Dec 062012
 

My younger, much more experienced partner and I were discussing fantasies last night. I have this pair of 4″ pumps she is particularly fond of, and she mentioned she might like to be fucked in the ass with the heel. They are not stilettos, they are wooden heels, not completely rounded, albeit fairly slender. While I am not one to pooh-pooh anyone’s fantasy, I can’t quite bring myself to believe that this would be safe. Pain factor aside, this seems like it has the potential to be very damaging, especially in the hands (or feet) of someone who has no idea what they’re doing, like myself. Do you have any thoughts as to how I could incorporate her fantasy into our sex life without actually hurting her (and not “hurt” in the good sense)?

–Feeling Like a Heel

You mentioned that you’re inexperienced, so before you approach this shoe fantasy, you’ve got to get some experience with basic anal penetration and sex toys. Start out with dildos and plugs, experiment with different techniques and what your bottom likes until you get really comfortable with them. One of the earliest letters I received for this column was about shoe fucking. A woman wanted to fuck her submissive with the narrow toe of her shoe. You’re talking about the other end, so you’re wise to be cautious.

Whether stiletto or not, a high heel is usually pointed and inflexible enough to make it a less than ideal penetration tool, and since you’re a beginner, I am going to recommend a safe option: the bait and switch technique. Put on the shoes, taunt her, step on her, tease her, tell her how you’re going to fuck her in the ass with those terribly menacing shoes. Then blindfold her, tell her it’s because you want all her senses to be on alert and concentrating on this new and unique sensation. Hidden nearby should be a wooden dildo, selected because you said the heel was wooden. Wooden dildos can be hard to find, but they’re out there (my picks: NobEssence and Jildos). With the image of your shoe heel firmly planted in her mind, the dildo can be firmly planted in her behind! It will have a similar weight and texture, and if you’re good at it, she will never know the difference. When you’re done, drizzle some lube on the shoe heel, take her blindfold off, and everyone will be satisfied!

Nov 272012
 

My wife and I are new to anal sex, but we’ve run into something I hope you can help us with. I’ve noticed that the normal hair around her anus can be kind of rough, as pubic hair can be, and this hair might be causing her some irritation. But we’re not sure if it’s a good idea to shave it off as that might make things worse or cause even more irritation. Any advice for us newbies?

–New and Hairy

Most people who shave their assholes do so for aesthetic reasons: they like a clean shaven asshole better than a furry one. However, the anus is a delicate little bugger, and can be irritated easily by many things, including cheap toilet paper, over wiping, and soaps and lotions. I suppose that some coarse hair could rub that puckered skin the wrong way and lead to some itching and discomfort as well, although I’ll admit it’s not a complaint I hear often.

You’re wise to be concerned about exacerbating the problem, since shaving can also be irritating to the area. I recommend you give it a try, though. Use a fragrance-free and chemical-free shaving cream that’s made especially for sensitive skin. Shave with the grain of the hair and don’t go over the same area too many times. Run cool water over the area after you’re done. If it feels irritated after you’ve patted it dry, apply a little Vitamin A & D ointment. Give it a chance to breathe and relax before you start to play with it. After you play with it, make sure she showers, washes with a mild soap like Castille Soap and reapplies the Vitamin A & D ointment.

Nov 132012
 

I’m a woman who loves anything anal especially having my ass tongued. In the past, I had a boyfriend that also liked it. I liked licking his ass because it turned him on a lot. How do I find out if my current boyfriend might be into a rim job without him thinking that I am a freak? He is very open, but I guess I am just afraid to ask. Is this a common thing with men, for them to like having their ass tongued?

–Aiming to Please

In the past five years, there has been a lot more dialogue on straight men receiving (and enjoying) anal pleasure. It’s what I like to refer to as the “Bend Over Boyfriend” movement, named for the great how-to video of the same name. So know that more men than ever are embracing this kind of stimulation and being more ‘out’ about it.

