Trying Anal For The First Time: How do I raise the subject?


It seems like anal sex is the final frontier for most couples. Maybe it’s the same for you and your relationship? Would you like to try it out with your partner, but you’re feeling a little unsure about what the first steps are? Then we have some tips for you.

First things first: the desire to try anal sex for the first time is nothing unusual. Many people, regardless of sexual orientation or identity, enjoy things “from behind” regularly. It’s only because it is still such a stigmatized topic that anal sex isn’t really talked about. Of course, it’s perfectly okay not to talk about topics that you do not wish to discuss. However, it is important that anyone in a relationship that is feeling curious about anal sex is definitely not alone.

Step #1: Educate yourself

There are an incredible number of myths online about anal sex. It’s unhygienic, it hurts – or even that the anal muscles can get too stretched out. None of that is true! However, there are a few things that are important to know. Essentially, if you would like to try anal sex, then it is definitely worth educating yourself through trustworthy online sources. A good example of this would be our article on anal sex for beginners, where we dispel some of the most ridiculous yet common myths. The more information you have, the more prepared you will feel when deciding whether anal sex is right for you – and for your partner.

Step #2: Find some quiet time

Most people think that it makes sense to start things up in the heat of the moment. We strongly advise against it in this case! Acting without preparation could destroy the mood and lead to some seriously hurt feelings. Instead, use a quiet moment to bring up your desires. For example, if talking in bed is when you’re most comfortable discussing sex, perhaps raise the topic then. Without any pressure, you can gently outline why you would like to try out anal for the first time with your partner. Additionally, because you’re already so well informed, you can also answer any questions on the spot.

Step #3: Stay in touch

We suggest that you approach your first time together slowly, rather than just going for it. It can sometimes feel a bit strange, especially when your partner is playing the “passive” role. Start by showering or bathing yourselves together. This usually ensures a safe and secure atmosphere to start things off.

After that, try offering a gentle massage. Let each other feel valued and respected in the moment. The more comfortable you both are, the more fun you will have. Now, you can slowly shift focus to the sphincter. It is a really elastic, yet strong muscle. If you’re tense, then your muscles will be too and this will render any penetration impossible. Therefore, it makes sense to massage this area with your finger or with an appropriate toy. The We-Vibe Ditto, for example, is a great toy to gently stretch and stimulate using deep vibrations.

Discover We-Vibe Ditto

Important: Don’t forget to use lubricants! Even when you’re only fingering the anal area for the first time. This is because, unlike the vagina, the anus doesn’t produce any liquids when excited. And this is usually the reason for partners experiencing any pain during anal sex.

Step #4: Maintain dialogue

Perhaps take a short break now and talk to each other. Is your partner enjoying this? Is there enough stimulation from your finger or the toy? Are they maybe enjoying it so much that they would like to keep going?

This is when you can try to introduce your penis (or strap-on) gently and slowly. The most comfortable position is for your partner to lie on their stomach. Keep talking during this and listen carefully to what they are saying. It is always up to the passive partner to dictate how far you go – never vice versa!

Most importantly: stay close to each other after your first time. Cuddle and kiss as this strengthens the feelings of togetherness. Moreover, it’s an important sign of affection for both partners. It’s quite common that people desire this feeling of security after “kinky” sex.

Photo by Toa Heftiba on Unsplash


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