Help My Turgid Member

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.

Dying to Get It In

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!

Double Penetration

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?

—Fingercuffs

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.

Making it Fun for Her

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?

—R.H.

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.

Warm Up

Sep 142000
 


A while back, my fiancee and I purchased your book The Ultimate Guide to Anal Sex for Women. We are hoping to include regular anal sex in our married sex life. As anal sex seems to take more preparation and time than other activities, we are planning to make the time for it and figured we’d shoot for once a week. Once the body is used to this activity, what is the best minimum frequency? Meaning, if we end up having anal sex say only once a month, will the body still be used to it or will we have to “re-train” it? We are open to having anal sex as often as we can to help make it an enjoyable experience always.

—Rick & Kristine

I applaud you for taking such a positive, healthy, and, most of all, realistic approach to anal sex. The reason that many women experience pain from anal penetration and vow that they’ll never do it again is because men rush the process, don’t work their way up, try to do too much too quickly, and end up hurting their partners. You are correct — anal sex does take time and preparation. The more patience and warm up you do, the better the experience will be for both of you.

But I know you must be thinking, “Do we have to go super slow, one little knuckle at a time, every single time?” The answer is yes and no. You always need to start out small, no matter how experienced you are. You cannot go from zero to sixty in five seconds flat. In other words, don’t just stick that big hard cock of yours in her ass. Tease her with your tongue, rub her clit, nibble her neck, open her ass up with your fingers, do whatever it takes to relax and arouse her. When she tells you she is ready for you, begin slowly.

The more you have anal sex, the easier and speedier this warm up will be. Your muscles do have memory. As long as you give them positive experiences, it will be easier for those muscles to relax and it will take less time for her ass to open up for your cock. I cannot give you a specific number of times you need to do it to keep in shape; that varies tremendously depending on the people and situations. The more you practice warming up to anal penetration, the more she’ll get used to how it feels when she is ready for you, and you will be well versed in all it takes to get her there.

Rimming Fears

Aug 132000
 


My girlfriend wants me to kiss and lick her anus. I find this difficult because I was raised by strict Catholic parents who taught me that shit is dirty. I sniffed her asshole and it did not smell. I also licked all around it, but I could not bring my tongue to her little rosebud. I kept imagining it opening up and shit coming out of it. But when my girlfriend licked my anus, I ejaculated uncontrollably onto her chest. It felt great! How can I get past my hang-up?

—Rosebud, San Simeon

It’s not just God-fearing Catholics who shy away from ass-to-mouth action; actually, plenty of folks have a fear of shit which prevents them from exploring many different forms of backdoor love, including being tongue-tied inside a sweetie’s ass. Porn star and anal queen Chloe says in my video Tristan Taormino’s Ultimate Guide to Anal Sex for Women (Evil Angel Video), “Get over your fear of shit!” I second that emotion, but I realize it may be easier said than done for many folks.

So, I first want to let you in on some basics about anatomy. When you penetrate someone’s ass with your tongue, your finger, a sex toy, or your cock, chances are you are not venturing beyond the rectum. You’d need something more than ten inches long or a good portion of your arm to move past the rectum and into the colon. So, for all intents and purposes, the rectum is your territory when it comes to anal play. And the rectum is not a storage facility. That’s right, you can’t stack boxes of old 45s in there or anything else. Feces are stored in the colon and move into the rectum when you are ready to have a bowel movement. So, if you feel like you have to go to the bathroom and you do, your rectum will be relatively clean and free of waste matter. Now, if you have the urge to poop, but instead stick something in your ass, well you are much more likely to find yourself with a mess on your hands (quite literally!). All this applies to people with good diets, regular, healthy bowel movements, and no chronic bowel or gastrointestinal problems. Empty bowels and perhaps a hot soapy shower will ensure that your anal romp will be nothing but good clean fun!

However, if you are especially concerned about cleanliness — and judging by those powerful poop images you are having, I’d say you are — then you may want to ask your girlfriend to have an enema before you go anywhere with that reluctant-yet-potentially-eager tongue of yours. You may also want to consider using a dental dam or some plastic wrap as a barrier between your mouth and her butthole. Since you have obviously experienced the ecstatic pleasures of rimming from the other end, you owe it to yourself and your girlfriend to give it right back to her. Sexual double standards suck, and it’s not fair that you should be sitting on her face without letting her sit on yours.

