Nov 142005
 

My wife seems to like the naughtiness of receiving my dick up her ass, but I don’t think she really likes it. We haven’t done it that much, but when I get it in there she does her sexy groan like when she’s going to come from a good licking. Part of it is we haven’t used much lube except her cunt juice. I don’t know if I really want to ask her if she wants to have it or not because she may say no, and I don’t want to go there. We’ve talked about it outside of the bedroom and she says she does it because she knows it turns me on and she likes to submit to my power over her. She’s very much in tune to her body and loves trying new things. Any advice on getting her more into it?

–Can’t Read Her Mind or Her Ass

Before you think about getting your wife “more into” anal sex, you need to figure out if she is into it at all. Although you’ve talked with her a little bit about the subject, you need to talk about it a lot more. She says she does it to please you, but does she enjoy any other aspect of it besides the pleasure it brings you? It troubles me that you have avoided asking her direct questions about it for fear that her answers might not be the ones you want to hear. You both need to be honest with one another about your desires and needs when it comes to anal sex.

As for the lack of lube, well, that’s not helping matters. You absolutely need lube for penetration to be comfortable for her; in this case, her cunt juice is not enough. But first and foremost, her desire must be there for it to work at all.

Jan 172005
 

My wife seems to like the “naughtiness” of receiving my dick up her ass, but I don’t think she really likes it. We haven’t done it that much, but when we do, when I get it in there, she makes her sexy groan like when she’s going to come from a good licking. Part of the problem may be that we haven’t used much lube except her cunt juice. I don’t know if I really want to ask her if she wants to have it or not because she may say no and I don’t want to go there. Any advice on getting her more into it? We’ve talked about it outside of the bedroom, and she says she does it because she knows it turns me on and she likes to submit to my power over her. She’s very much in tune to her body and loves trying new things. Any suggestions?

–I’m In There, But Is She Into It?

Where do I begin? I’m disappointed to hear you have not been using any lube except cunt juice. Lube is a must for comfortable anal penetration, and no matter how juicy a cunt is, its fluids just won’t cut it. So, my first piece of advice is to get your hands on some lube and use plenty of it. You’ll be amazed at how much better it will feel for your wife.

From the information you provided — both about your conversations with your wife about her submissive desires and her response when you fuck her in the ass — it sounds like your wife does indeed enjoy your backdoor adventures. But the fact that you have avoided asking her directly because you “don’t want to go there” is a problem. Honest, ongoing communication is critical to any relationship and opening up a dialogue about anal sex with your partner can only be a good thing. You’ll get the answer to the question directly from her, and, if all goes well, maybe she’ll elaborate on some of those naughty, submissive fantasies of hers.

Nov 122004
 

My wife and I have indulged in anal sex as occasional fun. Since becoming pregnant, she has had some vaginal soreness which has lead to an increase in anal play which I really love. My wife has admitted she really likes analingus and sometimes orgasms during anal penetration. My fear is that once she gives birth, anal sex will return to being only an occasional thing again. How can I persuade or convince my wife to let the good times roll?

–An Anal Lover

If your telling of the situation is accurate, it sounds like your anal play hasn’t just served as a “substitute” for vaginal penetration, but that your wife is having a pretty good time (orgasms being a clear indicator of a good time). I suggest you talk to your wife about exactly what she likes about anal, in addition to analingus, and keep doing more of it. The better time she has during your anal explorations now, the more likely she is to continue wanting you to fuck her in the ass post-pregnancy.

Oct 072004
 

I have fantasized about anal sex for years, and I finally think I have the courage to ask my wife to do it. What’s the best way to bring it up with her?

I think communication about sex is specific to the individuals involved, so there’s no one rule that will work for everyone. If you and your partner speak openly and directly about sex, then, by all means, be open and direct about your anal desires. If you’re unsure about how your partner may respond, then you might want to bring it up in a more indirect way; for example, “I just read something about anal sex in a magazine — what do you think of it?” rather than “I want to do this to you now” — which may feel more threatening or intimidating. It’s important for you to make your request as pressure-free as possible, and give her the opportunity to voice her concerns, if she has any. The one rule that I think can apply to all couples is that you shouldn’t bring up the subject in the middle of sex; pick a time and place that’s neutral for both partners.

