Red Alert

Oct 272004
 

I was just wondering if having anal sex while on your menstrual cycle is okay. If you do have sex during this time, how does it feel? Does it feel as good as it does any other time? I have been really horny this cycle and I was just wondering for next time.

–Red Alert

It’s absolutely safe for women to have anal sex while they have their periods. Usually, it’s more a matter of preference and comfort rather than safety. For some women, while they are menstruating, they have cramps, bloating, and other symptoms which don’t make them feel very turned on. Others, like you, can feel an increase in their sex drive and want to have more sex. As for how it feels, it really depends on the individual. Some women find that all their erogenous zones (including their asses) are more sensitive just before they bleed or during menstruation, while others don’t notice a significant change.

Absolutely Agnes

Oct 142004
 

I’m just starting to explore my butt with my partner and we’ve gotten hung up on the how and where of lube. Obviously, I know I need plenty of lube for comfort, but how do we use it exactly? Does it go on his cock? If it does, doesn’t it all just rub off at the entrance? What’s the best way to get plenty of lube inside my butt?

–Absolutely Agnes

You’re right — you need plenty of lube for anal penetration. I recommend a thick water-based lube because thicker lubes tend to stay wet longer and give the delicate rectum a little cushioning. First, you should lube up whatever your partner is using to warm you up (his finger, a small dildo or butt plug). He should coat his finger or the toy with a layer of lube. It shouldn’t rub off at the anal opening, since it will cling to his hand or the toy. When your ass is ready for his dick, he should squeeze some lube into his hand and rub it on his cock until it’s well-coated with lube. If you feel that you need more lube, he should come out of you and re-lube.

Broaching the Topic

Oct 072004
 

I have fantasized about anal sex for years, and I finally think I have the courage to ask my wife to do it. What’s the best way to bring it up with her?

I think communication about sex is specific to the individuals involved, so there’s no one rule that will work for everyone. If you and your partner speak openly and directly about sex, then, by all means, be open and direct about your anal desires. If you’re unsure about how your partner may respond, then you might want to bring it up in a more indirect way; for example, “I just read something about anal sex in a magazine — what do you think of it?” rather than “I want to do this to you now” — which may feel more threatening or intimidating. It’s important for you to make your request as pressure-free as possible, and give her the opportunity to voice her concerns, if she has any. The one rule that I think can apply to all couples is that you shouldn’t bring up the subject in the middle of sex; pick a time and place that’s neutral for both partners.

Pierced in Pennsylvania

Sep 222004
 

I have discussed with my wife the possibility of having anal sex. After a little discussion, she said she would try it. We agreed that if it hurt her too much, I would stop. My problem is I have my penis pierced with an ampallang piercing; that’s a horizontal piercing through the head of my penis. I would probably get stuck in her if I did not pull out before ejaculation, and then I’d lose my erection. Any suggestions?

–Pierced in Pennsylvania

Your question raises many more questions. How old is your ampallang piercing? Most piercers recommend an initial healing time of 8-10 weeks, and say it will be fully healed at 6-12 months. In the first couple weeks, erection or orgasm can cause the piercing to bleed. If yours is fully healed, my next question is, how big is the jewelry? You make it sound huge by saying you’re going to get stuck, and, if it is in fact bigger than about 10 gauge, that would be cause for concern. I have not heard of people with average-sized ampallang piercings getting stuck.

Although I do think you should be concerned that your piercing may tear the delicate tissue that lines the rectum or cause your partner pain. I recommend you wear a condom to prevent possible injury or discomfort. Again, all penis piercings with average-sized jewelry should not interfere with the safe use of condoms. Use a condom with a receptacle end to fit comfortably over the jewelry, and lubricate the inside of the condom as well as the jewelry itself to reduce friction.

Fucking a Fluid-Filled Bottom

Sep 132004
 

For the last few months, my lover had been hankering to try anal sex. After reading your advice, buying lots of lube, and experimenting with a host of toys, we finally managed to get his gorgeous cock all the way in my bottom and fuck me — and I had a fantastic orgasm! Since he’d never had anal sex before, as you can imagine, he is now a very happy bunny and wants more! He currently has a fantasy about filling my bottom with lots of creamy liquid, and then fucking me like that.

We’ve seen stuff like this in porn movies, but I’m curious about how they do it and how we should do it. What liquid do we use and how much would be safe? I’ve been giving myself brief enemas before our anal play so I’m kind of used to stuff being there. I’m not sure how long it’d stay there and if there are any safety concerns I should be aware of. Any suggestions would be appreciated, and thanks for all the great advice you give people.

