Questions, Questions…
First let’s talk about the different factors that influence the type of position that may work best for you.
What type of anal sex do you want? With someone else? More than one person? Just yourself?
Do you want to explore oral or are you more interested in penetration? With penetration what are you happy with? Fingers, toys, a penis? Perhaps you want to start with a toy and then move to something else at a different time, but it’s important to be honest about where you are at this particular moment.
Is it important for you to be able to look at your partner/s during anal sex?
What environment will you be in? At home in your own bed? Someone else’s place? At a party?
Are there any obvious things that might make certain positions tricky for you, such as a knee injury that may be aggravated during doggy style?
If you’re receiving penetration, do you want to be able to have maximum control of depth and speed?
Seems like a lot of questions to consider but this is to just highlight that there is no such thing as the best ‘top three positions’ for everyone. Knowing what suits your body can help you figure out what your top three might be in any given situation. And obviously you can have fun trying things out and exploring! You may already have one or two that you know you like, and then find with different partners or toys other positions flow better. Equally you may find that only one position suits you and that’s completely fine too – just because there’s a range of different positions doesn’t mean you have to include them all. Never disregard a position if its not deemed ‘exciting’ enough. It’s all about you, your body and what feels good.
Anal Sex Methods
Play around by yourself to work out the positions that suit your body best – on your back, side lying, on your knees, squatting, bent over. I’d recommend staring out with positions that make you feel the most relaxed – any tension around your butt will inevitably tense the sphincters and restrict blood flow, limiting your capacity to feel sensations and not allowing for easy penetration.
Positions for solo anal sex using your hand and fingers
Lie on your side and use pillows to prop your hip up. This allows easy access for your hand to reach your anus. Swap sides if your arms gets tired – make yourself a little nest so your whole body can be supported by pillows and blankets.
Many anal sex beginners prefer to self explore in the shower or bath – the warmth and not having to worry about any clean up can be a great way to start your anal pleasure journey. Lying down, squatting or with one knee propped up, leaning against a wall – you can try them all safely and in the privacy of your own bathroom.
Partnered Anal Sex Positions
Anal Massage
When I teach people how to give anal massage the main position for the giver is one where they are comfortable and can move around easily to change position. Sitting down cross legged leaning back against the headboard of your bed with your partner face down over your knees may work well initially but if the giver is uncomfortable or gets cramp then the massage isn’t going to be feeling good for anyone.
Generally the receiver is lying face down with their hips propped up with pillows or a rolled up towel – have a few extras handy if you need to add more support for you both. Massage the back to warm up and relax, before slowly making your way towards the butt crack and anus. Use massage strokes such as the ‘credit card’ swipe with nicely warmed and lubricated hands. This massage really allows blood to flow to the area, which in turn enhances sensations. Hand and fingers massaging the butt crack and anus externally can progress naturally towards doing the same type of strokes with your tongue.
Rimming – licking, kissing sucking the anus with your mouth/tongue
Rimming is great if you want to have your hands free to pleasure other areas at the same time. Depending on how much booty you’re blessed to be working with, you may need to spread the butt cheeks outwards or get the butt owner to do this for you. This ensures great, lickable access to the anus.
Explore bent over positions and experiment with what angle of propping up with pillows works best for you, thinking in particular about what position or positions can allow for a nice smooth transition from lush massage to rimming. You want your giver to have full easy access and for your both to feel relaxed and comfortable. For the yoga bunnies, ideal anal oral sex positions for receiving could include the main resting position of “child’s pose” with pillows to prop your hips up. Even a cheeky downward dog position is great and gives the ‘rimmer’ easy access. Face sitting allows the receiver to be in full control, and of course there’s always the classic 69 position if you want to give oral sex at the same time.
Positions for anal penetration with a penis or strap on
With any anal penetration for beginners I always recommend starting shallow, and moving the dildo/penis in slow circular movements to gently ease in. This allows the anus to adjust to the sensations and girth slowly and safely.
A position that allows for easy control of the depth of penetration so the receiver has full autonomy is really important. If eye contact and being able to see and read your partners face is important to you then have the receiver lying on their back. You can use pillows under the hips to help with obtaining the best angle for penetration. For more advanced, deeper penetration the receiver can put their legs on their partner’s shoulders. Alternatively, creative use of mirrors can be a great way to still have eye contact without needing to face each other.
Side-lying spooning works especially well for most people as it doesn’t matter if difference in height is a factor (standing up or doggy style can need some alterations if either party is a lot taller or shorter than the other). This position has a bonus in that it feels close and loving, with lots of skin to skin contact between you and your partner.
Positions that allow for hands to be able to easily stimulate the clitoris, penis, and nipples can be great. Standing up, doggy style, spooning, and reverse cowperson all are ideal for this.
Advanced Anal Techniques
Having explored ‘softer’ anal sex techniques such as anal massage and then ventured into penetration with fingers, a penis or toys, some people choose to go on to explore more intense forms of anal sex, such as fisting, gaping/stretching, or double penetration. These more intense forms of anal play are definitely not something to try on a first attempt! They take a lot of communication, trust and practise, so if intense anal sex is something you’re keen to try make sure you work up to it.
Whatever stage you wish to take your anal play to make sure you’re connected with your own pleasure boundaries, practice safe and hygienic sex and include aftercare for yourself and partners.
It’s All About What Works For you!
The best anal sex positions are the ones where you feel most comfortable, turned on, empowered and in pleasure! Different days, settings, partners, or toys may influence what position feels best in any given moment. My best advice is to take your time, breathe, connect and listen to your body before, during, and after anal play.
Never ‘put up with’ or push through anything that feels uncomfortable or painful for the sake of performance, or any other reason for that matter. Your body and butt is a beautiful playground ready to be explored when and if you want to!
Want to learn more about anal sex?
Make sure you check out our upcoming workshops and masterclasses for more chances to learn about anal pleasure!
Jessica Parker (she/her) is a highly qualified and experienced massage therapist, certified sexological bodyworker and sensual events manager. Essentially her work is based around supporting people to discover their true pleasure potential through tailored sex education and events, guiding people to experience and explore themselves within safe, beautiful sensory spaces.
Some events Jessica runs are: Ebony & Ivory sensual massage; Pleasure Island Parties; and Lady Liquid Love.