How to Have Anal Sex (With Anal Training Steps)

Curious about anal sex but unsure where to start? Learn how proper anal training, preparation, and progression can make anal sex safer, more comfortable, and genuinely enjoyable.‍

Anal sex tends to create two pretty decisive camps: people either love it or completely want to avoid it. Although it’s a relatively common sexual practice—at least compared to some of the other kinks we might write about—the majority of people seem to fall into that second camp.

A lot of the time, this is because it completely icks them out, which is fair enough. Others may have had terrible experiences trying it, or they carry fears about messes, anal tears, or enduring a lot of pain and discomfort. Done right, the chances of something bad happening are minimal—and it can feel very, very good for everyone involved.

This article is going to walk you through everything you need to know: the actual risks and how to minimize them, how to prepare for anal, positions to try, and how to train your way up to penetrative anal sex if you decide you want to venture that far.

Why Do People Enjoy Anal Sex?

Let’s talk about anatomy for a second, because anal intercourse feels quite different from vaginal intercourse.

The inside of the rectum is comparatively smooth, whereas the vaginal wall is somewhat bumpy and ridged. As a result, once inside, the head of the penis isn’t stimulated during anal sex in the same way it is in the vagina. You may not feel much at all.

The vagina also tends to wrap more tightly around the penis, creating pressure along the entire length of the shaft and head during penetration. The rectum doesn’t function the same way.

However, anal sex is often described as being “tighter.” This is due to the anal opening having two sphincter muscles—one internal and one external—which grip far more tightly than the vaginal opening.

The vaginal opening is designed to open as a woman becomes aroused and the area fills with blood. The sphincter muscles aren’t. They are primarily designed to stay tightly closed. This means that during anal sex, these muscles are continuously gripping a small section of the shaft of the penis. So while the rest of the penis isn’t being stimulated as it would be during vaginal sex, that concentrated point of contact can still feel pleasurable for both people.

For women, anal stimulation can create a unique sensation that feels pleasurable. There may be a sense of fullness compared to other types of stimulation, and orgasms may feel more intense—especially when anal play is combined with other forms of sexual stimulation.

The real thrill of anal sex, though, isn’t purely physical. It’s the taboo nature associated with the act. It’s a turn-on because it’s seen as naughty and wrong. The rectum wasn’t designed to be fucked.

Anal sex may be experienced as a very dominant act when associated with degradation, objectification, free use, or rough sex. But it can also feel profoundly intimate and emotional when handled with attention and care. It’s often this mental component that makes some people crave anal sex.

That said, you don’t have to like it.

The internet is already awash with articles implying that anal is as normal a sexual practice as “regular” sex. Reading these can be enough to make anyone who doesn’t want to go anywhere near an asshole feel as though they’re lacking in adventurous spirit. If it grosses you out, skip it—and don’t let anyone shame you for doing so.

Personally, the physical sensation of my cock being hugged by a wet vagina is far more enjoyable than the feeling of anal tightness. So I don’t really seek out anal sex at all unless my partner genuinely enjoys it.

How to Have Anal Sex

By practicing these recommendations, you’ll learn how to mentally and physically relax the sphincter, engage in anal stretching without pain, and discover just how good anal sex can feel.

Risks

Thousands of people have anal sex every day without issues, trauma, or trips to the emergency room. It can be done safely with minimal risk, so long as you follow good practices. That said, like anything else, anal sex is not risk-free.

Here are some risks you should be aware of:

• Pain and discomfort: Some mild pain or discomfort during anal sex—and for a short time afterward—is normal. If the pain is anything more than mild, if there is bleeding beyond very light spotting, or if pain persists for more than a day or two, consult a doctor.
• Anal injuries: This is an extreme scenario and is unlikely if you follow sensible precautions and play with care. The anus is not designed to lubricate itself for intercourse, which makes it more prone to painful tears (fissures), bleeding, and tissue trauma. If this happens, you will likely notice pain and blood, and you should seek medical attention.
• Getting toys stuck: A muscle spasm can effectively pull a toy into the rectum, making it very difficult to remove without medical intervention. To prevent this, be judicious about what you allow in your ass. Only use high-quality toys with a flared base or a secure handle.
• Higher risk of sexually transmitted infections: Because the lining of the rectum is thin, it can tear more easily, allowing viruses and bacteria to enter the bloodstream.
• Cross-contamination: Anal play carries the risk of transferring bacteria and other matter from the ass to other parts of the body—most notably the vagina or urethra. This can cause urinary tract infections or more serious complications. Avoid this by changing condoms, gloves, or toys before switching holes.
• Leakage and pregnancy: The chance is small, but semen can leak from the ass into the vagina or be transferred in other ways, creating a non-zero risk of pregnancy.
• Long-term complications: Chronic, untreated, or overly vigorous anal sex can lead to long-term issues such as recurring fissures or, in rare cases, incontinence.

