5 Ways To Get Your Partner To Try Anal

Anal play is more mainstream than ever—but let’s be real, it’s still one of the most misunderstood topics in the bedroom. Many people shy away from it out of fear, discomfort, or that one myth that refuses to die: “It’s going to hurt.”

Truth be told, anal sex shouldn’t hurt when it’s done right. With the right mindset, communication, and plenty of lube, it can be an incredibly pleasurable experience for both partners.

So, if you’ve been curious about exploring backdoor pleasure but aren’t sure how to bring it up (or ease your partner into the idea), here’s your guide to doing it right—step by step.

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1. Talking, Asking & Entertaining the Idea 

Before anything else, it starts with talking about it. Open, honest communication is the foundation of great sex—and that includes exploring fantasies or curiosities without judgment.

If anal play is something you want to try, explain why. Maybe it’s about new sensations, deepening intimacy, or satisfying mutual curiosity. Make it clear this isn’t about control or “taboo” thrills—it’s about shared pleasure and trust.

And don’t forget: both partners have the same sensitive nerve endings in the rectal canal, and men have the added bonus of the prostate—a pleasure point that can trigger powerful, full-body orgasms. Let your partner know this can be just as enjoyable for them as it is for you.

Pro Tip: Approach the topic with curiosity, not pressure. “I read something interesting about anal play—what do you think about trying it sometime?” works a lot better than “We should do anal tonight.”

2. Rimming (A.K.A. The Warm-Up)

Rimming, or oral stimulation around the anus, is often the best first step toward exploring anal pleasure. It’s intimate, gentle, and introduces the idea of touch in a low-pressure way.

You can use your tongue, lips, or even just the tip of a finger to trace soft circles around the area. The key here is to go slow—and always with consent.

If you’re playing with a vulva, remember: never go from anus to vagina without washing up or using a barrier like a dental dam. That keeps things clean and prevents bacteria transfer.

Try This: Combine rimming with oral sex for double the stimulation. A light anal touch while your partner is already melting from pleasure can take things to a whole new level.

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3. Fingers First

Even the most adventurous partner might get nervous about penetration—so starting small is everything.

Begin with a well-lubed finger (and yes, we mean well). Use small, circular motions around the rim to help the muscles relax. Once your partner feels ready, gently slide the tip of your finger in. Let them breathe and adjust.

This stage isn’t about depth or speed—it’s about comfort. As the rectum relaxes, the sensations become not only tolerable but deliciously pleasurable.

Pro Tip: Try this during oral sex or while your partner’s already turned on. Arousal relaxes muscles and makes everything feel better. Once a single finger feels good, you can explore two—or upgrade to a beginner-friendly toy.

4. Anal Toys

When it comes to anal play, toys are your best (and safest) training partners. TooTimid’s anal collection has everything from beginner-friendly plugs and anal beads to prostate massagers that hit just right.

Start small—like with a slim plug or soft bead set—and use plenty of lube. Let your partner control the depth and pace. The goal here is to make them realize, “Wait…this actually feels amazing.”

Once they’re relaxed, you can work up to more filling sensations or different textures. Remember: anal toys are designed to be safe, smooth, and easy to remove—never use anything that doesn’t have a flared base.

Our Top Pick: Beginner’s Silicone Anal Training Kit — the perfect starter set for couples curious about exploring comfortably and safely.

5. Pushing Penetration

If your partner’s feeling relaxed, turned on, and curious—then (and only then) it might be time for full penetration. Whether you’re using a penis, strap-on, or larger toy, the golden rule is simple: lube, patience, and communication.

Because the anal canal doesn’t self-lubricate, apply a generous amount of lube to both the toy and your partner. Go slowly—inch by inch—and encourage them to breathe and push out slightly during insertion. This helps the muscles open up naturally.

Once you’re in, move gently and check in often. With time and the right rhythm, that initial pressure turns into a deep, full-body pleasure that many describe as uniquely intense.

Pro Tip: If it hurts, STOP. Pain means the muscles are tensing up or you’re moving too fast. Take a break, add more lube, and never push through discomfort.

Final Thoughts

Anal play isn’t about shock value—it’s about trust, curiosity, and shared exploration. Whether you stop at rimming or go all the way to penetration, the goal is mutual pleasure and connection.

And remember: consent is non-negotiable. If your partner isn’t into it, respect that boundary. Pushing someone into something they don’t want is never sexy—and can damage the trust that makes sex great in the first place.

But when both of you are ready and relaxed? Anal can unlock sensations and orgasms you didn’t even know were possible.

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