zephyrrb: My wife loves anal sex but doesn’t orgasm, I don’t want to go back to vaginal but how do I get her to orgasm thru anal sex? Thx

Does she combine clitoral play with anal sex? Most women need clitoral stimulation to orgasm, at least without further practice/training. Some lucky women find themselves able to orgasm from anal alone, with zero clitoral stimulation, but in my experience at least that’s relatively uncommon.

Aside from that, here are a few (but not an exhaustive list of) things you can try to work towards a fully anal orgasm.

1. Try having her go a few days or more (actual length of time can vary depending on how long it takes her to get extremely horny) without any orgasm to boost her level of arousal and make her more sensitive. Edging can help during this time as well to amplify and speed up the process. Then when she’s so horny she can barely take it anymore, have anal sex and see if she can manage to orgasm from it in that aroused state.
2. Related to the previous, an edging session to get her aroused and sensitive, followed by anal sex with just a little bit of clitoral stimulation to try and get as close to the edge as she can and then letting go to try and let the anal carry her over the edge into orgasm. Repeated practice of this can lead to less and less clitoral stimulation needed, and may over time let her orgasm just from anal.
3. Try having anal sex while she has a full bladder. This can make her both more sensitive and reposition things a bit inside to make anal penetration more likely to also stimulate her orgasm trigger points.

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masters-rabbit-hole: Also try to have her not touch her clit at all until she cums some other way. That’s how I’ve trained all the women I’ve been with throughout the years to cum via penetration. Latest success is my slave can now cum via anal penetration alone. She says they’re the largest orgasms she’s ever had. She also now has a hard time cuming with her Hitachi on her clit. To her brain that is not ‘sex’ anymore; penetration is.

I think the biggest reason some women can’t cum via penetration is they can’t keep their fingers off their clit. This can be the same for men if they jack off too much. The brain is trained, over years for most people, to only associate masturbation with sex. You have to retrain the brain. Takes months, from my experience 4 or more.

There’s been a Ted talk on this subject. It was slightly different, about the association of young men with ED and their masturbatory habits. They removed masturbation and it retrained their brain on ‘what is sex’ ‘what should evoke a sexual response.’

Anonymous: I honestly thought there was something wrong with me. I learned early that the easiest way to cum was from anal stimulation. None of my partners until recently wanted to even try anal, but my current lover is a self proclaimed Ass Man & eagerly fucks my ass, but likes to play with my pussy when he does. I get very wet when my ass gets fucked, & he’s fascinated. The problem is I cum really easily from my clit, but the orgasm from anal is much better & stronger! How can I convince him “hands off”?

I would just come straight out—maybe not during sex itself, but before you have sex sometime—and explain the situation to him. Tell him that while you don’t dislike the feeling of him playing with your pussy or clit while he fucks your ass, you love cumming from anal itself, and when he rubs your clit it short circuits that process and prevents you from getting the bigger orgasm you’d enjoy even more because you cum from your clit before you can get the orgasm to build from just anal. Most people are eager to help their partner get the most pleasure they can from sex, and should understand the appeal of what you want.

You could also phrase it a bit differently—asking him if he wants to see you cum just from his cock in your ass and nothing else, and to avoid touching your pussy in order to try, then when you do, tell him that you enjoy cumming that way even more.

Anonymous: So I never did anal but my daddy wants me to become an anal and mouth slut only, and I can’t say no to my daddy. But he wants it to be hard for me so he makes me come every days by my pussy and my clit. He wants to be sure I’m ready to abandon everything for him so he makes me addict to pussy/clit orgasm before the day he will choose, I have to abandon that and become anal only. And he doesn’t want me to touch my ass because he wants to wait until he says so. So I wait for him.

This isn’t really an approach I recommend, because it’s generally advisable for most people to transition into anal only in order to best enjoy it, and while some find they do right away and can cum from it without clit play, most need a more gradual approach to get to that point, if they can at all. But, if you’re determined to do it this way, good luck.

Anonymous: How do you prepare for anal? It frightens me to think that something big would force in there.