How you bring it up with your boyfriend depends a lot on your personal style and how you communicate about sex as a couple. If you’re direct, by all means ask him about it; make sure you talk about how much it would turn you on. If you’re feeling unsure and want to test the waters, you could raise the issue indirectly, with a conversation starter like: “I read about women rimming men in a magazine, what do you think of that?” Find a hot erotic story that involves a woman rimming a man and read it to him as a bedtime tale. See what his reaction is to it. Or maybe you want to drop some hints during your next sex session. Try gently stimulating his asshole with your finger, and see what kind of reaction it elicits. Pay attention to his body language and the non-verbal cues he gives you. If he seems comfortable and turned on by it, the next time you’re down there licking his balls, venture farther down. Make sure after you do it to talk about it later to see how it felt for him and get feedback about what else he might like.

Oct 302012
 

Is ginger or toothpaste generally safe on, in, around the anus, clitoris, vagina? I haven’t yet summoned the courage to try figging or a paste made with ginger powder; however, I did try a dab of toothpaste on my clitoris and the perimeter of my anus. I read about it on some discussion board. I’m not sure what ingredient in the toothpaste caused it, but it produced QUITE the tingle in both places. If toothpaste does that, now I’m really afraid of the ginger! I know we put toothpaste in our mouths, but we aren’t supposed to swallow it. So, what’s the scoop?

–Ms. Toasted Buns

People who enjoy more extreme sensation play around the genitals (or even genitorture) use various substances — including sports creams, vapor rubs, Tiger Balm, fresh ginger, and, yes, toothpaste — to produce a tingle or even a burning sensation between their legs. Of course, the manufacturers of these products do not recommend their use on our private parts, and some even put warnings on the label to avoid mucous membranes.

The ingredient in the toothpaste which made you all a-quiver was most likely menthol or mint flavoring. You’re not supposed to ingest a whole tube of toothpaste since it could lead to a toxic level of fluoride in your bloodstream; if you’re worried about even a little fluoride, try a natural toothpaste that is fluoride-free. In general, natural toothpastes contain fewer if any other chemicals or potentially toxic substances than traditional brands.

There are some important safety issues to keep in mind with toothpaste and the other products I mentioned. You’re dealing with the delicate, sensitive genital tissue, so what feels tingly on your tongue will feel several times more intense on your labia, anus, or clit; be careful and use common sense. Begin with a tiny amount to see how your body reacts. External application is much safer than putting any of these substances inside your pussy or ass. One of the safest, albeit tamer, options to create a similar sensation is to try a warming lubricant or stimulating gel — these contain menthol (but in this case, they have been designed specifically for your naughty bits) which provides a warm feeling and helps stimulate genital engorgement and arousal by increasing blood flow to the area.

Oct 242012
 

My boyfriend and I have been dating for about two years, and he loves anal sex. Before him, I had never experienced anal anything. I really enjoy it, too. However there are times that no matter how bad I want to have anal sex and no matter how excited and ready for it I am, as soon as he enters me, the pain is so great, I can’t handle it. Other times, after the initial entry the pain subsides with pure pleasure and I can’t get enough.

I really would like to know why those times I can’t handle it are so painful and what I can do to lessen the pain. How can it hurt when I am so turned on and begging for it? I end up disappointing my boyfriend because I can’t handle the pain. This only happens about once out of every five times, but it is very aggravating for both of us. We don’t have anal sex all the time, usually about three to four times a month. We have tried using lots of lube. We have also tried Anal Ease — all that does is make his cock numb and he can’t keep an erection. Muscle relaxers don’t even seem to work. I am desperate for answers and help.

–Seeking Peace in Pennsylvania

Forget Anal Ease, it will make your ass and his cock numb, and that’s no fun for anyone. I also think muscle relaxants are not a good idea. There seems to be a mind/body disconnect going on for you, since it sounds like you feel extremely turned on, but your ass is not on the same page. Are you working your way up to it? Since you say that initial penetration hurts (even during those times when it eventually subsides), it seems like you’re not doing any warm up. If he just sticks his dick in your ass, no matter how well-lubed his cock is, it’s most likely going to hurt. Because our asses just don’t work that way. Your ass needs to be coaxed and seduced before a penis barges in.

