Enjoying Anal Sex: 5 Tips for First-Timers

On an instinctive level, most of us are aware that pleasure and pain occupy opposite ends of a spectrum. But that is not always the case when it comes to sex – anal sex, in particular.

If that sounds confusing to you, then you’ve probably never looked at yourself in the mirror while in the midst of climax. Had you tried, you’d have likely glimpsed a peculiar expression on your face. Many women look halfway between rapturous enlightenment and intolerable agony when they achieve orgasm.

If you happen to be one of them, we assure you that there’s nothing wrong with you. Many mystified witnesses to their own seemingly contradictory facial expressions during the peak of sexual gratification have wondered, “What’s up with that?”

If you’re thinking about engaging in anal sex for the first time, it’s important to know as much about the act as possible. Don’t let misinformation deprive you of the pleasure you might otherwise derive from the experience.
If you’re thinking about engaging in anal sex for the first time, it’s important to know as much about the act as possible. Don’t let misinformation deprive you of the pleasure you might otherwise derive from the experience.

The Surprisingly Natural Link Between Pleasure and Pain

The relationship between pain and sexual pleasure has sparked the imaginations of many writers and artists. It’s easy enough to see why: the unlikely association invites juicy undertones of forbidden, mischievous enjoyment.  Moreover, as a theme for fiction, this hint of delicious naughtiness can be rich fodder for profitable controversy.

But the truth is that the link between pleasure and pain is as natural as the birds and the bees. It is embedded deep in our biology.

Pain causes the central nervous system to release endorphins. These are proteins which act to block pain. They work in a way that is biologically analogous to the way opiates induce feelings of euphoria.

When anal sex is painful, your body releases endorphins to block the pain. These proteins work in a way that is akin to the way opiates induce feelings of euphoria.
Sometimes, anal intercourse can be painful. When that happens, your body releases endorphins to block the pain. These proteins work in a way that is akin to the way opiates induce feelings of euphoria.

How to Enjoy Your First Experience of Anal Sex

Much of the same can sometimes happen to women during anal sex. But, of course, it’s important to understand that – when it’s done right – fifth base can be painless. In fact, some women consider anal penetration as the cherry on top of a sexual parfait. It is the perfect precursor to something that is already pleasurable on its own.

So, if you’re thinking about engaging in anal sex for the first time, it’s important to know as much about the act as possible. Don’t let misinformation deprive you of the pleasure you might otherwise derive from the experience.  Below, doctors, sex educators, and real women give you five tips on how to enjoy your first experience of anal sex.

1. Once you’ve decided to try anal sex, give yourself time to think again.

Our first tip is to give yourself time to think about it. The worst thing you can do is to take anal sex lightly. Before you throw yourself into it, take a pause. Remember that there just might be a lot more involved in the act than you may have realized.

When done the wrong way, anal intercourse can be excruciating and unsafe. To be sure, a nasty first experience can be traumatizing. To avoid an awkward – or even unhappy – turn of events, we urge you to start small.

Shawntres Parks, a licensed marriage and family therapist in San Diego, suggests that you try a butt plug, anal beads, or fingers.

“If you’re comfortable with any of these things in your anus for about 15 to 20 minutes, there’s a good chance you’re at a point where you can successfully insert a penis,” she says.

In short, once you’ve learned to pleasure yourself with an anal toy, you can move to partnered experimentation. This will be good for you and it will be also good for your partner. Why? You will gradually gain the confidence to give pleasure even as you teach your partner how best to pleasure you.

2. If you’re worried about pooping while having anal intercourse, try a warm water enema.  

You’ve likely heard of that story involving a friend-of-a-friend-of-a-friend who had a particularly embarrassing, malodourous experience when she first tried anal sex. Your anus is where you expel digested waste, after all.

Can anything placate a first-timer’s jitters? Russel Stambaugh, Ph.D, a sex therapist in Michigan, says giving yourself a warm water enema a couple hours before the deed should permit you some peace of mind.
Can anything placate a first-timer’s jitters? Russel Stambaugh, Ph.D, a sex therapist in Michigan, says giving yourself a warm water enema a couple hours before the deed should permit you some peace of mind.

Yes, that can happen. But it’s unlikely. Your digestive system is an amazing, living structure that’s designed to keep waste up high until it’s time for a bowel movement. “A good wash in the bath or shower should take care of any stragglers,” says Gabrielle Kassel, a New York–based sex educator and wellness writer.

Still, worrying about leaving a foul-smelling crime scene behind can kill all the joy of your maiden voyage.

Is there a solution? Can anything placate those first-timer’s jitters? Russel Stambaugh, Ph.D, a sex therapist in Michigan, says giving yourself a warm water enema a couple hours before the deed should permit you some peace of mind.

But there’s one important caveat. “Leave time for your body to expel the excess water so it doesn’t come out during your big moment,” Stambaugh says.

You shouldn’t overdo it, too. Medical experts warn that performing enemas too often can be dangerous. There’s been concern in the past that anal douching could increase the risk of sexually transmitted infections. That is mainly due to the ingredients commonly used for enemas.

Tap water is fine for occasional use, says Pierre-Cédric Crouch, PhD, a former nursing director at Magnet for the San Francisco AIDS Foundation. Even so, “You don’t want to overdo it,” Douchie adds.

3. So, you’re ready for anal sex now? Well, guess what? You need to take another beat.

 Anal intercourse, like anything else that we do with our bodies, “should be consensual and taken slowly to make sure that everyone is comfortable,” says relationship and sexuality educator, Logan Levkoff.  
Anal intercourse, like anything else that we do with our bodies, “should be consensual and taken slowly to make sure that everyone is comfortable,” says relationship and sexuality educator, Logan Levkoff.  

So, let’s say you’ve followed our advice so far, done the necessary additional research, and taken all the needed precautions. You and your partner have talked about actual penetration a thousand times over. You think you’re ready and you’re excited.

Guess what? You need to take another beat at this point. Anal intercourse, like anything else that we do with our bodies, “should be consensual and taken slowly to make sure that everyone is comfortable,” says relationship and sexuality educator, Logan Levkoff.  

We hope this is obvious. But whether or not these common-sense rules are clear to you, it’s a good reminder to communicate with your partner openly and frequently.  This is especially true when you are about to try something new in the bedroom.

Whether you’re on the giving or receiving end of anal sex, “like anything else that we do with our bodies, it should be consensual and taken slowly to make sure that everyone is comfortable,” Levkoff says.

We hope this is obvious. Either way, it’s a good reminder to openly communicate with your partner while trying out new things in the bedroom.

On a similar note, don’t try any fancy anal moves on your first try. “The idea of stretching your sphincter may sound appealing, but unless you are seriously into intense sensation play, forego the risks of edgier play until you have more experience,” advises Stambaugh. “Remember, porn is fantasy, not technical training,” he adds.

4. Use proper lubrication when you engage in anal penetration.

Unlike the vagina, the anus doesn’t lubricate itself. This means you should always use a lubricant for anal sex. When you use proper lubrication, you reduce friction. This is beneficial both for you and your partner.

Without proper lubrication, you can get small tears inside the rectal lining of your bum. These tears make you more susceptible to contracting HIV or other sexually transmitted infections (STIs). The same goes for your partner, if your partner happens to own a penis. (Obviously, in this situation, there isn’t as much of a risk of STIs for a partner who uses a strap-on.)  

Proper lubrication likewise allows you both to enjoy anal penetration more comfortably.  Learning to relax and enjoy anal sex can take time. It doesn’t come easy for everyone. At the very least, appropriate lubrication will make it tolerable.

By applying lube to both your butt and any object your partner inserts into it – be it a finger, beads, or a sex toy, you ensure that you have adequate slippage. That’s one thing that’s sure to make you moan, “Oh, wow.”

Unlike the vagina, the anus doesn’t lubricate itself. This means you should always use a lubricant for anal sex. This is beneficial both for you and your partner.
Unlike the vagina, the anus doesn’t lubricate itself. This means you should always use a lubricant for anal sex. This is beneficial both for you and your partner.

5. Once it starts, more talking should start, too.

We know we’re getting repetitive, but it’s necessary.  Check in with your partner multiple times during anal sex. Communication is important in every relationship, but it is especially important when trying something new in the bedroom.

“A partner who takes feedback well, and backs off if anything feels uncomfortable, is just as important as preparing with anal toys before partner play,” Stambaugh says.

There are other reasons for communication, of course. Communicating with a partner about any discomforts can also reduce the likelihood of friction-related injuries. So, if it hurts, you must be comfortable telling your partner to slow down or stop.

Check in with your partner multiple times during anal sex. Communication is important in every relationship, but it is especially important when trying something new in the bedroom.
Check in with your partner multiple times during anal sex. Communication is important in every relationship, but it is especially important when trying something new in the bedroom.

If you want to try it, be sure you set the stigma around anal sex aside.

In many ways, we’ve reached an age of enlightenment when it comes to sex. It’s 2022 and just about everyone agrees that sex should be adventurous, fun, and guilt-free. From kinks to fetishes, pop culture has largely removed any embarrassment around whatever it is that turns you on and gets you off. 

Anal sex – an act that was once consigned by proud-to-be-ignorant bigots exclusively to couples in the gay community – is now on the rise among heterosexual couples. In 2010, the Journal of Sexual Medicine published a study that said 94 percent of the surveyed women who’d recently engaged in anal sex experienced an orgasm.

Yet, despite the fact that we seem to have entered a new era of sexual illumination, anal intercourse remains surrounded by an old – and still conspicuous – stigma. Why does this stigma and misconception remain?

 In 2010, the Journal of Sexual Medicine published a study that said 94 percent of the surveyed women who’d recently engaged in anal sex experienced an orgasm.
In 2010, the Journal of Sexual Medicine published a study that said 94 percent of the surveyed women who’d recently engaged in anal sex experienced an orgasm.

Certified sex therapist Aliyah Moore, PhD, believes that the misinterpretation is the fault of doctors. To be more specific, she blames how anal sex is discussed in medical journals.

“We live in a culture that continues to associate anal with homosexuality,” says Moore. And “homophobia very much persists,” she points out.

The sex therapist calls out the harmful language used by medical journals and experts. She claims that it shames people who engage in anal sex – even in instances where they’re attempting to be positive.

The problem is in the language the writers employ. Moore says some of the terms scientists use appear to shame those who engage in anal intercourse. She noted one study which refers to anal sex as a “risky sexual behaviour.” Some studies have even associated the act with binge drinking, she says.

Whether or not there is any truth to Moore’s claim, it’s important to remember one thing. If you’re curious about anal sex, or if you already you enjoy it, you should set that stigma aside.

Why? Simply because it’s not necessarily reflective of reality. Certainly, it does not reflect your individual experience. “Anal sex should never be a shameful practice,” says Levkoff. “Plenty of people enjoy it.”

Perhaps more importantly, it’s always best not to judge anyone’s sexuality – or anyone else’s private opinion about sex, for that matter. So, whether you enjoy anal sex or not, no one has the right to judge what’s right for you.

Now that, dear ladies, is our “bottom” line.