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?

Nov 262002

My boyfriend and I have been going out for 5 years. My boyfriend wants to have anal sex, but he is very big and thick. He hurts me when we’re just having regular sex. I don’t know why, since I’m 100% wet when we have sex, and it still hurts. We tried anal once but I told him to take it out because it hurt even when he put the head in. I’m just afraid that if we have anal sex he’s gonna hurt me. He says he will go slow, but he never listens to himself. Just before he’s getting ready to cum he starts to do it harder, so I don’t know if I should do it with him or not.

–I Want A Pain-Free Poke

First, I recommend you really focus on extended foreplay before your boyfriend even attempts penetration with his dick. Have him go down on you, rub your clit, use a vibrator, and work your body before getting inside it. The more aroused you get, the better your circulation; blood rushes to the genitals, the body relaxes, the pussy lubricates, and penetration becomes much easier. You say you are 100% wet, but I still really recommend using lube. Lube makes everything nice and slick, and eases penetration whether he’s well endowed or not. You also need to warm up both your ass and pussy with something smaller than your husband’s dick, like his fingers or a smaller dildo or vibrator. Start small and slow, and work your way up. Add another finger or go farther in only when you feel completely relaxed and ready for more. Don’t rush it.

Once you start having intercourse, make sure you are in the driver’s seat. You call the shots about how hard, how deep, how fast. Talk to your boyfriend and make sure he knows when something feels really good and when it does not. Penetration, whether vaginal or anal, should never hurt you. Take the time to make sure your body is warmed up, you are ready, and make sure he’s connected to you so he knows when the time is right.

For some men, in order to orgasm they need to take some very quick hard thrusts, which sounds like it may be the case with your guy. If he simply can’t slow down or when he does slow down, he can’t come, then I suggest this: when he’s ready to shoot, have him pull out. Then you can give him a hand job, he can jerk himself off, or he can thrust against you but not inside you.

Oct 252002

I never thought that I would enjoy anal sex as much as I do. I’ve been married over 15 years and my husband has suggested it a couple of times, and he even rubbed around my butt a few times, but as a “good girl,” I never wanted to go further. That changed on my husband’s 40th birthday. I offered him my butt to do as he wished and I have to admit I really really liked it (even though it was a bit sore the next morning). That was three years ago. Now, I often think that I prefer anal sex (but having both my butt and vagina filled is absolutely the best). Most of our intercourse includes some sort of anal play (I haven’t tried anything really big yet though). This leads to a question: Is it normal to like anal sex as much or better than vaginal sex (yes, I can orgasm both ways)? Thanks for any advice.

–Anal Addict

Welcome to the club! And what a great birthday present you gave your husband! To answer your question simply and directly, there is really no such thing as “normal.” Mainstream culture and media would have us believe that heterosexual cock-in-pussy intercourse is the most common activity and therefore normal, but we all know that is bull. The truth is that we like what we like. Whether it’s the smack of a riding crop on your butt, an enthusiastic toe-sucking, or anal play, if it turns you and your partner on, then go for it! For some women, anal penetration may feel as good as or better than vaginal penetration; lots of people tell me that anal play produces more intense orgasms. Plus, adding clitoral stimulation to backdoor banging or creating an angle for indirect G-spot stimulation can all help increase the pleasure of anal penetration. It sounds like you really enjoy anal sex with your husband (and congrats for being able to come from it); ignore those voices in your head which may be calling you deviant or weird, and just keep doing what you’re doing.

Jul 052002

Me and my partner have always enjoyed anal sex. We have been together for a while and are expecting our first baby in three months. I know people are supposed to have “cravings” when they are pregnant, but my craving is that I want to be fucked in the ass even more than I did before! It feels great, and I experience no discomfort, but we want to make sure that we aren’t doing any harm to the baby (and I don’t exactly feel I can discuss it with my doctor!). I find the most comfortable position is on my knees with my butt sticking up so I can support my belly properly, and this way I can get the most cock in my ass. Will it be alright to continue up to the time you would normally stop having vaginal sex?

–Preggo Anal-Addict

Many women say that their libido, sexual tastes, and orgasms can change drastically during pregnancy, so know that your new craving is perfectly natural. According to most physicians, throughout your pregnancy, penetration (both vaginal and anal) with fingers is safe and with a cock is safe in low-risk pregnancies. One of the challenges of sex during pregnancy is finding comfortable positions, and it sounds like you’ve found a good one, at least for now — it may change when you get bigger. Your mate should definitely avoid deep thrusting and really hard slamming of any kind. Use a water-based lubricant, but be extra careful in preventing bacteria from the ass transferring to the vagina. Make sure his fingers and cock are super clean, or you may get an infection, which is often harder to treat during pregnancy. If you feel any discomfort during any sexual activity, stop at once. You said you don’t feel comfortable talking to your doctor about this, but for the sake of your health, and the health of your baby, it’s probably a good idea.

