Anonymous: How do you have an anal orgasm? Do you have to push like you’re going to the bathroom, or do you just wait for it to happen?

There isn’t a straightforward answer, different people cum from anal differently and with varying levels of ease. Pushing out works for some. Others just have an orgasm build and climax naturally from anal without having to do anything else. A full bladder helps some. Some need to get very aroused by having no orgasms for a few days or a week (or longer) before they can cum from anal, some have to wean themselves off clitoral stimulation over a period of time, and still others find it too difficult or seemingly impossible to cum from anal alone and have to incorporate clit play during anal in order to cum.

Anonymous: So me and my girlfriend have been doing a lot of anal lately, she says that anal gives her more intense and powerful orgasms than in her pussy… The only issue is she tells me that after she ha/ the orgasm my dick starts to put her in extreme pain and makes me stop anal and go back in her pussy… Any ideas on why this is and how to stop that from happening?

It may be that she isn’t actually warmed up enough for anal and it’s causing her pain but when she’s aroused and stimulating her clit she’s interpreting that pain as pleasure, then when her arousal drops post-orgasm, she feels it as pain again. That can definitely happen. Is she sore and in pain after, or is she fine once you’re back out of her ass? How does she describe the pain? Stinging, like a cut? Burning, like a sore/strained muscle? Or something else? Do you engage in any pre-anal warmup/foreplay? Anal fingering, butt plug wear, etc.?

The original poster responded:

Yes we do anal fingering (usually two or three fingers) and she describes the pain like a sore muscle and once I’m out and back in her pussy she says the pain goes away

Have you tried taking it out briefly when it starts to hurt, wait for the pain to fade, and then putting it back in? Or does she stay sore and sensitive anally after? It may be that the orgasm gives her almost a muscle spasm anally which can hurt, and she just needs a moment without it after.

Unless you clean between or change condoms, going from ass to pussy is not really a good idea, it can lead to a urinary tract infection.

Anonymous: My gf is the opposite of anal only. We’ve had anal 4 times. 3 where she somewhat liked it and once where she felt in pain (my bad). Ever since the time I hurt her she refuses to try it again despite me telling her it would be different. I dream of entering her ass again, how could I convince her to try again?

Talk with her about it. Ask her why she doesn’t want to try it again. I’m guessing it was uncomfortable for her to begin with and then painful the last time, and now she doesn’t think it will get any better and doesn’t want to continue, having mostly done it for you to begin with.

Read up on anal and how a woman can enjoy it. There’s lots of information out there, some better than others. Read multiple sources. Once you’re confident you’ve got an understanding of the basics, ask her if she’d be interested in trying anal play again with a focus on her enjoyment of it. Don’t even try anal sex at this point, just introduce some anal play into your sex life if she agrees. Rub or finger her asshole during vaginal or oral. Rim her. Try to include some sort of anal play when she cums sometimes. Gradually work up with two fingers, etc., as she’s ready for it. If she’s enjoying the anal play, get her a small/medium butt plug.

If you approach anal play correctly, and she enjoys it, she’ll be more open to trying anal sex again. It’s got to be enjoyable for her too, and it can be.

Anonymous: Anal Only September girl here! It’s only the 9th, I’ve been strict about not putting anything inside my pussy, not even my fingers, and I’ve started to notice a fundamental difference… when I get turned on, I’m far more aware that I have two holes. It’s not an “I want something inside my pussy” feeling anymore, it’s a more diverse desire to just be filled… More and more often I find myself just craving something in my ass – to be honest, I’m starting to forget I even have a hole in my pussy.

Anonymous: How do I get my boyfriend to abandon my pussy? I asked for a week of anal only and he said he didn’t want to be limited like that

Some people just aren’t into the idea and may not be able to be convinced. How often do you have anal sex currently? Is it something you’re able to do fairly easily with minimal preparation? Some guys like anal but don’t want to eliminate vaginal because anal can take more prep time before and they feel going anal only will eliminate the spontaneity. However, with practice, that doesn’t necessarily have to be the case—after a few weeks of regular anal, possibly supplemented by regular wearing of a butt plug, it’s often not hard to quickly be ready for sex.

Perhaps there’s something he wants to do as well which you could offer in exchange for trying a week of anal? If he’s still hesitant, perhaps a shorter length of time? Explain to him that it’s something you want to try because you think it sounds hot, not to be limiting. Or, if you have other reasons driving that desire, like pain or discomfort or a lack of pleasure from vaginal, be very clear about that as well.

