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.

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.

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.

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.

Mar 202004

I just started having anal sex with my girlfriend. We did it the first time with lots of lube and I was able to get the entire shaft inside her with little to no pain. She told me that she could feel the fullness but she got no pleasure or pain from it. She said that if I wanted to do it again later it would be no problem since it does not hurt her; however, I would like for her to get some pleasure out of it. I cannot touch her vagina with my fingers because she is very ticklish there. If you have any suggestions, I would appreciate it them.

–Pleasure With My Probe

Bravo to you for realizing that anal sex should be pleasurable for both people involved. My suggestion is that you add some clitoral stimulation to the mix. While you are doing her ass, rub her clit, or, if it’s easier, have her do it herself. You could also use a vibrator for more intense, focused sensation. Many women (me included!) love the combination of clitoral and anal stimulation, and lots of girls say that they don’t experience pleasure from anal penetration without something on their clit.

I’m not sure what to make of your girlfriend’s ticklish pussy. That sounds more psychological than physical to me. Perhaps it’s a reaction to her feeling shy about receiving pleasure; if that’s the case, then you should encourage her to relax and give herself permission to experience being touched and pleasured. Or, it could be that when she’s turned on, her genitals become super-sensitive, and stimulation of any kind feels overwhelming. Then, try softer, more indirect kinds of stimulation, like rubbing her clit from one side, rather than directly on top.

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.

Aug 202003

My boyfriend and I decided to try anal sex for the first time. We did it for about 5 or 10 minutes. He loved it. I, however, found it very uncomfortable and painful, and I didn’t have very much fun. Although at one point it almost felt good in a way. I want to try it again (he loves the idea so much), but I want to have fun while doing it. I’ve heard such good things about it. Is there anything we can do to make it more enjoyable for me or get me used to it without the pain?

–Clueless and Curious

First, I want to commend you on remaining curious and open to anal sex even after you had a not-so-memorable first experience. Most women have a negative anal de-flowering and never try it again.

It sounds to me like your husband may have made the most common mistake that I hear about: he rushed the process. Unlike your pussy, the ass is not self-lubricating, so you absolutely need to use lube, and plenty of it. I prefer a thick water-based lube that’s similar in consistency to hair gel; thicker lubricants stay wet longer and have a cushioning effect inside the delicate rectum. And speaking of the delicate rectum, your ass is very sensitive and needs plenty of slow, patient warm up to get it ready for your husband’s cock. That means activities like oral pleasure, gentle penetration with his finger or playing with a small butt plug or dildo to start. He needs to err on the side of caution, especially in the beginning, to get your ass used to having something inside it.

Take your time, and make sure you let him know if you want him to slow down or stop. As you relax (lots of deep breaths help), your ass will, too, and penetration should feel pleasurable, not painful. During this foreplay, experiment with adding other sensations to the mix: many women like (even need) clitoral stimulation in order for anal to feel good. Some like to have vaginal penetration or direct G-spot stimulation at the same time. See what works best for you.

Aug 142003

My partner likes anal sex very much, she has had plenty of experience and we practice it regularly. But, despite extended warm up sessions, a lot of lube and communication, she cannot accommodate my penis every time. I am always very gentle and caring. I know that even with the same partner each day is unique and different even if the mood and environment is the same. The situation is even more frustrating for me (and probably for her too) as we have often to stop after the tip of my cock has gotten inside her. It’s almost like some sort of reflex in her body just “rejects” me. What is the best way to achieve full anal sphincter relaxation, allowing an easy and guaranteed penis insertion?

–Patient in Paris

There are no guarantees in life, especially with matters of the heart and ass. It sounds to me like your partner’s body still isn’t relaxed enough which is why her ass is rejecting you. A surefire solution is to increase the amount of foreplay. I suggest more warm up with fingers and toys, plus you should add clitoral stimulation to the mix. Using a vibrator, your hand, or hers to manually stimulate her clit while you play with her ass can increase her arousal and help her rectum expand for penetration.

Once you first get inside her, don’t make any sudden moves. Stay put and give her a chance to adjust to the feeling before you start moving in and out. When she feels relaxed, then start with gentle thrusting, and let her call the shots in terms of speed and depth. Take your time, listen to her body, and don’t put so much pressure on yourself and her to make it happen every time.

Jul 132003

My boyfriend and I love anal sex. When he penetrates me, I come and squirt all over the place. It’s not pee, but I definitely soak the bed. We both love it, but is this normal or am I special?

–Gushing Girl

Congratulations — it sounds like you are a female ejaculator! Many women have the ability to ejaculate either through direct or indirect stimulation of the G-spot, also known as the urethral sponge. The urethral sponge sits around the urethra, and its paraurethral glands produce ejaculatory fluid which can comes out of the urethra (which is why many people mistake it for urine). You can definitely achieve indirect G-spot stimulation through anal penetration, especially during certain positions which angle the body toward that all important spot, like doggie style with your head down and ass in the air. You and your guy have obviously found the magic spot, so keep on doing what you’re doing. Women who ejaculate often soak the bed, so I suggest you put down a towel or an absorbent bed pad before you get going.

Apr 142003

I am big fan of anal sex. It is the best kind of sexual stimulation for me. I think that it is the top way to emotionally connect for a couple. My girlfriend was very reluctant to have anal sex when we first started to date, but she eventually agreed. I think it’s important for the man not to be an assailant, but to be patient. We now have anal sex about once a month. Last time we had it she said that she has a more intense orgasm with anal than with vaginal penetration. Is it possible that anal offers a better orgasm for women than vaginal penetration? Do you prefer anal over vaginal sex?

–Ass Man

Different women have different kinds of orgasms. Some women say that they experience different orgasms through clitoral stimulation alone, versus vaginal penetration alone, versus anal penetration. When sensations are combined, women may have still other kinds of orgasms. Many women experience indirect G-spot stimulation when they get fucked in the ass, and others like to add clitoral stimulation during anal penetration.

Yes, it is absolutely possible that for your girlfriend, anal penetration produces the most intense orgasm she’s ever felt. That may mean the orgasm feel like it’s rocking her entire body, rather than localized in her genitals or it may mean that the orgasm lasts longer, or it may mean the sensation feels stronger than when she comes other ways. As for me, well, I have never made it a secret that I love anal sex, and I have much more intense orgasms through anal penetration than I do from anything else. Why do you think they call me Butt Girl?