Question: What are the best ways for simultaneous penis and anal play?

I love receiving questions and am happy to answer them. The more details I get, the better my answers can be. This time the question was quite universal, so my answer is a bit longer, so that I have more chances to find the best option for the person.

The person who asked for my help is a kinky man, and he is looking for tips to have anal and penis pleasure while he is masturbating. 

If I would talk to this man in person I would ask questions like:

Do you have any toys at the moment?

What is your experience with anal play so far?

And my tips would be based on his answers, but we don’t know, so let’s start from this place, add tips for beginners and also for the more advanced, and here is my answer.

Anal play can be a deeply satisfying experience when it is done well. Combining it with other forms of masturbation is mindblowing, so prepare for some stunning orgasms.

Give yourself time to explore and listen to your body

Anal pleasure comes from a space of deep relaxation, and while in your kinky fantasies you already go big, in real life listening to your body is crucial. Consciously withdrawing is as important as penetrating. Create a space of freedom and play for yourself. 

When you are exploring and creating this new way of pleasure for yourself, stay present. Don’t use porn at the beginning, because it is much more challenging to stay in your body and get all the feedback and act accordingly. It is ok to use your fantasies or “just” really be in the moment with yourself. This is what makes you an expert in your own body, pleasure and orgasms. 

Start anal penetrations only when you are already aroused and prepared

Your reaction to penetrative anal play is very different when you are already relaxed. Give yourself the best start possible. External anal stimulation and penis play are going to open your backdoor even more. Don’t underestimate them.

Strategize wisely and be practical

You have 2 hands, so when you play with 2 parts at the same time, it is important to find the right toys. From a very practical view some automation can expand your opportunities. Keep your attention more on pleasure than managing. I’m not saying that this always has to be the case for you, but when you do something that is new to your body, you can for example easily lose your erection temporarily, until you get used to the feeling. This can also be true for your orgasms. It can be harder to have your “usual” ejaculatory orgasm when you have new, intense sensations at another area of your body. You are not broken and nothing is wrong with you, you “just” have to get used to the new level and area of pleasure. The more you are aware of the possibility the more relaxed you can be when this happens. 

Explore anal orgasms and prostate orgasms as well

So many of male anal toys are mate for the prostate and focus on prostate stimulation. I get this, the prostate is an amazing source of pleasure and orgasms, but so is your whole anal area, what is also wired for pleasure and orgasms and you can have both. So explore all of your options and this will mean more variation of intense orgasms for you.


Try not to create a pattern or you loose on erotic potential


When you try something new and it feels amazing it is natural, that you want to repeat it, so that you can enjoy it even more. And this itself is awesome. But when you repeat it again and again without experiencing other ways of orgasms and pleasure journeys it becomes a pattern that is keeping you stuck. Try to experiment with different things still so that you can keep your pleasure gates open.

 The next post is going to be about concrete products and tips so that you can choose your favourite ways to explore. Click here to check it out.


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