Anonymous: My gf is the opposite of anal only. We’ve had anal 4 times. 3 where she somewhat liked it and once where she felt in pain (my bad). Ever since the time I hurt her she refuses to try it again despite me telling her it would be different. I dream of entering her ass again, how could I convince her to try again?

Talk with her about it. Ask her why she doesn’t want to try it again. I’m guessing it was uncomfortable for her to begin with and then painful the last time, and now she doesn’t think it will get any better and doesn’t want to continue, having mostly done it for you to begin with.

Read up on anal and how a woman can enjoy it. There’s lots of information out there, some better than others. Read multiple sources. Once you’re confident you’ve got an understanding of the basics, ask her if she’d be interested in trying anal play again with a focus on her enjoyment of it. Don’t even try anal sex at this point, just introduce some anal play into your sex life if she agrees. Rub or finger her asshole during vaginal or oral. Rim her. Try to include some sort of anal play when she cums sometimes. Gradually work up with two fingers, etc., as she’s ready for it. If she’s enjoying the anal play, get her a small/medium butt plug.

If you approach anal play correctly, and she enjoys it, she’ll be more open to trying anal sex again. It’s got to be enjoyable for her too, and it can be.

dirtyndelicious: What are the pros / cons to being an anal only slut? Can you have an orgasm anally? Do you enjoy it more?

you-should-dp-me: I can’t have an orgasm exclusively through anal yet, but I’m trying! I enjoy anal more because it makes me feel like a true slut. Any old slut can stick a bunch of dicks in her cunt, but only a real slut can stay anal only. It’s a lot of extra work to prepare your asshole however the pay off is intense. I’d say that’s the main con of being anal only though, it’s difficult to be spontaneous. If I want to have anal sex or masturbate I have to carve out a large portion of time for prep. But if you’re patient and motivated then it can produce some incredible orgasms

Anonymous: I’ve been training my ass and can handle one fist already!! Should I keep going and try for 2??

Well, since you enjoy anal fisting, you clearly enjoy anal stretching and large insertions, so why not? As long as you go about it safely and without injuring yourself, go for it! Then you can answer the question for us of whether two fists are better than one.

Anonymous: I joked about having an Anal Only September with my long-distance boyfriend and we ended up actually deciding to try it… now I’m only allowed to touch my clit if I have a toy inside my ass and in two weeks I’m going to go pure anal only with no pussy stimulation whatsoever… I’m really nervous but also super excited… any tips?

Congratulations! A month of anal only is a wonderful way to experience the benefits of an anal only relationship without making a long term commitment up front. I’m sure you’ll love it! I like the idea of incorporating clitoral denial but easing into it over a couple of weeks, and I’d like to hear more about how this goes for you as you transition from being able to use your clit during anal play to going pure anal only.

I would suggest starting out with a higher frequency of clitoral stimulation during your anal play but working towards tapering it off as you approach the two week point where you will abandon it fully, in order to help with that transition rather than it being a sudden removal. Try, during the first two weeks, to get close to orgasm with as little clitoral stimulation as possible, and see if you can continue to push that more and more until you’re only using your clit the absolute bare minimum needed to cum.

Once you do go into the clit denial stage, whenever you feel the urge to touch yourself, rub your ass and your asshole instead. Finger your ass, use toys, do whatever it takes to redirect that urge to touch your clit to your ass instead, until it feels natural to go for your ass instead when you feel aroused. The urge to touch your clit is a habit, and it can be changed.

If you haven’t already, I would suggest joining the Anal Only Lifestyle Forum and creating a thread in our Challenges forum where you can post updates and receive encouragement from other users. Those who have done so find it helpful to maintain momentum towards their goal. Good luck, and enjoy!

Anonymous: The more I get fucked in my ass the more I realize how much I hate getting fucked in my cunt.

That’s not an uncommon result of moving towards more and more anal — while some women certainly enjoy both, many don’t get all that much from vaginal and as they discover anal pleasure they dislike vaginal even more. Before anal it may have been the best sex they’d experienced, but after, anal is so much better as to make vaginal seem pointless.

So, this is a great sign, because it means you’re discovering something so much more pleasurable. Undoubtedly, before long you’ll be going fully anal only, if this trend continues.