Feb 052000
 

Can you recommend a particular lube for someone just learning to receive anal sex? I find that I chafe very easily, and I am thinking that a better lube might be the answer. Is baby oil safe for anal sex? What about Vaseline?

–M.S., Los Angeles, CA

No more chafing after this column, I promise! Lubricant is one of the most important ingredients to pleasurable anal sex, and the general rule is: you can never use too much lube! Remember that, unlike those juicy pussies we all love, the rectum is not self-lubricating. You need lube, and spit will not cut it this time. First, the bad news. Baby oil, Vaseline, olive oil or Crisco were not made for sex. Since they are oil-based, they are not safe to use with latex condoms and gloves. Also, if either you or your partner is a woman and an oil based lube gets inside the vagina, it will be very difficult to flush out and will likely cause an infection.

The good news is that there is a huge selection of great lubes on the market. I recommend a thick water-based lube that is similar to the consistency of hair gel. Water-based means that the lube is latex compatible, non-staining, odorless, and can be easily washed out. You want a thick lube — instead of a thin, watery one (like Astroglide or KY Liquid) — which will coat the delicate, sensitive lining of the anal canal and rectum. Many people reach right for that tube of K-Y Jelly; if it’s the only one available, then it will do the job, but there are better lubricants out there with more staying power. My favorite lube is ID, and there are also plenty of others: Probe (Thick and Rich formula), Wet, Foreplay Lube de Luxe (Gel or Cream). If you or your partner are sensitive to glycerin (a common ingredient in most water-based lubricants), try Maximus or Slippery Stuff Gel, which are glycerin-free.

The newest kind of lubes are silicone-based and keep things slick for a very long time. They are safe for use with condoms, but not with many silicone toys (silicone lube bonds to a silicone toy and ruins it). They also aren’t as thick as the water-based lubes I mentioned, but still worth a try; brand names include Eros, ID Millennium, and Wet Platinum. It’s a good idea to get sample sizes of a few different lubricants from places like Good Vibrations or Babeland. Try them out to discover the perfect lube that works for you!

Jan 152000
 

My husband and I have been married for six years. Although he has always played with my ass while we were making love, about three weeks ago, he actually put his cock in my ass. We’ve been doing it ever since, and it’s been great! He’s rather large, but we do a lot of warm up. Generally, we do it doggie style because I enjoy looking in the mirror, and seeing him behind me pumping away. Here’s my dilemma. Dennis always pulls out when he is about to come. This is very disappointing to me, and I would like to have him continue and shoot his juice into me. Would there be any problem with allowing his sperm to get into me that way?

–V.P., Bennington, VT

Congratulations on discovering the pleasures of butt bangin’! Once you open this particular flood gate, things will never be the same again. The question about your husband coming in your ass is a popular one (I got the same query from five different people this month). There really is nothing like the feeling of having a man’s hot load burst from his cock and fill that tight little orifice. He doesn’t have to feel worried or anxious about pulling out at the right moment — he can concentrate on working his way up and just letting go. He can stay inside until he has ridden his climax all the way to its end. As the receptive partner, the feeling of a firm dick inside my ass is out of this world, and I especially like to feel the moment before the climax, when that dick gets rock hard and ready to explode; if the guy pulls out at that moment, I feel empty, deprived, hungry, left on the side of the road to walk home alone. If we can share his coming together, I feel more connected with my partner, and his peak usually pushes me right over the edge into my own ecstatic orgasm.

But I understand that you are concerned about the safety of such a slippery through-the-sphincters delivery. If you are monogamous, and both of you have tested negative for HIV, STDs, and hepatitis, then your husband can come in your ass, and it is relatively low risk for both of you. If, however, you don’t have current negative test results for all these diseases, then either of you could transmit something to the other person through unprotected anal intercourse. This is true whether he comes inside you or not. You said you are married, but since this is the new millennium, I will not automatically assume that you are monogamous — you or your husband may have sex with multiple partners. If that is the case and for other readers out there who may be non-monogamous, anal penetration without a condom can put both people (and especially the receptive partner) at risk for contracting HIV, STDs, or hepatitis. Condoms and lube are the way to go. Let’s play it safe, folks!