You don’t force anything in, to begin with. You start with something small and lubricated (always lubricated) that you can fit in comfortably (like a finger), and you combine gently inserting that with rubbing your clit or using a vibrator. You masturbate like that often, trying to orgasm while something is in your ass. As you become more comfortable with that, you try something a little larger (maybe two fingers) and repeat. After you can fit around the size of three fingers in without difficulty, buy a small/medium buttplug (something around the size of the Tantus Ryder) and work towards being able to insert that easily and wear it during masturbation or sex and even other times as well.

Continue gradually increasing in size until you feel comfortable trying with a trusted partner who will take care to go slowly at first and let you adjust and get used to his size. If anything hurts, take a break and do more warmup with something smaller.

dumbandpretty: A fellow mom, whom I’ve gotten close to the last little while, asked me how I keep B interested in sex.

I said one word:

Anal.

She said “oh” and that was the end of that. I am optimistic, however, because it was more a curious “oh” than a disgusted or disappointed “oh.” I will update you guys when I speak to her again this weekend.

Anonymous: Confession: to train myself into an anal slut, I’ve started inducing pain on my clit, like clamping it and leaving the clamps there for a long time… to learn that my clit is something filthy and unpleasant and awful. Anal is where the pleasure is.

I definitely encourage people to experiment with clitoral denial once they’ve become familiar and comfortable with enjoying anal. Not everyone needs it at all, but many can benefit from clitoral play during their initial introduction to anal. After the initial stage and when you can regularly enjoy anal, it can be beneficial to experiment with enjoying anal stimulation entirely on its own and learning more about its subtleties without the distraction of clitoral. Not everyone will decide it’s for them, and that’s okay, but some will find they love the experience of pure anal, uninfluenced by clitoral stimulation alongside and over the top of it.

Anonymous: How do you prepare for anal? It frightens me to think that something big would force in there.

You don’t force anything in, to begin with. You start with something small and lubricated (always lubricated) that you can fit in comfortably (like a finger), and you combine gently inserting that with rubbing your clit or using a vibrator. You masturbate like that often, trying to orgasm while something is in your ass. As you become more comfortable with that, you try something a little larger (maybe two fingers) and repeat. After you can fit around the size of three fingers in without difficulty, buy a small/medium buttplug (something around the size of the Tantus Ryder) and work towards being able to insert that easily and wear it during masturbation or sex and even other times as well.

Continue gradually increasing in size until you feel comfortable trying with a trusted partner who will take care to go slowly at first and let you adjust and get used to his size. If anything hurts, take a break and do more warmup with something smaller.

Anonymous: I’m so glad to hear chastity piercings are something the two of you are now considering. I think you’d be a perfect candidate for them, and even though I know you don’t need them to stay devoted to anal only at this point, they would provide lovely symbolism.

dumbandpretty: I know, right? I’ve had all the kids I want to have, my vagina has served its purpose. I think forced retirement is in order!

Anonymous: So bored with vaginal to be quite honest. If I don’t get the back door enough from my girlfriend and another girl offers it should I take it?

Don’t cheat on your girlfriend, that’s never okay. If you’re unsatisfied with your relationship, either try to improve things or do her the favor of officially breaking things off before doing anything with another partner. You’ll have to decide how important anal is to you, and whether not having it as much as you want outweighs everything else you have with your girlfriend. Sex isn’t everything in a relationship, even though it is an important component.

Anonymous: I have had anal before, but my boyfriend hasn’t. I really enjoyed it and want to have anal with my boyfriend. I’ve mentioned it before and he said he wanted to try it. He’s never tried it or said anything about it though. Is he maybe waiting to see if I bring it up again? How do I bring it up to him? I enjoy vaginal sex with him, but I want his dick in my asshole. Any advice?

Most guys want to try anal if they haven’t already, if only out of curiosity. Many, however, are also sensitive to the myth that women don’t like anal and so may have a hangup about doing it if they think it’s going to hurt their partner or she won’t enjoy it. Since you brought it up, he probably does want to do it but may not want to appear too eager or selfish for bring it up again himself now. I would mention it again, and be sure to reinforce it with the fact that you really enjoy anal and want to share it with him.

You could also take the more direct approach and prepare yourself for anal before having sex sometime and asking him partway through to put it in your (pre-warmed up and -lubed) ass.