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How to have painless anal sex: tips and tricks

By: sextoys.co.uk

How to have anal sex

It's the most wonderful time of the year. In celebration of Anal August, we've gathered a list of steamy tips for embarking on your first booty adventure in a safe and painless way. Although some people are nervous to try it, exploring anal play can open up a whole world of pleasure and intimacy between you and your partner.

What is anal sex?

Anal sex is generally the act of an erect penis or strap-on penetrating a person’s anus. It can also be any anal play involving mouths, toys, or fingers. People of all genders everywhere love anal stimulation with the tongue and lips, known as rimming.

The receiver of anal sex can be any gender. However, in cisgender men, anal sex can massage the prostate, which is known as the male G-spot, and create a new kind of orgasm. 

Preparing for painless anal sex

Unlike the vagina, the anus is not self-lubricating. It can also tear more easily due to having thinner walls, so anal sex prep is key. The sphincter sits inside the anus and is a powerful muscle. This muscle tightens up when it's not ready, so you need to coax it into relaxation.

That can be accomplished through practices like good hygiene, breathing exercises and lots of lube. Oh, and plenty of time getting hot and bothered by your partner.

Clean nails and hands

Most anal sex, especially for beginners, will need to be prefaced with some fingering. For that reason, hands should be and nails should be short and filed smooth without any rough edges.

Relax

The first step in understanding how to prepare for anal sex is relax, relax, relax! Relaxing the mind will lead to relaxing the body and will stop you from “tightening up” down there. 

Start with deep, slow breaths and give the person who is receiving penetration a sensual rubdown. Rub the inner thighs, lower back, and butt cheeks before arriving at the entrance of the anus for the ultimate anal massage.

Once the sphincter has slightly loosened up, it’s time to move on to foreplay.

Foreplay

Don’t be afraid to take your time with long anal foreplay. Low and slow is the best way to get heated up for this act, so keep things on simmer for a while and don’t rush. Rimming is a great way to please your partner without penetration and introduce them to sensation during anal play.

The anus is a treasure trove of nerve endings that are begging to be woken up by hands, mouths, and more. 

Explore rimming first

Play with your tongue to arouse their bum, and don’t be afraid to use your hands (or a vibrator) on other body parts as well.

Stimulating erogenous zones like the vulva or penis before or during anal sex can add a new level of comfort and enjoyment to your session. Explore lighter anal play. This can be done via rimming or stimulating the outside of the anus with fingers and anal toys. This can help set the mood for insertion, arousing the receiver.

Communication and consent

Rather than just a yes, it should be an enthusiastic “Oh yeah, baby!” to ensure that everyone is having a good time. Coercion is not okay. There’s also no shame in acting questions—in fact, this can be just as hot as dirty talk!

Asking your partner what they’re enjoying or not enjoying can hone the technique and make for a smoother session next time. It creates a comfortable, safe space that makes them feel their desires are being listened to and addressed. Use a safe word to establish and vocalize boundaries. 

Many people use cues using the traffic light system. For instance, green means keep going, red means stop, and yellow means that it might be time to pause and communicate.

You can also have your partner play with themselves. Practice makes perfect, and there’s nothing like some sensual solo play to offer constructive feedback!

How to have safe anal sex

Is anal sex safe? If you take the right measures, absolutely! There are two definitions for safe anal sex: it should be pain-free, but it should also protect you from bacteria and STIs. 

Injury prevention

Overly rough anal sex or not using enough lubricant can result in bleeding, tears, and more. Even if you follow best practices, be on the lookout for injuries. Most importantly, do NOT work through the pain! Anal training takes time.

Infection prevention

If you experience unusual discharge, warts, or sores around the anus in the days following sex, it could mean you’ve contracted an STI. If you’re unsure of your or your partner’s status, it’s best to use a condom for penetration or a dental dam for rimming. 

Say no to cross-pollination

If you’ve done anal penetration first, never switch to vaginal penetration after without either switching condoms or thoroughly rinsing off in between. This can prevent the spread of bacteria. 

Don’t use numbing creams

Although some penis owners like to use numbing cream to last longer during sex, this can be hazardous during anal play. It can increase the risk of injury and stop your body’s pain signals from indicating that something is wrong. When you’re numb, you can’t tell what damage is being done. Instead, listen to your body in its natural state.

How to have clean anal sex 

Although addressing this isn’t necessarily the sexiest part of anal, it is critical to address it. After all, hygiene is hot! There is some stigma that anal sex is “dirty,” but this is not the case. If this idea is holding you back, there are several measures you can take to make the experience more enjoyable.