Dec 151999
 

What are your thoughts on anal fisting? I know some women can do it, but isn’t it very rare?

–R.C.

Most people think anal fisting is either a gay urban legend or some freakish sexual circus feat. Actually, it is a very real sex act, and while it is more popular among gay men, certainly there are heterosexual couples and lesbians who are fisting lovers. I recently had the opportunity to teach a seminar on anal fisting at one of the only national events of the S/M community: The 14th Annual Living in Leather produced by the National Leather Association.

When I say the words anal fisting, most people’s immediate reaction is a wide-eyed, half terrified-half titillated “Yikes!” Take a deep breath. (It’s all in the breathing.) Anal fisting, also known as handballing, is the gradual process of putting your hand (and for very experienced players, sometimes your arm up to the elbow) inside someone’s ass. Fisting as a term is misleading since you don’t go inside all at once like a punch and usually your hand is not in a clenched fist once it is in there. Gay men popularized fisting in the late 60s and 70s during the sexual revolution, and founded private fisting clubs in major urban areas. I’ve read and heard tales of these sex clubs, filled with hungry men, waiting slings, and cans of Crisco. Although it is an intense exchange of power between two people, fisting isn’t exactly S/M. Because it is an outlaw sexual practice popularized by gay leathermen, it remains associated with and practiced by S/M folk, although not exclusively. Yet, like S/M, anal fisting explores and tests the farthest reaches of the mind and body’s inner limits.

While vaginal fisting is practiced among women and has been represented in classes, books, erotic stories and videos, anal fisting is a rarity. We’ve concentrated all our energy and efforts on one fabulously flexible orifice and overlooked the other. As a result, unlike gay men, women don’t have a history to hang on to like a sturdy sling, a legacy of fisting pros, role models to pass the skills from generation to generation.

I was scheduled to teach the anal fisting class with leatherman and leading handball expert Bert Herrman, author of the only book devoted exclusively to the subject, Trust: The Hand Book (Alamo Square Press). He also publishes Trust: The Handballing Newsletter. Bert, a fisting legend, has been putting his hands in men’s asses since I was in diapers. A true meeting of the minds and asses, the workshop proved to be a unique bridging of different perspectives, genders, and generations. In our opening, when we talked about warming up for fisting, our differences were readily apparent. An old school fister, Bert’s into getting high on pot and poppers and stuffing gobs of Crisco, whereas I am into endorphin highs and a nice, thick water based lubricant.

We viewed Handball Loving (Alamo Square/Erospirit Institute), which is unlike any video I’ve ever seen. Bert’s approach to fisting is very spiritual; he sees it as a path to enlightenment and higher consciousness, a way to connect with a higher power, and soul bond with another person. He draws on Eastern religions, particularly the principles of tantric sex. In that way, he is at the forefront of future sex, incorporating spirituality into sexuality.

Then there is the simple amazement factor seeing his arm almost to the elbow up his partner’s ass, then later with both hands inside him. It really is a different kind of sex; yes, there’s pleasure and intimacy and even orgasm, but that’s not all. Their bodies melding, their souls merging, both men were transported into a deep trance.

That night, after the workshop, I was inspired. I’ve been anally fisted before, but it was a long time ago and I wanted to do it again. My girlfriend Red and I had already decided to host a small sex party in our room. I started with a medium sized butt plug (appropriately called Voyager) in my ass which I wore for a while, then switched to a larger, very thick red plug. Whenever that one slides in my ass, it feels too big at first, but inevitably I take a deep breath and in it goes. When I felt like my ass was relaxed and ready for more, Red put on a latex glove, slipped out the butt plug, and started working her fingers inside me. I took lots of deep breaths, concentrated on relaxing and opening up. She eventually got all five fingers in to the final knuckles — the widest part of the hand, the dreaded sticking point. At one point I wanted to flip over from my back to my stomach and I was so absorbed that I tried to turn over with Red’s hand inside me not realizing that I would’ve broken her arm if I kept going. I kept asking for more lube but finally she let me know gently that there was plenty of lube, just no more room! At that point, I had moved beyond the point of orgasm, so we just relaxed, ate cheese and crackers with our guests, then fell asleep.

