allstrawberry: every time i see porn with something in a vagina, my brain goes “that would be better if it was in her asshole”

Anonymous: Hi! Me and my boyfriend have been trying anal recently and it has been incredible, but last time it started out really good but then it started feeling uncomfortable. When I went to the bathroom to wipe up, I noticed some very, very faint blood on the tissue and it was just a little spot. Is this normal, or something I should be concerned about?

It’s not abnormal while starting to have anal for the first time, and it’s not generally serious, but it is a sign that you may have been doing a little too much too fast without enough warmup or practice. Once it starts to become uncomfortable or you notice blood, I recommend always stopping and reassessing. If there’s blood, stop immediately and wait a few days (or until any pain is gone) before trying again, just to make sure it heals well. Very few injuries from regular anal sex are serious on their own, but they can get aggravated and harder to heal if you continue stressing them by pressing on through the pain or continuing to have anal sex before they’ve healed. A tiny spot of blood is likely just a minor abrasion/tear that will heal in a few days, however, and I wouldn’t worry about it.

Do make sure that you’re both using enough lube and engaging in enough warmup before sex. Wearing a butt plug for half an hour or so before sex can really help with getting relaxed and warmed up, but fingering can as well. Sometimes you can seemingly do everything right but still—especially when relatively new to anal—notice a little spot of blood here or there. When that happens, just take a little break from anal and try again in a few days.

Anonymous: I tried anal for the first time yesterday, and loved it! so much, we did it a second time. it’s definitely going to become a regular thing now. and who knows, eventually I might try anal only for a bit

Congratulations! Anal can be a lot of fun. Have fun with it, explore it further, discover your limits, and once you’ve really gotten familiar with it over a period of time, then consider trying anal only for a while.

While it certainly works for some to go anal only with little experience—for example, those who do so while still vaginal virgins—in general I recommend more of an easing into it just because anal can require a little more care, practice and patience at first for the best results for everyone, so if you have the opportunity to do so, learning to love anal and discovering its nuances without any obligation to have it every time just yet is my recommendation to most, then if you still really love it down the road, try a month of anal only.

That’s not to say that’s the only way to go about it, though—some people just really want to try going anal only, and if someone is motivated to do that, it can work for them!

thedirtycode: What was your first anal experience?

sweetcumkitten: I was really horny one night in my room that I was rubbing my pussy against my big fluffy stuffed bear. Grinding and felt it rubbing against my ass which made me go nuts. Got some cream and started fingering it. I enjoyed out so much I went and got a toy. Prefer anal sex over my pussy fucked. ?

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.