Anal beginner

First Time at Anal Sex? Here’s the Ultimate Guide

Published: FEBRUARY 26, 2019 | Updated: AUGUST 29, 2021
With a little preparation, some realistic expectations, and careful communication, anal play can be a great addition to your sexual repertoire.

Anal sex can be scary. For some people, it’s the ultimate taboo. For others, there’s concern about pain or mess. But, with a little know-how, it’s a lot more accessible than you might think.


Don't Do It Because You're Being Pressured

It’s important to note you never have to do anything you don’t want to do. A partner’s interest isn’t a good reason to try anal sex if it isn’t something you’re excited about. However, if it is something you want to try, here are the steps to make it as comfortable and fun as possible.

Read: A Step-by-Step Guide to Negotiating Consent

Relaxing Is Important

If you decide to go for it, the first thing you need to do is relax. And that’s easier said than done. Here’s the thing about anal anatomy: there’s an outer sphincter you can see, and a second one a little further inside. The outer one you have some control over, the inner one does it’s own thing. So you can’t fake relaxation; you really need to feel it for your body to allow penetration.

For people who have had painful attempts at anal play, this is the most common problem - penetration happening before the body is ready.

In order to relax you genuinely need to be up for the things that are happening. You need to put your mind at ease around any anal sex concerns.


Address the Potential for a Mess

A lot of people are concerned about the potential mess when trying anal. It’s true, sometimes there’s a little mess. This is something you and your partner should be prepared to address with discretion and compassion if it becomes an issue. If you can’t both agree to that, anal might not be for you. You can further prepare for mess by throwing a towel down on the bed and using gloves on hands, and condoms on toys or penises.

That said, anal sex usually isn’t as messy as people fear, and sometimes it isn’t messy at all. For folks without any stomach issues, fecal matter doesn’t generally hang out in the rectum. So if you’re getting plenty of fiber and feeling pretty regular, you’re probably in good shape. The only prep you need to do is shower. Don’t bother with an enema. They’re likely to cause more distress to your body than they’re worth, especially on your first try.

Read: How to Do An Enema Before Anal Play

Once your mind is at ease, focus on physical relaxation. A combination of arousal and deep breathing is helpful here. If you’re game for a visualization, imagine breathing in through your nose and out through your pelvic floor. I know it might sound silly, but it really helps.

Start Small

When you’re ready to dive in, start small. Many people only realize their eyes are bigger than their butts after choosing what seemed like a reasonably sized toy in the store. If you’re looking for toys, remember that anything used for anal play must have a flared base that’s significantly wider than the widest part of the toy. Luckily you don’t need toys to get started, fingers work just fine — either yours or your partner's.


Looking for safe anal toys? Check out Kinkly's recommended butt plugs for beginners.

While the choice is yours, gloves are a great idea. Not only do they make clean up a snap, but they help smooth fingernails and any other rough edges that might cause discomfort or even little micro tears in the delicate tissue of the rectum.

Once you’re gloved up, add lots of lube, both to the fingers and to the outside of the anus. Be sure you’re using a body safe lube, and one that’s compatible with barriers and any toys you’re using.

Start with External Touch

Start by just focusing on external touch. The anus and surrounding area are incredibly sensitive. External massage can be very pleasurable, even if you never add penetration. In fact, sometimes it’s best to stick to external touch the first couple of times you explore so that your body can get used to touch in this area.

Move Forward Using One Finger

If you decide to try penetration, start with just one finger. Try to aim with the soft pad of the finger rather than the tip (where the nail is.) Gently tip your finger into the opening and then pause, just one knuckle deep. This process should go very slowly with a pause at each step so your body can keep getting used to what’s happening. Any time your body tenses up or something feels uncomfortable you should pause, back up, or even stop the process.

Once having a finger or two inside your body feels OK, you can start exploring what feels the most pleasurable. For people with a prostate, there is often a lot of pleasure to be had by exploring that area with gentle massage or toys made specifically for prostate play. For people with a vagina, the G-spot area (and much of the clitoral urethral vaginal complex) can be stimulated from within the rectum.

Beyond G-spot or P-spot pleasure, many people find the feeling of fullness enjoyable, as well as pressure and possibly friction around the area of the anal opening. To know what feels good for you, you’ll simply have to experiment.


Always Use Protection

Keep in mind that anal sex is still sex, and all your usual precautions still apply. In fact, some STIs are more frequently passed through anal sex because of the likelihood of small fissures forming in the lining of the rectum, which can open you up to infection. So make sure you’re still having your safer sex talks, and using whatever barriers apply to you.

As you continue to play, remember to progress slowly from one activity to another, and not to rush sizing up to bigger toys or body parts. When you are playing with something bigger, it can be especially helpful if the person being penetrated is the one who controls how quickly penetration takes place.

With a little preparation, some realistic expectations, and careful communication, anal play can be a great addition to your sexual repertoire.

Stella Harris

Stella Harris is a certified intimacy educator, coach, and mediator, who uses a variety of tools to guide and empower her clients and she teaches everything from pleasure anatomy, to communication skills, to kink and BDSM. Stella has appeared at conferences across the US and Canada, and regularly provides workshops and guest lectures to colleges and universities. Stella’s writing has appeared widely, including a weekly sex advice column in her local paper. Highlights of her...

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