This is just one part of our Anal Sex Advice & Guide to the Anal Only Lifestyle section. Be sure to read the rest as well to get answers to our most frequently asked questions! New! This guide is also now available as a Kindle ebook!

So you want to have anal sex! Congratulations—this is a great idea. Anal is one of the best and most pleasurable ways to have sex, but it can take a little more practice and understanding of proper technique before you do it in order for it to be an enjoyable first few experiences. If you rush into it unprepared or without the knowledge of how to do it properly, it can hurt or be uncomfortable and discourage you from trying it again.

While some people are able to go straight to having anal sex as their first real anal experience and have it be enjoyable for everyone involved, this typically isn’t a good idea for most people, and it’s better to start slow and small and work your way to anal sex over time.

If you can, start solo

While you can certainly start with a trusted partner, it’s often best to first start exploring anal pleasure on your own, so you can be completely in control of the situation. A lot of people have fears and self-consciousness about anal play and sex, and if you do it entirely on your own, you can bypass those fears long enough to start experiencing anal pleasure.

So, the next time you masturbate, add some anal play into the mix. Take a bath first to wash yourself and relax, and clean yourself out with a small douche/enema if so desired or needed (see our page about anal hygiene and cleanliness techniques for specifics), and then start masturbating your favorite way. If you are able to enjoy multiple orgasms and remain aroused after to keep masturbating, give yourself an orgasm first to relax further, otherwise start adding the anal play in once you start really feeling turned on.

While you masturbate, take a finger or a equivalent small toy and apply a liberal amount of lubricant to it, then press it against your anus and start rubbing it lightly while you continue to masturbate with your other hand as normal. After a short amount of time, you should feel yourself relax somewhat and as you feel comfortable doing so, start to gently slip the finger or toy inside. If it starts to hurt, slow down or back out until it no longer hurts and gently move it in and out while continuing to masturbate.

Once you can fit the finger or toy all the way inside, just combine both forms of masturbation together until you reach orgasm. Typically, an orgasm while you’re receiving anal penetration is more intense and powerful than on its own, but it can take some experimentation and practice to figure out what sort of penetration and what spots to target with your penetration cause the most intense orgasms for you.

Start making this a regular part of your masturbation routine. Regular anal practice makes it a lot easier to progress and continue to find it enjoyable as you start introducing larger penetration into the mix and work your way towards anal sex with a partner. It doesn’t have to be every time you masturbate (though there’s nothing wrong with doing it every time if you want to, so long as you aren’t sore from the last time you did it) but at least weekly if not several times a week is a good idea to begin.

Advancing your anal play

Once you can comfortably and regularly do anal masturbation with a single finger or small toy—which might be on the first day or it might be a week or two into regularly masturbating, depending on your body and personal needs—it’s time to start adding more into the mix. If you’re using your fingers, it’s easy and you can just add a second finger. Start each session by warming up with a single finger first, then after a few minutes, try the second. If using a toy, you’ll need to find another toy that’s just a little bit larger. Usually you want to increase toy sizes in approximately 1/4″ to 1/2″ (6mm to 12mm) increments to have enough of an increase that it’s worthwhile but not so much that it’s too big a challenge for you.

From there, it’s really just a repeat of the process. Warm up to your current comfort level, increase in size, masturbate at that level until you’re always comfortable at the new level, and repeat until you’re at your goal. For most people, if anal sex is the goal, that’s going to be about the size of their partner’s penis or a toy they want to use regularly.

As you feel ready, you can start introducing a partner into the anal play routine if you haven’t already and have them taking control of the fingering or the toys, and helping you push your limits further.

Another thing you can start exploring with a partner as you feel ready to do so is rimming/analingus, where your partner licks your anus either on its own or in combination with rubbing your clit. This can be an incredibly pleasurable and intimate act, and there are those who enjoy it even more than cunnilingus! If it feels like it tickles rather than being pleasurable, try a bit more foreplay first and get a bit more turned on before trying again. In addition the pleasure involved, it can be very beneficial for associating your ass with pleasure and helping you to relax.

Avoid pain and injury

Anal shouldn’t hurt. If something hurts, you’re not warmed up enough, aren’t prepared for that size, speed or depth yet, or you aren’t using enough lube. If you’re training and reach a point where it’s painful, stop and just hold in place for a moment to see if the pain fades. If it does, and you can resume, you probably just needed time to adjust. If it doesn’t, or resumes when you start again, back off a little bit and either go a little slower, more shallow, or reduce to a smaller size again. Don’t ever force your way through pain. A bit of discomfort at first won’t harm you, but pain is a warning that something is wrong and you should pause and reassess before continuing.

Don’t use numbing lubricants. They don’t help you relax, they just mask pain and hide the fact that you may be potentially injuring yourself, making it so you can’t listen to your body and adjust your approach accordingly. One exception to this which some people report positive success with is using a mild numbing spray such as those intended for prolonging male endurance during sex. When applied to the anus a few minutes before training or sex, it can numb initial discomfort while not masking actual pain or risking injury, and can get you past the edge and learn how to relax more easily at first until you don’t need it anymore.

If you encounter bleeding as a result of anal play, your best bet is usually to stop and try again another day. It’s not a serious concern, usually just a minor abrasion or microtear that will heal in a day or two, but if you ignore it and keep playing and aggravate it further, it can develop into something that takes longer to heal. Always allow time to rest and heal if you injure yourself and you’ll be back at it in no time.

While maintaining a regular frequency of anal training/play is very beneficial to advancing towards your goals, so is taking care of yourself. If you’re particularly sore after an anal training session, give yourself a few days to recover before going at it again. The more you do it, the less sore you’ll get, and the easier it will get long-term to do anal play or have anal sex as often as you want.

Have a suggestion for an additional topic you’d like to see covered here, or a missing or incorrect detail that you’ve found or have concerns about in one of the guides? Please let us know and we’ll do our best to continue improving these guides over time!