Mistress of His Ass

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.

Questioning Her Anal Love

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.

Pleasure With My Probe

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.

I Have an Anal-Crazed Girlfriend

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.

Stubborn Submissive

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.

I Want A Pain-Free Poke

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.

Mr. Softie

Feb 122002
 


My girlfriend has hinted that she wants to try anal sex, but she is too shy to talk about it. She likes me to finger her ass, and she goes crazy when I lick it as well. The problem is that every time I try to penetrate her ass, I lose my erection! I think I must be too nervous or something, but I don’t have this problem when we have vaginal sex. Because of my problem, we have never been successful in anal penetration. I think it takes me such a long time to try and position my dick that I just lose my excitement. Anal sex is one of the most arousing fantasies for me—please help me so I can do it!

—Mr. Softie

If you have a less than solid erection, you can often “stuff it” into her vagina, and, once you’re in, you achieve a full hard on. It’s a little trick which plenty of men do. However, that same shortcut simply does not work with anal penetration. The bottom line is that you need to have a rock hard cock to get it into someone’s ass.

Well, since you have no erectile issues during vaginal sex, then your problem is probably not physical but psychological. My initial question for you is do you have any fears about fucking your girlfriend in the ass? Some men are anxious about hurting their partners. Somewhere in the back of your mind, you may be afraid you’ll cause her pain or perhaps a past lover has told you that you hurt her. If you think you might have this fear, reassure yourself and your girlfriend that you’re going to warm her up, use lots of lube, and go slow, so that it won’t hurt.

Speaking of going slow, it sounds like that may also be part of your problem. You wrote about how much time it takes to get in position, and you may be losing the momentum of the moment. If that is the case, perhaps your girlfriend can stroke your cock as you’re maneuvering it or talk dirty to you to keep the fantasy and the anticipation going while y ou get ready. I’m concerned that you say she’s too shy to talk about anal sex. You may have poor communication both in and out of bed, and that could be contributing to your anxiety or ambivalence about anal sex. Talk to her in a safe, non-threatening aware, share your desires and fears, and agree to work on this issue together.

Wanting to Play Ball

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!

Negotiation and Switching

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?

—Brian

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.

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.

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