During the experience, I remembered Bert talking about what it feels like when you’re all the way up to someone’s transverse colon (which is beyond the rectum and descending colon). I realized I’m definitely a below-the-transverse-colon kind of girl. Hey, even Buttgirl has her limits.

Nov 231999
 

How do I identify a woman who is open to anal sex? Are there groups or organizations whereby consenting adults meet who are of like mind?

–Mark T.

I am a heterosexual man who loves anal sex. It occurred to me that it would be a good thing to have a society of sorts in which people who enjoy anal sex could meet each other and not have to bring the matter up later only to be disappointed by the reaction. There ought to be a forum for people who enjoy it to meet each other under safe and embarrassment-free circumstances. So far as I know, no such organization exists. Have you come across such a thing in your work?

–Brooke

Guys, I feel your pain. Unfortunately, you cannot tell if a woman is into anal sex just by looking at her. And these days, at the dawn of a new century, you really can’t make assumptions about anyone loving or hating anything sexual. You just never know.

Your concerns bring up several valid points. First, you are both feeling the stigma associated with anal sex in our society — it’s not an easy topic to bring up with people, especially a new sexual partner. If you ask about it during sex, your partner might feel pressured or raising the topic might kill the erotic moment altogether.

Instead, I recommend approaching the subject in a non-sexual context, where you can take the pressure off. Ask an innocuous question like “Have you heard about this book on anal sex for women — what do you think?” to see where she’s coming from. Give her the space to voice her opinions before you then ask the more personal question like “Do you want to try it with me?”

I don’t know of any organizations a la “Anal Lovers Anonymous,” but if there are any, you’d find them on the Internet. Or, start your own and see what happens. Sex toy stores like Good Vibrations, Babeland, Stormy Leather, and Grand Opening and SM organizations like QSM, The Eulenspiegel Society, and others offer workshops on a range of topics including anal sex; get plugged into your local community and see what resources are available. Good luck, and remember that there are women out there who love anal sex and others who I know are willing to try it and be converted.

Oct 041999
 

I want to learn how to make anal love to my girlfriend in such a way that she doesn’t describe it as hurting. Should we try a different position? I want it to feel so good. You are the woman who can help me.

–P.J., Reading, PA

I wish I could hop on a plane and give a personal tutorial to each couple who seeks my advice and guidance. I would arrive with a fully stocked briefcase of lube, latex gloves, condoms, vibrators, and butt plugs. I would let you two get revved up with lots of foreplay, and when you were both ready, I would lead you through anal penetration step by step. Go slow and be gentle. Use lots of lube. Work your way up, beginning with a finger or slim butt plug or dildo. Ask her if she wants clitoral stimulation; some women like to have their clits played with while getting fucked in the ass, others like their partners to concentrate solely on the butt. If she wants your hand or tongue or vibrator on her clit, give it to her. Talk to her the whole time, see what turns her on and what doesn’t work.

When you are ready to fuck her with your cock, find the best position. People always ask me: “What’s the best position for anal sex?” My answer: the one that works for both of you. Missionary position can be great, unless keeping her legs in the air or over your shoulders isn’t comfortable for her. Spooning works if your bodies line up naturally, and the man can get a good angle. If you choose doggie-style (my personal favorite), you can do traditional on-all-fours or do head-down-ass-in-the-air. With doggie-style, you can get a great angle to hit her G-spot, just remember not to go too deep at first. When you first enter her, just put your head inside, stop, and stay where you are. Let her sphincter muscles and anus get used to the feeling. Sometimes, she will actually suck you inside — when we are aroused, our anal canals and rectums start to contract and we can often pull a dick or a toy right in. If she doesn’t suck you in, slide into her very slowly. Many men make the mistake of trying to just shove it in there, and even with the most experienced woman, that just won’t work!

