kneeling on the floor while R was tied down. “It is the signal whip then looped cane for you now R.” I said as I reached under her and tugged on the chain hanging from the nipples clamps she’d worn for several minutes already. She cried out. “How do your nipples feel, bitch?”
“They were throbbing Master, but then they started to feel better, but when I was tied down they hurt a little at first when they pushed against the couch cushion but that subsided until you grabbed the chain and then they hurt terribly.”
“They started to go numb. Of what use is the absence of feeling to me? I can fix that though.” In a quick movement I reached under her again and pulled both clamps from R’s nipples and she screamed out in pain. “Brought the feeling back to your tits, whore?”
“Yes Master, thank you sir.”
“You will be feeling that for a little while, but don’t worry, in a few moments I will take your mind off of that. By the way, R and M, I hope you noticed that big fat cock hanging off C while she untied and tied you. After R’s whipping, and before C is punished some more, youwill both bw feeling that cock, as well as my own!” I rubbed R’s ass with the whip. “Get ready bitch.” I said and raised the whip and brought it down very hard. R cried out as I remembered that this was possibly the hardest stroke she had ever received. Then raised the whip and brought it down again, up and down, for a total of 15 times, but not nearly as hard as the first stroke and not as hard as I whipped M or would whip C. Her ass was red and striped and so were her upper thighs because I apparently missed twice, and her lower back which was marked by one stray lash. I rubber her ass and said, “Just warming up,” Then whipped her ass another 15 times about the same severity and not quite as rapidly. I pulled her head up by her hair and said, “You were looking to be whipped like a real slave, how does it feel slave?”
“It hurts Master, thank you.” After she answered I stuck two fingers roughly into her pussy. It was wet and when I pulled them out I put them in front of her face. “See how wet you are bitch? Only a true slave whore is wet when she is whipped, and that is the only kind of whore who can serve me!” Before she could say anything I shoved my fingers in R’s mouth and she greedily sucked and licked them. Then I pulled them out, grabbed the cane and got back behind her. “It is a taste of the looped cane now, slave!” I brought the cane up and then brought it firmly down. The looped landed squarely on her right cheek. It was not that hard a blow but she gasped. The loop at the end of the cane tends to make quite an impression. I raised it and brought it down on her left cheek. Then I began to do it in succession, one after the other, her right cheek then her left cheek then her right cheek then her left, increasing the force a little each time. By the last couple of strokes they were landing pretty hard and she was crying out after each one.
“What did you think of the looped cane slave?”
“It is very effective Master. I believe I will remember it for a long time.”
“Excellent. M, untie R.” She did so, and soon I had three slaves kneeling at my feet, C with that big fat rubber cock jutting out of its harness.
“M and R, turn to face each other.” After they had done so I commanded them to “Kiss and make out.” They pulled each other close and began to kiss, their tongues roaming each other's mouth. Then I commanded, “M lay on the floor on your back, R, sit on M's face and lean forward in a 69.” I watched the two slaves eat each other's pussies. They were both very good at it, which was good because I needed them very wet. “Both of you adjust your positions and start licking and tonguing each other's asshole. Make them very wet!” I demanded.
I touched C’s shoulder and gestured for her to come with me. We retrieved a heavy padded bench in the bedroom I keep just for this purpose. We placed the bench in the middle of the room and instructed M and R to both bend over and lean across the bench, opposite each other, so that R's face was next to M's butt, and M’s face was next to R’s ass as well. I retrieved two small wooden paddles and gave one to C.
“You're both going to get well used now. No hole will be spared. I expect wet pussies, open holes and no hesitation. To punctuate my point I brought the small wooden paddle down really hard 5 times across M’s ass, then did the same to R’s ass. Any performance lacking will be met with an immediate paddling. My only question, which is from M, is who gets your Master’s cock up her pussy and ass first and who gets the even bigger and harder rubber cock strapped to C up their pussy and ass first? Before you answer I have a question for R, which is, have you ever been fucked up the ass before?”
“No master.” R answered.
“Well then M, you have a decision to make. As you know my cock is certainly large and will make an impression the first time, but as you also know that dildo’s even bigger, and for an inexperienced asshole that hasn’t even been opened and prepared by a smaller cock first, you know that's going to be a brutal experience. So M, it's up to you, who gets your master's cock first?”
Without hesitation M responded, “Please fuck me with your cock first Master.”
R looked a little dismayed and nervous. I knew M was as anxious to be fucked as I was to fuck her, and never liked seeing my cock in another woman though she certainly dealt with it. I was glad to see that she would choose what she wanted even if it meant her friend would have a rougher time, because she certainly didn't owe this to R. Not only did R understand what she was getting into and do it completely of her own accord, but M had spent time serving R and being punished by her. She had licked R’s feet, asshole and pussy, and had been whipped and fucked up the ass by R. So in keeping with the spirit of doing everything with M first, I walked around in front of her and took off all my clothes. My cock was already jutting straight out in front of me hard and throbbing. I held onto M’s head as I thrust my cock into her mouth, deep into her throat. I slowly moved my hips gently fucking her throat as her tongue and lips caressed the shaft . “C, kneel behind me and get your tongue up my ass. Make sure you keep it in there while I fuck M's mouth.” C did as she was told and I started to fuck M’s mouth much harder, deeper and faster. Then I pulled out and pushed C away from my ass. “Fuck her mouth with that big strap- on too.” C fucked M’s mouth, stretching it wide with that big, fat dildo while I walked behind M. I entered M’s pussy and immediately started to fuck her hard and deep. M was getting it deep up her pussy and deep down her throat at the same time. Finally, I pulled out of her pussy and thrust my cock hard into her ass. She cried out, muffled by the cock in her mouth. “C, pull out of M's mouth and start fucking R's pussy.”
C did as she was told and I could see she slid easily into R’s soaking wet pussy. R started to moan. I started to fuck M’s ass as hard and deep as I could. She was biting her lower lip and moaning loudly. I looked over to C and said, “Work that big, fat, wet cock up the bitch’s asshole now!”
C slid out of that wet pussy and started to slowly and carefully work the big, fat head of that cock into R’s tight virgin asshole. “OH! Oh, that hurts Master, please!” R began and C instinctively removed the cock from R’s aching ass.
“Please what?” I asked. I expected her to immediately beg us to stop, in which case we would've stopped and found a suitable punishment for making us change our plans. But she paused and turned a little towards M’s ass, then looked straight ahead, and finally said, “Please continue to have me fucked up the ass, sir. I'm sorry I complained, Master, I've never done this, and I know I'm not near the slave M is, but I'm trying to learn from her…”
“I think you're doing a good job.” I replied, and then nodded to C, who brought the head of the cock back to R’s asshole. She started to work it in again and R was clearly distressed but she was able to relax and finally take it in.”
I reached over and caressed R’s face and said, “You're doing very well slave, keep it up.” After a little bit, I pulled out of M’s ass, and everything looked good as I brought my cock to R’s face. “Clean and suck my cock, whore!” I commanded as I presented my cock to R's mouth. R hesitated while she looked down at my cock, presumably for her to decide if it was acceptable. This was met with my immediately gesturing C to pull out of R’s asshole, which she did quickly and unceremoniously causing R to let out a pained gasp. Then I leaned forward and brought the paddle down hard and fast five times on each of her ass cheeks. She cried out a couple of times, then kept her mouth open until I was back in position and could shove my cock inside. I pushed my cock deep into her mouth and felt her working to rub her tongue all over my shaft and clean my cock as I commanded. I started to slowly fuck her mouth to give her tongue access to the tip of my shaft that was moments earlier buried in her throat. When I was satisfied, and also afraid I might cum, which I was not ready to do yet, I pulled out of her mouth and asked R : “Did you ever think you’d be bent over with your ass paddled then cleaning your Master’s cock from another girl’s ass, slave?”
“I’d fantasized about things like this, but it wasn’t until the first time I got to stay with you and M that I ever thought, even for a moment, that any of this would be possible.”
“And does reality match your fantasies?” I asked.
“In real life the punishment hurts more, but everything also feels better. Things take longer to set up, people are always instantly tied in my fantasies and you never have to go far to find the right whip or paddle, but overall I would have to say dominance and submission is every bit as exciting and satisfying as I imagined it would be. But I am not prepared to say which I like more yet, being Mistress or slave, because it is all so new and so exciting!” R responded.
“Excellent. Probably best that you did not decide which you like better because being a naked, tied down, slave whore at the moment, I may have decided to paddle you again if I did not like your answer.” I said.
