Jun 152004

My boyfriend is ultra submissive in just one area: his ass. He doesn’t go for the Mistress thing, lick-my-boot mentality, but when it comes to his ass (which is the focus of his fantasies and always how he’s able to come) he’s full sub. I know exactly what he needs that way, pain and humiliation. Directed at his ass. Insulting HIM gets us nowhere, but insulting HIS ASS does. My snag is this: there are only so many ways to insult an ass. Degrading his ass, calling it a cunt or pussy gets him off in a snap. Is there any way to get good ideas to boost my imagination so play is not monotonous for either of us?

–Mistress of His Ass

Plenty of people get off on pain, humiliation, degradation, and overall submission. Clearly your boyfriend’s submissiveness is tied directly to his ass and anal play. There are many ways to combine submission and anal pleasure. You’ve already insulted his ass, but have you also tried to insult and humiliate him for wanting his ass penetrated, for being a naughty butt boy? Take all the cultural baggage that comes with anal pleasure, and use it to your advantage, as a psychological tool: it’s dirty, taboo, dangerous, and will make him gay. Of course those aren’t true, but these myths can make for great mindfuck material.

If he likes extreme submission, you may also want to explore forced anal penetration or anal rape scenes; that’s tricky territory, so tread lightly. It also sounds like there is an element of gender play in your man’s fantasies, since he enjoys having his ass be called his pussy. Try to explore that part of his desire further. Does he want to crossdress, to be girl? Does he want to be forced to do it? Forced feminization is quite popular and may be part of what he’s try to express in the anal play you’re currently having. See if he will open up about and be specific about his submissive anal desires, and use what he gives you to take things to the next level.

Jan 162004

My Master wants to give me anal training so that I can take a lot of use that way. I am not a virgin, but it has been some time since I have had any anal contact. What would be the best way to do this? He thought that putting a butt plug in me for five minutes twice a day would do it. I have tried this, but have only had problems with it. Perhaps it’s the plug. I am not sure what the plug is made of — it’s a hard-but-flexible plastic on the outside with a different type of plastic on the inside. It hurts when I stick it in, and that’s not helping my ass get properly trained. What should I do?

–Slave Butt in Training

Your Master has the right idea: anal training is a great way to mentally reinforce the Dominant/submissive dynamic as well as physically prepare your ass for extended anal play. I, too, use butt plugs as part of my anal training regimen.

The method I think that works best is to set up a plan for a bottom, where he or she gradually increases a number of elements. First, start with a very small plug and wear it for fifteen minutes. Continue to wear the small plug each day, adding fifteen minutes to the ritual. After a week, switch to a butt plug that’s slightly bigger, and start back at the fifteen minute mark, working your way up for another week. With each week, increase the size of the plug and the duration that you are wearing it. When you reach a large plug, with each new week, instead of changing the size, just up the amount of time you wear it. Use plenty of lube, and, if your Master allows it, play with your clit to make the experience more pleasurable (this will also relax your entire genital region and help you take more for longer). If it still hurts, honor your body’s response and go back down to the smaller sized plug, staying with it until you feel ready for more.

As for the type of plug, toys made partially or entirely of hard plastic aren’t a good idea for anal novices or the beginning of training. I recommend something soft and flexible made of either latex, vinyl, or silicone. Once you’re a pro, then you can move on to bigger, harder, heavier toys.

Dec 112003

My Mistress would like me to wear a butt plug daily. I’ve agreed to a small one, but she really wants me to wear a large one because she thinks that a bigger plug will make me more submissive to her. Is it possible and harmless?

–Plugged-up Slave

Wearing a butt plug every day is possible and harmless, as long as you use plenty of lube, and you warm up your ass with fingers or a smaller toy first. You should be aware of a butt plug, but it should not feel uncomfortable or painful at all. If you plan to wear it for several hours, you should work your way up in small increments in order to allow your body time to adjust to the new activity; in other words, if you’ve only ever had a plug in for fifteen minutes, don’t try it for four hours. As to the matter of your level of submissiveness, only you and your Mistress can really answer that. A bigger plug may make you more aware of your ass, and, by extension, help you focus on your dedication and service to your Mistress. But the size of a butt plug alone does not affect one’s level of submission — bigger does not always inspire better.

