How to make anal sex less painful

Do you avoid anal sex because it’s been painful in the past? Are you curious to try anal sex with your partner but hitting a pain barrier after those first 1-2 inches of penetration? A client recently asked me about how to overcome this pain point and enjoy anal sex, which is actually something I hear a lot from clients (and friends)! So, in this blog I’m going to outline all the tips and tricks I’ve learned over the years, both as a giver and receiver of anal penetration. Anal sex, or anal play of any kind, can be an enjoyable part of a healthy sex life but is never something you should feel pressured into. Some people really enjoy it, and for others it just doesn’t do much for them. Some people love to give, some prefer to receive, others are really happy to switch. Wherever you are on that spectrum, this article will give you some ideas if you want to bring more relaxation and pleasure to the experience!

Things to consider before anal sex

I have a couple of suggestions on what you can do before you’re having anal sex with a partner that will reduce pain and increase pleasure in the moment. Think of it like this: if you and your friend want to run a marathon together do you just turn up on the day and expect that you will be able to run all the way round in a good time? No. You do some training to prepare yourself for the event – some on your own and perhaps some with your friend.

1. Do you play with your own arse?

If you don’t include anal play in your solo sex/self-pleasure experiences then it’s way more likely that you’ll experience pain when a partner is penetrating you. Including regular anal massage, with fingers and toys, in masturbation/self-pleasure makes it easier when you’re with your partner. Even just inserting a little finger into your arse during your morning shower can be a good start! Getting used to the feeling of deeper penetration when you are in charge of the speed, the depth and the size of the object penetrating you is a great way to build familiarity with the sensations, and train your body how to relax. 

2. How much empathy does your partner have?

Does your partner have any idea how it actually feels to be penetrated? I personally do not trust anyone to put anything in my arse if they have never had anything in their own! If you partner doesn’t already enjoy receiving anal stimulation I would really encourage you to discuss this. It will build empathy for you both and make them far more skilful and present to what you are experiencing. This doesn’t need to descend into full blown ‘pegging’ (where a female partner wears a strap on and penetrates her male partner) if your male partner isn’t comfortable with that, but I suggest – at the very minimum – some external anal massage and penetration with 1-3 gloved fingers.

Things to consider during anal sex

1. Preparation

If you experience pain during that initial part of anal sex, it could be because you’re not taking enough time to prepare. If you’re just trying to shove a cock or dildo straight in there with no warm up then it’s not surprising it hurts. The muscles are not relaxed, there’s limited arousal and therefore less blood flow to the area to help the tissues feel supple and soft. I recommend that you spend at least 20-30 minutes on anal massage before moving to penetration with a penis or dildo. It’s like stretching before you run. To get my free guide to anal massage subscribe to my mailing list HERE.

Start by working on relaxing the hips, the butt cheeks, the thighs; then introduce external anal massage to relax the pelvic floor and the external sphincter; then start with inserting 1 gloved finger and applying gentle stretches in a criss-cross movement, slowly move to 2 fingers, then 3 fingers, and maybe up to 4 fingers (which is probably a bit thicker than the average cock). I recommend these latex free gloves for anal massage from Amazon*.

At this point you could maybe introduce a small butt plug (like these ones from Amazon) whilst your partner plays with your pussy for a while before you dive in to anal penetration – some nice slow oral with the butt plug in can be a great way to get you a bit aroused whilst helping the sphincters to relax.

2. Breath

Generally when we experience pain we contract and stop breathing to try and avoid it. This is counter productive during anal sex because you don’t want your muscles to be contracted. There are two sphincters within the rectum, the first is under your conscious control: you can contract it or relax it (think about what you do when you’re trying to hold in a fart…). The second sphincter is not under your voluntary control. It relaxes when your nervous system is in the a relaxed state, this happens every time you exhale so focussing on the breath and letting the exhale be long and slow will help that second sphincter open up. As the receiving partner, focus on exhaling through your mouth so your jaw is relaxed: this has a knock on effect down through the chest, belly and pelvis. As the giving partner it’s important for you to stay relaxed and connected to your breath as well. 

3. Communication

Once you’re all warmed up from the massage, the fingers, and maybe the butt plug, the penetrating partner needs to go in really slowly. The receiving partner needs to communicate as soon as there is pain. At that point the penetrating partner just holds still – doesn’t go deeper, doesn’t pull out – and the receiving partner can focus on just relaxing the belly, the pussy, the butt cheeks and pelvis. 

I often feel a lot of emotion at this stage, but rather than panicking and tightening my body up, I practice to open up to the emotion and let myself soften. It takes presence and patience from the penetrating partner, trust and a willingness to surrender from the receiving partner. Making sound really helps with this: when you are holding on the tension it will relax and release more easily if you allow yourself to make long raw ‘aaaaaah’ sounds and express any emotions.

4. Positions

  • My favourite, and most relaxing position for anal sex is with the receiving partner lying on the belly with a cushion under the hips to slightly elevate the pelvis. Pulling one knee up to the side from here can also feel good. The receiving partner can reach back and spread the butt cheeks, or the penetrating partner can do it, which also helps to open up the sphincters. 
  • I find that being on top as the receiving partner means there’s a lot of tension in your thighs and pelvis, which I don’t find optimal – but some people prefer this as they’re in control of the speed/depth of penetration. 
  • Lying on your back in ‘Happy Baby’ yoga pose can be nice as well, but for me this can get straining on my hips. 
  • Spooning is a good option to focus on shallower penetration.

Other things that affect enjoyment of anal sex

You might like to consider that penetration with the full length of the cock or dildo doesn’t have to be the ‘goal’: focussing on those first couple of inches and playing slowly with ‘just the tip’ can feel really pleasurable too.

Using plenty of lube is absolutely vital during anal sex – unlike the vagina, the anus does not self-lubricate. However, the kind of lube you use is important. Water-based lube will get absorbed into the skin more quickly than silicone lube, and turn into ‘glue’ basically – not a nice sensation. I recommend a high quality silicon based lube such as Pjur Original.

Hygiene fears are often a subconscious cause of tension in the body when it comes to anal play. Making sure that you clean and prepare beforehand can help to alleviate those concerns – I really like this humorous and informative article about ‘How to clean your arse before anal sex’! Ultimately though, sometimes a bit of poop does appear, it’s not a disaster – having a box of tissues or wet wipes to hand will quickly clear that up. Other than that, I suggest always using gloves for anal massage (check out these ones from Amazon*) and putting a condom on all toys and appendages that might be used internally 🙂

Carry on exploring!

I hope these tips help you to continue exploring, and enjoying, anal sex with less pain and more pleasure. If you have any other tips that you’ve picked up along the way that you’d like me to add then feel free to drop me an email on

With Love, 




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