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.

Mar 222001

It’s wonderful that you are so pro-anally inclined. I am a connoisseur of fine posteriors (my wife’s being on top of the list — sorry, don’t feel bad!). We watched your video,
The Ultimate Guide to Anal Sex for Women, and enjoyed it very much. As I was trying to coax my wife into the act, somehow, she tightened up and it became a painful ordeal. We’ve had anal sex before, and she enjoys plugs in her butt when we are having vaginal sex. But she can’t take my turgid member as frequently as I would like.

—Help My Turgid Member

Glad to hear that you worship your wife’s ass. Now, you need to take a little extra care so that both of you can enjoy anal sex. First of all, if she’s experiencing pain during penetration, there may be several different causes. In general, you need to concentrate on giving her a lot of foreplay before you move on to putting your dick in her ass. Use your fingers, then a dildo smaller than your dick, and let her get used to that first. Go slow, and make sure everything feels good to her before graduating to more fingers or a bigger toy. If she experiences discomfort or pain, there may be too much friction. Add some more lube, and see if it feels better when you slide back in. Or you could stop the movement of your finger or the toy, but stay inside; see if the pain subsides. If she’s still hurting, stop penetration altogether and focus on more external stimulation — a hand job, oral sex, more foreplay.

Let her know that she’s the one in control of the situation, and if she needs to, stop the activity altogether. She needs to relax, take some deep breaths, listen to her body, and tell you when she’s ready. After she is warmed-up and ready for your cock, lubricate your turgid member and re-lube her ass. Place your cock at her anal opening and hold it with your hand to help you guide it. Now, you have a few options:

  1. Have her move her body toward your cock (forward or backward depending on your positions), while you guide it inside.
  2. Rub your cock against her opening. This external stimulation should relax the anus. As the sphincter muscles contract, the opening appears to “wink” at you. As it winks open, take the opportunity to slide in.
  3. Press your cock against her opening and gently push against it (she may want to either relax or bear down in order to let you inside).
  4. Penetrate her ass with your finger, withdraw it, and while her anus is open, gently insert your penis.

Have her stimulate her clit as you penetrate her. This will relax and arouse her, making penetration easier. Deep breathing will help her relax and concentrate on opening her ass to you as well as circulating blood to her genitals. (Taking shallow breaths tightens the muscles and inhibits the engorgement process.) If you’re having trouble hitting your intended target (hey, those two holes are close together and it’s slippery with all that lube), have her wrap her fingers around the head of your cock and help to guide you inside her ass.

When you first get inside her ass, don’t go too deep. Again, you want to give her ass an opportunity to get used to your penis. Keep your movements slow, gentle, and subtle at first. When she’s ready, you can venture farther inside and start some slow thrusting. She should tell you if she wants you to go deeper or faster or both. Then, it’s simply a matter of exploring what feels good for both of you.

Feb 142001

For a long time, I have been trying to give it to my wife up the ass. But when I start to put it in her ass, I am only able to get the head part of the way in, then it won’t go much further.

We found an ad in a swinger’s magazine for a guy who said he was a pro at ass fucking. He promised if it hurt her, he would stop. He was a black man with a very large cock, and I was sure that he couldn’t get it in. He started by playing around with her, then they had vaginal intercourse. He slowly worked a finger up her butt. He told her to get on her hands and knees doggie-style, then he worked another finger inside her ass. He pulled his fingers out, then placed the head of his cock against the opening of her butt. I was amazed at how easily he got his dick in her ass. But since then, I have tried, and she just flinches and tightens up. I want to get my dick in my wife’s ass, can you please help?

—Dying to Get It In

Well, the good news is that your wife seems to be physically capable of taking and enjoying a cock up her ass, according to your story about her romp with the swinger. The bad news is that cock wasn’t yours.

Well, I think you can learn a few things from your swinger friend. First, let me applaud him for saying that if it hurt her, he would stop, and I encourage you to give her the same reassurance. It will help her relax and put her mind at ease. He engaged in lots of foreplay before the anal deed, including vaginal penetration and using his fingers to warm up her ass. Both activities probably got your wife aroused, relaxed, and ready for more. Follow his lead, and make sure you use plenty of lube (in both of her holes) when you do. Ask her when she’s ready for your cock, and let her be the one in control of the action from there. Ask her what position she wants to be in, or maybe suggest doggie-style, since that worked for her before. Rub the head of your cock at her opening, tease her with it, and let her prepare herself for the penetration. Have her reach back and guide your cock with her hand. This way, she can control the pace and depth of your entry. She can also come back on your dick from the position. You may need to help her out by pressing firmly, but don’t rush it and definitely don’t just shove your cock in her. With patience, I have hope you are on your way to assfucking delight!