You sound like a very sensitive, caring, anal-sex-loving partner. Have you communicated your desires and concerns to your girlfriend? If she knows that you are caring and promise to be gentle, it will definitely set her mind (and her sphincter muscles!) at ease. You need to emphasize that, as the receptive partner, she’s the one in control of the action: it’s her call on how fast or slow, how deep or not-so-deep, and how much. That’s how I’d handle the situation in person. But, alas, my schedule just doesn’t permit it! Listen to her body and her verbal cues, go slow, and pretend I am there guiding you through it!

Aug 181999
 

My wife is 28 and I am 30; we have been married for three years. We are starting to get into anal sex. We have your book and want to experiment more — we even want to try fisting. Our problem is that we need more toys. The biggest plugs and dildos we can find are 2 1/4″ which feels like my max, but she thinks she can take more. Why is it that a big six foot man can only take a 2 1/4″ plug? Also, where can we get a speculum? Are there different ones for the ass and the vagina? How do you use it safely?

–Mr. G.

Wow, you’ve got a lot going on. I don’t know where you live, but I am assuming you’ve visited your local sex toy store and bought everything it’s sellin’. For more toys, I encourage you to check out two of the best sex toy purveyors in the world — Good Vibrations located in Berkeley and San Francisco  and Babeland in New York and Seattle. They both have an incredible selection of butt toys, from anal beads to high-quality silicone butt plugs and dildos by great manufacturers like Vixen Creations and Dils for Does. You may also want to check out some of the inflatable butt plugs and dildos on the market; you can go from slim to super with a few squeezes, making it a very versatile toy. As for the size issue, some of the lines of plugs and dongs marketed toward gay men seem to be of the size queen variety. Some of them are downright scary, even to Buttgirl.

So, it seems your wife can take a bigger plug than you, huh? Well, your height has little to do with how much you can stuff in your ass. My recommendation to you: practice, practice, practice.

As for your speculum request, you can find the disposable clear plastic kind and the metal re-usable type at medical supply stores (Babeland also carries them). Technically, a speculum is a speculum, and you should select a smallish one for anal use. If medical equipment and scenes are your fetish, you can also get some more expensive menacing-looking stainless steel speculums, and you can ask a medical supply house for an anal speculum. Make sure to use plenty of lubricant, insert the speculum slowly, and open it even slower.

Jun 121999
 

Help! Buttfucking hurts unbearably! It didn’t hurt so bad the first couple of years, but now, 5 years later, it does. It has never been my favorite thing, but it is my partner’s. He feels deprived and almost desperate. We’ve tried Anal-Ease and Anal Easy, but no luck! There must be something a girl can try. Could I use OraGel? Could I stretch my anus by using butt plugs daily? Would stretching exercises work? Please help!

–Kimberly, Spokane, WA

There are so many elements which you need to have a pleasurable, pain-free anal sex experience: lots of foreplay and warm-up, plenty of lubrication, and communication and trust between you and your partner. Anal sex should never, ever be painful. If it hurts, stop. Pain is your body’s way of telling you that whatever you’re doing isn’t working. You should always listen to your body. Your butthole knows what is best for you. At the first sign of pain, you may want to stop all activity or simply slow it down: maybe use one finger only, change to a smaller butt plug, decrease the depth of penetration, or switch to external anal stimulation only. Work your way back up, but never force anything. Go as slow as you need to, continue to add more lube, and talk to your partner so he knows exactly what does and doesn’t feel good.

I’d also like to address your mention of using products like “Anal Ease” or even OraGel. Anal Ease is the brand name of a lubricant (of which there are several) marketed for anal sex which contains a numbing agent. I absolutely do not recommend using products like Anal Ease ever. Because they have the effect of numbing your anal area, you cannot feel your ass literally and you are in danger of hurting yourself. Using products like these often lead people to go farther than they normally would, take something bigger in their ass than they should and the result is a sore ass, possible tearing and damage to the delicate lining of the anal canal and rectum, and pain after the fact that isn’t exactly going to want to make you rush right out and try anal sex again. There are plenty of great water-based lubricants that are thick and work well for anal sex (like I-D, Maximus, and ForPlay Lube de Luxe Cream), so use one of those. As for the OraGel, common sense and warnings on the label should let you know the answer: no. Just don’t go there.