Preparing for Anal Sex

Preparation makes a big difference when it comes to calming nerves around messes, discomfort, or safety. Here are a few helpful steps to make anal sex easier, cleaner, and more enjoyable.

Douching

A douche is a tool you can use to clean your ass before receiving anal sex. This is done by squirting water into your ass and then expelling it, which cleans the rectum and helps ensure there’s a minimum of ick when you later have anal sex.

There are a number of different methods available, but the type of douche I most recommend is a bulb-style squirty douche.

How to Use a Standard Bulb-Style Douche:

1. Fill a sink with water at a comfortable temperature. Err on the side of slightly cool rather than too hot.
2. Squeeze all the air out of the douche bulb, fully submerge it, then release. It will fill with water.
3. Remove the bulb, dry it off, and apply lube to the tip. Lube up your asshole as well.
   Get into a comfortable position. Gently squeeze the bulb until a small amount of water comes out (to expel any remaining air), then insert the tip about an inch into your ass.
4. Squeeze the bulb and fill yourself with a comfortable amount of water. You may be able to take the full bulb, or you may prefer less.
5. Remove the douche.
6. Hold the water inside for about a minute while you move to the toilet, then sit down and release. Bear down gently to expel the water.
7. Clean yourself up and repeat the process until the water you’re expelling runs clear.

Do you need to douche?

Whether or not you douche is ultimately up to you and your partner. Douching can allow you to have anal sex with little to no mess, which can help you relax and make penetration easier.

That said, douching takes time, energy, and equipment, and doing it too frequently or too aggressively can strip moisture from the rectum and cause irritation.

Not douching does not mean you’re guaranteed to end up with shit everywhere. The rectum is not constantly full. In fact, it only contains waste shortly before a bowel movement. The rest of the time, residue is usually minimal.

Fingernails

If you’re planning to insert fingers into your partner’s ass, file down your fingernails beforehand. Smooth nails help prevent discomfort, pain, or tears during entry.

Condoms & Gloves

Using condoms for anal sex helps reduce the slightly higher risk of sexually transmitted infections for both partners. Condoms also help prevent the accidental leakage or transfer of semen from the ass to the vagina.

Gloves are another good option if you’re planning to insert a finger—or fingers (or a whole hand)—into your partner’s ass. Gloves protect any cuts or abrasions on your hands and make cleanup easier. They’re also useful if you want to play with your partner’s ass, remove and dispose of the glove, and then touch them elsewhere without cross-contamination.

Lube

How much lube should you have on hand? A lot of lube.

Apply lube generously to the outside of the condom and to the anal area. If you pay attention during initial penetration, you’ll notice that when you pull your cock out the first time, her ass will have wiped most of the lube off. Because of this, you’ll want to reapply lube two or three times after the first penetration.

If you don’t end up with a big wet patch of lube on the sheets afterward, you were probably using too little.

If you’re not using a lubricant specifically designed for anal sex, there’s a chance it will dry out during play. You may need to pause periodically to reapply for comfort and safety. To minimize this, use an anal-specific lube—and use plenty of it.

Anal Training

Anal training is the practice of preparing the anus for anal play or sex. While the usual end goal is penetrative anal sex, that isn’t always the case.

Especially for beginners, you shouldn’t jump straight into penetrative sex. Instead, go through an anal training sequence, with each step building on the success of the last. Do not advance to the next level until you’re fully comfortable with the previous one.

The benefit of anal training isn’t primarily about stretching the anus to accommodate larger objects. The rectal cavity is actually quite large—larger than the vagina, in fact—so once you’re inside, there’s plenty of room.

