Anal Sex Tutorial: An In-Depth Guide for Beginners

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Anal Sex Tutorial: An In-Depth Guide for Beginners

Anal sex… for years it was a taboo subject, even when spoken of in private with your partner. In recent decades, though, anal sex has grown in popularity. And not just among the kinkier crowd, but even the more vanilla couples.

This article will provide a blueprint for beginners, an anal sex tutorial if you will. You’ll learn all about anal sex, tips and tricks for beginners, and techniques for the more advanced crowd. In this article, I’ll also share some great anal sex positions to try.

Okay, now let’s dive in!

What You Need to Know About Anal Sex

Let’s look closely at all angles of the topic… the good, the bad, and the ugly.

The Good

This one’s quite obvious… anal sex feeds good!

There’s this idea that because women don’t have a prostate gland, they don’t get the same pleasure from anal penetration as men do. For many women, though, anal sex is a pleasurable (or even preferred!) sexual experience.

One reason for this is the a-spot, a sensitive spot found deep in the vagina. Anal penetration indirectly stimulates the a-spot which can lead to an intense anal orgasm.

The Bad

Anal sex does come with some medical risks, which I’ll get into more in-depth below.

However, perhaps the most relatable “bad” thing is the discomfort and pain that can be associated with anal training. Even when training in the safest way possible, you’re likely to experience some discomfort.

The only thing you can really do here is to take it slow, pull back when necessary, and have patience.

The Ugly

As the saying goes, “shit happens.”

With anal sex, poop is always a possibility. There are things you can do to reduce the chances of it happening during sex, such as using an enema a few hours prior. However, there is no way to eliminate the possibility of its appearance completely.

Anal Sex: Health and Safety Recommendations

It’s true that anal sex can be a fun and pleasurable experience. However, it does come with some risks. With the proper precautions, though, you can minimize these risks.

Just like unprotected vaginal sex, unprotected anal sex can lead to the spread of sexually-transmitted diseases (STDs). This is especially true for blood-borne diseases, like Hepatitis C and HIV.

The anal lining is much thinner and more delicate than the vaginal lining. It also lacks natural lubrication. This means tears, even small ones, can happen easily which can make the spread of blood-borne diseases more likely.

The good news is you can almost completely eliminate these risks by wearing condoms each and every time you have anal sex.

Anal sex may also increase the incidence of urinary tract infections (UTIs) in both male and female partners. In male partners, anal sex without a condom may introduce bacteria into the urethra. In female partners, bacterial infection may happen if the penis or sex toy is inserted in the anus and then inserted in or near the vagina.

So once again, the recommendation is to wear condoms and practice common sense.

10 First-Time Anal Sex Tips and Tricks

If you’re preparing for your first time receiving anal sex, you may be nervous. The tips below will help to ease your concerns and prepare you so you can have an enjoyable experience.

1. Relax

Relaxation is important for anal sex. After all, tensing of the anus will only make anal penetration more painful. And you don’t want your first memories of anal to be painful or else they may be your last.

Anal training (more on that below) will help with physical relaxation. Beyond that, you can also focus on breath training and full-body relaxation techniques (i.e. clenching and then releasing all muscles in the body).

2. Communicate

Intimacy and sex of any kind require clear and direct communication. This is perhaps more so important for anal sex if pleasure is the goal.

Share your concerns and fears with your partner and, if they have any, ask them to do the same. You should also openly discuss expectations so you can level set.

The most important thing here is that there are no surprises.

3. Start with Anal Training

Anal training is the practice of training the anus and the anal muscles to relax during anal penetration. This is necessary because the anus is not biologically meant to be penetrated, so it requires a bit of training to get it ready.

There are two main benefits to anal training:

  1. The prevention of injury to the anus and the surrounding tissues.
  2. An increase in pleasure during anal penetration and anal sex.

So how do you get started with anal training?

First and foremost, find a lubricant you like. We’ll cover lubricants more in-depth in a later section. Second, create a plan of action whether that’s anal training by yourself, with a partner, or a mix of both. Third, practice proper hygiene by cleansing the anus, trimming your nails, and washing your hands after each session.

Whether training by yourself or with a partner, I recommend a four-step approach that includes anal fingering:

Step 1

Insert your lubricated fingertip into the opening of your anus. Press down and hold for five seconds. Then push upwards and hold for five seconds. Repeat four or five times.

Step 2

Insert your lubricated fingertip up to the first knuckle. You’ll feel a muscle constricting around your finger – that’s your external sphincter. With your finger still inserted, bear down as if you’re using the restroom. You’ll feel the external sphincter release.

