Jun 202001

Since I have been old enough to jerk off, I have been attracted to exceptionally buff and athletic women. The first time I ejaculated, I was fourteen and I was watching women’s gymnastics in the summer Olympics on television. Since then, I have desired a non-stereotypically-feminine woman. As my sexual development progressed, I discovered that I wanted such a woman to sodomize me—to fuck me in the ass with a strap-on. I have thought long and hard about this. Buff, athletic women are the most amazing, sexy creatures on the planet.

The desire has remained totally unsatisfied throughout my life. Recently, though, I was able, through some miracle, to go on a couple of dates with this girl who is on the diving team of my university. She is my ideal woman, and I really like her, but I’m afraid if I ask her for anal sex, I will lose a relationship with the sexiest, coolest, sweetest girl I have ever had the chance to be involved with. Help! How do I find out if she would be into anal sex with me? And, if not, how in the world will I ever find another as buff and beautiful as she is that might just be into anal sex with me? This girl is amazing, and I don’t want to lose her, even if that means sticking my thumb up my ass while thinking about her, and settling for strictly vanilla sex with the girl of my dreams.

—Buff Girls Rock My World

Well, it sounds like you really like athletic, assertive, maybe even butch, heterosexual women. I commend you for figuring out the unique type of person that floats your boat (and obviously gets your dick hard). As for seeing if she’s into fucking you in the ass, well, I think you need to take the plunge and ask her. I understand that you don’t want to lose her, but you also want to have your anal desires fulfilled, and those anal desires seem pretty fucking strong to me. So, approach her honestly and in a non-confrontational way, and tell her what you want. Hopefully, she will make all your dreams come true, and strap it on.

Mar 052001

I dated a woman for three years. We had a wonderful, rich, loving sex life. We had a lot of anal play, and we both enjoyed giving and receiving. I am ready to start dating again, and I am worried about anal sex. I like it, but I know not everyone does. I have been told (and I know it is true in my case) that a lover who really cares about me will want to fulfill my sexual desires, but the idea of “pushing” anal sex on anyone makes me nervous. At the same time, I like it.

When I dated this woman, we started slow and gentle (and very caring), and after a year or so, we were using handcuffs, talking nasty — for fun. I want to love a person first, and the sex second, but I am afraid I won’t get what I want. I have a feeling you are going to tell me that I am reasonably normal, and that I shouldn’t worry about it. If that is the case, fine, but I need to be told by someone knowledgeable in the field.

—Loving Anal Slut

You’re right, you are a reasonably normal guy, a reasonably normal guy who happens to really like anal sex. It sounds like your three-year relationship was very fulfilling for you, and that you approached anal sex in the right way, with plenty of love, communication, and patience (and lube, I hope!).

I think it’s absolutely okay that you want anal sex to be a part of your next intimate relationship. Your desire for buttfucking is obviously part of what makes you tick sexually, and bravo to you for identifying it and owning up to it. But I see your dilemma: what if you find the perfect girl and she’s not gung ho about you doing her bunghole? Well, presumably you are looking for a mate who has a similarly liberal and adventurous attitude about sexuality as you do; if you like anal play, bondage, and dirty talk, you obviously need a partner who’s inclined toward experimentation beyond the missionary position. As you date and hunt around for a new relationship, be confident in who you are and what you like, and be honest with your partners. I find that since I’ve gotten seriously into anal sex, I have not landed in bed with anyone who isn’t into some backdoor lovin’. I’m obviously putting some kind of vibe out there that people are picking up on, and I find that I tend to be attracted to people with whom I am very sexually compatible. Rather than feeling worried, obsessed, or even a little guilty about your anal desires, why not embrace them fully? Once you do, you have a greater chance of attracting women who will not only fulfill your desires, but may even exceed your wildest expectations!

Jan 072001

My wife and I have not delved into anal sex. She’s hesitant, while I’d like to play. I’d like us to play both ways, hers by me and mine by her. I’ve read your advice before and get the gist of how to do things. I need to open the conversation about anal in an attractive and fun way. Any suggestions on how to talk about what would be a new sport for us?

—Wanting to Play Ball

Well, I am glad to hear that you are already approaching the subject with an open mind and ass — mainly, that you’re willing to go both ways when it comes to anal pleasure — and I am sure your wife will be, too. Obviously, I want to let the world know about how awesome anal sex can be, but, as a sex educator, I don’t want to coerce anyone into doing something they don’t want to do.

You wrote that your wife is hesitant — have you talked about this subject with her? An honest discussion may be what both of you need. There could be a variety of reasons why she’s not gung-ho about anal sex. Like so many of us, your wife may have certain misconceptions about buttfucking — that it’s dirty, painful, or only for a man’s pleasure — which prevent her from wanting to dive right in. You should correct those myths with the facts: anal sex doesn’t have to be a big mess; if you do it right, it won’t hurt; and women can get off on it in plenty of ways.

Or, perhaps she has had a bad experience in the past. If a boyfriend before you tried to go from zero to 60 in five seconds by sticking his dick in her ass without warm-up, lube, or communication, then chances are it hurt a lot and she never wants to do it again. Here’s your chance to reassure her that this time, with you, it will be different. You will take your time, use plenty of lube, and work her ass up to your cock. If you want to be sexy about this whole conversation, why not whisper in her ear a fantasy you have about fucking her in the ass. That, coupled with communication and information, ought to get her revved up!

