Tips & Techniques

Anal Sex: Your Questions Answered

You asked, and Jessica Parker is answering. All you've ever wanted to know about anal sex - and then some
by Jessica Parker
4 Aug 2021

UPDATED: 3 Apr 2023


The great thing about butts is that everyone has one! Our bodies can learn and adapt to many different types of activities, and anal sex is one of them. You need consent from everyone involved, an awareness about what is going to happen and communication throughout anal sex to give your body the best opportunity to adjust, learn and safely explore.

Slow down and give yourself space and time to integrate and relax into new sensations. Taking your time can help to understand what suits your body, and you and your partner can listen and adapt to make anal sex a great experience.

What is anal sex and can you get used to it?

Anal sex is usually defined as:  ‘sexual activity involving penetration of the anus’. Penetration could also be with fingers, a dildo, or other sex toys.

Anal sex can be used to describe other types of anal pleasure such as pegging, rimming and using butt plugs. You can totally have butt-fun and pleasure without any anal penetration. For first-timers who may be nervous, it can be great to experiment with anal pleasure externally before building up to any type of internal penetration.

What other types of anal play are there if I don’t want penetration?

Anal massage and rimming are great examples of ways to include anal play without needing to have penetration of any kind. I almost always start with teaching people how to do anal massage with their hands first before introducing oral rimming and any type of penetration.

Learning anal massage not only sets people up to explore their own and their partner’s anus in a relaxed way to prepare for anal sex, it also gives them another skill to add to their sex/play menu!

What’s your advice for first time anal sex?

Number one is to make sure that you actually want to try it. Anal sex has had a surge in popularity recently and isn’t as much of a taboo topic as it was in the past. More and more people seem to be interested or more open about including anal sex in their lives. Exploring anal sex should be your own choice that you journey into at your own pace. If anyone is forcing, convincing or putting pressure on you to have anal sex or penetration before you’re ready this is at worst sexual assault and at best over-riding your own body wisdom.

If you’re unsure about if you’re having anal sex to please yourself or appease someone else that can be a sign that you need to take some time to really listen to your body and decide what you want. Take some time and space to ask yourself these questions. You can even write answers down in a dedicated journal. Take your sex, pleasure and wellbeing seriously!

  1. Am I ready to have anal sex?
  2. Does my body tense up or react positively when thinking about anal sex?
  3. What are my fears?
  4. What am I ready to try now?
  5. What am I curious about trying in the future?
  6. What do I definitely not want to try?
  7. What would make me feel safe?
  8. What would make me feel comfortable and sexy? 

Start With Yourself!

Secondly, the safest and easiest way to begin to explore anal sex is with your own anus. Common fears first-timers have is that anal play will smell, there might be poo or accidental farts or it might hurt.  If you have a lot of fears going on in the background it will usually cause tension. You won’t be able to switch off the brain chatter in order to actually notice or feel (or enjoy!) sensations.

When we make time to explore our own bodies we can build a pleasure map of what feels good to us. What positions and angles do we like? What type of lube suits our bodies best, what depth and width of penetration feel right, what type of foreplay and warming up works well before we explore anal penetration?

Lots of potential worries that beginners may have about having anal sex for the first time can be safely explored solo, helping you to feel ready when it comes to having anal sex with a partner for the first time. 

How can I explore anal play solo?

One of the easiest and most accessible ways to begin to explore your anus is in the shower or bath. Start by exploring different types of touch and pressure around your butt and anus to get familiar with the sensations. Remember, if you’re planning on any penetration you’ll want to use lube, and lots of it, as the water from the shower or bath can (counterintuively) be pretty drying. 

Different positions you may like to try are standing up, squatting down, lying down with your legs braced up, side-lying, or lying with one leg bent up resting on a ledge/step. Ideally you want a position that gives you the most relaxed support without needing to tense up your muscles, in particular those of your buttocks and legs.

You can never have too much…lube!

The anus isn’t self-lubricating and the number one top tip for any type of anal penetration is lube, lube and lube! Lube will not only help make penetration more pleasurable it can also enhance sensations.