Ultimately, you’ll be able to relax the external sphincter naturally. However, it helps to know the sensation so you can practice.

You will also notice a continued constriction on your finger. That’s the internal sphincter. This is normal as the internal sphincter cannot be controlled voluntarily. However, as you continue training, it should learn to relax.

Step 3

Now slowly insert more of your finger inside your anal canal.

As mentioned above, you can’t force your internal sphincter to relax. But there is a special breathing technique that can help.

  • Inhale deeply through your mouth for two seconds, taking in as much air as possible. Then, slowly exhale through your nose, counting to five seconds as you do.

Repeat this five to ten times.

Step 4

The main goal of anal training is to get you to the point where you can take the girth of the average-sized erect penis. You can mimic this by inserting two fingers into your anus at once.

You can follow steps one, two, and three again, only this time with both your index and middle fingers together. Once you reach stage three and are able to slide both fingers inside your anal canal, you can curl your fingertips and move your fingers back and forth to help the internal sphincter muscles relax and stretch.

If you need to prepare for a larger penis or want to train yourself to accept a larger toy, you can repeat the above with three or even four fingers.

Reminder: If at any point you feel pain or discomfort, stop the exercises and resume at a later time. It can take longer for some people than others to train their anus to stretch. Listen to your body.

4. Foreplay

The anus doesn’t naturally lubricate itself, so no amount of foreplay or arousal will prepare your anus for sex. However, arousal can help you to relax your body (and, as a result, your anus) and make anal penetration more pleasurable.

What do I recommend for foreplay? Foreplay preferences vary, so take time to explore the different options with your partner.

  • Talk dirty to each other
  • Send naughty text messages
  • Dress up in lingerie
  • Have a makeout session
  • Watch adult entertainment
  • Read erotic literature together
  • Play sex games
  • Roleplay different scenarios

As you and your partner get more aroused, you can begin to get more physical. For example:

  • Use your fingers to trace your partner’s curves
  • Nibble on their ear lobe
  • Ask your partner to suck your nipple or rub your clit
  • Tease your partner by brushing against their lower stomach and upper thighs but avoiding their genitals

Once you’re fully aroused and ready for more, it’s time to move on to anal play. It doesn’t have to be full-on anal penetration to start. Just try to incorporate anal play more regularly in your intimacy to get used to the sensations.

5. Use High-Quality Lube

Lubricant is a must-have for most types of sexual activity, but especially anal.

Not all lubricants are created equal, though. There are different types of lubricants, all of which have pros and cons. The main types of lubricants are:

  • Water-based lube
  • Silicone-based lube
  • Oil-based lube
  • Desensitizing lubes

Here’s a brief breakdown of each.

Water-Based Lubes

Water-based lube is often considered to be the most universal type of lubricant. It can be used in any orifice, and it’s also compatible with sex toys (of all materials) and condoms. Water-based lubricants are also easy to clean and non-staining.

The greatest downside of water-based lubes is they don’t last as long as other types. This means frequent reapplication is necessary, especially when it comes to anal sex.

Silicone-Based Lubes

If you want a longer-last lubricant, then silicone-based is the way to go. Silicone lubes are also hypoallergenic, so great for those with sensitive skin. And like water-based lubricants, they are safe to use with any type of condom.

The one downside to silicone-based lubes is they are NOT compatible with silicone sex toys.

Oil-Based Lubes

For the longest lasting lubrication available, oil-based lubricant is the way to go. However, while you’ll benefit from the longevity, they are NOT compatible with latex condoms.

Oil-based lubricants are also staining. They can also clog the pores which may cause irritation or ingrown hairs.

Desensitizing Lubes

Desensitizing lubes are a water-based lubricant, but I though they deserved their own mention on this list.

These types of lubricants have special ingredients which temporarily numb the area. They also reduce friction.

Desensitizing lubes should NOT be used by beginners. Pain is your body telling you when you’re pushing past your limits and this is important to know as a beginner so you can avoid severe injury and scarring.

6. Take It Slow

Whether you’re completely new to anal sex or you’re a seasoned vet, it’s always a good idea to take it slow at the start. This is, of course, even more so important for beginners as their anal muscles need time to accustom themselves.

What does this look like?

For starters, ensure you and your partner are comfortable and aroused. It also means not pushing yourself or your body past its limits. It’s possible to be mentally ready but not physically ready, and the reverse is also true. So listen to your body and only go as far as it allows.

During one session, that may mean only using a finger or two to penetrate the anus. Or maybe just the tip of a dildo or penis. Just remember to continue to communicate with your partner and stop when you need a break.

7. Don’t Forget Other Stimulation

It’s easy to focus solely on anal penetration when you’re a beginner. But you don’t want to forget about other stimulation which you can do while also being penetrated anally.

You may think this will take away from the pleasures of anal penetration. However, stimulation of the nipples, clit, or vagina can only add to the experience.

If you’re alone, then you may have to get creative with your approach. Sex toys are an option, and there are even some that penetrate both the vagina and the anus simultaneously. You can also use an anal dildo or vibrator and use your hands to touch yourself elsewhere.

With a partner, you have a few more options. If your partner is penetrating your anus, they can reach around and play with your nipples or clit. You can also play with your nipples or clit, or even penetrate your vagina with your fingers or a dildo.

8. Know Your Limits

As you experiment with anal training and, eventually, anal sex, it’s important to know your limits.

You won’t be able to take your partner’s full girth and length overnight. That’s not a failure on your part. Anal training can take weeks, or even months. So give yourself permission to enjoy the journey as you safely explore anal penetration.

And while it’s important to know your limits, you should also take time to reevaluate them every so often.

In the beginning, the idea of taking your partner’s penis can seem daunting. But eventually you’ll get there. In the same vein, you may be able to take more in the future than you ever anticipated. So if you’re looking for more, don’t hesitate to attempt greater lengths and depths as you get more comfortable.

Advanced: Anal Sex Techniques

Once you feel comfortable with anal penetration, you can consider more advanced techniques like those below.

Bring in the Toys

Toys are a great way for beginners to become accustomed to anal penetration as they can control the girth, depth, and speed. However, there are also anal sex toys for those with more anal experience.

Butt Plugs

For beginners and advanced alike, butt plugs can be a fun way to spice up things in the bedroom. They can also help to prepare you for the upcoming night’s events if you put them in a few hours before you get started.

Dildos

Anal dildos are a special type of dildo with a flared base. It’s important to only use anal dildos in the anus as dildos with non-flared bases can get lodged in the anal cavity and even travel up into the colon.

The great thing about dildos is their variety. You can find anal dildos in just about any girth and length combination, from the typical male size all the way up to horse size.

These are a fun way to incorporate anal play into your own solo time, or to use during vaginal intercourse with your partner.

Anal Beads

Anal beads are perhaps one of the most pleasurable anal sex toys out there. With anal beads of almost any size, as well as vibrating anal beads, you can have fun alone or with a partner.

And because the size of anal beads increases incrementally, they can be used by people with most levels of anal training experience.

Prostate Massagers

For men looking for a good time, the above toys are certainly useful. But there’s something about prostate stimulation that brings anal play to a whole new level.

Enhance your sex life. Close up of silicone prostate massager on a black silk fabric. Male sex toys

Prostate massagers come in many different styles, including those that attach to the penis like a cock ring, those that look like dildos, and those that vibrate.

Fun with Fisting

Even if you’ve never cummed directly from anal penetration, you may just enjoy the feeling of fullness. That’s definitely something that anal fisting can achieve.

Fisting should only be practiced by those men and women who have sufficient experience with other types of anal penetration. After all, fisting is probably the most girth you’ll ever take anally.

Even with that experience, it’s a good idea to prepare yourself in the days leading up to a fisting. Use various sizes of dildos to increase your anal canal’s stretching abilities. You should also work the dildos in circles to further stretch the external sphincter.

Never exceed your limits. If you try fisting for the first time and it’s just not happening, then back off and continue to prepare over the next few days. You never want to force anything larger than you can take into your anus as this can cause irreparable damage.

Pegging for Pleasure

When discussing anal sex, it’s often seen in one of two ways: between a male partner (the giver) and a female partner (the receiver) or two male partners. However, pegging allows the female partner to be the giver to either their male or female partner.

Pegging is the act of penetrating a partner’s anus with a strap-on dildo. This way the receiver can experience anal sex just as they would if their partner had a penis.

While heterosexual men may be initially hesitant to try pegging, it’s a great way to increase intimacy between partners. This is especially true if the female partner has recently prepared for anal sex herself and she now wants her partner to experience the same pleasure.

Anal Sex Positions for Beginners

Now that you’re ready for anal sex, what are the best positions for beginners? Use these positions as an anal sex tutorial and you’ll be sure to have a good time.

Laying Down Doggy

The receiving partner lies face down on the bed. The giving partner enters from behind and uses their arms to hold themselves up. The receiving partner can shift their hips forward or backward to vary the depth of penetration.

In the Laying Down Doggy position, the penetration is shallow.

The majority of the nerves in the anus are within the first two inches or so. Beyond that, the receiver may feel pressure but not necessarily pleasurable stimulation. So shallow penetration is a treat, especially for beginners who are hesitant about going too deep.

Lap Dance

The male partner sits on the edge of a chair or bed. The female partner, facing away from the male partner, eases herself down onto the penis.

This position is great for beginners who are looking for deep anal penetration but who still want to control the speed of their partner’s thrusting. In the lap dance position, the female partner is largely in control of the movements. This can help her to discover the types of anal stimulation she enjoys most.

Spoon

The receiving partner lies on their side. The giving partner lies directly behind the receiving partner and facing toward their back. They then enter from behind.

You may think facing away from your partner decreases the intimacy, but the skin-to-skin contact in and of itself is highly intimate. This position also makes it easy to stimulate the clit of the receiving partner while they’re being penetrated.

Anal Sex Positions for Advanced

The anal sex positions below are for anal penetration that is deeper and that gives the giving partner more freedom to thrust.

Reverse Cowgirl

The giving partner lies on their back. The receiving partner positions themselves facing away from the giving partner and shimmies themselves into a kneeling position and onto the penis.

The best thing about this position is the receiving partner’s ability to control the depth and thrust speed with ease. They can lift themselves up higher for a more shallow depth or grind down further for a deeper level of penetration.

Standing Doggy

The giving partner stands directly behind the receiving partner. The receiving partner bends over at the waist. The giving partner enters from behind. For greater leverage, the receiving partner holds their arms to their sides so the giving partner can hold onto the wrists.

This position is a fun foray into BDSM as the giving partner exerts a certain level of control. Of course, be sure to set boundaries with your partner before you begin.

The Intimate Launch Pad

The Intimate Launch Pad position is quite… intense. This is why it should be reserved for those who are used to anal penetration but looking for something more sensational.

The receiving partner lies on their back and holds their legs up with their knees bent. The giving partner will kneel in front of you and enter.

This position is one of the more advanced ones as it requires you to be able to take the full length of your partner.

Anal Sex: The Three Elements Most Important to Pleasure

If you’ve attempted anal sex multiple times but it’s just not doing it for you, the reason may come down to these three elements. That is, you’re not hitting one or all of these elements and it’s throwing you off your game.

The three elements most important to anal pleasure are:

  1. Anal positioning
  2. Penetration angle
  3. Stroke speed and length

The good news is that all of these elements are fixable with experimentation.

Anal Positioning

Here you can experiment with different anal sex positions like those mentioned above.

Start somewhere in the middle and experiment with your partner by changing the position of your anus slightly, either up or down. You both may have preferences, both in terms of comfortability and pleasure. However, the receiving partner should certainly get more say in positioning as it’s a huge factor in how much they enjoy anal sex.

Penetration Angle

Once you’ve found an anal position you’re both happy with, it’s time to consider the angle of penetration. This will require some work from the giving partner as they work to change the angle with new body positions.

If the receiving partner is laying down, then the giving partner can adjust themselves higher up for a shallower penetration or lower down for a deeper penetration. If the receiving partner is standing up, then the opposite is true.

Experiment with different body positions for both partners until the penetration angle is just right.

Stroke Speed and Depth

Stroke speed and depth is probably the easiest element to control. It’s also one of the more fun elements to experiment with.

Start off with short, slow strokes until you get into a rhythm. Slowly work up to faster, deeper strokes. Do you or your partner have a preference for either one? Do you both prefer to alternate (first going slow, then fast, then slow again)?

There are no wrong answers here. Just have fun experimenting until you find what works for you.

Conclusion

There are often a lot of preconceived ideas around anal sex, including who has it and why they do it. Far from the depraved, sex-crazed individuals that some will have you believe, anal sex is for anyone who enjoys a good time and who’s looking to explore other types of pleasure in the bedroom.

Whether you’re a beginner or advanced, we hope this anal sex tutorial will give you some new ideas to spice up your sex life.

Laura Rose Halliday

Laura Rose Halliday started The School Of Squirt back in 2012 and has been running the website and digital courses along with Jakob Wulfe since then. She is a full time sex writer, researcher and practicer.


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