Your boyfriend should start with his mouth, tongue, or one finger. When you’re ready, add another finger or move on to a small dildo or butt plug. He should not progress to the next step until whatever he’s doing feels really good and the penetration is comfortable. My hunch is that if you take things at a slower pace, you will give your ass a chance to catch up with the rest of you.

Oct 162012
 

My paramour seems to be preoccupied (to say the least) with the idea of anal sex. We’ve tried before a couple times, none of which ended well. I blame it on my own trust issues and the lack of lube. But it’s been a while and I’m feeling better (and braver) about it all. I recently read something about the possibility of semen finding its way from your anus to your vagina and impregnating you. I need to know if I’m gonna have to consider a contraceptive before allowing my beloved to go-a-spelunking in my magic cave without a raincoat! I’d hate to have to explain to my kid someday that he or she was conceived by mommy and daddy getting freaky in the butt!

–So Not Trying To Have A Butt Baby

First let me say that I am pleased that you’re willing to give anal another try — I promise you that lube will go a long way to making it a lot better! If I only received a question like yours once a year, I’d chalk it up to an ill-informed young person or an Internet jokester. But, believe it or not, I get at least one question about becoming pregnant from anal sex nearly every day. So let me reassure you that you’re not the only one who’s heard this rumor or is concerned about it.

Technically, the scenario you pose is possible, but it’s very, very unlikely and improbable. Semen would have to drip out of your ass and into your pussy and survive the transfer outside the body (sperm cannot live very long when exposed to air). Then, a cock or finger or toy would have to push the semen inside, so it had a shot at getting close to the cervix, through the cervix, into the uterus and fallopian tubes. It’s a long journey and beginning in another place doesn’t help matters for those poor sperm.

If you are seriously concerned but want to go condom-free, I recommend taking a few precautions. Have your partner ejaculate in your butt in a position where gravity is working in your favor, like missionary or spooning. As soon as he pulls out, make sure to have a baby wipe handy to catch any dribble and prevent it from migrating toward your puss. Use another baby wipe and give yourself a full swipe from front to back. That ought to cover you!

Oct 102012
 

I know the ass is sensitive, but how many nerve endings are there in the ass? Is it the same in guys and girls? And are the “good feeling nerves” located in the sphincter or the rectum?

–Curious About Anatomy

The anus (the anal opening), the anal canal (the first few inches inside), and the rectum are all sensitive in different ways, which is why anal stimulation and penetration can be so pleasurable. The external and internal sphincter muscles surround the anal opening. These muscles can work together or independently of each other, and these are the muscles we must learn to relax in order to achieve comfortable anal penetration. When we talk about the sphincter and pelvic muscles and how they play a role in anal pleasure, we discuss them less in terms of sensitivity and more in terms of how tone and “in shape” they are and how tense or relaxed they are. The anus and the outer part of the anal canal are made of the same sensitive soft tissue and this tissue contains the most concentration of nerve endings of all our anal anatomy. In general, this tissue tends to be more sensitive to touch and vibration. The inner part of the anal canal and the rectum are mucous membrane and have a lot less nerve endings; however this tissue is much more sensitive to pressure (like from penetration).

Men and women have nearly identical anorectal anatomy except for one important difference: men have a prostate gland, which can be stimulated directly via anal penetration. The prostate gland surrounds part of a man’s urethra; it’s behind the pubic bone, below the bladder and above the base of the penis. A mass of muscle, glands, and connective tissue, the prostate is about the size and shape of a walnut; it produces ejaculatory fluid that combines with sperm and fluid from the seminal vesicles to create male ejaculate. Men can experience direct prostate stimulation when they are anally penetrated. It can be found by sliding a finger (or toy) about one to two inches inside a man’s ass and aiming toward the front of his body.