Silicone-based lube is often described as best for anal penetration, as it doesn’t absorb into the skin and tends to be of a much thicker consistency. However, it isn’t always compatible with toys and condoms, in which case you’d want to use a water-based lube. These lubes are great as they are widely available and easy to rinse off, unlike silicone or oil-based lubes which can stick around. Just be prepared to reapply with this one as water-based lubes absorb into the body. There are so many different types of lube on the market – it’s really all about finding what works best for you. Some people prefer to use organic coconut oil for example. Just remember you can’t use oil lubes with latex condoms, or silicone lubes with silicone toys. 

My recommendation for any beginner is to think carefully about what lube will meet your needs. Playing with a hand or in the shower? You’ll want a silicone-based lubricant that doesn’t wash away so easily. Playing with silicone toys, or penetration with a condom? Stick with water-based lube, and just make sure to reapply as often as you need. 

You can never have too much lube with anal sex so always have some nearby within reach.

How can I start to explore internally?

Once you’ve taken time to explore your own anus externally you may like to start trying different types of penetration. Butt plugs come in all sorts of wonderful shapes and sizes – a helpful tip would be to always make sure you use one with a flared base so it doesn’t get lost inside the body. Vibrating plugs can also be a great way to relax and massage your anal sphincters internally and help you to become familiar with the feeling of movement inside your anus.

Getting familiar with the feeling of something inside your anus is different for everyone. Take your time and be gentle to allow yourself to notice any areas of tension. You don’t want to be pushing through any pain. Allow your body to gently accommodate the penetration and pause any movement to breathe, soften and relax before noticing if you’d like further penetration, remain still or pull out completely.

How quickly can I work up to anal penetration?

With penetration as well as pulling out it is important to go super slow. Literally millimetre by millimetre.

You want to be really in tune with your anus so that you’re ‘breathing’ in whatever is penetrating you and ‘breathing’ out as it/they slowly pull out. This allows your anus to adjust and enables you to really notice every sensation. Communicate with yourself or your partner if any pace/pressure needs to be changed or if you need a break. This point is especially important for people new to anal sex as you don’t want to override your own body’s response by going too hard, too fast, too soon.

Always remember you can always go faster/stronger and build up but using stillness and starting super slow gives your body a chance to stay in a ‘pleasure’ zone and for you to notice what feels good in each moment. Never override or ignore your bodies response in order to ‘get it in’ or to perform or please a partner.

What is the best way to have anal sex?

Have it with yourself first. Then you can articulate from a tangible and real reference point to your partner(s) exactly how, what and where works for you, letting them know what pressure, pace, amount of lube, positions and warm-up that you enjoy.

Communication before and throughout any anal sex is a must. A great way to clear the air about any fears or anxiety that you may have around your first time having anal sex with a partner can be chatting about it at a completely separate time to actually doing it. This can help you both get really clear on what you want to try rather than in the heat of the moment.

Checking in with questions or statements that need exact answers or include specific direction rather than a generic ‘is this ok?’ can be really helpful for beginners.

Try some of these examples:

‘Would you like me to lick inside or on the outside only?’

‘Can you guide me with your hand when you’re ready for me to go inside?’

‘I’ll only move when you tell me.’

‘Do you want me to move or stay still?’

‘Would you like it slower or faster?’

As you get more experienced with certain partners some people prefer to have hand signals/taps and ‘safe words’, words which both you and your partner can agree to mean specific things before engaging in any anal play. 

There is no ‘right way’ to have anal sex – what may look really hot and enjoyable (or acrobatic!) in porn doesn’t necessarily mean it will feel good or work for you.

What are the best positions for first time anal sex?

It can be fun to first try out a few different positions without actual penetration so you can see what works for your bodies. Every body is different so having a play around first can be a great way to see what is going to be most comfortable for both the ‘giver’ and the ‘receiver’. Just because a position looks great in a picture or porn doesn’t mean it will suit your particular combination of bodies!

A great position for first-timers is sideways anal sex. This is like a spooning position when the penetrator is behind and you’re both lying on your side. It’s great because it’s close and intimate, and the position helps to keep things slow and gentle with both bodies very relaxed. Bonus points as the receiver can stimulate their clit or penis at the same time as being penetrated. 

Facing each other in a missionary style position is also a great first-time anal sex position as it allows you to read each other’s reactions in real-time and adds another level of intimacy with kissing and lots of verbal and non-verbal communication. 

Whatever position you choose, make sure it works for both of you and continue to check in with one another throughout your play.

For more support in learning about anal sex & anal massage tuition please contact Jessica via her contact page: