Buttlyn: Ok. This is the second message I send to the blog and I hope you answer it too.

I’m the brazilian girl who had a broken pussy and a anal addicted boyfriend (nowadays my husband), but wanted to try v****** “sex”. It’s improbable that you remember, but ok. Here I go.

I have a soft brain palsy what made almost every muscle of mine more rigid than normal, including my butthole. It sucks.

At this point, I suppose that you already can guess what my problem is. Yeah, I discovered that’s the reason why I can’t be penetrated in my wronghole. But it also disturbs my pleasure while doing anal.

I don’t want to fuck using a anesthetic lube or this kind of shit, but I cannot train my butthole’s endurance because I have no control over it. Sometimes I watch those porn girls doing huge insertions, fisting and hatefuck and I feel like crying, full of envy. I feel myself impotent, like I’m not enough, like I’ll never become a more-than-good buttslut to my husband. My ass does not even loose up if I’m not rubbing my clit, and I cannot masturbate my asshole at the same time because I have only one functional hand.

I couldn’t give my man a nice Christmas assfucking due this problem. I’m about to freak out! Please, help me! My case is too specific for Google.

I suspect I would remember your earlier message, but I’m not sure offhand from just what you’ve said here. If you find your previous message in our archives, feel free to send a link to me and I can cross-link or tag them so that readers can easily follow the full conversation across posts.

Definitely don’t use an anesthetic lube, as that will only mask any pain, not prevent the root issue of muscle tightness/cramping. And where there’s pain, there’s risk of injury as a result of those tight muscles. What you need is a way to relax and warm up your muscles instead.

While it sounds like you’re experienced with anal sex at this point, you might want to go back to the early stages of anal training for solo play on your own and as warmup before sex. Lie on your side and rub your clit or use a vibrator on it while rubbing across and around your anus with a finger from your other hand and try to relax your anal muscles as you do so, then slip your finger inside as you feel ready to do so, and keep gradually going up in size from there. If smaller sizes cause you no trouble, try working around the edge of where larger sizes cause difficulty and discomfort. Even without such a medical condition, everyone has some anal muscles they can learn to consciously control and others that are involuntary, so while it may be more difficult for you, there may still be some benefits to working on this more often. Read our new anal training guide for more details on this topic if needed.

Depending on how much warmup you do before sex, you may need to do the above before you start a session, as well as rubbing your clit while your husband performs oral sex on your ass to further help it relax.

For clitoral stimulation during anal masturbation, you might look for a clitoral vibrator that attaches and stays in places so you don’t need to hold it. Venus butterfly vibrators and others similar to this sit in place over your pussy with bands that go around your legs to hold it there so it can keep vibrating against your clit hands-free.

Similarly, a dildo with a suction cup can help you to masturbate hands-free while you have one hand on your clit and ride up and down on a dildo without needing to hold it.

Finally, a doctor may be able to suggest exercises to help with pelvic floor muscle tightness or spasms, and may be able to prescribe muscle relaxers as well. I am not a doctor, a while I can offer suggestions on adapting certain techniques to help with people who have difficulty with tightness, discomfort or pain, I’m far from an expert on specific conditions.

I hope this is at least somewhat helpful, however, and I absolutely wish you the best in figuring out a way to effectively and consistently enjoy anal sex to the full extent of what you want. Do please feel free to follow up if you have more questions or updates.

I’ve also sent this post to someone from the Anal Only Lifestyle Discord server who can provide more perspective and a more detailed answer regarding your condition, and they will be responding in the comments of this post, so be sure to check back there as well.

Merry Christmas! For years, we’ve been answering questions about anal sex and the anal only lifestyle and giving advice to countless people through this blog, and that’s never going to change! But, while manually migrating nearly 1,900 posts off Tumblr to the new version of this blog, it became clear that many of the same questions got answered over and over again over the years.

To prevent redundant posts going forward, we’re happy to announce a new section on this blog, accessible via the Guide link in the menu at the top of each page, Anal Sex Advice & Guide to the Anal Only Lifestyle. Broken into a number of key topics, this page attempts to answer in detail most of the frequently asked questions about anal training, myths about anal sex, hygiene and enemas, types of lubricant, butt plug and dildo recommendations, how to have anal sex for the first time, how to have anal orgasms, how to go anal only and why one might want to do so, dating and finding new partners for an anal only relationship, and more.

More topics will be added in time, and more details will be added to pages as relevant additions come up or are recommended. If you see anything missing or that you believe is incorrect or should be amended, please feel free to send a message or leave a comment on this post and let us know.

Asstronaut: I have currently been with my girlfriend for 6 years. At the beginning of our relationship we had one amazing anal experience(her first) she had an orgasm so intense she said her toes went numb…. The sounds she made…. On the other side of the coin, I had purchased her a tail plug which caused her a lot of pain. Long story short, after seeing that I had hurt her I didn’t ask again until last month. She is very receptive… But it’s been so long(almost 6 years)and her ass feels better than anything I’ve ever experienced in MY LIFE that I can not last any longer than it takes to get the head of my cock past her inner ring. The moment that I’m inside of her I cum….. Stamina is only an issue when we have anal. Any ideas?

I’ll start by saying that while anal certainly shouldn’t hurt and definitely doesn’t have to, encountering a painful experience once doesn’t mean you should just end it altogether. Pain means someone simply isn’t warmed up enough or prepared for what they’re doing, or the plug in question may have been an uncomfortable shape for her. Going forward, if there’s pain I’d say to stop and reassess in the moment but not give up on anal entirely.

Getting to your question, however, I suspect that it’s a combination of extreme tightness for her and your excitement about getting anal again. That excitement is understandable, and there’s not too much you can do about that, but the tightness you can work on together with some anal training and helping her better relax and open up for you. If it’s taking effort to get inside her, she could probably stand to have some more training and warmup before sex to help her relax.

If it really is just that it feels so much intensely better than anything else you’ve ever done, you may need to practice more to build up that stamina, which can mean more regular anal sex. Perhaps start with a lot of anal play for her and get her close to the edge, then switch out for yourself and finish there while getting her off at the same time, and over time work to last longer.

See also this past answer to a similar question: How to Last Longer With Anal

Perhaps some other readers could offer their suggestions as well.

Anonymous: I’m a virgin in both senses and I’ve tried to masturbate using my vag but I never can reach orgasm even when playing with my clit. How ever doing anal really excites me is there any tips of how to start trying anal?

With anal you’ll want to use some sort of lubrication, whether saliva, vaginal juices, or actual commercial sexual lubricant of some sort. (There are many options out there, and it’s very much personal preference as for which is “best”.)

Start slowly, with a finger, and just massage gently around and across the outside at first. When you feel yourself relax and maybe even start to open up slightly, gently press your finger into your ass and let it slide in slowly, then gradually in and out. Explore from there and adjust your pace depending on your comfort. If something hurts, slow down or back off. Add another finger as you feel comfortable and ready to do so.

From there, once you’ve gotten 3 or so fingers in and can comfortably masturbate with them, you might look into toys like butt plugs and dildos for your ass.

Just remember: lube, start slowly, and if something hurts, you’re trying to go too big or too fast and need to work up to that point from something smaller and slower first.

Anonymous: What’s the best way to introduce your female partner ( who is interested in anal just a bit scared) to the pleasures of anal?

Communicate and start slowly. Don’t try to go straight to anal sex, start with rimming, gentle rubbing externally along with clit stimulation, and fingering and small toys. Build from there at a pace she’s comfortable with. If something hurts or gets uncomfortable for her, back off and go slower or smaller for a while before trying again.

There are a lot of other good anal advice posts on this blog which you can read in the Anal Advice category.

Anonymous: I have vaginismus (a really tight pussy too tights to have sex or it hurts a lot) and my doctor had my try stretching it out and I tried but it just hurts so bad and turns me off more every time, so she suggesetd I try anal instead. I found your blog when I was looking, and it sounds great if people really do anal only, any tips? I’ve fingered my ass some and I like it more than my pussy.

Anal has proved a welcome option for a lot of women with vaginismus over the years, and it’s great to see that it’s being encouraged as a serious alternative to vaginal. We in the anal only community often come from adopting anal as the primary form of sex by choice because it’s better than vaginal, and it is, but it also can provide an outlet for pleasure and intimacy for women incapable of having vaginal, and that’s wonderful.

It sounds like you’re on the right track by starting slow and exploring with your fingers. Keep doing that, be sure you’re using some sort of lube, and start to add more fingers. From there, start with a dildo or a vibrator and gradually work up further in size as you’re comfortable and ready for something bigger. Butt plugs are also good for a more passive approach, and you can wear them in your ass while masturbating clitorally or even while doing other things.

I’d suggest only trying anal sex with a partner once you’re comfortable using a similarly sized dildo and are confident you’re ready and can do it without pain.

Anonymous: My Fiancé and i really want to try stretching out my ass and you seem to be knowledgeable about these things. Ive done a little research on my own but I’d like to see what tips, cautions, and thoughts you have on going about this.

If you’re just starting out and want to stretch/train it for anal sex, start with a finger and work up in size from there. If you’re already experienced with anal sex and want to go bigger, the same basic principles apply.

Essentially, increase in small size increments, generally no more than 1/4″ diameter at a time, warm up through smaller sizes before jumping to the larger sizes, and stop for at least a few days if you become particularly sore or if there’s any bleeding.

Feel free to follow up if you have any more specific questions!

Anonymous: I try to convince to do anal but she said I’m bigger then the ones she been with an it hurts like how do I convince her

Start with anal play, not sex. Eat her ass, get her relaxed, use a lubricated finger to gently massage and then penetrate her ass, gradually add more fingers as she’s comfortable and ready to go ahead, get her some butt plugs and dildos to use, and over time work up in size until she can fit a dildo close to your size. Then, and only then, start on anal sex.

If it hurts, she’s not ready for it and you’re getting ahead of yourself. Anal should not hurt.

Anonymous: Hi I had a couple questions , how do I get my girlfriend to want to do anal and like it more ? She loves it when I lick her lil butthole and rub it and put my finger in when I’m making love to her but other then that she says it hurts and I try to tell her to relax … we use lube and what not but her being anxious makes her scared … is there anything I can do? I recently bought her a princess plug but we haven’t used it yet. Thanks

Keep doing the things she likes and make them regular parts of sex for the two of you. Start using the plug as well. From the baseline of what she enjoys, gradually work up in size at a pace that she’s comfortable with. Encourage her to play with her ass as well and masturbate anally, and to tell you what feels good, what’s comfortable, and when things start to not be. Push her limits, but gently and slowly. As you work up in size and get near your own size, only then should you try going ahead with actual anal sex.

Play with her clit and give her lots of orgasms during anal training, and that will help her relax and develop the association between anal penetration and pleasure, and she’ll start wanting more and more.

Anonymous: I fuck my girlfriend in the ass about once a week. We both enjoy it, and she has great orgasms, but she says it makes her too sore to have it more often. I really want to be able to fuck her ass every time we have sex. She said she would too if she didn’t get so sore. Is there anything we can do to keep her from getting so sore so we can be anal only? It’s the only time we can fuck without using a condom.

It sounds like you need to spend some more time on warmup and ease into things a bit more, as well as perhaps doing some lower intensity anal play more often. I would suggest that you let her go a week or so to get over any soreness after her last anal session, but then rather than having anal sex, start doing lots of anal play alongside other sexual activities. Have her wear a plug, both during oral/vaginal sex, and at other times. Doing this 3 – 5 times a week, if not daily, can really start to make a difference over the course of a week or so, even if just for a relatively short amount of time each day.

When you do have anal sex the next time, have her wear her plug first, then warm her up some more with fingers or a toy before having sex. This helps warm up her muscles and relax so that soreness is less likely to occur.

From there, return to your once a week anal session but keep up the anal play in the meantime as long as she’s not too sore for it. If after a week or two she’s able to do both with less soreness, try going to anal sex twice a week, and keep working up from there. You can absolutely get to the point where she can have anal sex daily, if not more than once a day, without getting sore, it just takes time and gradually working towards that goal, and then maintaining a relatively consistent routine so that her ass stays in that state where it’s ready for sex regularly.