Oct 082003

In Anne Rice’s erotic novel The Claiming of Sleeping Beauty, there is a scene where Beauty was made to play a game: twenty roses were scattered all around a room where the Queen sat, and Beauty had to crawl around and pick the roses up and return them, one-by-one to the Queen, all the while being flogged to keep up her pace. Every time Beauty would bring a rose, the Queen would stick a large gold marble in Beauty’s ass. The trick being that the further along she got, the harder it was to keep going without dropping the marbles.

My husband and I thought this was really hot, and we’d love to play it out, but we are concerned with the idea of losing a marble inside my ass. Could that happen, and if so, what could we do to prevent it? We have worked with anal beads before, but there are only so many on a string, and those knots can sting! What can you suggest?

–Losing My Marbles

While I love erotic fiction as much as the next kinky reader, when it comes to representations of bondage, sadistic sensation play, and other BDSM activities, you need to remember that half of the stuff that fictional characters do in books isn’t even physically possible, let alone safe or meant to be instructional. Many, but not all, writers of leather smut have never actually done any of the things they write about. Or, even if they are players in real life, often they still indulge in fantastic fantasies they know are great to jerk off to; they don’t mean for anyone to try to replicate them.

The scene you describe from The Claiming of Sleeping Beauty is an example of a sexy scenario that’s not practical, and could be physically harmful. In general, anything you put in the ass should have a flared base (like on a dildo or butt plug) or another way to stop it from going all the way inside (like the ring on the end of a string of anal beads). Obviously, marbles don’t qualify, and they could get lost inside your ass. You’ve already played with anal beads, and you’re right, most people find the knots of the nylon or cotton rope pretty uncomfortable.

I have several suggestions for scenes that may appeal to you. If you want to be surprised, now is the time to stop reading and hand the magazine over to your husband. Several sex toy manufacturers sell toys which are a continuous series of beads, but the toy is all one piece (no string, no knots); some have several beads of the same size, while others have graduated beads which get larger and larger. Your husband can insert the first bead, send you off to retrieve rose #1, then slide the second bead inside, and so on. It creates a similar effect as the marbles with a toy that’s completely safe.

Or, if the goal is to make it increasingly difficult to keep the object inside your ass as you retrieve the roses, he can begin with a silicone butt plug, and, each new round, replace it with a plug made of a heavier material, moving from clear acrylic to glass to marble to stainless steel. I’ve used all of these high-end toys, and can tell you that when you stand up with a steel butt plug in your ass, it feels like a barbell that’s fighting gravity! A similar effect can be achieved with only one butt plug and a series of small weights usually used for cock and ball play or genitorture. Find a way to attach the weights to the base of the plug (I suggest a small piece around the rounded base), you can keep increasing the amount of weight each time a rose is retrieved. Use the story in the book as inspiration, but then be creative and create a scene that’s clever, cruel, whatever works for you. Most important, make it safe.

Apr 302003

My boyfriend and I have a Dom/sub relationship (he is the Dom). We also play with some “special friends” from time to time. Since I feel no hesitation having anal sex with him because of our love and trust, I am not really interested in engaging in it with others. He seems to see this as resistance to his control and it has led to some heated discussions. I have told him I am not interested but his challenge is, “How do you know you won’t like it if you don’t try it?” Do you have any advice on a good response or two that I can have ready the next time the subject comes up?

–Stubborn Submissive

While I understand that complete control and surrender of one’s free will is a goal for many people in Dominant/submissive relationships, I’m also practical: very few human beings can be 100% submissive and surrender all their free will to another person. That’s why it is quite common in the leather world for people to negotiate ground rules in scenes and relationships. I appreciate your Dominant’s desire to have your complete obedience, to push you to expand your erotic horizons, and to see other people fuck you in the ass; however, I am siding with you on this one. You have communicated a clear boundary to him, and I think that boundary needs to be respected. He needs to see that you having limits does not mean you are resisting him, but that you are taking care of yourself, listening to your instincts, and communicating clearly — which are all great qualities for a submissive to have.

Oct 122002

Receiving anal penetration and being sexually submissive has always been the focus of my sexual fantasies. More specifically, I like the anal penetration to be painful. I always imagined it that way and was disappointed when my partner was too gentle at first. He knows me better now, and I have been able to fulfill my anal fantasies with him for the past six months. We usually start with fingers, dildos or plugs, but unlike everything else I’ve read, we use these to make me sore, not to warm me up, and we use as little lubrication as possible. I can only feel totally aroused when it begins to burn, sting, or ache and I feel I want my partner to stop. This particular pain, coupled with some light to medium flogging, is the one thing that makes me really orgasm. I also love the feeling of soreness the next day.

I always recover after a day or so of restraint, but I am now worried after reading more about the dos and don’t of anal sex that over time I could cause permanent damage to myself. I love it so much, and it is so sexually satisfying to me that it would be a problem for me to lessen this behavior. I would like to know if anyone else has enjoyed such rough anal penetration over a long period of time, and if they have or haven’t had any problems.

–Rough Anal Player

Thank you for writing to me. I think it is incredibly brave of you to be so honest about your sexual desires and practices, especially when many people might see them as sick, twisted, and politically incorrect, even fellow BDSM players. I appreciate your candor, and I think that yours is an important letter to print, because I am sure you are not the only one out there. As kinky people who practice all kinds of BDSM, we know that there is a fine line between pleasure and pain, and that line is different for everyone. People who enjoy flogging, spanking, piercing, and other forms of intense sensation play know the high from the rush of endorphins we get, the thrill of pushing the limits of our bodies, and the orgasmic potential of these activities which non-kinky people would see as cruel and painful.

As a community, BDSM players often reiterate ad nauseum that our activities are “safe, sane, and consensual” and we frown upon “unsafe” players. With most forms of sensation play, you can paddle, whip, beat, pierce and cut fleshy, well-padded areas of the body. You should never strike joints, boney areas, areas around internal organs, the neck, head, or face. I think the ass would fall into the latter category as an area we shouldn’t deliberately hurt simply because unlike fleshly parts of our body which may redden, bruise, or bleed but eventually recover completely, the ass is not so resilient. The rectum is quite delicate, which is why sex educators like myself encourage people to go slow, warm the body up, and use plenty of lube. It’s a matter of comfort — I assume that the majority of people do not want to experience pain through anal penetration. Anal sex has long been mythologized as violent and painful for women, and I am attempting to counteract that stereotype by teaching people to have pain-free anal penetration.

Your desire for pain puts you in the minority but that doesn’t mean it is not valid. However, you need to know the risks of your practices. Through repeated penetration with little warm up, no lube, or deliberate roughness, you can scrape or abrade the rectum, develop anal fissures and other ailments, and cause permanent damage to your ass. Permanent damage could mean no more anal play at all, which doesn’t sound like what you want. Yours is a difficult dilemma. I want you to do what turns you on and makes you come, but I don’t want you to hurt yourself or damage your body in the process.

I think you should explore other kinds of play which may produce similar sensations for you, but happen on a less fragile part of the body. But even as I write that recommendation, I realize that part of the turn on for you may be that you don’t want to feel pain in the “safe” places on your body, but in the very places we’re told are too delicate and off limits. You and your partner should explore new ways to approximate the pain sensations while still taking good care of your ass. Adding warm up and lube to the equation will protect your body and won’t prevent you from feeling the burn or the ache, especially with especially large toys. You need to find that unique line for yourself where the sensation is intense enough to satisfy you, but you are mindful of not hurting yourself.

Apr 182002

I’m a professional dominatrix, and have several clients into forced feminization and anal play.
 Some of them have requested that I insert tampons into their (anal) “pussies.” Can this be done safely? I know that there is a risk of toxic shock syndrome when tampons are used vaginally, and I am wondering if it can happen in the ass as well.

–Mistress Mean

Toxic Shock Syndrome is a blood-borne bacterial infection caused by the bacteria Staphylococcus. We most commonly hear about it in relation to using tampons, and symptoms can include fever, chills, vomiting, sore throat, headache and more serious conditions. It is treated with intravenous antibiotics to prevent shock and kidney failure. TSS colonizes skin and mucous membranes, and the rectum is a mucous membrane; however, I had a difficult time locating any documented cases of TSS through the use of tampons anally. Since tampons are used to absorb moisture, it could be uncomfortable and dehydrating at the very least.

I have an easy solution for you. In fact, it’s for anyone who has a client lover who wants something in his or her ass which you know is either unsafe or potentially dangerous (other examples include glass bottles, candles, baseball bats, just to name a few). Find a sex toy with a similar size and feel to the desired (but unadvisable) object. Blindfold your bottom before inserting the toy in his or her ass, and make sure to talk about whatever the fantasized thing is in great detail. If you’re a good Top, you can convince a submissive of almost anything.

Apr 042002

My partner and I are in a permanent Dominant/submissive relationship, and have been experimenting with anal sex for over two years now. We both get a lot of pleasure out of it. He likes to have me wear a locking harness to keep a butt plug in place while we go out to dinner and a movie. The trouble is, after about an hour, I need to use the restroom and must remove it. What can I do prior to ‘harnessing up’ that will allow me to be able to wear the harness for a longer time? Should I change my diet prior to the excursion?

—Anal Slut in Texas

The amount of time you can wear a butt plug depends upon your personal bathroom schedule, and everyone’s particular time table varies greatly. It sounds like you’re an evening bathroom goer, and that you’ve got a pretty fast metabolism (because shortly after eating, you have to go to the bathroom). In order to prolong your butt plug wearing, I suggest that dinner time be moved. You could eat dinner, wait to have a bowel movement, then get locked in your harness for several hours. Or perhaps you can have an outing with the butt plug in your ass that doesn’t involve food, then, after the scene is over, treat yourself to a meal. If the outing must include dinner, than perhaps your Top should insist that you watch him eat, while you’re limited to water only (sorry to give him tips from my sadistic Top self, but you did ask). If you’re a good girl, maybe he’ll feed you after you’ve held that butt plug in long enough!

Dec 162000

My wife and I of nine years have been experiencing trouble for some time in our relationship. Upon my search to get a new fire rolling, I sought out new ways to please her, which in turn brought us to the world of BDSM. We are both intrigued by anal play (giving and receiving), but she is a little concerned. I think it might be too painful for her. I myself believe we are well on our way to restoring and incorporating this new volcano of sexual energy, but I want to make it happen safely. Also, what are your thoughts on switching?


It makes perfect sense to me when people want to combine anal sex and BDSM. Anal play can be very emotionally and psychologically charged, and it can be a perfect activity in which to explore the erotic dynamics of power and control. We learn early on that our assholes are a source of embarrassment and shame or that our buttholes are private, dirty, and shouldn’t be thought of in a sexual way. Anal sex is taboo, forbidden, shrouded in mystery and misinformation. Our asses are also very delicate, sensitive areas that require an extra level of communication, trust, and skill. In other words, you can hurt someone if you don’t do it correctly. When I say hurt, I mean not in a good way.

When I teach anal sex workshops to people who aren’t into BDSM, I try to help them overcome all those negative feelings so they can move on and have pleasurable anal sex. But if you are into BDSM, it’s a different story. As tops, we can take advantage of all these elements of anal eroticism in a scene. We can play on all these different psychological angles to make anal sex a hot BDSM experience. You can taunt a bottom, telling her that she’s nasty and perverted for getting fucked in the ass. You can take a level of control and comfort away from your bottom. When I bottom, I find that giving up my ass to my top can be the ultimate act of submission. Giving over such a delicate part of my body to another person magnifies the inherent power in penetration.

In a non-BDSM context, I recommend lots of communication, but the kinds of things I recommend people say don’t necessarily translate while you’re in role. A top can’t ask “How does that feel honey, am I hurting you?” A bottom can’t say “Go slower, I don’t like it so fast; Okay, I’m ready for more now.” That kind of banter could throw off the dynamic. So I recommend prior communication and negotiation. You can also incorporate different ways to warm up your bottom’s ass into your scene — for example, if you develop a system where the bottom needs to tell you when she wants something bigger in her ass, you’ll know she’s ready without having to ask her (she’ll be the one who has to ask!).

As for my thoughts on switching, contrary to some popular thinking, switches are not just wishy-washy folks who can’t make up their minds. Switches are people who like to see things from both sides and take different positions depending on the particular situation. You may start out wanting to experience different aspects of BDSM from both ends, doling it out and taking it, then find you come to see you really do fit into one or the other. But don’t feel like you have to choose right away or identify yourself to the world at large. Focus on what you want rather than what label applies to you.

Jul 182000

I would really like to have my wife perform anal pleasure on my ass but she doesn’t seem to be very into it. She enjoys receiving anal sex, and I have mentioned in the past what I would like her to do, but I can tell she’s a little weirded out by my request. Any suggestions?


Congratulations on coming out of the backdoor closet! I think it is especially revolutionary for straight men to admit their desire to be the receivers of anal pleasure. You join plenty of men who want to get done in the ass, and I promise you that once you’ve had your prostate gland stimulated, you’ll never be the same again! For men, it’s a chance to be penetrated, to give your body over to a woman in a new way. Seriously, I think every man should be fucked in the ass at least once in their life, and I am so glad you are ready to try it. I truly believe that getting fucked in the ass is one of the greatest gifts you can give a woman and yourself.

Now, on to your wife. I am not sure exactly why she is “weirded out” by your request. I can tell you that she doesn’t know what she is missing. Giving men anal pleasure gives women an opportunity to be the aggressor or the penetrator for the first time. Your wife has the chance to experience her sexual power as a woman and a giver of pleasure in a wholly unique way. Have you asked her directly why she might be hesitant to do it? Many people can buy into the myth that if men want to be fucked in the ass, then they are really gay. This is ridiculous, of course. Because anal sex is falsely linked with gay men and gay sex, there is a myth that if men want anal sex, then they must be gay. In most cases, men who identify as heterosexual and desire giving and/or receiving anal sex with women are not repressing homosexual desires or tendencies. Their desire for a particular sexual activity does not rely on or “cancel out” their sexual preference in a partner. According to research, more gay men regularly practice fellatio than anal sex, and as my friend Audrey says, “How come no one ever asks: if a straight guy likes blow jobs, does that mean he’s really gay?” Your wife may be a victim of this stereotype, and you need to assure her that you love her, are attracted to her, and want her to do you in the ass.

Different men also want to be fucked in different ways. Some want to be submissive as part of an SM scene, and giving up your ass can be an ecstatic way to submit. Men have lots of issues to get over when it comes to being penetrated (feeling passive, receptive, plus homophobia), so sometimes being “forced” to do it by a Mistress or dominant woman helps them take that leap. These are specific to SM, and may or may not apply to you. Either way, men don’t necessarily have to be bottoms to be fucked in the ass. I have personally fucked plenty of tops in the ass without flipping them — it’s all in the way you play it.

There are a few superb resources that I recommend you and your wife check out. They will help to open up a dialogue about this subject, and will also give you great information, tips, and techniques for doing the deed. The book, The Ultimate Guide to Strap-on Sex by Karlyn Lotney is informative and very useful. There are two videos: Bend Over Boyfriend is heavy on super instruction and stars real life couples. Bend Over Boyfriend 2: Less Talkin’, More Rockin’ has a title that says it all. Both are produced by S.I.R. Video.