Jun 072002

My girlfriend and I have been having anal sex for about four or five months. In fact, the first time I penetrated her was anally. After that, it’s been a once-in-a-while ritual where I get to have the pleasure of making love to her sexy ass. I enjoy it very much and she doesn’t mind letting me have my way, even though she says she receives little to no pleasure from it. We use plenty of lube and always warm up with shallow and slow penetration, deep breathing and lots of communication. We now do it now once every three weeks to a month, which is kind of my problem. I’d like to do it more often, but not too much.

I have two questions for you: How much anal sex do you think is healthy for a couple that wants to have a nice balance between the three major forms of sex (oral, vaginal and anal)? What kind of ways can I pleasure her when I do her in the ass? How can I make her come from anal sex?

–Booty Lover

There is no mathematical equation to determine “a nice balance,” nor is there any common recommendation about how much of one kind of sex a healthy couple should have. Sexuality and our particular practices are extremely unique to the individuals involved, and therefore so are our preferences and how often or little we indulge in them. I say if both you and your wife are content with how much sex you’re having, and the kinds of sex you’re having, then why mess with a good thing?

But it does sound like you’d like to add more anal sex to the menu, and your second question is the key to getting there. Because if you start to give her tremendous pleasure while you’re fucking her in the ass, then chances are she’ll want to do it more often. There are a number of ways to get a woman off while you’re fucking her ass. You can play with her clit while you penetrate her, or if the position you’re in makes that too difficult, encourage her to jerk herself off or even use a small vibrator. Clitoral stimulation combined with anal penetration is one of the ways some women can orgasm. If she likes double penetration, try putting a few fingers in her pussy or a slim dildo while you’re in her ass; this often increases the sensations in both places. Experiment with different positions in order to find her G-spot. Many women experience indirect G-spot stimulation through anal sex. You want to angle fingers, toys, or your cock toward the front of her body to find and stimulate the spot. Also, ask her what she’d like to do to make it feel not just better, but fantastic. Together, you can discover what will turn you both on.

Nov 072001

My girlfriend had recently asked me to have anal sex with her since we had never done it before. I complied, and after two tries (on separate occasions), we succeeded. We enjoyed it so much that we attempted it twice more with success. But we can’t do it anymore. We’ve tried, but we haven’t been able to do it for months. I am supportive as I can be. I give her control, soothe and relax her, question, encourage. But lately she says I have been hurting her. She says I get stuck just after my head goes in, and she can’t continue. The first time we went at it slowly, but near our climaxes, we started to really go at it, and she took all of it in. I have suggested some form of foreplay, but she refuses. She says it is all penis or nothing at all. Please help!

—Frustrated in Florida

You are absolutely doing the right thing by giving your girlfriend control and warming her up. Her insistence that it’s all or nothing just isn’t realistic, and you need to somehow make her see that. Remind her that the ass is not like the pussy: it requires a lot more delicate handling and more foreplay before she can relax it enough to make penetration comfortable and pleasurable. Licking her ass, penetrating with your fingers, or playing with a small butt plug, dildo, or vibrating toy are all good ways to get her ass ready for your cock; of course, remember to use plenty of lube! As for her theory that you are “getting stuck” after the head of your cock goes in, again, with a gradual progression to penetration, her ass will feel more relaxed and open. Because it is the head of your cock she complains about, it sounds like her sphincter muscles aren’t relaxed enough to accommodate your dick. With more warm up, she’ll be more aroused and it should feel much better.

Aug 052001

I am in a relationship with woman, and we both want to try anal sex. But I have one concern. I know that it’s going to feel really good for me, because I am a guy, but what will it feel like for her? Do women get off on anal penetration, and if they do, then how exactly? Can my girlfriend come from it?

—What’s In It For Her?

Rest assured that there is plenty in it for her. First, let’s talk about the physical aspects of anal sex. Anorectal anatomy is nearly identical in men and women, and the entire area — the anus, anal canal, and rectum — is extremely rich in nerve endings and sensitive to stimulation of all kinds, including penetration. Because of this level of sensitivity, exploring our asses can bring us incredible sexual pleasure.

The one distinction in men and women’s anal anatomy is that men have a prostate gland, which can be reached and stimulated through the rectum. Although women don’t have a prostate, they do have a G-spot. The G-spot is reached through the front wall of the vagina, but it can also be indirectly stimulated through anal penetration. Since all that separates the rectum and the vagina is a thin membrane, if you angle a finger, toy, or penis toward the front wall of the vagina, women still may experience G-spot stimulation. Many women find that the G-spot stimulation they get from anal sex is one way they can have an orgasm. Another way for her to orgasm is to add clitoral stimulation as you penetrate her. Give her clit some rubbing action or let her jerk herself off with her hand or a vibrator while you do her in the ass, and see what happens.

In addition to the bundle of physical pleasure that anal stimulation brings, there are complex emotional and psychological issues that contribute to the erotic experience. For some people, the idea that anal sex is naughty, forbidden and taboo is very exciting, and adds to their enjoyment of it. For others, the great amount of trust one must have in a partner heightens the physical pleasure; allowing your partner to penetrate you in this special place says, “Here is a delicate part of my body, and I trust you not to hurt me but to make me feel very good.” That power exchange can be very intense for lovers. Anal sex is often represented in popular culture as violent and degrading; however, in reality, it can be extremely intimate, connecting, and even spiritual.