Size Queen

Dec 152004
 

I started doing anal play about ten years ago. It was somewhat uncomfortable, but I persisted. Well, my persistence paid off. I am now able to take a dildo about 10 inches long and about 7.5 inches in circumference. I thoroughly enjoy it, but I have a question about how deep you can go. I tried inserting it to about 12 inches, and I got it worked in, but after about five minutes, I removed it, and there was blood. It shook me up big time. It stopped immediately, but I didn’t insert anything for week for fear of starting something I couldn’t stop. I felt no pain and it felt good. Is the blood a big deal?

–Size Queen

Since the rectum is quite delicate and covered by mucous membrane, even the gentlest of penetration with the smallest of toys can cause a small tear and a little bit of blood. It’s usually not cause for concern as long as the amount of blood is small and there’s no serious pain or discomfort. However, in your case, you’re using very long, thick toys for penetration that give you more of a chance of causing an abrasion or tear; you must realize that a twelve-inch dildo or one that is nearly eight inches thick is huge and not common. When you penetrate your ass with something longer than about ten inches, you move beyond the rectum into the sigmoid colon, which is made up of fragile tissues. Technically, anything bigger than 10 inches could perforate this, especially if it’s inflexible. Plus, an extremely thick dildo can stress the rectal lining. My advice is that at the first sign of blood, you should stop immediately and give your ass a few days to recover. If these big dildos continue to make you bleed, then I suggest you select smaller ones.

Wanting But Wondering

Nov 202004
 

I’m a guy, I like women, and I’ve never been attracted in any way to men. I want to try anal sex (with me on the receiving end) with dildos and even a strap-on. Does this action means I am gay? I have heard that men can have orgasms by prostate manipulation. How would my wife be able to do this to me? Is there a specific method or do I just hope that she does it right?

–Wanting But Wondering

The idea that men who like getting it up the butt are gay is absolutely a myth, one fueled by our society’s homophobia and misconceptions about anal pleasure. Plenty of heterosexual men enjoy receiving anal pleasure, whether with tongues, fingers, or toys. As I’ve said before, anal sex can be an incredibly powerful experience, but it’s not powerful enough to change your sexual orientation! I think that men who enjoy strap-on action especially have anxiety because of the implication that they are getting fucked by a cock, whether it’s silicone or not. The truth is that it feels good, and when you turn around, you want a woman on the other end of that cock.

Men can definitely have orgasms through anal penetration. The prostate gland is about an inch to an inch and a half inside the rectum on the front wall. So, if your wife slips her finger inside and heads toward the front of your body, she’ll find an area (about the size of a walnut) that feels differently textured than the rest of the rectal wall. She should gently rub the spot as you give her feedback about how it feels. Every guy is different, so your communication is critical to helping her stimulate you in exactly the way you want. As you get more aroused, the prostate will swell and become more sensitive. For prostate stimulation with a dildo (whether strapped on or in her hand), select a curved toy and make sure the curve is always toward the front of your body. Some guys like to have their cocks and balls played with, others want anal play alone — that’s something for the two of you to experiment with.

An Anal Lover

Nov 122004
 

My wife and I have indulged in anal sex as occasional fun. Since becoming pregnant, she has had some vaginal soreness which has lead to an increase in anal play which I really love. My wife has admitted she really likes analingus and sometimes orgasms during anal penetration. My fear is that once she gives birth, anal sex will return to being only an occasional thing again. How can I persuade or convince my wife to let the good times roll?

–An Anal Lover

If your telling of the situation is accurate, it sounds like your anal play hasn’t just served as a “substitute” for vaginal penetration, but that your wife is having a pretty good time (orgasms being a clear indicator of a good time). I suggest you talk to your wife about exactly what she likes about anal, in addition to analingus, and keep doing more of it. The better time she has during your anal explorations now, the more likely she is to continue wanting you to fuck her in the ass post-pregnancy.

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.

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