The pleasurable way to start anal sex

Anal sex doesn’t need to start out painful or unpleasant, there are ways that will open you the gate for mind-blowing anal pleasure when you will crave for more.

Anal pleasure feels different from anything. Of course the taboo factor can make it even hotter, but when you have a connection to the anus and everything that happens aligned with the pleasure pathway, fulfilment opens naturally.

The usual way to backdoor exploration is following the mainstream pathway: you need lube, a butt plug, you have to overcome the pain/discomfort, and pleasure will inevitably win. And maybe this works for some, but I know a lot of people who are not wired for this, especially if they’ve already had some bad anal experiences.

What if you started differently the next time? What if you didn’t expect yourself to follow a predetermined route, but you would allow your body to show you the way?

Be present in your own asshole

Some find this funny and some can’t even imagine how they can make this happen. (I have other tips for you as well, so don’t be stuck here, if you feel like this is too much.) 

Even just checking in a couple of times every day to see how your anus is feeling. Bring your attention there. Try to stay present for a while. Breathe. You don’t need to intentionally relax your rosebud, “just” feel. And then go back to your everyday life.

Check in also when you are in the shower, but not “just” with your attention, but touch yourself and feel into this. Don’t penetrate the anus (unless you are called to it), stay outside, but let your hand stay there a bit. You can explore the outer texture, your response to the touch. Feel yourself.

If you have a partner you can also do some connecting moments like what I recommended in the shower. Don’t penetrate. Create safety, connection and be present for this. Breathe slowly and let yourself feel. 

This is not a waste of time. This is building a stable foundation for pleasure, awareness and connection. Pleasure is not about how much you want something or following a script. It is about how open you can naturally be. When you have a strong, stable and intimate foundation you can experience bliss that you have never even thought was possible for you. 

When was the last time you saw your anus? Maybe it is time to be curious and see yourself.

Being present without expectations

Freedom is essential for pleasure. Expectations and agendas create judgment and pressure (very probably not the juicy kind). So is curiosity. Allow yourself to react authentically. 

Whatever comes up it is ok. You can stop anytime. You can come back anytime.
If you feel nothing that is ok too. Don’t judge yourself, but ask what would feel good to try? 

First flow with pleasure

Pleasure is your leader here. Do what feels good. Make your heart pound faster. Let your blood rush and make your body feel more alive. Tease yourself. Orgasm if you can. When your body is turned on and you feel open and safe you are ready to explore anal pleasure further.

Spoil your backdoor

You have already connected with your anus. What if you would make it feel amazing and want more? 

Add some lube and explore what feels really good. From “just” holding to circling around and enjoying different sensual textures you have plenty of options. I wouldn’t recommend ice though as initiation because cold closes you down. So let’s leave ice for later. 

Rimming can be super pleasurable, and if you don’t have a partner, a rimming toy, like the Skins - Rose Buddies Bums n Roses Rotating Rimming Toy will fly you into paradise. 

When you are deeply craving for more, you are ready for penetration. 

Start slow and small. When you feel pain, withdraw. When I say withdraw I mean with tenderness not disappointment or anger. Allow your body to react naturally and accept it with grace. It is up to you to decide to try to move deeper again or explore pleasure somewhere else.

Smooth or beady?

When it is about anal toys the ones used first the most often are the rounded plugs. These usually are not ideal for starting, because they tend to be too wide too fast. 

If you are looking for a plug to start, choose something more elongated and narrow like this plug or this with a safe base of course, like the Fant-ASS-tic Anal Training Kit - Silicone.

I like the Smoothy Prober because one side is smooth and the other side is beady and you can experiment with it to see which one your body enjoys the most.

These anal toys with a handle allow you to keep the toy at the most pleasurable part and provide some pressure there. It is all about exploration and seeing what your body is into. Just because you see something more often it doesn’t mean that it is for you. 

Enjoy what your body is into instead. And you will know this when you allow yourself to discover and feel without expectations.

Say a nice good bye

You put lots of effort into initiating anal sex, why wouldn’t you close with fulfilment. You don’t need a whole ritual (except if you want it), just an acknowledgment of how you feel. What did you enjoy the most? What would you do differently the next time?

Your body is wired for pleasure. And the more open you are to discover it, the more you will experience. 

Back to blog