Using butt plugs on a daily basis is a good way to get your butt used to having something inside it. Butt plugs don’t actually “stretch” your butt; they simply help you learn to relax your pelvic and sphincter muscles. In terms of exercises, many women find that Kegel exercises (which exercise your PC muscles) are very helpful. In order to locate your PC muscles, pretend that you are trying to stop peeing (or while you are peeing, you can actually stop the flow of urine). The muscles you contract to stop the flow are your PC muscles. If you put your finger on your perineum — the area between your vagina and your anus — while you do this exercise, you can feel the contractions.

Kegel exercises (named for the scientist who studied PC muscles and popularized the theory of exercising them) can help you to become more aware of your sphincter and PC muscles and learn to control and strengthen them. They will help you get in tune with the feelings in your pelvic area, increasing your sensitivity and responsiveness. The exercises will also tone the pelvic muscles, making them more flexible and more receptive to pleasurable sensations; when you exercise the PC muscles, other muscles in the area also are exercised and strengthened.

Women who regularly exercise their PC and pelvic muscles report some very positive benefits: heightened pelvic sensations and greater anal sensitivity; increased pleasure during clitoral stimulation, vaginal and anal penetration; more control over orgasms; and better, more intense orgasms. For more information on Kegel exercises, check out Anal Pleasure and Health by Jack Morin and The Complete Guide to Safer Sex from the Institute for Advanced Study of Human Sexuality. There is also a masturbation tool called the Kegelcisor, designed like a barbell for your pussy, which works wonders on those muscles!

But there is another crucial ingredient to great anal sex, the most important one — which may be missing for you, according to your letter: desire. You really have to want to be fucked in the ass.

First, you may want to think about why you don’t enjoy anal sex. Many people have fears and anxieties which, when kept to themselves, can result in tension and a butthole that just won’t let anything inside. Meditate on your feelings about and associations with anal sex, your past experiences with buttfucking, what you liked and disliked about it. Share your thoughts with your partner — sometimes talking about things can help you assuage your fears and relax. If you come to the conclusion that you don’t want to do it, then don’t do it. All the exercises, butt plugs, and lube in the world won’t do a damn thing if your heart’s not in it.

May 221999
 

Is it true that too-frequent insertion of penis/dildo/plug into the anus will lead to an enlarged and/or loosened sphincter? I have fantasies of anal sex which now include toilet training. Am I going to have to see a psychiatrist? Or am I going straight to hell?

–Paul

Your first question is one that I get asked over and over. As I say in my video: Let’s put this myth to rest once and for all. If you have a lot of anal sex, you are not going to end up in adult diapers. In others words, frequent backdoor banging — when done properly with care and lots of lube — will not lead to “an enlarged and/or loosened sphincter” or a loss of bowel control. In fact, having a lot of anal sex may do just the opposite: you may find that you actually have better bowel control than you did before. You see, in order to take something inside your rectum, you have to learn how to relax your sphincter muscles. The more you practice controlling these muscles, the more you are exercising and toning them (just like any other muscle). You are not stretching out or loosening the sphincter muscles, you are simply relaxing them to allow penetration. Have no fear, and keep opening up that back door.

Now, on to your second point about your fantasies involving anal sex and toilet training. Since you weren’t that specific, my mind went in several different directions. Some people who fantasize about anal sex also find the idea of shitting, playing with shit, smelling shit, eating shit and various other kinds of shit play (also known as “scat play”) highly erotic. There are plenty of people out there who share that fetish (especially on the web). Other people into anal sex are also into piss play (or golden showers) and combine the two into very hot scenes. There is a great erotic story in the anthology Hot Off The Net (Black Books) where one guy pisses into another guy’s ass after buttfucking him.

I recently did a scene where four dommes topped two subs, culminating in three of us taking turns fucking one of the subs in the ass and peeing on him. He was covered in plastic and we were wearing latex gloves. I remind you that both piss play and scat play involve exchanging bodily fluids, and you should practice safer sex when engaging in these activities. Still other anal enthusiasts like to combine butt play with infantilism or other “age play,” where the submissive can be a baby or a little boy or girl. Age play can be very hot, a great way to be a kid again, and toilet training is a frequent part of this fantasy.