Nov 052000

My boyfriend and I want to have a three-way experience—he and his best friend (a guy) and me. It has always been a fantasy of mine and he too wants to go through with it. We both swing, so we don’t mind seeing each other with another person. I have never really done this before. I have sucked another guy off while my boyfriend fucked me. However, I have never had two guys penetrate me at the same time, but I really want to do this. I think the idea of having two cocks in me—one in my pussy and one in my ass—would be an unbelievable feeling. However, this seems to be a hard thing to pull off. Do you have any tips on how to make this experience as pleasurable as possible?


Congrats for being able to voice your fantasy out loud and tell your boyfriend. Fantasies can be incredible forces in our lives. When you share a fantasy with your partner, it can bring you closer together — and you can have a hot time in the process!

My first piece of advice is that maybe the two of you should practice some double penetration before you invite your friend over. Use a flexible vibrator or dildo in one of your holes and your boyfriend fills the other. Use lots and lots of lube, go slow, and work your way up to it. Communication is extremely important: you’re testing the limits of your body, so make sure you give your man plenty of feedback about how it feels.

Also realize that some women can easily and comfortably accommodate something of size in their pussy and in their ass. Others will take some effort, with lots of warm-up. But some women may not be able to do it at all, since double penetration really depends on your internal map, and if there’s room for two. You are the one who will know best if it’s possible, so make sure you’re the one who’s in charge and calling the shots. Work out the kinks on your dildo before you plan your threesome.

When you are ready to tackle two flesh cocks at once, use plenty of lube and go really slow. Depending on the size and height of all three of you, some positions will work better than others. You may want to straddle one man and have the other nail you from behind. Try to take one cock about halfway inside your pussy, then angle your body to take the other one in your ass. Both men should start with shallow penetration, so you can get used to the feeling. Remember that porn stars make it look easy in adult movies, but they are seasoned professionals! You may be much more awkward your first time around. Practice makes perfect.

Oct 192000

I love it when my wife wears a strap-on and gives it to me in the butt. My problem is that she only does it occasionally. I wish she would do it more and enjoy it more, but I think maybe it’s not to be. I’ve even thought about having a gay encounter so I can get fucked in the ass more. Any suggestions? Are there any women that like screwing guys?


Are there any women that like screwing guys? R.H., is the sky blue? Do I love getting fucked in the ass? Yes, yes, of course there are women who enjoy turning the tables and being on the other end of a nice butt fucking for a change. Unfortunately, your wife may not be one of these dildo-wielding divas. Since you’ve already gotten your ass plowed by her before, I think it’s fair to ask her directly why you’re not getting the backdoor gift from her more often. Have you told her how much it turns you on? Your wife may have some issues with being the penetrator (instead of the penetrated), since it is not a straight woman’s typical role; however, you can reassure her that there are plenty of other women giving it to their guys and loving every minute of it.

Perhaps she hasn’t realized her own potential for pleasure during strap-on sex. In addition to being a real turn-on upstairs (in her head), there are also plenty of ways for her to get off while she’s got her cock in your ass. For some women, when the base of the dildo rubs against the clitoris and vagina, there is enough friction there to feel fantastic. Your gal should also consider the power of having balls. Some women simply don’t choose a dildo with balls because they prefer a more non-realistic style dildo; however, balls do more than make it look real, they extend the base of the dildo and cover more surface area — which means more for you to rub up against. Think about it.

If she wants to add a vibrator to the equation, she has several options. She could select a vibrating dildo, which will deliver vibration to both of you. She could try to don a wearable vibrator beneath her harness, but this may be awkward and interfere with the harness being tight enough. A better idea is the Buzz Me harness made by Stormy Leather and equipped with a pocket for a small vibrating egg. Vixen Creations has several dildos, among them “Treasure Chest” and “Bobby Sue,” with hollowed-out bases. Stick a vibrating egg in the base of the dildo, tuck the battery pack in the side of the harness and she’s ready for vibrating action, his and hers style!

For double penetration (one for you, one for her), there are harnesses with two holes, one for the dildo to penetrate you with, another for a dildo pointing in her direction. The”Nexus by Vixen is not an extra long jelly dong like you see in adult novelty stores. Instead, it’s a two dildos-in-one package: she can have a dildo inside her pussy or ass while simultaneously penetrating your ass. I just love sex toy technology!

If you want to learn more about strap-on anal sex, I highly recommend the videos Bend Over Boyfriend 1 & 2.

Now, as for your idea about having a “gay experience” in order to fulfill your anal sex desires, don’t you think that switching teams might be a little too extreme? Unless you are actually bisexual, and looking for a way to express your desire for men, if it’s anal sex you want, I stay stick with your wife and see if both of you can get what you want and need out of the assfucking experience.