Try to have a bowel movement

Don’t force yourself, but if you can manage to, use the bathroom before you get started. It can make for a cleaner and more comfortable experience.

Take a shower or bath

Using a gentle soap and a clean cloth, clean the area while in the shower. Don’t be afraid to soap up a fingertip to clean the entry of the anus before rinsing off. Be extra-gentle and use a mild soap because this is a delicate area.

Enemas and anal douches

An enema is a handy tool that introduces water into the anus and rinses out the area. An anal douche does the same. These devices are often used before and after, but it’s important to note that they should be used at least two hours before your rendezvous rather than immediately before.

Condoms

To avoid fecal matter from spreading, consider wearing a condom during anal sex, which also protects against STIs. Condoms are also a must if you plan on switching between anal and vaginal sex - remember to dispose of a condom and put on a new one before you switch!

Baby wipes on hand 

Don’t have shower access? Wipe the area beforehand or during play with unscented baby wipes. This is basic etiquette if you’re going to be on the receiving end of some rimming.

Clean sex toys after use

Always clean your sex toys after use with an antibacterial toy cleaner or warm water and antibacterial soap. This is especially important for toys that come into contact with fecal matter. Otherwise, you can spread bacteria and potentially contract an infection.

How to have anal sex for the first time 

The first step to pain-free anal play is lube. Lots of lube. The wetter the better. When it comes to penetration, always work your way up slowly in size.

Don’t start with the penis - instead, generously lube up one finger and slowly insert it. If this feels good, add another finger. Once you’re ready to add a third, you can experiment with penetration. Begin with “just the tip” before going any deeper.

Prioritize pleasure over orgasm

If you orgasm from anal play, great! But making it about the destination versus the journey can place pressure on everyone. Get out of your head and focus on the individual sensation rather than having a goal-oriented mindset.

Anal sex positions

Just like for vaginal sex, there are different strokes for different folks. Preferences vary, and as a result, so will positions. Here are some popular anal sex positions for beginners and beyond.

Receiver on top

If you’re a beginner, being on top is the best position for anal sex. You can control the speed, depth, and rhythm of the movement, customizing how you feel.

Spooning sex

This is another position that puts the receiver in control. It lets them push back against the penis or sex toy rather than solely having a partner thrust into them. Spooning requires less muscular engagement than being on top.

Doggy style

If you’re comfortable giving up a bit of control, this position can be incredibly erotic. Decide on a safe word or specific body language with your partner. This will signal if things are getting too intense since your partner can’t see your face.

Laying flat on your stomach

Many vulva owners enjoy masturbating on their stomachs. It can open a whole new realm of pleasure to stimulate the vulva with hands or a toy during penetration. Plus, the view isn’t too shabby for the person penetrating, either!

Do women like anal sex? 

Not everyone has had a great anal sex experience. This might be because their desires, boundaries, and comfort zones were not acknowledged. With tenderness, sensuality, and taking things slowly, anal sex can lead to some mind-blowing sensations and orgasms. 

Cis women don’t have a p-spot like men, but they do have many nerve endings. It can also be erotic to explore what many consider a ‘taboo’ or submissive experience. 

Booty play can be a pleasurable alternative to vaginal sex when cis women are menstruating. In fact, some women report that wearing a menstrual cup during anal sex can be a game-changing, euphoric bonus. 

That said, this is a personal choice, and not all women are the same. Rimming and fingering are also forms of anal sex for women who don't enjoy anal penetration.

Can you get pregnant through anal sex?

Although many people have anal sex to not get pregnant, there is a chance that semen could drip into the vaginal canal. It’s highly unlikely but not impossible, so using a condom is best. Doing this will also make the cleanup process a breeze.

Best lube for anal sex  

Beyond consent and taking things slowly, lube is the most important part of anal play. It eases friction and creates the groundwork for pleasure to happen. It’s a myth that using too much lube takes away friction and, hence, pleasure, so don’t be afraid to be generous!

Using a lube tube can also help dispense lubrication more precisely. These tubes reduce the likeliness of a mess, which is helpful with oil or silicone-based lubes that can stain bed sheets.

Silicone based lube

Due to its long-lasting and plush nature, silicone based lubes like Swiss Navy Premium Anal Lubricant are often considered the best lube for anal sex. They don't require reapplication and have a silky feel.  You can also use them with latex condoms.

Swiss Navy Premium Anal Lubricant

Swiss Navy Premium Anal Lubricant

Water based lube

Although popular with vaginal sex and safe for latex condoms, water-based lube doesn’t last as long as a silicone onr. Interrupting for reapplication can ruin the mood, but if you’re using anal sex toys, it’s a safer option. There are also thicker water-based anal lube formulas like JO H2O Anal Thick designed for this purpose.

JO H2O Anal Thick

JO H2O Anal Thick

Hybrid lube

Hybrid lubricants are a combination of water-based and silicone-based lubricants. Combining the best of both worlds, they’re the holy grail of anal lube. They’re safe for all sex toys and condoms and provide long-lasting moisture.

Warming lube

Warming lube and arousal serums can bring more blood flow to the anus and boost stimulation. Using one can wake up all those delicious nerves and help bring you to ecstasy. Flavored lubes are also fabulous for rimming and are available in different formulas.

Using anal sex toys 

Variety is the spice of life, and there's no shortage of it with anal sex toys. These products come in every shape, size, and material, providing different sensations for every experience level. Most anal toys have a flared base so that they don’t disappear inside you.

The sphincter is a powerful muscle that can act as a vacuum, so this is absolutely a possibility. ER doctors have plenty of stories about this, so remember only to insert toys that are explicitly labeled as anal-safe!

Anal training toys 

Anal training kits or dilators contain several sizes of graduated anal plugs, like this set by The One. They are designed to relax and romance the sphincter. These kits can be a helpful tool for any beginner. They're versatile for use alone or with a partner.

The One Anal Plug Set

Get 40% Off The One Anal Plug Set

Butt plugs 

Butt plugs don’t just help you explore penetration; they are designed to stimulate the opening of the anus, which can be incredibly sensitive. Instead of moving in and out, they nestle inside and sit there. Beginner plugs like this one by Luxe are slimmer and more approachable to start with.


This can create a sensation of fullness and rub against you from the inside out. Most plugs have a narrow tip that gets larger before tapering back down before the base. However, more advanced plugs may have different shapes that you can explore with experience.

Luxe - Beginner Plug

Luxe - Beginner Plug

Glass anal toys

Glass anal toys are durable, easy to clean, and allow you to explore temperature play. They retain heat or cold, and a warm introduction to penetration might be just what you’re looking for. They’re more lightweight than metal toys and have an eye-catching design, which makes them one of our bestsellers. The Chrystalino Doubler, which is currently on sale, offers two plugs in one.

Chrystalino Doubler

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Metal anal toys

Like glass toys, metal butt plugs are perfect for temperature play. However, they have more of a weighty feel, adding to the sensation of fullness. Aluminum plugs (like this Rose Gold Heart) are lighter than stainless steel plugs. Unlike silicone toys, you can safely apply silicone lube to metal and glass toys. 

Rear Assets - Rose Gold Heart

Rear Assets - Rose Gold Heart

Inflatable anal toys 

Whether you’re unsure of girth or savor the feeling of a toy gradually expanding inside of you, inflatable anal plugs slowly inflate with each pump. Inflatable butt plugs are perfect for those exploring anal stretching or looking for personalized pleasure. Starter products like the Booty Call Booty Pumper are a great alternative to training kits.

Booty Call Booty Pumper

Booty Call Booty Pumper

Vibrating anal toys 

As mentioned before, the entrance of the anus is packed with sensitive nerves. The result can be insanely satisfying when you add vibration into the mix. Some even perform a thrusting motion

The most popular vibrating butt plugs use materials like silicone, but you can also find options made from glass or steel. Some toys even contain rotating beads to simulate the sensation of rimming. 

Anal beads 

Anal beads are vibrating or non-motorized series of beads that make you shudder with pleasure. They feel just as good coming out as they do going in, which is why many people love them.

The beads may get larger in size to create a more intense feeling during insertion.  Some, like these Black Silicone Anal Beads, are more flexible, while others are larger. Advanced users may want to explore larger or longer beads.

Black Silicone Anal Beads

Black Silicone Anal Beads

Prostate toys and pegging 

For cisgender men, when the prostate is stimulated in the right way, it can create an explosive and full-body climax. Many vibrating anal toys are specifically designed to stimulate the prostate. Some even come with remote controls, which makes them easier to control while inserted. Remote-controlled toys also allow you to play with power dynamics and edging.

Looking to explore gender role reversal? Cis women can do pegging via wearing a strap-on harness to penetrate their partner. As with any anal play, slowly work your way up in size. This is especially important for those who haven’t tried this before.

Anal Adventures Platinum - Silicone Vibrating Prostate Massager 04

Anal Adventures Platinum - Silicone Vibrating Prostate Massager 04