How to Do It
Dear How to Do It,
I’m a straight, cis woman, and honestly, vaginal sex has never really excited me much. I enjoy foreplay; my clitoris is sensitive and I can get turned on easily. But during actual intercourse? It can range from feeling like nothing special to being uncomfortable. I’ve consulted doctors, but the symptoms of conditions like vaginismus and vulvodynia don’t fit what I experience. It’s almost as if I lack sensation down there entirely. I’ve been with enough men to understand it’s not just about them, and even toys don’t do much for me either.
A couple of months ago, my boyfriend and I decided to explore something different.
We tried anal sex. I had always hesitated due to some digestive issues, but I was curious, so we went for it. And wow, it felt like whatever sensations I was missing in my vagina were suddenly alive in a new way back there. I finally got what people meant about the pleasure of penetrative sex, and to my surprise, it was pain-free. I even experienced orgasms, like, several back-to-back, without even touching my clit. It’s not just about the orgasms; it’s the enjoyment of penetration that I never felt before. Interestingly, the deeper my partner went, the more pleasure I experienced, which isn’t the case for me with vaginal sex.
While I’m excited by this discovery, it does complicate things. My digestive troubles haven’t improved, and I’m not sure my boyfriend wants anal every time we have sex—would that be healthy? Why does anal feel so much better for me compared to vaginal? Everything I read suggests that even cis women who enjoy anal generally prefer vaginal sex.
—Surprised
Dear Surprised,
I contacted Dr. Evan Goldstein, a pro in this field and author of Butt Seriously, who had a few insights for you.
So, here’s the positive takeaway: many people find anal sex to be a pleasurable alternative. The anatomy of the anus and rectum has different nerve endings compared to the vagina, leading to different sensations. For some, stimulation of the “A-spot,” along with the surrounding nerve-rich areas, could lead to powerful orgasms. The key often lies in proper anatomy understanding, muscle relaxation, and pacing.
Since the anal canal is surrounded by muscles that should be relaxed, and its skin is delicate, lubrication, time, and taking it slow are vital. Tools like anal dilators can really help prepare the body for this experience. Starting small and gradually increasing size allows everything to adapt comfortably. Many also find that experimenting with various positions and thrusting styles during play helps identify what feels good while keeping control. I really advocate for personal exploration since it helps individuals discover what they enjoy without pressure.
People often worry about how their digestive health might affect this. Typically, with regular anal play, the rectum is clear. Good digestive health, such as adequate fiber intake and hydration, significantly helps. If someone wishes to prepare, I recommend safe douching methods, as over-cleaning could cause issues. I’ve developed a cleansing solution that’s designed to be gentle and effective for those looking for confidence in their anal experiences.
I also want to point you towards my co-columnist Rich Juzwiak’s comprehensive article from 2019 about anal hygiene, which includes expert advice too.
Even if you only occasionally feel mild discomfort, it’s wise to consult a health professional. Dr. Goldstein suggests seeing a gynecologist for vaginal pain, a proctologist for anal concerns, and a pelvic floor physical therapist for muscle-related pain. Each specialist provides a unique perspective and can collaborate for a comprehensive approach.
If you’re wondering whether your boyfriend would enjoy anal every time, the best approach is to simply ask him. His preferences will likely rely on his feelings about anal sex itself and your pleasure, and he’s the only one who can clarify his perspective.





