Fellow Anal Lover

Feb 052005
 

I’m a 21 year old male anal sex lover. First off, I’d like to say that I respect your work a lot. It’s awesome that a woman like you does so much work to turn women on to accepting anal pleasure. With that said, here’s my dilemma. My girlfriend loves anal pleasure, but cannot handle it. When I finger her asshole, and or touch her pussy at all, she says it’s too much. She has to stop me because she says it feels too good, and that she can’t handle it. It is because of this we have never gotten past the two-finger mark. But she wants to have my cock in her ass, and, of course, so do I! I just recently ordered her some new toys, but my question is how can I get my girlfriend to relax? We think we have tried everything short of drugs, which we don’t want to try. How can I get my girlfriend to give in to the pleasure and loosen up? We both really want to get my cock into her ass without hurting her!

–Fellow Anal Lover

The ass is an incredibly sensitive erogenous zone, so it’s not surprising that some women can find anal stimulation or penetration too intense. Believe it or not, the more aroused your girlfriend gets, the more stimulation she’ll be able to take; blood will rush to her genitals and the entire area will get swollen and be more receptive to pleasure. Try to bring her close to orgasm before you play with her ass, and see if she responds any differently. If anal play still feels overwhelming to her, than you may want to investigate the situation further. Sometimes when a person is super-sensitive during sex, there may be an emotional component at work. One more tip: there are a few steps between the two-finger mark and your cock. One of the most common mistakes people make is that they rush penetration which leads to discomfort or pain. If you make it to a pleasurable two fingers, try adding a well-lubed third or try a small butt plug or dildo. When that feels great — and not before — you can consider your cock.

I’m In There, But Is She Into It?

Jan 172005
 

My wife seems to like the “naughtiness” of receiving my dick up her ass, but I don’t think she really likes it. We haven’t done it that much, but when we do, when I get it in there, she makes her sexy groan like when she’s going to come from a good licking. Part of the problem may be that we haven’t used much lube except her cunt juice. I don’t know if I really want to ask her if she wants to have it or not because she may say no and I don’t want to go there. Any advice on getting her more into it? We’ve talked about it outside of the bedroom, and she says she does it because she knows it turns me on and she likes to submit to my power over her. She’s very much in tune to her body and loves trying new things. Any suggestions?

–I’m In There, But Is She Into It?

Where do I begin? I’m disappointed to hear you have not been using any lube except cunt juice. Lube is a must for comfortable anal penetration, and no matter how juicy a cunt is, its fluids just won’t cut it. So, my first piece of advice is to get your hands on some lube and use plenty of it. You’ll be amazed at how much better it will feel for your wife.

From the information you provided — both about your conversations with your wife about her submissive desires and her response when you fuck her in the ass — it sounds like your wife does indeed enjoy your backdoor adventures. But the fact that you have avoided asking her directly because you “don’t want to go there” is a problem. Honest, ongoing communication is critical to any relationship and opening up a dialogue about anal sex with your partner can only be a good thing. You’ll get the answer to the question directly from her, and, if all goes well, maybe she’ll elaborate on some of those naughty, submissive fantasies of hers.

Ass-eating Cotton Mouth

Jan 132005
 

I am a newcomer to analingus, and I’ve only performed it on my girlfriend a few of times. Every time I do, my mouth gets extremely dry. Why is that?

–Ass-eating Cotton Mouth

As an avid ass-eater myself, I’ve never run into the problem you describe. But that doesn’t mean it’s not possible. There is nothing inherent to rimming that leads to a dry mouth, but there are a few possible explanations for your condition. As you lick your lover’s butthole and spread your saliva around, you may be sharing more spit than your mouth is producing, leading to an imbalance. You may also be dehydrated, which is easily rectified by drinking plenty of fluids before you dive back in. If it’s still uncomfortable, then I suggest you rub a small amount of lube (either a flavored one or one with a taste you don’t mind) on her pucker before you kiss it. Your dry mouth is most likely unrelated to your asslicking altogether: many medications can cause dehydrated mouth, as can common substances like tobacco, alcohol, and caffeine. If this parched condition persists, you should see your doctor.

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.

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