–Fucking a Fluid-Filled Bottom

Congrats on joining the anal bottom brigade, and thanks for sharing your fun fantasy with me and your fellow readers. In general, I am a purist about what people should put in their asses: I endorse only plain water, lube, ejaculate, fingers, cocks, tongues, and toys. I discourage exotic enema ingredients, ice cream sundae toppings, and other equally wacky substances.

But, in the case of your sweetheart’s idea, you’re in luck. He can fill your ass with lube! There are several great water-based lubes on the market – including Hydra Smooth, Sensual Power, and Liquid Silk — which have creamy consistencies. In fact, they have a look and feel that’s a lot like a man’s cum (which I think may be what your guy is going for). Plus, they are lubricants, designed for penetration, and therefore, totally safe! If he wants to really fill you up, you may want to buy a plastic disposable syringe (available at medical supply stores and some drug stores), which he can fill with lube, and “shoot” up your ass.

If he succeeds in filling your ass, remember, what goes in must come out. You may be a little runny for a day, as all that lube works its way out of your ass, so keep that in mind; I’d avoid, say, silk pants, for a few days.

Cut Cock

Aug 292004
 

About 6 days ago, while having anal sex with my girlfriend, I had an odd thing happen: it felt like I hit something sharp inside her ass. It was not a painful feeling, just sharp, so we continued and had no other problems. Two days after this incident, I noticed a red mark on the head of my penis, in the exact spot where I’d felt that sharp sensation. The mark doesn’t hurt, the area has not been any more sensitive than usual, and I don’t feel odd otherwise. As the days passed, the mark seemed to be healing, however now I realize that it looks like it is leaving a scar. Have you ever heard of anything like this happening before? What could I have hit inside her that could have scarred my penis? I am uncircumcised, so I have a fairly sensitive penis, but this is definitely not a lube allergy, it’s more like a cut. What do you think it is and what should I do?

–Cut Cock

What you describe is pretty perplexing for several reasons. First, the only “things” that should be in someone’s rectum are bacteria, possibly fecal matter, and anything your girlfriend stuck in her own ass. Let’s rule out bacteria. Let’s assume that there was nothing else in her ass but you. Did she play with a toy recently that somehow broke into pieces in her ass? Since you did not mention it, I will assume the answer is no.

We are left with the concept that you ran into some fecal matter in her rectum, and that fecal matter contained something sharp. That scenario first makes me wonder, was your girlfriend in any pain? Because if there was something truly sharp in her fecal matter, she would have to have swallowed it, meaning it passed through her intestines, which would cause great discomfort before it even made it as far as her rectum. It seems to be she would not have been in the mood to get fucked in the ass if that was the case.

Let’s say she felt fine. The next clue you gave is that you have a sensitive cock. You may have encountered something harmless, like an undigested seed from something she ate, and the feeling it produced was magnified because of your sensitivity. But, even in the case of a seed, which could feel sharp to an engorged cock, it shouldn’t do any permanent damage. The scrape that you described (that is beginning to scar) is mysterious. If by now it has indeed scarred, then I suggest you have it checked out by a doctor.

Perplexed About A Butt

Aug 182004
 

Are some women’s butts more pre-disposed to anal intercourse than others? I know we are all different, with different bodies, needs, and desires, but I wonder if there is a physical component to achieving success in anal penetration. My current partner loves anal sex, and she can have these long, all-over-her-body orgasms when I fuck her that way. With my last girlfriend, however, I wanted on many occasions to have anal sex, but could never get it right. We did loads of foreplay, including massaging, oral with loads of clitoral stimulation, anal rimming, licking, loads of lube etc. With all that said and done, her butthole never loosened up very much, and didn’t get vaguely close to me getting myself in there. Is she just not an ‘A’ candidate, or was I missing something somewhere?

–Perplexed About A Butt

Yours is a very interesting question, one I think could be asked about all sorts of sexual desires and acts, not just anal penetration. You’re correct about how individual we all are; while our anatomy may be similar, our sexuality — how we liked to be touched, what turns us on, what combinations of sensations and scenarios brings us to orgasm — can be almost as unique as our fingerprints. Certainly, there are some women who seem to enjoy anal pleasure more than others, and I can say from experience that some women have an easier time than others. When I say easy, though, know that all the same rules still apply; you still must use lube, go slow, and make sure her body is warmed up. Likewise, there are plenty of women who tell me that they enjoy anal, but it takes them a lot of time to relax and open up, and on some occasions, it just won’t happen.

I appreciate your dedication to your previous girlfriend; it sounds like you made all the right moves, but even with the best effort, sometimes foreplay isn’t enough. In addition to the physical aspects of anal play, there are psychological and emotional components that cannot be ignored. If a woman is feeling unsure, nervous, anxious, or conflicted about receiving anal pleasure, then no amount of expert cunnilingus or rimming may change her mind. Sometimes, working through a partner’s fears about anal play — whether it’s the potential mess or pain, or feeling dirty for just wanting it — are the key to opening up. Free her mind, and (hopefully) her ass will follow.

Waiting to Come

Aug 052004
 

I am a heterosexual married man, and I have been occasionally stimulated myself with a finger during masturbation for years. I recently convinced my wife to try a strap on a dildo and fuck me. As I expected, I enjoyed both the physical stimulation and the psychological joy of giving myself up to her as the penetrator. But try as we may, the buttfucking could not get me to orgasm. I have heard that direct prostrate stimulation can cause orgasm and ejaculation. But for me, even though we reached a point where a modest, 5-6″ dildo was all the way in and being generously worked, I could get just at the edge of orgasm but not quite there.

Not that I’m complaining, because the whole encounter was great. If I was at the same point of arousal and pleasure as I was fucking my wife, I couldn’t have held back. But anally, to put it bluntly, I was able to be buttfucked at that same pinacle of near orgasm delight for as long as my wife could go and I could take NOT coming. The whole time it felt like “just a little faster, or harder, or deeper and I’ll come.” It was incredible, but also disappointing. Am I going to have to have my penis stimulated to get an orgasm, or is it a matter of working up to a larger dildo to hit the prostate?

–Waiting to Come

Before I answer your question, thanks for your testimonial about the joys of being buttfucked by your wife; I hope it serves as an inspiration to all your hetero-male bretheren! This is not a problem of size, I can assure you, because the prostate is just a few inches inside the rectum, so something bigger or longer is not going to solve this quandary. First, I want to encourage you to add cock stimulation to the mix since guys like to be stimulated in both places at once; try working your dick as she fucks you and see if the result is different. Second, you may experience a different kind of orgasm from prostate stimulation than you do from having your penis stimulated manually, orally or via penetration. Many men report that they have all the sensations of an orgasm without ejaculation. So, it may be simply a matter of re-orienting your mind around a different expectation of an orgasm. Third, you may still be able to come and shoot from a good assfucking, and in that case, practice makes perfect!

Burned Butt

Jul 282004
 

I’ve had a black vinyl butt plug for two years and I think that a chemical film or something has developed on the surface that makes it burn when I insert it into my girlfriend’s ass. Would an automotive-type vinyl restorer make my butt toys last longer?

–Burned Butt

Latex rubber, jelly rubber, and vinyl sex toys are inexpensive for a reason: they do not last forever. I recommend that folks replace toys made of these materials after twelve months for the exact reason you report: the material starts to break down, and often causes stinging, burning, itching, and other discomfort when used.

No, a vinyl restorer sold in automotive supply stories is not a good idea; not only will it not help stop the toy from deteriorating, but you do not want any product like that (or traces of it) in your ass! Throw the toy and buy a new one, or, for your next purchase, try a higher quality silicone toy. Silicone can be much more pricey, but it’s also a lot more resilient. My silicone toys have lasted for many years, and some brands even come with lifetime guarantees.

Enema Edge Player

Jul 142004
 

I bought a simple Fleet enema at the drugstore, and I have a few questions. Can I use it as is, or should I replace what’s in the bottle with water? Here’s why I am asking: I like to experience some good hard erotic cramping during enema play. My girlfriend and I often do enemas together, and we like to see which one of us can hold it the longest and who can handle the cramps without showing much discomfort. Is that safe? Because it’s awfully fun.

–Enema Edge Player

When I teach a basic class on enemas, I instruct people on two important points: the ingredients of an enema and the temperature. A Fleet enema (or most other brands you buy at the local drugstore) contains a laxative, and you do not need a laxative. You just need plain, warm water, which is why you should empty the contents of the store-bought enema bottle, rinse it out and refill it with warm water. If you’ve heard of more exotic enemas, with ingredients like champagne, espresso, wine, or other things, beware: these can make you very, very sick. So stick to plain water only.

I recommend that the water be warm so it’s as close to body temperature as possible; usually, the warmer the water, the more comfortable the enema. Most people will have little or no cramping when the temperature is right. Cold water causes discomfort and cramps that most people won’t like. I say most people because I do know enema fetishists who like to deliberately inflict discomfort and cramping on themselves or their partners.

Let me first say that this is considered “edge play” among enema fans, and inexperienced enema givers and receivers should not try this at home. I can tell that you’re a much more seasoned enema player, so I won’t admonish you for your sadomasochistic twist on this intimate form of play. One word of caution: don’t overdo the cold-water, cramp-inducing sessions. You can stress your gastrointestinal tract and disturb the delicate balance of your insides, which is never a good idea. As for you and your partner’s little game, it sounds like a great endurance contest for the BDSM Olympics! Again, a good rule of thumb for all this kind of play: everything in moderation.

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