How to try anal for the first time

Here’s the very first thing you need to know about anal sex: it’s is not the kind of thing you want to rush into.

Anal sex, without the proper preparation, can be painful, risky and unpleasant. However, if you know what to expect and you prepare yourself properly, you may actually enjoy it – after all, plenty of people do!

Before you get down to the deed, here are five critical ways to warm up.

Five things to do before you have anal sex for the first time

1. Talk, talk, talk

You and your partner need to be able to trust each other completely before you go down this road. It takes patience, care and gentleness to create an enjoyable – or at least not terrible – first time anal sex experience for the recipient. And yes: your first time may not be fun. Your first few times, in fact, may be quite uncomfortable. Which is why it’s so important to do it with someone who’ll treat you with care.

2. Always lube up

We can’t over-stress this: use plenty of water-based lubricant – even more than you think necessary. Unlike the vagina, the anus is not self-lubricating, so you need to provide loads of moisture yourself. Lube won’t only help you avoid discomfort but could also increase your pleasure and satisfaction.

3. Use protection. We repeat: use protection

Anal sex is one of the riskiest types of intercourse because, as mentioned above, the anus isn’t a self-lubricating body part. This means that it’s susceptible to tearing during sex – and tears, as you know, lead to bleeding.

Any time bodily fluids or blood are exchanged, you’re exposing yourself to the risk of HIV and other STIs. Always use protection when you’re having anal sex, whether as a straight or gay couple, and even if you’re using a sex toy rather than a penis.

Bottom line: unless you’re 100% sure of your partner’s status and that you’re both monogamous, never ejaculate into their anus or allow them to do it to you.

4. Relax

If you do it slowly and with plenty of lube, anal sex shouldn’t hurt. Get used to the sensation by asking your partner to insert their finger first, or to use their tongue (don’t forget protection!) or a small sex toy.

Spoiler alert: it will feel like there’s something strange in your butt. Even the first several times may just feel odd. However, as you relax and get accustomed to the sensation, you may suddenly start to experience a whole new type of pleasure that adds a new element to your sex life.

Important: at this stage, your partner should be inserting only the tip of their tongue, finger, penis or sex toy. That way, you get used to the feeling without experiencing discomfort. Also, going ‘all the way in’ too soon will probably make you feel like you need to go to the toilet – not the sexiest sensation!

5. Don’t cross-contaminate

The easiest way to get a UTI is by spreading germs from the anus to the vagina. Make sure that any toys or body parts inserted into the anus are properly cleaned before being inserted into the vagina. Always wash well with clean water (and a mild soap if you must) before and after anal sex, and never mix anal with vaginal or oral sex.

Butt first, get tested

The best thing you can do before having anal sex for the first time is get tested with your partner. At Marie Stopes, we offer quick, confidential STI and HIV screening, plus a wide range of protection options. The safer you are, the better the sex will be.

Find your nearest Marie Stopes centre and make an appointment online.

Let’s be real. Even for those of us who have a generally open-minded, been-there-done-that attitude about sex, the thought of anal sex can still seem a little intimidating if you haven’t gone there before. For one reason or another, anal penetration is frequently a final sexual frontier — and there can be a whole lot of buildup (and nerves) that comes along with it.

But our greatest fears often lie in anticipation, and once you give anal a go, you might just find that you’ve been missing out on something that can actually be really hot and satisfying. After all, some studies have found that mutual satisfaction was high across the gender orgasm gap in a sexual encounters that included anal, as FiveThirtyEight’s Mona Chalabi wrote in 2015: “100 percent of men and 94 percent of women say they orgasmed during encounters in which they received anal sex.” This could be because anal is something that requires a bit more foreplay and preparation to execute well or that the people who are having anal sex are maybe a bit more concerned with getting their partner off.

We checked in with some experts and asked them to take the mystery out of anal sex for beginners, and they schooled us on some positions that can help ease you into your first time to actually make it an enjoyable experience.

Arm yourself with these tips and a lot of lube, and you’re on your way to one kick-ass time.

Cowgirl (or cowboy)

In the traditional cowgirl position, your partner lies down while you mount on top — yeehaw! As the partner on top, you can ease into anal penetration by moving up or down as needed. Pro tip: Make sure your bottom partner does not begin to thrust until you’re good and ready.

Certified Master Sex Expert and Educator, Sex Coach and “So Tight” Sensual Fitness Personal Trainer Nikki Ransom endorses the cowgirl position for anal newbies. She explains, “This position will allow you to control the pace and depth that his penis goes inside of you. Remember to go at an easy pace and stay relaxed. It helps to have had an orgasm already and be highly aroused.”

Jessica O’Reilly (a.k.a. Dr. Jess, Ph.D.), author, international speaker and PlayboyTV’s sexologist, offers an alternative to the cowgirl in her book The New Sex Bible, “If she doesn’t like the sensation of deep penetration, but he desires more stimulation against the base of his shaft, she can reach backwards with a warm, wet hand to grasp the lower half of his shaft. Her hand becomes an extension of her butt while providing a physical buffer to ensure only shallow penetration.”

Doggy style

This position is most often associated with anal because it has major advantages. As the partner on the bottom, you can stay loose as you control penetration to increase pleasure. Getting busy on all fours may be your best bet if you have attempted and found anal painful in the past.

Patricia Johnson and Mark Michaels, co-authors of Designer Relationships, Partners in Passion, Great Sex Made Simple, Tantra for Erotic Empowerment and The Essence of Tantric Sexuality, recommend doggy style for first-timers and those who may have had an unpleasant experience before. The couple says, “Anal sex should never be painful. Always use plenty of lube and proceed slowly and gently.” Ransom adds, “Rub and stimulate your clitoris too to make it even more pleasurable.”

In The New Sex Bible, Dr. Jess has a different take on doggy-style anal sex. She recommends the modified doggy to give the receptive partner more control, support intimacy and provide the opportunity for double penetration. Dr. Jess explains, “She assumes a kneeling position with her butt cheeks on her heels and her knees spread wide open. She places her hands on her knees or the bed for support. He assumes the same position behind her and adjusts his height so that the head of his [penis] rests below her bum. He remains static as she lowers herself onto his head and takes a few deep breaths before sliding farther down his shaft. She drives her butt and hips up and down at her own pace as he reaches around to fondle her breasts or rub her clitoris.”

Face to face

This position is preferred if you are looking for extra intimacy during the act. Start with your partner sitting as you mount his lap, face-to-face. Once again — as the partner on top, you can control depth of penetration to stay comfy. Face-to-face anal has the added bonus of extra stimulation for a woman:  breasts, clitoris, go crazy!

Johnson and Michaels love face-to-face anal for the toe-tingling intimacy it provides. They confirm, “This position facilitates using eye contact and breath to build even more arousal.”

Dr. Jess agrees. She says, “I like this position as it allows the ‘mounter’ to exercise a good amount of control of the depth and rhythm of penetration. Wear a vibrating c*** ring for this one to provide extra pleasurable sensations as the top partner grinds against his shaft.”

A version of this post was originally published January 2015. 

Still want to change things up in bed? Our sex position bucket list has all sorts of moves to try: 

Good old missionary with a twist

When it comes to anal, missionary will never steer you wrong. Approach this favorite vanilla sex position with a backdoor twist: In the missionary position, place your legs on his shoulders. With the right amount of lube and relaxation, even initial penetration should be pleasurable.

Missionary is easy-peasy for most maiden voyages, but Johnson and Michaels caution that this anal move may not work for everyone, “Some people may not be sufficiently flexible for this position.” For those who are flexible and looking to try new things, Dr. Jess explains her take on missionary, “Better yet, place the soles of your feet against his shoulders so that you can push back and release according to your preferences.”

On the stomach

Anal on the stomach is comfortable and easy, with the right prep work beforehand. First-timers can relax and make penetration enjoyable by lying on top of a pillow placed under the stomach. For women, this elevates the backside nicely and still gives enough room to stimulate other body parts.

Johnson and Michaels recommend incorporating sex toys into the act to keep things interesting, “This is a great position for stimulating your own clitoris or using a vibrator.”

Because of the opportunity for sex toy play, Dr. Jess adds that on-the-stomach anal can be especially favorable to the ladies. She says, “This is one of the best anal sex positions for women (as the receptive partner), as she can reach down to stimulate her pubic mound and clitoral shaft with her hand or a flat vibrator (try the We-Vibe Touch). The dual stimulation helps to increase arousal, which heightens relaxation to create a cascade of orgasmic sensations.”

Spooning, with a twist

We are all familiar with spooning for some great side-by-side action. Spooning is also a top choice for anal since both partners are more likely to be relaxed. As the “little spoon,” you can make penetration easier by curling up and pulling your upper legs slightly toward your upper body. And while you’re at it, here’s a naughty little secret to double your pleasure — use a vibrator to get to the finish line.

According to Dr. Jess, spooning is the perfect first-time anal position for lovers. Johnson and Michaels add a helpful tip from their own bedroom experience, “You can give your partner a better view of the action by holding your upper leg just below the knee and opening up.”

Ransom also believes that spooning is ideal for a pleasurable beginner anal experience. “This is a great position to stay relaxed in. It also allows for clitoral stimulation and vaginal stimulation for a trigasm.” She advises, “Stay relaxed — your partner should enter you an inch at a time. Then, allow your anus to become accustomed and relax around his penis. Then [he can] enter you another inch and another, and continue until he is all the way in. Be sure to have plenty of lubrication with any anal penetration.”

A version of the story was published August 2020.

Before you go, check out 69 more sex positions to try before you die: