Feb 242004
 

My girlfriend has a severe anal sex fetish. She prefers it over vaginal intercourse. Fortunately, I don’t mind it one bit. We’ve done some ass-to-mouth stuff, since we are monogamous and STD-free. I’d like to experiment eating food out of her anus — either food shoved partially into the anus or food that has been completely inserted and then pushed out. I’m wondering what food products would be safe for this, since I don’t want anything to get stuck up there. So I’m looking for something that would be semi-rigid, but would also melt or dissolve if it got lost. I was thinking about things like M&Ms (the non-peanut variety) and other chocolate things, but I can only stomach so much chocolate.

–Butt Buffet Boy

Usually I advise people against sticking food in their ass, since food items are not sex toys and are better left in the kitchen. But you seem pretty invested in this food fantasy, so I’ll suspend my anti-food stance for this response. But before I go there, I just have to say that what you describe is an interesting twist on one of the most taboo desires in the world: scat play. Scat play involves people defecating into other people’s mouths, eating shit, and generally eroticizing it. It sounds to me that you like the idea of stuff coming out of your girlfriend’s ass, even stuff that resembles what typically comes out of our asses (you suggested chocolate, not me), but you want it to be previously undigested.

As long as you take care to insert your chosen edibles just inside the anus and not too far up, there’s no great danger of soft or small foods getting lost. What goes in will inevitably come out. You should avoid foods like jalapeno peppers, seeded breadsticks, and others that are spicy, abrasive, or could break into sharp-edged pieces, which could all irritate the delicate rectal tissue. Also stay away from salami or sausages, since nitrites used for preserving meat aren’t good for you. I’m glad to hear that you’ve both been tested for STDs, but it’s probably still a good idea if your girlfriend has an enema a few hours before your feast, since her ass contains bacteria that may be fine in the lower intestine, but may cause problems if you ingest it.

Feb 172004
 

I thought you might be able to shed some light on a long time unanswered question. About two years ago, I was a having a sexual relationship with a woman. The sex was mind-blowing and we were very sexually compatible. Probably one of the best compatibility I have had with a partner. One evening while having vaginal sex, I was penetrating her from behind. Just before she was about to have an explosive, gushing orgasm, her ass expanded to about the size of a baseball, or maybe a bit bigger, and then contracted again. I had never experienced this before with another woman, and subsequently never had. She did enjoy anal sex, but I didn’t even touch her ass on that occasion. Any ideas?

–Perplexed About Her Butt

No worries! You may have witnessed one of two things, and since I wasn’t actually there when your girl’s ass amazed you, I’ll explain both possibilities.

First, there’s a chance that her asshole was gaping with delight. Usually, this happens after an intense session of ass pounding when a woman’s ass has gotten open and relaxed. When all is said and done, it can achieve the gape, which you often see in porn. You admit that you didn’t deliver any buttfucking that time, but it is still possible, if rare, that her ass was relaxed enough during her orgasm that she’d get a gape.

Another scenario is one that looks even more dramatic. When a woman begins to orgasm, especially if she’s a gusher (as you described your girlfriend is), she often she bears down. And this bearing down can cause an effect in certain women where the rectal tissue actually pushes briefly outside the body. It looks almost like a rose, with multiple layers. I have actually experienced this phenomenon with one of my lovers, and although it was shocking to see, it’s really okay.

Feb 102004
 

Have you heard of figging? Do you think it’s safe to do? My submissive and I are headed to a party next week where figging is to be the central theme. Any information you could provide would be very useful.

–Liar, Liar, Ass on Fire?

For readers who may not know what it is, let me begin with a definition. Rumored to have been practiced as early as the Victorian era (they were so kinky!), figging involves sticking a ginger root up someone’s (or your own) ass, and most people I know do it in the context of a BDSM scene. The idea is that the ginger illicits an intense, long-lasting burning sensation in the sensitive, delicate tissue of the rectum. I’ve heard of some Dominants who insert the root into a submissive’s ass before a spanking, paddling, or caning. The longer the root is inside the butt, and the more blood that rushes to the area, the stronger the burning. Plus, any kind of movement — including clenching the sphincter muscle s– increases the fiery feeling.

This is not an activity for anal play novices or people with extra-sensitive behinds. I consider it an internal form of genitorture; if your bottom enjoys sensation play like ice cubes or metholated sports creams on her pussy lips or her anus, figging takes this “torture” one step further. Plus, you should not use creams like Ben Gay or Icy Hot inside the pussy or ass. While some bottoms say that figging feels warm and tingly like the creams, most report that the sensation is ten times more intense.

There are a few safety tips that go along with this practice. You should begin with a fresh, whole ginger piece (also called a hand), and peel off the brown rough skin before slicing a “finger” to use for penetration. Because it obviously does not have a flared base (and therefore could get lost in the ass), select the largest piece you can find, and either carve out your own shape with a base or attach a string to it in order to make it easy to retrieve. After handling a peeled root, you shouldn’t touch your eyes or your slave’s eyes. Some figging fans say that lube can seal in the moisture and prevent it from releasing, thereby defeating the purpose, but you know my stance on lube: you need it! Other than those precautions, as with all perverted activities, use your common sense.

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 052003
 

I am very aroused by the anal jewelry worn by one of the actresses in Evil Angel’s The Fashionistas. I would like to get something like that for my girlfriend, but the only ones I can find start at around $75. This is a little bit much for a broke college student. Are there any alternatives that come to mind which are cheaper and safe?

–Jonesin’ for Jewels

I assume that the ones you found are Rosebuds Erotic Jewelry by designer Julian Snelling. Based in France, Snelling creates truly unique butt plugs made of stainless steel or bronze; each base is crafted with precious metals and semi-precious stones (like amethyst and malachite) to look like jewelry. When you slide the plug inside someone’s ass and all that remains is the base, the effect is kind of like a pierced ear but for your butt! It’s like wearing a work of art in your ass. No one has even tried to copy Snelling, so unfortunately there aren’t any cheap Snelling knock-offs.

If an artsy anal plug is what you’re after, lots of silicone sex toy manufacturers have risen to the call: Vixen Creations makes its Buddy plug in sparkly sliver, gold, or pink glitter; Tantus has stunning metallic colored plugs; and there are several other multi-colored swirled anal toys.

Nov 182003
 

My girlfriend is a bit crazy for anal. When we’re out shopping at the mall, in broad daylight, with no concern for who hears her, she’ll say something like “I’d like that up my ass.” She will say this about video game controllers, sports equipment, household appliances, children’s toys — you name it. I think she gets a kick out of this. I just imagine the look on people’s faces when they overhear it, and I cringe. It’s embarrassing! She just doesn’t care. Would you recommend threatening to take away anal from her? Should I just end the anal ritual altogether? Or, God forbid, should I fuck her ass so hard that she never wants to do it again?

–I Have an Anal-Crazed Girlfriend

I can’t decide why I chose to answer your letter: to illustrate that I receive some of the best letters in the sex advice business or to indulge you because you might just be fucking with me! I’m going to embrace the former, and assume that your girlfriend’s behavior is, in fact, an issue.

First, all the men out there who can’t get their wives to agree to anal play at all are reading this and shouting out loud, “Dude! I wish I had your problems!” Count your blessings that you have not just a willing, but a clearly enthusiastic, anal sex partner.

It sounds to me like your girlfriend is not simply “anal crazed,” but she’s also a verbal exhibitionist: she enjoys saying bold, sexually suggestive things in public, and she wants those around her to hear her and be shocked. There is only one potential problem with this situation: there are many public places where it’s really inappropriate for her to talk her tushy trash, especially when she’s within earshot of children. Threatening to “take away anal” or actually doing that will only fuel her bratty inner-schoolgirl and hurting her during anal sex is just mean and stupid. Let her know that her explicit public chat bothers you, but also offer a solution: encourage her to save all her naughty little ideas for when you get into bed, where she can whisper them to you or shout them out loud. In that erotic context, you too will probably get off on her mouthing off. If she can’t keep her thoughts to herself the next time you go out, then a spanking and a gag are in order.

Nov 082003
 

My girlfriend and I have tried anal sex multiple times, but she doesn’t like it unless I rub her clit. As soon as I stop rubbing it, she says it’s very painful and wants to stop. She is also afraid to try doing certain anal positions. We only do it lying on our sides, facing the same direction. She claims that doggy style hurts too much from our one time of trying it. I am desperate for help!

–Anal Addict Denied

It fascinates me that you consider yourself an “anal addict denied,” because you are, in fact, having anal sex — just not necessarily in the exact way you want to be. If your wife doesn’t like it doggy style, that’s most likely because that position offers the deepest penetration, and it obviously doesn’t work for her; fucking her in “spooning position” — which you say works for you — may mean less deep thrusting for you, but a lot more comfort for her. If you’re simply dying to do it to her doggy style, then I suggest taking more shallow strokes, and seeing if that feels better.

As for your problem that she doesn’t like anal unless you rub her clit, well, what exactly is the problem? Rub her clit! The majority of women need clitoral stimulation in order to orgasm, and most would say it enhances all kinds of penetration. I know lots of women who can’t take anything in their ass without something working their clit; it helps them relax, get aroused, and it just feels great. If rubbing her clit is difficult because of your body position, then let your wife work her own clit while you concentrate on her ass; that way, it’s a win-win situation.

Oct 232003
 

After a long night (or weekend) of intense anal play, usually culminating in anal fisting, my ass feels worn out, sore, and sometimes it even stings a little. Do you have any advice for caring for it after such a workout?

–Ass Needs TLC

We’ve all been there: your ass has taken such a good reaming, you feel that you might never sit down again. First, a few days of rest are in order to give your butt a chance to reflect on all the festivities. Next, I recommend a fabulous product that I never leave home without: Preparation H or Tucks brand Hemorrhoidal Wipes, pre-moistened wipes with witch hazel and aloe. I like the Preparation H wipes better because they are about twice the size. Many drugstores also carry the generic or in-store brand which contain the exact same ingredients but is a lot cheaper. They are cool, soothing, and almost immediately calm an itchy, sore, or irritated butthole. They are also great on a well-used pussy!

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.

Sep 172003
 

Since you’ve recommended in previous columns that a person not go directly from anal intercourse to vaginal intercourse, I am wondering if I can go from analingus to cunnilingus without spreading germs. Also, can I still orally pleasure my girlfriend’s ass after I’ve used lube to penetrate her, or is that bad for me?

–More Than A Mouthful

The reason that going directly from ass to pussy is not a good idea is because you can introduce bacteria from the rectum into the vagina, where it will cause an infection. There is a much greater risk of this transfer of bacteria during penetration because your dick has been inside the rectum (the deeper you go, the more likely you will come into contact with bacteria or trace amounts of fecal matter).

When it comes to oral stimulation, if you are simply licking the outside of your girlfriend’s ass, then her outer lips and clitoris, there is less (but not zero) risk of cross contamination, as long as her ass was clean to begin with. If you want to be super safe, you can rinse your mouth out with mouthwash in between oral acts. Once you have penetrated her ass, you can still orally pleasure her, although I recommend a quick swipe with a baby wipe or damp towel just to clean any lube that may have come out of her ass as you withdrew your dick. Also, pick a lube with a taste that either doesn’t bother you or you actually like so if you do get a mouthful, it won’t make you wince.