Most complications with anal sex arise at the anal opening, which is guarded by the sphincter muscle. This muscle clamps down hard when it perceives intrusion. The key to enjoyable anal play is learning to mentally relax this muscle and become comfortable with something in your ass—relaxing as it goes in and comes out, breathing properly, and gently pushing out to open up.

Once you can do this, anal sex doesn’t hurt, because the muscle isn’t being strained. But this does take practice, which is why anal training is designed to progress from small to larger objects over the course of weeks, while consistently practicing breathing, awareness, and mental relaxation.

Step 1: Talk About It With Each Other

As with anything you want to explore in sex or BDSM, start with a conversation. It’s important to understand whether your partner has had bad experiences in the past so you can navigate the process with sensitivity.

Try asking what it is about anal that turns your partner on—or off—and whether there are any fears or concerns you can address together. Completing a sex menu can also help both of you communicate clearly and identify any limits around different types of anal play.

Bonus: Here’s a free sex menu created on Google Sheets containing over 350 kinky sex acts for you to discuss and rate with your partner. Use it to instantly improve communication in relationships and have a better and more satisfying sex life!

Step 2: Try It on Yourself

Not everyone is going to do this—but if you do, you’ll gain real empathy.

Switch roles and experience it firsthand. Stick a finger in yourself, or use a small toy, and notice how it feels. Nothing will give you a deeper appreciation for what your sub is experiencing than trying these techniques on yourself.

Beyond that, because of the position of the prostate, anal play can be very pleasurable for men. Even if you do it purely for the sake of becoming better, more experienced, and more educated at what you do, this step will teach you more than anything else.

Step 3: Exterior Touches

The first milestone is becoming comfortable with external touch. This can happen during sex or during a session specifically dedicated to anal training.

If you’re introducing it during regular sex, a bit of warning can help. Start by lightly touching or resting a finger on the anal opening. Keep the stimulation brief and check in with your partner to ensure she’s comfortable.

Step 4: Finger Penetration (No Movement)

Once she’s comfortable with external touch, practice sliding your little finger inside her. You must use plenty of lube. This applies to every step from this point forward. Insufficient lubrication will cause pain and discomfort—the exact opposite of what you’re trying to achieve.

Once your finger is inside, keep it still. Don’t slide it in and out. The goal here is to get used to the sensation of fullness and to practice relaxing the sphincter muscle. Movement adds stimulation to the sphincter and can trigger involuntary contractions, which may lead to pain.

How and when you insert a finger is up to you, but I recommend starting while you’re giving your sub oral sex. Clitoral stimulation helps associate anal stimulation with pleasure, making relaxation much easier.

After a few sessions, you can progress to using your index finger for a wider and deeper sensation. At this stage, still avoid sliding in and out, aside from initial insertion and removal.

Step 5: Introduce a Small Butt Plug During Play

At this stage, you want her to get used to the feeling of a slightly girthier object stretching her rectum, without the sphincter being stretched too wide or placed under significantly more strain than it was with your finger. This is where butt plugs come in.

I recommend purchasing plugs with a flared base. This prevents them from disappearing completely inside your ass. Naturally, you’ll want to start with the smallest size, which is typically just slightly wider than your little finger—something she should now be accustomed to feeling inside her.

Take it slow and don’t rush. The plug should slide in comfortably and without pain. If it doesn’t, stop and relax for a minute. Being turned on helps a lot here. You’ll feel the plug going in, and there will usually be a moment where it slips fully into place. Most plugs have a narrow “neck” that the ass grips, which helps keep it seated.

Once the plug is fully in, you can let go—assuming you’re using one with a flared base. The shape should ensure that her ass grips it snugly and doesn’t push it out.

At this stage, don’t leave the plug in for long periods. Aim for five to ten minutes.

Step 6: Increase Plug Size and Build Endurance

Once she’s completely comfortable with the small plug, move up to the next size. It will be thicker and may be trickier to insert, but once it’s in place, the base is usually only slightly wider than the previous size.

Gradually increase how long the plug is worn—from around five minutes up to twenty minutes. At this point, it should still be worn during sexual activity, when she’s aroused.

Only advance to the next size once she can comfortably take the current plug without discomfort.