Aug 182004
 

Are some women’s butts more pre-disposed to anal intercourse than others? I know we are all different, with different bodies, needs, and desires, but I wonder if there is a physical component to achieving success in anal penetration. My current partner loves anal sex, and she can have these long, all-over-her-body orgasms when I fuck her that way. With my last girlfriend, however, I wanted on many occasions to have anal sex, but could never get it right. We did loads of foreplay, including massaging, oral with loads of clitoral stimulation, anal rimming, licking, loads of lube etc. With all that said and done, her butthole never loosened up very much, and didn’t get vaguely close to me getting myself in there. Is she just not an ‘A’ candidate, or was I missing something somewhere?

–Perplexed About A Butt

Yours is a very interesting question, one I think could be asked about all sorts of sexual desires and acts, not just anal penetration. You’re correct about how individual we all are; while our anatomy may be similar, our sexuality — how we liked to be touched, what turns us on, what combinations of sensations and scenarios brings us to orgasm — can be almost as unique as our fingerprints. Certainly, there are some women who seem to enjoy anal pleasure more than others, and I can say from experience that some women have an easier time than others. When I say easy, though, know that all the same rules still apply; you still must use lube, go slow, and make sure her body is warmed up. Likewise, there are plenty of women who tell me that they enjoy anal, but it takes them a lot of time to relax and open up, and on some occasions, it just won’t happen.

I appreciate your dedication to your previous girlfriend; it sounds like you made all the right moves, but even with the best effort, sometimes foreplay isn’t enough. In addition to the physical aspects of anal play, there are psychological and emotional components that cannot be ignored. If a woman is feeling unsure, nervous, anxious, or conflicted about receiving anal pleasure, then no amount of expert cunnilingus or rimming may change her mind. Sometimes, working through a partner’s fears about anal play — whether it’s the potential mess or pain, or feeling dirty for just wanting it — are the key to opening up. Free her mind, and (hopefully) her ass will follow.

Jun 152004
 

My boyfriend is ultra submissive in just one area: his ass. He doesn’t go for the Mistress thing, lick-my-boot mentality, but when it comes to his ass (which is the focus of his fantasies and always how he’s able to come) he’s full sub. I know exactly what he needs that way, pain and humiliation. Directed at his ass. Insulting HIM gets us nowhere, but insulting HIS ASS does. My snag is this: there are only so many ways to insult an ass. Degrading his ass, calling it a cunt or pussy gets him off in a snap. Is there any way to get good ideas to boost my imagination so play is not monotonous for either of us?

–Mistress of His Ass

Plenty of people get off on pain, humiliation, degradation, and overall submission. Clearly your boyfriend’s submissiveness is tied directly to his ass and anal play. There are many ways to combine submission and anal pleasure. You’ve already insulted his ass, but have you also tried to insult and humiliate him for wanting his ass penetrated, for being a naughty butt boy? Take all the cultural baggage that comes with anal pleasure, and use it to your advantage, as a psychological tool: it’s dirty, taboo, dangerous, and will make him gay. Of course those aren’t true, but these myths can make for great mindfuck material.

If he likes extreme submission, you may also want to explore forced anal penetration or anal rape scenes; that’s tricky territory, so tread lightly. It also sounds like there is an element of gender play in your man’s fantasies, since he enjoys having his ass be called his pussy. Try to explore that part of his desire further. Does he want to crossdress, to be girl? Does he want to be forced to do it? Forced feminization is quite popular and may be part of what he’s try to express in the anal play you’re currently having. See if he will open up about and be specific about his submissive anal desires, and use what he gives you to take things to the next level.

May 122004
 

I have been with my girlfriend for six years, going on seven. The sex is really amazing, but something is missing: anal. I love to eat her pussy a lot. The taste of her and just being down there can make me come. For the past year, when we 69, as I lick her pussy, I have been playing with her ass, and she moans louder when I do that. One time, my whole thumb was in her ass and she loved it. But when we talk about it, she seems hesitant. When I go down on her, I tend to give her a small rim job. Or, when we are in missionary position and I swivel her left leg over so her ass is exposed and play with her ass. She gets into it, and then stops. I’m very confused. I think she loves it, but I don’t know.

–Questioning Her Anal Love

It sounds to me like you two need to have a conversation about anal pleasure. According to your account, your girlfriend isn’t opposed to it, though it seems that you want to go further than she is comfortable going. It may be that rimming and penetration with a finger feels great, and she has no desire to do any more. But the fact that you’re getting mixed signals means she may have some unexplored issues that prevent her from fully enjoying the anal play you already do and stop her from further exploration. Be open, compassionate, and non-judgmental when you approach her. Ask her if she has fears or misgivings about anal pleasure; she may have concerns about hygiene, safer sex, penetration, and other common issues associated with butt sex. Talk through these issues, and see if you can get to the bottom of her feelings.

