Having Anal Sex For the First Time

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!

If you’ve already gone through the initial anal training process and feel confident that you’re ready to try anal sex with a partner, the first step is communication. Tell them that you’d like to try anal sex with them and make sure they understand the process involved, the warmup required, to start out going slow and let you adjust, and to stop anytime you need them too. Sitting down together and reading through this guide isn’t a bad idea either.

Always warm up first

Even if you’ve been practicing and training for a while, you still want to start each session with some warmup and foreplay. Just like with exercise, you want to warm up and stretch your anal muscles before having sex to make sure they’re limber and not too tight, which can cause an injury/muscle strain. Get turned on, do some rimming, and use some toys to relax and warm up your anal muscles. Wearing a butt plug even before you begin can help as well! Once you have warmed up with toys to a similar size as your partner’s penis, you can begin.

Good positions for first time anal sex

Some positions are better than others for beginners, allowing you to relax and open up more easily for your partner. With a bit more experience, just about any position works for anal, but some can take more practice than others to be comfortable.

Some find doggy to be a good position as it lets you push yourself backwards onto your partner at your own pace as you adjust to being penetrated.

Cowgirl, with you on top of your partner, also allows gives control over the penetration, and any squatting position helps to straighten and relax your rectum and anus for easier penetration.

Spooning, with both of you on your side, is also a very relaxing and intimate position that many couples find works well for anal sex.

Getting started with anal sex

After you’ve warmed up, apply additional lube to yourself on and in your anus, and to your partner’s penis, and then have him gently press against your anus, applying slow pressure until he slides inside. If you’ve warmed up appropriately, he should just slide inside without pain. If it starts to hurt, have him stop and hold position inside you for a moment until the pain passes.

Once he’s all the way inside, or as far as you can comfortably go, pause again for a moment to fully adjust to his size inside you, then slowly start to move him in and out. If you can manage this after a few minutes of going slowly, start to give him more control and let him do some of the motion as well, still going slowly but gradually increasing pace to something that works well for the both of you. If you have to stay going very slowly, do so, and in time you’ll be able to go a little faster if that’s desired. Stay in communication and listen to your body and adjust as needed.

Avoiding pain and injury from anal sex

If it becomes extremely painful, stop and rest before reassessing and seeing if you can continue. If you notice bleeding during sex, stop and take a break for several days before trying again to allow yourself to heal.

If you were able to have sex without pain but are sore afterwards, this is somewhat normal, especially when starting out. Just like with exercise, muscle soreness after you start a new routine can be very noticeable. Let yourself rest a few days before having anal sex again, and increase the frequency over time as that soreness becomes less noticeable.

You can also apply aloe and other similar healing substances to the outside of your anus after to help with soreness or swelling if there is any.

Orgasm, ejaculation, and post-anal sex cleanup

Some people can orgasm just from anal sex without any additional stimulation, and it’s worth exploring whether you are able to do this, but many people find that it’s very beneficial to combine anal sex with clitoral stimulation, especially when starting out, both to help yourself relax and to be able to orgasm easily. Orgasms from clitoral stimulation along with anal penetration can be very intense and pleasurable!

It’s perfectly safe for your partner to ejaculate inside you during anal sex, so long as both partners are tested, and there are no health risks of doing so. It’s extremely unlikely for semen that leaks out of your anus to enter the vagina and get you pregnant, but it’s not impossible. With a little bit of care and cleanup after, you can mitigate that risk. Some go to the toilet after sex and push their partner’s semen out, while others want it to remain inside and get absorbed. There are some studies that suggest that anal absorption of semen is a very healthy and beneficial thing for women, with mood-enhancing and arousal-boosting effects. Others take it a step further and insert a butt plug after sex to help it stay inside and absorb as much of it as possible.

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!