Step 7: Wearing a Butt Plug for Prolonged Durations

By this point—which will likely have taken several weeks to reach—she shouldn’t need to consciously focus on relaxing. It should be happening automatically. Having something in her ass should feel pleasurable and be associated with positive sensations that increase arousal.

This step is about wearing a butt plug for longer periods of time, including during non-sexual activities, so that the sensation becomes completely natural.

If she enjoys the feeling, she can wear a plug for a few hours without issues. Most plugs fit discreetly under clothing. If it’s been in for a while, you may want to reapply a bit of lube before removing it.

This is also a great opportunity for long-distance or public play. She can pop it in and go about her day.

Step 8: Penetration Training with Dildos

If anal penetration is your ultimate goal, she’ll need to get used to the sensation of something moving continuously in and out of her ass. Up to this point, the focus has been on relaxation, associating anal play with arousal, and learning what fullness feels like.

You should never have to force penetration. If you can’t get something in, the solution isn’t to push harder—it’s to slow down, help her relax more, or return to earlier training steps using fingers, plugs, or smaller toys.

Warm your sub up with anal play, a finger, or a plug, then carefully insert a thinner dildo. Begin by slowly sliding it just a few inches in and out. Over multiple sessions, work toward her being able to take the full length of the dildo and tolerate more continuous movement.

If she starts tensing up, that’s a sign you’re moving too fast and need to back off.

Step 9: Anal Sex

As with dildo training, anal sex is far more enjoyable when the receiver is aroused. You can stimulate her with a clean hand, or she can stimulate herself to help the process along. Most people find anal sex significantly more pleasurable when they’re turned on.

When you first penetrate her, enter only a couple of inches and then stop. Hold still and allow her to adjust to the angle and sensation, which will feel different from a dildo.

Do not try to replicate porn at this stage. Pounding her ass mercilessly is the fastest way to undo weeks of patience and careful training. Accept that you likely won’t be able to thrust the way you want to for quite some time.

Only move deeper once she gives clear consent. Pause again and check in to make sure she isn’t in pain and is enjoying the process. If she isn’t, stop.

Once you’re fully inside her, how things proceed is up to the receiver. Some people find a faster, rougher pace more comfortable than slow thrusting. Others need manual stimulation to enjoy it. Some will find it painful; others won’t. Ask. Experiment. Learn what works for you.

Two Steps Forward, One Step Back

When doing anal training over weeks or months, don’t resume each session exactly where you left off.

For example, if your submissive was comfortable with one index finger inside her during the previous session, don’t start there next time. Take a step back and work your way up again.

Begin with external touch, then your little finger, then your index finger—then progress to the next level, such as two fingers. This approach reinforces relaxation and prevents setbacks.

Positions for Anal Sex

Many first-time receivers assume that getting on all fours is the best position, but that can be surprisingly intense if you haven’t done anal before. It’s also not ideal for staying as relaxed as possible during the process.

A better option to start with is the spooning position—where the receiving partner lies on her side and the penetrating partner lies behind her. This position tends to be far more relaxed and can feel more intimate for a first experience. You can keep your face close to hers, whisper encouraging dirty talk, remind her to breathe, and help her stay aroused and relaxed throughout.

Another popular position is with the receiving partner lying flat on her stomach, with the penetrating partner on top. While this doesn’t give the receiver much control, it’s often more comfortable than doggy style and naturally limits depth, which can make it a good early option.

The opposite variation is to have her lie back on top of you, with her back flat against your chest and her weight resting on your stomach. From here, you can easily reach around and stimulate her clit, which may help her have her first orgasm with a cock inside her ass.

Once she has more experience and confidence, you can start experimenting with doggy style or other more vigorous positions.

Slow Is Smooth, Smooth Is Sexy

Anal sex doesn’t have to be painful, intimidating, or chaotic. When approached with proper preparation, patience, and gradual progression, it can become a deeply pleasurable experience for those who choose to explore it. By respecting the body’s need to relax, training the sphincter rather than forcing it, and prioritizing arousal, communication, and comfort at every stage, you dramatically increase the odds of anal sex being enjoyable rather than endured. If anal is something you’re curious about, doing it right makes all the difference—and if it’s not, that’s perfectly valid too.