“Yes sir.” R responded, smiling.
From here the dildo looked acceptable as I said to C, “C, I believe you have a cock that needs cleaning!” C said “Yes sir, I do.” As she glanced down and made sure it was ready, then she presented the large phallus to M’s mouth, and of course she opened wide and accepted the cock deeply. I looked at C, then down at M, then at R then back to C and C took the hint that I wanted to hear more and said to M, “That’s right Bitch, clean your Mistress’ ass off my big hard cock!”
As I was anxious to put my cock somewhere, and to see M’s ass stretched over that big hard rubber cock, I said to C, “That cock looks clean, but it looks like it really should be fucking some whore, or maybe that’s just my cock talking but either way it is time to switch….”
C got behind M and I got behind R. I eased my cock into R’s pussy for the first time. I was glad to see she was very wet despite having never experienced this much pain and submission before. I looked down and watched M’s face as she got fucked by that big dildo. She closed her eyes but she did not look as happy getting fucked by that big cock as R did. M loved to get fucked, but not by a piece of plastic. She could not just let go and enjoy the act if it was not how she wanted it. It was very hard for her to cum when another woman was eating her or engaging in any sexual contact with her, and only if I commanded it and she really wanted to please me was she able to cum under those circumstances.
“M looks bored. I should probably punish you for not fucking her better, C, but I will let you redeem yourself by finding something to get her attention now.” C knew exactly what I meant, as I am sure M did too, and she pulled the cock, now slick with M’s juices, out of her pussy and began to work the large head into her asshole. M took a deep breath and bit her lower lip and relaxed as best she could. She groaned and let out a quick “Ooohhh!” and then the cock was in and she was groaning as C impaled her ass with that big cock, driving it in and sliding it out almost all the way, then plunging it in. Although C liked to be the focus of the punishment and attention as much as M, and never evidenced the slightest dominant desires, it sure seemed to me like she was enjoying making M suffer. I didn’t notice her enjoy it so much when she was helping me punish R. As for me, as nice as R’s pussy was, it was time for me to feel how tight her ass was. I slid my cock out of her pussy and used it to spread her cheeks as I began to work the thick head into her asshole. She was tight and I told her to relax and she said she was trying and finally I pushed the head through and she cried out and drew in a deep breath and groaned as I worked the shaft all the way deeply into her ass. I pumped in and out and could feel her relaxing more. At that point I pulled out of her asshole and after checking, presented myself to M’s mouth. She dutifully opened and stuck her tongue out so she could begin to clean my cock before I shoved it in her mouth. M knew that I had trained her how I liked her to clean my cock after it had been inside her or another woman, and that was to lick it thoroughly from base to tip before sucking it. The only time she was allowed to go right to sucking was during this scenario, when she was expected to hold her position.
I was ready to move on but I was trying to figure out how to do the two things I wanted to do next, but at the same time. I decided the small wooden paddle I used to paddle R when she was slow to suck might work out.
“M, go kneel on the couch with your ass sticking out. C, kneel on the couch with your ass sticking out about 2 feet to the right of M. R, kneel on the floor next to the couch on the other side of M.” They all got into position. I got behind M and worked my cock into her pussy once again. I started to fuck her slowly, and in my right hand was the small, heavy wooden paddle. To my right was C, sticking her ass out, waiting for whatever I chose to do. I raised the paddle and brought it down hard on C’s ass, once, twice, three, four, five times---all the while thrusting away inside of lovely M. Then I pulled out of M’s pussy and worked my cock back into her beautiful, tight ass. I started thrusting again and I started paddling C’s ass again. It did not take long of this to make me explode inside M’s ass. Before I pulled out I gave C’s ass 10 more hard strokes. As I pulled out I told M, “Lean forward and stick you ass higher in the air.” As she did so I sat down on the couch and told R and C to clean my cock. They eagerly licked my cock and I enjoyed watching them work together so much that I told them to kiss each other for a while before I let them finish with my cock. Then I had them both kneel behind M and told her to lean back so her ass was now pointing down, and I had R and C, R first, take turns sticking their tongue into M’s asshole and licking my cum out of it. As soon as I saw some of my cum dripping onto R’s tongue I had C switch places. It took her longer, and she really had to work her tongue deep up M’s ass before she came out with some cum, but they both got to clean my cum out of M’s ass just as I had promised her!