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How Do I Start Having Anal Sex?

Dear Jen,

I have heard from several women that anal sex is amazing, but every time I try it with my boyfriend, it hurts so much that he can’t even get it in. I just don’t understand why any woman would like this?! And why do men want to do it so much? Every guy I’ve ever dated has wanted to try it, but my boyfriend is the first one that I’ve ever actually let try. Please help! Should I just tell him to give up already or is there something I can do?


Anal Virgin

Dear Anal Virgin,

First and foremost…congratulations on even trying!! For so many women, it’s an automatic no to their partner(s), which is a shame because anal sex can be very rewarding!

For many women, anal sex can deliver more intense orgasms than vaginal sex. This is, in part, due to the positioning of anal sex wherein your partners penis is, potentially, able to hit the elusive g-spot and/or a-spot, anterior fornix erogenous zone. The a-spot is commonly called the female prostate, as it is located in about the same are that the prostate is located in cisgender men. Both the g-spot and the a-spot are theorized to be zones associated with the internal parts of the clitoris, the vestibular bulbs. On top of this type of clitoral stimulation, there are a great amount of titillating nerve endings near the anus itself.

Finally, from an emotional stand point, many women may find that anal sex creates a deeper intimacy with their partner, as some women choose to only have anal sex with a partner they trust and allowing them to enter a space that only certain persons can go. As to why so many men seem to want to try anal sex, the answer varies. Some like it because the anus may be a tighter than the vagina, thereby creating more stimulation to the penis. Some like it because it feels taboo and that seems exciting. Some men may feel more special or closer to their partner when engaging in anal sex for similar reasons that some women like it. Still, other find that it makes them feel more dominant in the bedroom. As these are just a few of the possible reason, I suggest talking to your boyfriend and asking him what anal sex means to him.

While I never want you, or anyone, to do something they are wholly against or uncomfortable with, there are some that you can do to improve your anal sex experiences. First, you must use a good lubricant!!! I suggest a silicone based lube, but any quality lube with aid just fine. Never use spit or water as a lubricant. And keep adding more lube, as needed, throughout the entirety of the anal sex experience. Second, toys and/or fingers to train your anus. Start with a small, thin butt plus or specialty anal trainers or even just the tip of a finger. Then gradually increase the size of the toy until you can handle one that is about the same size as your partner’s penis. Third, with either toys, fingers or penis, go SLOW! You can massage the anus opening before penetration. Upon insertion, take deep breaths and work on relaxing your body and your anus with each SMALL push inward. Finally, make sure your bowels are empty before getting started. This will make you feel more comfortable, overall, and decrease the likelihood of any surprises.

Fun tips- you can practice anal sex and anal training on your own, so when you are ready, you can teach your partner how you like it. Always remember, you never want to insert anything into your vagina that has been in the anus without a thoroughly cleansing first. And I highly suggest not inserting anything into the mouth from the anus without a thorough cleansing. The anus will contain some fecal matter which contains bacteria that is unhealthy for the vagina and stomach.

Best of luck to you and to anyone trying anal sex for the first or even fifth time!



*Disclaimer: this is not meant to act as or replace therapy in any way. Questions sent in may be edited for de-identification purposes, length, and/or grammatic coherency.

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