In my experience, most women are either into anal sex or they aren’t. Most women I know who like anal sex have done their research before diving in. They have read books, gone to workshops, watched educational videos. In other words, they know how to approach this delicate area with the amount of respect and consideration it deserves.

Most women who I have spoken with who are not into anal sex have usually had it, ahem, “thrust” upon them in the throes of passion. One minute they were having hot sex, and the next, something was being shoved up their butt. I can say with utmost confidence, this is NOT the way to approach anal sex with a partner for the first time.

There are many ways to find out if your girlfriend might be interested. One of the easiest ways would be to bring up the conversation outside of the bedroom. Begin by sharing your sexual likes and dislikes and within that conversation you could simply ask for her thoughts about anal play.

If her reaction is, “ewwww, gross,” you could ask her why she feels that way. It might be she’s had a bad experience or she has simply had years of receiving negative messages about that part of her body. This doesn’t necessarily mean that she wouldn’t be open to exploring anal play if it is done slowly and safely in a trusting environment.

However, if she is totally opposed to it then you have to accept that may never change, no matter how you feel about it.

Another way to explore this would be when you are intimate, you can try gently touching around that area to see how she feels. If she squirms away, you’ve been given a clear message. However, it may just be that she isn’t feeling especially into it on that particular day so again, it’s worth asking about later on.

If, however, she gives physical or auditory cues that indicate that she is enjoying herself then you can gently try working the tip of your finger in. You need to be prepared to take the tiniest of baby steps when it comes to this and continue to be open to chatting about her feelings/concerns/likes/dislikes afterwards.

And, in addition to patience and sensitivity, I cannot stress enough the importance of lube in all anal play.

I also spoke with sex educator Cory Silverberg about your question and he added this:

There’s a school of thought that says that if one person is interested in anal play, that person should be open to exploring being on both the giving and receiving end. Expressing that you’re open to this can dramatically change how a conversation like this goes. Of course it has to be a genuine offer, so you’ll need to think about this for yourself first.

In other words, if you’re interested in her being open to you exploring that part of her, you should also be open to the possibility that she may want to explore that part of you as well.

And for more tips and techniques, I would highly recommend Tristan Taormino’s Ultimate Guide To Anal Sex For Women.

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Outspoken, hip, irreverent – yet enlightening, Cynthia Loyst is a TV host, advice columnist & relationship coach who likes to ask uncomfortable questions. She’s also a certified life/relationship coach and guest expert on a variety of shows including The Marilyn Denis Show, CTV Newsnet and Etalk. Follow Cynthia on Twitter.