Mar 202004
 

I just started having anal sex with my girlfriend. We did it the first time with lots of lube and I was able to get the entire shaft inside her with little to no pain. She told me that she could feel the fullness but she got no pleasure or pain from it. She said that if I wanted to do it again later it would be no problem since it does not hurt her; however, I would like for her to get some pleasure out of it. I cannot touch her vagina with my fingers because she is very ticklish there. If you have any suggestions, I would appreciate it them.

–Pleasure With My Probe

Bravo to you for realizing that anal sex should be pleasurable for both people involved. My suggestion is that you add some clitoral stimulation to the mix. While you are doing her ass, rub her clit, or, if it’s easier, have her do it herself. You could also use a vibrator for more intense, focused sensation. Many women (me included!) love the combination of clitoral and anal stimulation, and lots of girls say that they don’t experience pleasure from anal penetration without something on their clit.

I’m not sure what to make of your girlfriend’s ticklish pussy. That sounds more psychological than physical to me. Perhaps it’s a reaction to her feeling shy about receiving pleasure; if that’s the case, then you should encourage her to relax and give herself permission to experience being touched and pleasured. Or, it could be that when she’s turned on, her genitals become super-sensitive, and stimulation of any kind feels overwhelming. Then, try softer, more indirect kinds of stimulation, like rubbing her clit from one side, rather than directly on top.

Nov 182003
 

My girlfriend is a bit crazy for anal. When we’re out shopping at the mall, in broad daylight, with no concern for who hears her, she’ll say something like “I’d like that up my ass.” She will say this about video game controllers, sports equipment, household appliances, children’s toys — you name it. I think she gets a kick out of this. I just imagine the look on people’s faces when they overhear it, and I cringe. It’s embarrassing! She just doesn’t care. Would you recommend threatening to take away anal from her? Should I just end the anal ritual altogether? Or, God forbid, should I fuck her ass so hard that she never wants to do it again?

–I Have an Anal-Crazed Girlfriend

I can’t decide why I chose to answer your letter: to illustrate that I receive some of the best letters in the sex advice business or to indulge you because you might just be fucking with me! I’m going to embrace the former, and assume that your girlfriend’s behavior is, in fact, an issue.

First, all the men out there who can’t get their wives to agree to anal play at all are reading this and shouting out loud, “Dude! I wish I had your problems!” Count your blessings that you have not just a willing, but a clearly enthusiastic, anal sex partner.

It sounds to me like your girlfriend is not simply “anal crazed,” but she’s also a verbal exhibitionist: she enjoys saying bold, sexually suggestive things in public, and she wants those around her to hear her and be shocked. There is only one potential problem with this situation: there are many public places where it’s really inappropriate for her to talk her tushy trash, especially when she’s within earshot of children. Threatening to “take away anal” or actually doing that will only fuel her bratty inner-schoolgirl and hurting her during anal sex is just mean and stupid. Let her know that her explicit public chat bothers you, but also offer a solution: encourage her to save all her naughty little ideas for when you get into bed, where she can whisper them to you or shout them out loud. In that erotic context, you too will probably get off on her mouthing off. If she can’t keep her thoughts to herself the next time you go out, then a spanking and a gag are in order.

Apr 302003
 

My boyfriend and I have a Dom/sub relationship (he is the Dom). We also play with some “special friends” from time to time. Since I feel no hesitation having anal sex with him because of our love and trust, I am not really interested in engaging in it with others. He seems to see this as resistance to his control and it has led to some heated discussions. I have told him I am not interested but his challenge is, “How do you know you won’t like it if you don’t try it?” Do you have any advice on a good response or two that I can have ready the next time the subject comes up?

–Stubborn Submissive

While I understand that complete control and surrender of one’s free will is a goal for many people in Dominant/submissive relationships, I’m also practical: very few human beings can be 100% submissive and surrender all their free will to another person. That’s why it is quite common in the leather world for people to negotiate ground rules in scenes and relationships. I appreciate your Dominant’s desire to have your complete obedience, to push you to expand your erotic horizons, and to see other people fuck you in the ass; however, I am siding with you on this one. You have communicated a clear boundary to him, and I think that boundary needs to be respected. He needs to see that you having limits does not mean you are resisting him, but that you are taking care of yourself, listening to your instincts, and communicating clearly — which are all great qualities for a submissive to have.