Willing Anal Virgins

Apr 232000
 

My girlfriend said she is willing to have anal sex, but neither her nor I have done it before, and I was just wanting some start up tips. I hope you can help us because I am looking forward to doing it.

–Bob

Two willing anal virgins! Yippee! I am very glad you wrote, Bob, because I receive so many letters from backdoor beginners and first-timers seeking advice. You didn’t specify which of you will be doing the fucking, and who will be taking it up the ass; however, I’m going to assume that you want to fuck her in the ass. (The majority of men who contact me wanting to get fucked in the ass are usually pretty specific about it.)

I cannot stress enough that going slow and having patience from the start will really pay off for both of you in the end. One of the keys when trying something new is not to forget the tried and true techniques that are already working. Before you even go near her ass, get her revved up in the usual ways — her favorite oral technique, her favorite position, her favorite sex toy, etc. The more relaxed and turned on both of you are, the easier it will be. Make sure you have trimmed your nails (sharp edges suck!) and have plenty of water-based lubricant on hand — lube is an absolute must for anal penetration of any kind. Tease the outside of her ass with your fingers, your tongue, maybe a vibrator.

When she’s ready for you to penetrate her, use one well-lubed finger. Instead of going straight inside, touch the pad of your finger to her opening; this trick usually relaxes the anus, allowing you to slip your finger in. Don’t go too far too fast! Go up to the first knuckle and just stay there, letting her ass get used to having something inside. When she’s ready for more, slip farther inside her ass slowly and gently. Make sure that she’s the one in control of the action — and she should let you know if she wants more or less, slower or faster, deeper or not-so-deep.

You should set some realistic goals, because most women can’t go from zero to sixty in one session. Decide to work your way up to one finger, two, or a small butt plug on your first try; that way, you won’t rush things. Going too fast or trying to do too much is a surefire route to pain and discomfort, which we don’t want. Practice a few times with fingers or small toys before you whip your dick out. Repeat as necessary. When you’re both ready for you to put your cock in her ass, again work your way up to it, go slow, and let her guide the action. Use plenty of lube and have a blast!

Women’s Anal Pleasure

Apr 052000
 

I just wanted to know if a woman actually gets any pleasure out of anal sex or is it just the guy? I’ve buttfucked some women who like it but others think it’s absolutely disgusting.

–Alan, Dubai

I am always slightly surprised by this question when I get it, and my gut response is: do people think that I have devoted my life to anal sex just for my health? Of course it’s pleasurable for me, why would I do it, write about it, talk about it so much if it didn’t bring me mind-blowing orgasms? The myth that women don’t enjoy receiving anal sex and that they just do it to please their partners is particularly prevalent among heterosexuals. Often, when we do hear about women having anal sex, the story goes something like this: the long-term boyfriend begged and begged and finally his girlfriend gave in to his demands. Her boyfriend was pleased, but she didn’t enjoy herself one bit. We never hear stories about women who crave and enjoy anal play or women who initiate anal sex. Author Susan Crain Bakos said, “Buttfucking is seen as the ultimate male sexual fantasy. We, as a culture, don’t understand how much women can like taking it up the ass.” She’s right: there are plenty of women who love buttfucking.

From a purely physical standpoint, the anus, anal canal, and rectum are wonderfully erogenous zones, rich in nerve endings and super-sensitive to stimulation and penetration. At the right angle, many women find that you can indirectly stimulate the G-spot (the spongy tissue around the urethra located on the front wall of the vagina) through anal penetration. G-spot stimulation feels great and even makes some women orgasm.

As I say in the introduction to my book on anal sex:

The first time someone put their finger in my butt, I almost went crazy from the pleasure. The sensations I experienced were so intense, incredible, and heavenly, that it was nearly mind-blowing. I felt high from the experience, and I couldn’t wait to do it again. The first time I put my finger in someone else’s butt, the results were just as fabulous — I felt entrusted with my partner’s deepest vulnerabilities, in awe of the ecstatic pleasure I could give. Each time I could take a little more and give a little more, the more sexually alive and powerful I felt. As I incorporated anal eroticism into my sex life, my sex life became better and better. The sex got hotter, my partners extra adventurous, my orgasms fierce and explosive. The physical sensations were undeniably some of the best I’d ever felt in my life. I confess too that beyond the deep body gratification, the naughtiness of it all really turned me on.

