Hi Yana,

My husband just started letting me put a finger up his anus for stimulation and he’s loving it. Now, how do I make sure I’m pleasuring him in the best way possible?

—Derriere Digiter

Dear Digiter,

My two main pieces of advice for making sure your partner is loving what kind of sex acts you’re dishing out are:

1) Do your homework!

2) Ask your partner for feedback!

A simple Google search of “anal stimulation” might bring you to more adult entertainment than education and/or just too much content to navigate. It’s helpful to know some good basic places to look that you can trust will offer solid information about sexual pleasure such as Scarleteen.com (designed for teens but also just a great resource), lil ol’ me at yanatallonhicks.com, and, for anal sex specifically, bvibe.com which, has an entire anal pleasure advice section featuring some work by yours truly. Locally, Oh My Sensuality Shop has a great section of carefully curated educational books and supplies plus a well-trained staff who can answer your questions.

My short-and-sweet anal education for you is:

Move slow — the best anal sex is never rushed.

Start small — whether that’s fingers or toys.

Use lots of lube — Sliquid Sassy and Slippery Stuff are my anal faves.

Communicate often — now’s not the time to be tightlipped.

Make sure all toys have a base — meaning, a wider flare at the bottom of the toy to prevent it from being accidentally lost in the rectum (it happens, people — Google it).

The prostate is the place to be when it comes to anally pleasuring penis-havers. As was just (re)published a few weeks ago in the Best of the V-Spot series Prostate Power — The Not So Dirty Truth, the prostate is a soft, walnut-shaped piece of pleasurable anatomy that can be felt by inserting a finger or toy up the bum, preferably with a curved shape that’s angled towards the receiver’s belly button. Explore stimulating the prostate by inserting your finger about two-knuckles deep and pressing “down” towards the belly button (check with your partner about pressure) until you feel a soft-yet-firm round “walnut” (that’s the prostate!). Once you find it, gently “hook” your finger over it and try rocking, “dragging,” or other digital dance-moves to see what feels best to your partner.

Though hands and fingers are great ways introduce ourselves to new sex acts, if your husband likes to combine anal stimulation with penetrating you or oral sex or other types of stimulation that might be easier done if you didn’t have one hand oh-so-busy, then I would highly recommend The Aneros which is an anal toy specifically designed for hands-free prostate stimulation that comes in several svelte shapes perfect for beginners.

Most importantly, to truly know what’s bringing your husband pleasure in the best way possible — ask him. You can ask him for feedback about what you’re trying out during anal play, after, or both! I think more people need to make Sexual Feedback Conversations part of their regular sex life — a time outside of sex itself (whether directly after whilst cuddling, over tea a couple days later, or even via text) to talk about what went well, what could go differently, and what you might want to try next. This is especially true and helpful when you’re adding new things to your sexual repertoire.

A successful Sexual Feedback Conversation is more about sharing information about your experiences with your partner and less about critique. Rather than focusing on what so-and-so did right or wrong, look at a Sexual Feedback Conversation like a collaboration between the two of you to make sure your sex life is as pleasurable and satisfying to you both as possible.

And if it’s not quite there yet? Return to item #1 — your research and development phase, where you go back to your trusted sexual pleasure education sources and gather more information about what to try next or instead. Remember — sexual exploration and learning can be challenging (with no help from societal sexual shame) but if we keep the goal of sex as being authentic pleasure, this process should mostly be fun, enjoyable, and safe for you both.

Yana Tallon-Hicks is a relationship therapist, sex educator, and writer living in the Pioneer Valley. You can find her work and her professional contact information on her website, yanatallonhicks.com.