Well, Paul, it sounds like you may want to end up in diapers, just not the adult variety! Your fantasies can be worthy of analysis, but not necessarily require you to see a shrink. Instead, I might recommend sharing your cravings with a partner or making an appointment with a professional dominatrix.

Apr 141999
 

I recently visited my local hip sex shop, and was amazed how many sex toys there are! There was a whole shelf of “butt plugs” — are those the best for anal penetration? Are there other particular toys that are good?

–Overwhelmed by the Selection, Jamaica Plain, MA

Well, the Anal Advisor happens to work in a sex toy store (Babeland) which helps me keep my finger on the pulse of sex toy trends and affords me a discount to purchase and test all the sex toys my little perverted heart desires! Let’s just say I know a thing or two about toys. In fact, my toy box is overflowing right now with all kinds of tools to shove into various orifices — my own and those of my loved ones. One of my favorite toys to use right now is a butt plug called “Voyager” and manufactured by a company called Dils for Does. It has a flared based, a skinny bottom portion and a very bulbous head at the top; it comes in four different sizes, all the same shape. The great thing about Voyager is that because of its unique shape, it is very easy to hold inside. Even with the strongest of muscles, sometimes butt plugs tend to slip out, especially if other activities are going on. This plug stays in place no matter what. I’ve been spanked, flogged, paddled, and caned with the plug inside. I’ve even been made to stand upright, do household chores, and run around — all the while with Voyager nestled in my ass!

Now for my advice:

There are lots of different toys on the market, and you should make your selection based on what you want to do with your toy. Butt plugs come in many different sizes, but all have a similar shape with slight variety: they are usually narrow at the top, thickest in the middle, and narrow at the base, which is flared. Some are diamond shaped, others are rippled with segments going from small to large. The great thing about butt plugs is that they were made for your butt. The flared base insures that a plug won’t get “lost” or go too far inside your ass. Butt plugs can be inserted in the ass and worn for a period of time. Because of their shape, they are designed to stay in place rather than be pushed in and out, as the sphincter muscles close around the narrow bottom. Butt plugs are good for two things. Many people like the feeling of fullness they get from having something in their ass, while other activities are going on. Butt plugs are also a great way to get your ass used to having something in it; the longer the plug stays in, the more the anal muscles tend to relax and open up. Using a series of different sizes of plugs can help you work up toward having something larger in your ass, like a dildo or penis.

Dildos come in so many different shapes and sizes that there is practically one for every individual taste, need and desire. There are dildos that look like dicks (with balls and realistic-looking heads), dildos that look like torpedoes, and even dildos that look like dolphins. Dildos that curve up from the base (instead of straight out) are often better suited to anal intercourse because they nicely mirror the curve of the rectum. Dildos are the best tools for the in-and-out variety of fucking.

Vibrating butt plugs and dildos have all the pluses of their non-vibrating counterparts, with the added attraction of a little buzz. Vibrators are also great for anal penetration, and vibration can actually relax the anal sphincters. Just make sure that the vibrator is long enough — like over 7″ — for penetration, and, ideally, has a flared base.

Anal beads are latex or plastic beads on a string with a ring on the end. The beads can be the size of marbles all the way up to the size of golf balls. Regardless of their size, make sure the balls are clean, smooth (file the edges if they’re not) and well-lubricated, and that the string is at least seven inches long. Many people like to insert the beads in the rectum while having their genitals stimulated. You should insert one bead at a time, giving the rectum a chance to adjust to the sensation; plus, it can be quite intense to feel the anus contract around each bead. Some people like to feed the balls inside and then pull them out just as they are climaxing; others like to climax with the beads in and then remove them. Remember, withdraw the beads slowly and gently, and don’t try to pull the entire string of beads out in one motion too quickly or it may be uncomfortable.

The majority of these toys are made of either silicone or latex. Silicone is the best material for toys because it is completely non-porous and therefore very easy to clean and disinfect. It’s also very resilient and conducts body heat. Latex rubber is less resilient and more difficult to clean, however does tend to be less expensive than silicone. There are also toys made of lucite, pyrex glass, wood, and leather.

