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.

Early Cummer

Feb 232001
 


My boyfriend and I have been exploring anal sex together, and it’s been really great. We have come together, and it is totally awesome. A couple of times, I have come before him, and my insides feel as though he is doing damage. If I come before my husband does during anal, why is it that it hurts for him to continue thrusting to his climax? It is really a mood breaker for us both, especially if he hasn’t come yet. It’s like I want his cock out of me right that very minute. What can I do (besides not coming) to maintain the comfort and pleasure waiting for him to shoot his load?

—Early Cummer

I get so many letters about people being shy or scared about anal sex or having trouble making it work. Every woman should be so lucky to have your problem!

One explanation for this feeling is that your ass, like your pussy, has contractions during orgasm. After you climax, all the blood that rushed to your genital area disperses, and your ass returns to its non-aroused state (which doesn’t want a cock inside it).

Well, I’ve have first-hand experience with your particular dilemma; I too sometimes come first and find it difficult to go on. So, what can you do about it? Well, you already identified one option, which is to delay your orgasm until after his climax. That way, you extend your pleasure for even longer, and don’t have any discomfort. But, you indicated that you want another strategy. Well, one thing to consider is, after you come, have him slow down his movement or even stop thrusting, but still stay in your ass. Take a few minutes to recover from your mind-blowing orgasm, then concentrate on relaxing your ass and taking lots of deep breaths. Keep your mind on the pleasure and not on the fear that he might be “doing damage,” which will definitely help you relax. To extend your arousal, play with your pussy and clit, and have him slowly resume his in-and-out. Continue to breath deeply, work your clit, and relax your ass. As he pumps your ass, talk to him and let him know how it feels. Hopefully, you can have a second orgasm in the process!

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.

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.

Loss of Bowel Control

Aug 212000
 


My husband and I have been together for over 18 years and we have an amazing sex life. We love to explore and try new things. The only thing we haven’t tried is anal sex. I’ve always been a little bit nervous about trying anal. Lately, I’ve been contemplating it more because I’m curious. And it’s sort of exciting, trying something that we haven’t done before. Does anal sex cause problems later on? Will I have control over my movements as I do now? Will it affect my tissues in any negative ways?

—Dee Anne

First of all, congratulations on such a long and pleasurable partnership — may you be an inspiration to couples everywhere!

Your questions about negative side effects from anal sex are very common ones. Let me assure you that if you do it right — go slow, have lots of warm up, use plenty of lubrication, and start out with something small — anal sex is not going to cause you any problems later in life. Being able to take something in your ass requires relaxation of the sphincter muscles, and like any other form of exercise, the more you use those muscles, the better shape they will be in.

No, you will not lose control of your bowels; in fact, you may even have better bowel control once you begin getting fucked in the ass since you’ll be more in touch with that area of your body and more aware of your muscle control. The tissue of the rectum is quite sensitive and delicate and does take extra care; however, as long as you don’t rush penetration, as long as you listen to your body and stop if it hurts, you will not damage the tissue in any way. Anal sex can be a healthy, positive, pleasurable part of your erotic life. Take it one step at a time!

Husband Wants Anal Pleasure

Jul 182000
 


I would really like to have my wife perform anal pleasure on my ass but she doesn’t seem to be very into it. She enjoys receiving anal sex, and I have mentioned in the past what I would like her to do, but I can tell she’s a little weirded out by my request. Any suggestions?

—D.D.

Congratulations on coming out of the backdoor closet! I think it is especially revolutionary for straight men to admit their desire to be the receivers of anal pleasure. You join plenty of men who want to get done in the ass, and I promise you that once you’ve had your prostate gland stimulated, you’ll never be the same again! For men, it’s a chance to be penetrated, to give your body over to a woman in a new way. Seriously, I think every man should be fucked in the ass at least once in their life, and I am so glad you are ready to try it. I truly believe that getting fucked in the ass is one of the greatest gifts you can give a woman and yourself.

Now, on to your wife. I am not sure exactly why she is “weirded out” by your request. I can tell you that she doesn’t know what she is missing. Giving men anal pleasure gives women an opportunity to be the aggressor or the penetrator for the first time. Your wife has the chance to experience her sexual power as a woman and a giver of pleasure in a wholly unique way. Have you asked her directly why she might be hesitant to do it? Many people can buy into the myth that if men want to be fucked in the ass, then they are really gay. This is ridiculous, of course. Because anal sex is falsely linked with gay men and gay sex, there is a myth that if men want anal sex, then they must be gay. In most cases, men who identify as heterosexual and desire giving and/or receiving anal sex with women are not repressing homosexual desires or tendencies. Their desire for a particular sexual activity does not rely on or “cancel out” their sexual preference in a partner. According to research, more gay men regularly practice fellatio than anal sex, and as my friend Audrey says, “How come no one ever asks: if a straight guy likes blow jobs, does that mean he’s really gay?” Your wife may be a victim of this stereotype, and you need to assure her that you love her, are attracted to her, and want her to do you in the ass.

Different men also want to be fucked in different ways. Some want to be submissive as part of an SM scene, and giving up your ass can be an ecstatic way to submit. Men have lots of issues to get over when it comes to being penetrated (feeling passive, receptive, plus homophobia), so sometimes being “forced” to do it by a Mistress or dominant woman helps them take that leap. These are specific to SM, and may or may not apply to you. Either way, men don’t necessarily have to be bottoms to be fucked in the ass. I have personally fucked plenty of tops in the ass without flipping them — it’s all in the way you play it.

