How to Explore Anal Sex

A woman's legs abstractly contorted with a red background.

Anal is one of those sex acts that can’t help but carry a charge. 

We know that booty-gasms are a thing, for all genders – and that if you’re a penis-owner, a prostate orgasm can feel especially amazing. But if you’ve just recently crossed the line, from “I don’t if I could ever do that” to “y’know…actually….” then allow me to help you. 

See, anal is not something you want to go from zero to sixty with. The rewards (orgasms) are fantastic, but I definitely recommend a lil’ prep. So here’s how to start exploring, in a way that’s safe – and – highly, highly erotic. 

1. Get a butt plug

Listen, if you’re curious about anal, start on yourself with light insertion. Butt plugs come in a variety of sizes, and what they do is gently stretch out your sphincter muscles to accommodate what you’re putting in there. And don’t worry; just like your legs aren’t permanently loosey goosey after you’ve done a stretch session, the same is true with sphincter muscles: they will look, feel, and function exactly the same, but be more pliable, thanks to our friend the butt plug.

Also, they’re cute! You can find bedazzled butt plugs, unicorn tail butt plugs, and even heart shaped plugs. Always look for a handle (let’s not get any butt plugs lost in our anal walls) and if you’re an absolute beginner, get a small size. The idea is that you can work your way up to bigger sizes, the more comfortable you get.

2. Also try anal beads

I’m recommending these and a butt plug right now, largely for your solo sex (masturbation), so you can touch yourself on your own and figure out which sensations you like. To that end, anal beads are exactly what the name suggests, starting small at the insertion point and getting larger toward the end. Why? Because while you’re having an orgasm, the beads can be pulled out slowly, which stimulates the clenching sphincter muscles…creating a radically intense O, like an orchestra between your booty and your pelvic floor muscles. 

If you’re a penis-owner, your solo sex can be “acoustic” or electric (again, tons of toy options at Shop With Emily), but if you’re a vulva-owner, might I recommend the Je Joue Mimi Soft. Its ergonomic shape offers handheld pleasure, whether you’re using the tip for pinpointed stimulation, or the broad sides to stimulate your whole vulva.

4. Be hygienic

The thing that scares most people from trying anal is probably exactly what you think it is: “um, I go to the bathroom with that body part…” 

To be totally honest, I’ve interviewed doctors specializing in anal care, and getting clean for anal is not nearly as challenging as most people think. I encourage you to listen to my interview with Dr. Evan Goldstein, for peace of mind on that front. What he points out is that waste is actually not stored in your anus, but your upper bowels — so the chances of a toy, finger, or penis interacting with it in a major way are quite low. 


Still, fecal matter can be present in the lower bowels, so it’s a good to go to the bathroom 30 to 60 minutes before anal play, and wash your entire booty (anus opening, crack, cheeks) afterwards. And a word here, about enemas: it’s completely understandable why folks turn to these, just know though that the wrong enema method can damage the protective lining of your anal walls –  pre-disposing you to injury, and possibly STI’s. So if you’re planning on using an enema, look for one that will clean you out, without damaging your body, with a well-balanced pH solution.

5. Communicate – a lot

Alright, let’s say you’ve trained your booty, you’ve cleaned up, and you’re ready for action with a partner. It’ssssss showtime!

Anal sex can be incredibly hot, owing to the taboo factor and the novelty of sensations – but listen to me, when I say *talk to each other.* You’ve got a ton of options for how you approach anal play, from analingus, gloving up and experimenting with fingers, or full-on penetration with a toy or penis. Position-wise, the most common options are face-down (receiver lying on their stomach with legs slightly apart), or “deep spoon” if you want something more cuddly.  

The most important thing though is that you’re staying communicative, both leading up to and during the act itself. Relaxation helps the ultra-responsive muscles of the sphincter release and open up, so if you’re the receiver, don’t be afraid to ask for anal massage during foreplay – progressing from gently rubbing the anus, to insertion with a finger or toy. Your body will react faster than your mind can, and will clench if you move too fast – so don’t be afraid to take your time here.

As all of us get a little more open-minded about anal, it’s freeing to realize that this body part can be a portal to pleasure too, if we want it. So try these steps above if you’re curious, and if you do experience the not-at-all-elusive joy of a bootygasm…congratulations! Even if you don’t, clitoral / penile orgasms can be that much more intense and exciting, with anal in the mix. So explore, keep an open dialogue with your partner, and enjoy the fun of seducing the booty.