In general, when choosing a toy, keep the following rules in mind:

  1. Never put any sharp objects or anything with rough or jagged edges in the rectum.
  2. Always use a lubricant with a toy; remember, the rectum is not self-lubricating. I recommend a thick, water based lube like I-D, Slippery Stuff Gel, Lube de Luxe Gel, Probe (Thick) or Maximus.
  3. Make sure that your tool is flexible enough to maneuver the curves of the rectum. Very hard, rigid things (like candles, metal or wooden objects) are not a good idea for your ass.
  4. Make sure that you clean your toys after each use, with sex toy cleaner, antibacterial soap and hot water, or bleach (diluted one part bleach, ten parts water).
  5. Never put anything in a rectum that may get lost or will be difficult to retrieve. Make sure dildos, plugs, and vibrating toys have flared bases.
  6. It’s really not a good idea to put something of an unrealistic width, length, shape or size in someone else’s or your own ass. Use common sense.
Mar 081999
 

I have just started working as a professional dominatrix, and some of my clients (men) want me to fuck them in the ass with a strap-on. Any advice for a novice in that area?

–Mistress Scarlett, Minneapolis, MN

I am so glad you brought this subject up! I just went to a play party at a small dungeon, and watched an amazing anal scene. A tall, gorgeous dom with fiery red hair and thigh-high PVC boots had her sub on his knees sucking her strap-on cock with his hands tied behind his back. He was a little wisp of a thing, but boy could he fit that big cock in his mouth. After he serviced her, she put him on a bondage table on his back, and basically tied his knees to his chest with some beautiful rope work (red, of course). When she snapped on a latex glove, you could see his eyes get big and glassy. She started working her fingers in his ass, and he squirmed and moaned, but couldn’t go anywhere. She came to the edge of the table and started teasing him with her greased-up cock. He went nuts. Finally, she gave it to him, all eight inches, and he was in heaven.

Now for my advice:

There are so many men out there who enjoy having their assholes stimulated, played with, licked, and penetrated. And, according to lots of men I’ve talked to who are into power play, they especially love to be anally penetrated as part of being dominated, disciplined, even punished or humiliated. In addition to all the nerve endings in the anal area, men have a pleasure spot that’s just too good to overlook — the prostate gland. You can stimulate the prostate with your finger or a dildo.

First, you want to choose a harness that fits you well — the snugger and more secure the better; there are many different kinds (usually made of nylon or leather), and you should definitely try them on in a sex toy store if possible to see which works best for you. For beginning anal players, I would recommend a smaller dildo to start out, but of course, you should find what works best for you and your clients.

As the one doing the penetration, you should also experiment with different positions. I know that the first few times I fucked someone in the ass with a strap-on, I had the person in traditional doggie-style position for several reasons: 1) doggie style gives you a clear view of the butthole, so you can see what the hell you’re doing 2) the position allows for a good angle of penetration, towards the prostate in men (and towards the G-spot in women); and 3) it’s an easy angle to get your balance, establish a rhythm, and get some good thrusting going. So, you may want to start out that way, but you can also try missionary (usually with legs over the shoulders) or man-on-top. Although, as a dominant, I would say that putting him in a position with his ass in the air and head down is probably the best way to go, both practically and for its obvious submissive possibilities.

Anal penetration requires patience, practice and lube, lots of lube. Make sure your bottom is warmed up with lots of teasing. When you start out, you want to go slow and let the butt get used to having something inside it. Always work your way up, adding more lube as you go. When he’s finally read for that big silicone dick, be gentle at first; the more you go easy in the beginning, the more his ass will open up and trust you later on when you really want to ram the guy!

For more on this subject, definitely check out the fabulous video series: Bend Over Boyfriend (Fatale Video) and Bend Over Boyfriend 2: Less Talkin’, More Rockin’ (S.I.R. Productions). There is also a good book called The Strap On Book (Greenery Press) and another called The Ultimate Guide to Dildo and Harness Sex (Cleis Press).