Skip to main content

Anal Sex Tips for First Timers

Anal Sex Tips for First Timers

So, you want to dive into anal sex? How fabulous! Plenty of pleasure awaits — from tongues, fingers, and toys on the outside to insertion of fingers, a variety of toys, and penises. The butt has so many possibilities for sensations. As for any other sexual activity, it is best to get to know your own body and responses first so that you can tell a partner what you like. Butt play can feel really different than other kinds of pleasure so if you can get familiar with what your butt likes and how it feels, you will be more relaxed and welcoming of those sensations during partnered sex. 

Getting Clean

Yes, we poop out of our butts. As long as you have “goldilocks poops” (not too hard, not too soft, just right!), there won’t be much fecal matter left inside. If you want to be extra clean for internal play, then you can rinse out the area with a rectal or bulb syringe/douche, however this is not necessary. You might want to at least have a shower though to get rid of any dirty bits (a.k.a. “resipoo”) left behind after your last toilet paper cleaning. Alternatively, a baby wipe will also do the trick pretty well in a pinch. 

Outside First

Tongues, vibrating toys, and fingers make awesome external anal pleasure tools and are essential for butt seduction and relaxation, especially for first-timers. The slower you go while listening to your butt, the more it will enjoy the pleasure and welcome you back. A nervous butt will tense up, making penetration painful or even impossible. We need to seduce the butt like any other body part. In fact, the first butt date can be just exploring external play!

Start Small

Your best chance for pleasure is to insert toys of progressively larger sizes after external play.  Start with a finger or similarly-sized toy. Massaging the walls of the anus with a finger in an around motion is often is more relaxing and pleasurable than in-and-out action. To build to larger insertables, use a butt plug and let the sphincters relax while you play with other erogenous zones such as vaginas, clitorises, penises, and/ or nipples. After a few minutes, remove the plug and the anus will be relaxed and more open. Repeat this process with progressively larger plugs until the move to a penis or desired dildo is not a big jump in width. You can even get kits with multiple size plugs to work up to.

Lube is Your Friend

There is no natural lubrication in the rectum so lube is essential. It is hard to use too much, so be generous. You ideally want a thick variety that stays in place well. Silicone (compatible with condoms but not with many silicone toys) and oil-based lubes (not compatible with condoms) are longer-lasting and thus great choices, but a good water-based lube will work as well. Don’t use a desensitizing lube; you wouldn’t use a desensitizer for any other areas you want to feel pleasure, would you?  Plus, if you desensitize the area it means that you might be ignoring any microtears — that you will surely feel later. Go slowly instead and enjoy all of the sensations.


Don’t put anything near a vulva or vagina after it has been in the butt (unless you clean it first or use a condom). Don’t put ANYTHING up the butt that does not have a flared base: the rectum has a habit of swallowing things that can only later be removed in the emergency ward. If you are unsure of your partner’s STI status, use a dental dam or piece of saran wrap for safer analingus, and use condoms on penises and sex toys.

The Goal is Pleasure

Our body has pain receptors for good reason: to prevent us from harming ourselves. Listen to your butt. If you feel pain, change the angle of penetration, add more lube, do a few squeezes of your anal sphincter muscles. If those don’t help, then stop and try another time, using extra warm-up and smaller insertables. If you force your butt to endure pain, it will tense up more and more each time such that anal sex will always be painful. 

Focus on ensuring pleasure for everyone, not just trying to get a penis or toy inside. The more you invest in taking the time to ensure it feels good the first time(s), the more incredible pleasure awaits for you and your butt every time thereafter.