There are a few superb resources that I recommend you and your wife check out. They will help to open up a dialogue about this subject, and will also give you great information, tips, and techniques for doing the deed. The book, The Ultimate Guide to Strap-on Sex by Karlyn Lotney is informative and very useful. There are two videos: Bend Over Boyfriend is heavy on super instruction and stars real life couples. Bend Over Boyfriend 2: Less Talkin’, More Rockin’ has a title that says it all. Both are produced by S.I.R. Video.

Burning During Penetration

Jun 252000
 


Yesterday, my lover and I settled down to watch your video (loved it!). We played during the video, and the idea was that I would take her strap on anally. But a strange thing happened. When she inserted a lubed, gloved finger into my butt, I felt an intense burning sensation. After a few minutes, I had to ask that we change the scene. (I wound up giving her a blow job, instead. [Happy dance!])

That’s never happened before, that burning sensation. I can still feel it a little bit now, twelve hours later. I’ve taken things before, like my own fingers, and a medium sized butt plug. Once, a guy even inserted a finger completely into me without lube, and that didn’t hurt. But for some reason, yesterday I got a really intense burning sensation.

The lube we used was Eros lube, and it was a latex glove. I know I don’t have a latex allergy, at least not a system wide one, because I work as an EMT and use latex gloves every day. I also used to cover one of my toys with a latex condom before inserting it (that goes back to when I was fourteen, though). I don’t know what happened. We were so in the mood, too!

Have you ever encountered a similar situation? If so, what was the problem, and how did it get fixed?

—Neptune

Hmmm. It sucks that you were so inspired by my video, but your anal play was a bust! I have a few theories about what might be going on. First, you probably do not have a latex allergy since, as you say, you’re an EMT and you’d know it by now. But have you considered that you may have had an allergic reaction to the lube? Different people have different sensitivities to lubricants; you may want to try a water based lubricant (since Eros, the one you tried, is silicone-based) to see if it makes a difference.

If it’s not the lube, it may be some kind of anal ailment. Hemorrhoids, anal fissures, even a minute tear in the delicate lining of the rectum can cause itching, irritation, burning, or pain. In that case, give your ass a vacation from butt play for about a week, then try it again. If your burning persists, you should see a doctor, because it may be a symptom which requires more extensive treatment (besides just giving your ass a break).

Now, there’s one other possible explanation: your ass just didn’t want to be fucked that night and the “burning” was a form of pain. In other words, sometimes we register pain in different ways: as soreness, as tightness, and, in some cases, as burning. Remember that our butts can be sort of finicky, and we need to respect them. I am glad that you stopped the scene and moved on to something else — listening to your body is so important! There are times when no matter how much you’ve prepared, no matter how much warm up, no matter how much you want it, your ass just won’t cooperate. Sometimes, there are issues or anxieties your haven’t resolved and those psychological issues are manifesting themselves on a physical level. Or you could have been particularly stressed out about something entirely different, but the stress affected your ass. Or, your ass just didn’t want to go there, for no explainable reason.

I hope I have given you some options to explore — good luck next time!

Bleeding After Penetration

Jun 022000
 

My boyfriend and I have been having anal sex for a few months now, and have been enjoying the new sensations that it produces. However, the past two times that we engaged in it, I’ve been bleeding afterwards. What is causing this? Will it ever heal, and if so, how long will it take? What treatments can I use to stop the bleeding? The blood is evident mostly on toilet paper (bright red) and occasionally in the toilet (after a bowel movement). Please help!

–JP

At the first sight of blood, no matter how little, most people become alarmed. It’s only natural. If you have a little bit of blood on the tissue when you wipe yourself, chances are there is no real cause for panic. The lining of the anus and rectum is quite delicate and even with the most gentle touch sometimes we can tear the tissue slightly and not even know it or feel any pain. As long as this spotting goes away in a few days, you should be fine.

If, however, there is more than just a little blood, or you have other symptoms with the bleeding — like pain, cramping, or extreme soreness — then you should definitely go see a doctor. You may have something more serious like an anal fissure or a ruptured hemorrhoid. Listen to your body, use common sense, and see your doctor if you are concerned.

Pesky Fingernails

May 222000
 

My boyfriend seems to like my finger up his butt when I suck his cock. I’d like to finger him, and maybe fuck him with my fingers. I am worried, however, that I might hurt or scratch him because I have nice long fingernails, and I hate to cut them. Any advice?

–Donna

Congratulations on finding your man’s ass! And kudos to him for not freaking out when you reach back there during a blow job! So much pleasure awaits both of you, but you’re smart to be concerned about your nails. The tissue of the anus and rectum is very delicate and requires gentle handling. Don’t despair — you can keep your talons and still give him a good ass fucking.

First, you need to invest in some disposable latex gloves; you can get them at drug stores and sex toy stores. They come in different sizes, and make sure you get the correct size with a good fit; you’ll have better sensitivity so you can feel what you’re doing and he won’t feel a wrinkled baggy glove inside his ass. If you are allergic or sensitive to latex, you should get vinyl gloves; they are harder to find and a little more expensive.

Many women with long nails like to stuff cotton balls in the fingertips of the gloves in order to protect their manicure and their partner’s delicate asshole. Others wrap their nails in gauze before slipping on a glove. One woman recently told me she’s found a finger bandage which she puts on underneath a latex glove. Whichever option you choose, make sure you use plenty of lube on your glove.

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