When you add the emotional aspects of anal sex — trust, tasting the forbidden, surrender, submission — to the physical sensations, you’ve got a very powerful sexual experience.

Ejaculation Inside Ass

Jan 152000
 

My husband and I have been married for six years. Although he has always played with my ass while we were making love, about three weeks ago, he actually put his cock in my ass. We’ve been doing it ever since, and it’s been great! He’s rather large, but we do a lot of warm up. Generally, we do it doggie style because I enjoy looking in the mirror, and seeing him behind me pumping away. Here’s my dilemma. Dennis always pulls out when he is about to come. This is very disappointing to me, and I would like to have him continue and shoot his juice into me. Would there be any problem with allowing his sperm to get into me that way?

–V.P., Bennington, VT

Congratulations on discovering the pleasures of butt bangin’! Once you open this particular flood gate, things will never be the same again. The question about your husband coming in your ass is a popular one (I got the same query from five different people this month). There really is nothing like the feeling of having a man’s hot load burst from his cock and fill that tight little orifice. He doesn’t have to feel worried or anxious about pulling out at the right moment — he can concentrate on working his way up and just letting go. He can stay inside until he has ridden his climax all the way to its end. As the receptive partner, the feeling of a firm dick inside my ass is out of this world, and I especially like to feel the moment before the climax, when that dick gets rock hard and ready to explode; if the guy pulls out at that moment, I feel empty, deprived, hungry, left on the side of the road to walk home alone. If we can share his coming together, I feel more connected with my partner, and his peak usually pushes me right over the edge into my own ecstatic orgasm.

But I understand that you are concerned about the safety of such a slippery through-the-sphincters delivery. If you are monogamous, and both of you have tested negative for HIV, STDs, and hepatitis, then your husband can come in your ass, and it is relatively low risk for both of you. If, however, you don’t have current negative test results for all these diseases, then either of you could transmit something to the other person through unprotected anal intercourse. This is true whether he comes inside you or not. You said you are married, but since this is the new millennium, I will not automatically assume that you are monogamous — you or your husband may have sex with multiple partners. If that is the case and for other readers out there who may be non-monogamous, anal penetration without a condom can put both people (and especially the receptive partner) at risk for contracting HIV, STDs, or hepatitis. Condoms and lube are the way to go. Let’s play it safe, folks!

Anal Lovers Anonymous

Nov 231999
 

How do I identify a woman who is open to anal sex? Are there groups or organizations whereby consenting adults meet who are of like mind?

–Mark T.

I am a heterosexual man who loves anal sex. It occurred to me that it would be a good thing to have a society of sorts in which people who enjoy anal sex could meet each other and not have to bring the matter up later only to be disappointed by the reaction. There ought to be a forum for people who enjoy it to meet each other under safe and embarrassment-free circumstances. So far as I know, no such organization exists. Have you come across such a thing in your work?

–Brooke

Guys, I feel your pain. Unfortunately, you cannot tell if a woman is into anal sex just by looking at her. And these days, at the dawn of a new century, you really can’t make assumptions about anyone loving or hating anything sexual. You just never know.

Your concerns bring up several valid points. First, you are both feeling the stigma associated with anal sex in our society — it’s not an easy topic to bring up with people, especially a new sexual partner. If you ask about it during sex, your partner might feel pressured or raising the topic might kill the erotic moment altogether.

Instead, I recommend approaching the subject in a non-sexual context, where you can take the pressure off. Ask an innocuous question like “Have you heard about this book on anal sex for women — what do you think?” to see where she’s coming from. Give her the space to voice her opinions before you then ask the more personal question like “Do you want to try it with me?”

I don’t know of any organizations a la “Anal Lovers Anonymous,” but if there are any, you’d find them on the Internet. Or, start your own and see what happens. Sex toy stores like Good Vibrations, Babeland, Stormy Leather, and Grand Opening and SM organizations like QSM, The Eulenspiegel Society, and others offer workshops on a range of topics including anal sex; get plugged into your local community and see what resources are available. Good luck, and remember that there are women out there who love anal sex and others who I know are willing to try it and be converted.

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