While women don’t have a prostate, but we do have a G-spot and can experience indirect G-spot stimulation through anal penetration. The G-spot is the urethral sponge which sits around the urethra; to find it, slip a finger inside her vagina an inch to an inch and a half and toward the front of her body. The G-spot can be stimulated through the front wall of the vagina or indirectly though anal sex.

Oct 022012
 

I have been told a million times by my mother (who’s a nurse) that no amount of wiping will clean the penis enough to make it safe to go straight from the ass to the pussy. She says a shower is all that’ll do. I have never had anal sex for this reason, but for years, I have been dying to get fucked in the ass. But even more than that, I want to have a bacteria and infection-free pussy. A shower, no matter how warm, seems like it would be a mood destroyer. Is what my mother says true? Is a handy wipe enough? I really want my ass fucked!

–Horny Virgin Ass

Your mother has the right idea: you should never, ever put a dick — or anything else — that’s been in your ass directly into your pussy. Bacteria that lives in your rectum will be transferred to your pussy and very likely give you an infection. You can swipe the cock with a baby wipe, but, technically, no wipe is going to kill bacteria, so some could still be hanging around. (By the way, you should always use baby wipes, which are designed for the delicate genitals. You should never use anti-bacterial wipes that are meant to clean your hands or household surfaces.) A shower with some anti-bacterial soap is the best way to assure yourself that the dick is bacteria-free. And actually, I think a shower can be sensual and fun if you do it together. Your other option is to use condoms, and simply change the condom when you change the orifice.

What puzzles me about your letter is that you have been avoiding anal penetration because of the ass-to-pussy restriction. Who says that anal sex must always include that particular kind of action? It’s safe to go from pussy to ass, or to have anal intercourse all on its own.

Sep 252012
 

Are anal suppositories effective in getting unwanted waste out of the ass? Or is a Fleet enema a much better way of cleaning out the ass? I’m trying to decide what would be the better choice if I want to clean my butt before anal sex.

–Clean Freak

Anal suppositories are small plugs designed to be inserted anally that contain a liquid compound. You stick a suppository in your ass and the liquid, usually a medication, is absorbed through the tissue of the rectum. Anal suppositories may contain different kinds of medications to relieve a variety of conditions, including constipation and hemorrhoid pain and irritation. I assume you are asking about glycerin anal suppositories, which are used as a laxative. A store bought enema (like the Fleet brand) is a bottle of liquid that contains a laxative; the bottle is equipped with an anal douching tip. You don’t need either. Laxatives are made for people who are constipated, and since you did not say anything about being constipated, I’m going to assume you’re not.

The best way to clean your ass in preparation for anal play is not to use a laxative, but just to rinse your ass with plain warm water. So, I do recommend buying a bottled enema, but you should always dump out the contents, rinse the bottle well, and refill it with water. Fill your ass with water, go to the bathroom, and repeat until all that comes out of your ass is clear water. Remember to wait several hours between the conclusion of your enema and anal sex, in order to make sure you’re fully cleaned out and to give your body a chance to recover.

Sep 182012
 

I love the idea of anal sex but my wife will not allow it. We have done it a few times, but she will no longer let this happen. On the last occasion we did, I was ever so gentle with plenty of lube, but this was the last time for her. Is there any hope in the future for me, or am I doomed in this particular act? It is not a topic she will discuss with me. Are there any ways I can convince her to try again?

–One Sided Affair

It sounds like your wife’s sphincter muscles aren’t the only thing that have clamped down in this situation. The lines of communication need some major lubrication before you can talk about lubing up her butthole. Knowledge is power, dude, and the only way to really know what is going on is to ask. Talking about sex can be difficult, uncomfortable, and, well, painful, for some couples, but you’ve got to do it — not only to get some answers on this subject, but to talk about other things that come up as well. Since you said you have fucked her in the ass before, did she enjoy it? You didn’t indicate what the past experiences were like for her. If she didn’t like it, ask her if there is something you could do differently so it would feel better. If she refuses to talk about it, then you should ask why? Does she think it’s perverted (not in a good way)? Does she have fears or anxieties about it that you could talk about with her? You need to find out where she stands and what she thinks before you proceed.