Dec 162000

My wife and I of nine years have been experiencing trouble for some time in our relationship. Upon my search to get a new fire rolling, I sought out new ways to please her, which in turn brought us to the world of BDSM. We are both intrigued by anal play (giving and receiving), but she is a little concerned. I think it might be too painful for her. I myself believe we are well on our way to restoring and incorporating this new volcano of sexual energy, but I want to make it happen safely. Also, what are your thoughts on switching?


It makes perfect sense to me when people want to combine anal sex and BDSM. Anal play can be very emotionally and psychologically charged, and it can be a perfect activity in which to explore the erotic dynamics of power and control. We learn early on that our assholes are a source of embarrassment and shame or that our buttholes are private, dirty, and shouldn’t be thought of in a sexual way. Anal sex is taboo, forbidden, shrouded in mystery and misinformation. Our asses are also very delicate, sensitive areas that require an extra level of communication, trust, and skill. In other words, you can hurt someone if you don’t do it correctly. When I say hurt, I mean not in a good way.

When I teach anal sex workshops to people who aren’t into BDSM, I try to help them overcome all those negative feelings so they can move on and have pleasurable anal sex. But if you are into BDSM, it’s a different story. As tops, we can take advantage of all these elements of anal eroticism in a scene. We can play on all these different psychological angles to make anal sex a hot BDSM experience. You can taunt a bottom, telling her that she’s nasty and perverted for getting fucked in the ass. You can take a level of control and comfort away from your bottom. When I bottom, I find that giving up my ass to my top can be the ultimate act of submission. Giving over such a delicate part of my body to another person magnifies the inherent power in penetration.

In a non-BDSM context, I recommend lots of communication, but the kinds of things I recommend people say don’t necessarily translate while you’re in role. A top can’t ask “How does that feel honey, am I hurting you?” A bottom can’t say “Go slower, I don’t like it so fast; Okay, I’m ready for more now.” That kind of banter could throw off the dynamic. So I recommend prior communication and negotiation. You can also incorporate different ways to warm up your bottom’s ass into your scene — for example, if you develop a system where the bottom needs to tell you when she wants something bigger in her ass, you’ll know she’s ready without having to ask her (she’ll be the one who has to ask!).

As for my thoughts on switching, contrary to some popular thinking, switches are not just wishy-washy folks who can’t make up their minds. Switches are people who like to see things from both sides and take different positions depending on the particular situation. You may start out wanting to experience different aspects of BDSM from both ends, doling it out and taking it, then find you come to see you really do fit into one or the other. But don’t feel like you have to choose right away or identify yourself to the world at large. Focus on what you want rather than what label applies to you.

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.

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?


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.

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?


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.

Oct 041999

I want to learn how to make anal love to my girlfriend in such a way that she doesn’t describe it as hurting. Should we try a different position? I want it to feel so good. You are the woman who can help me.

–P.J., Reading, PA

I wish I could hop on a plane and give a personal tutorial to each couple who seeks my advice and guidance. I would arrive with a fully stocked briefcase of lube, latex gloves, condoms, vibrators, and butt plugs. I would let you two get revved up with lots of foreplay, and when you were both ready, I would lead you through anal penetration step by step. Go slow and be gentle. Use lots of lube. Work your way up, beginning with a finger or slim butt plug or dildo. Ask her if she wants clitoral stimulation; some women like to have their clits played with while getting fucked in the ass, others like their partners to concentrate solely on the butt. If she wants your hand or tongue or vibrator on her clit, give it to her. Talk to her the whole time, see what turns her on and what doesn’t work.

When you are ready to fuck her with your cock, find the best position. People always ask me: “What’s the best position for anal sex?” My answer: the one that works for both of you. Missionary position can be great, unless keeping her legs in the air or over your shoulders isn’t comfortable for her. Spooning works if your bodies line up naturally, and the man can get a good angle. If you choose doggie-style (my personal favorite), you can do traditional on-all-fours or do head-down-ass-in-the-air. With doggie-style, you can get a great angle to hit her G-spot, just remember not to go too deep at first. When you first enter her, just put your head inside, stop, and stay where you are. Let her sphincter muscles and anus get used to the feeling. Sometimes, she will actually suck you inside — when we are aroused, our anal canals and rectums start to contract and we can often pull a dick or a toy right in. If she doesn’t suck you in, slide into her very slowly. Many men make the mistake of trying to just shove it in there, and even with the most experienced woman, that just won’t work!

You sound like a very sensitive, caring, anal-sex-loving partner. Have you communicated your desires and concerns to your girlfriend? If she knows that you are caring and promise to be gentle, it will definitely set her mind (and her sphincter muscles!) at ease. You need to emphasize that, as the receptive partner, she’s the one in control of the action: it’s her call on how fast or slow, how deep or not-so-deep, and how much. That’s how I’d handle the situation in person. But, alas, my schedule just doesn’t permit it! Listen to her body and her verbal cues, go slow, and pretend I am there guiding you through it!