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!