FREE Shipping on orders over $59
Anal Sex For Beginners: Tips, Tricks & Advice for Anal Sex

Anal Sex For Beginners: Tips, Tricks & Advice for Anal Sex

Anal sex is kinky, exciting, and a bit scary all at once. If you’re considering it, wonderful! Anal sex, done the right way, can be an amazing experience. In fact, it could transform your relationship with your sexual partner. On the other hand, anal sex inspires a bit of fear for a reason. If you aren’t careful, anal sex can be painful and uncomfortable. 

If you want the kind of anal sex experience that leads to amazing orgasms and heightened relations, keep reading. This anal sex guide will tell you exactly how to do anal the right way starting with sex toys for anal, the most important accessory for anal play pleasure.

Everything You Need to Know About Anal Sex: Fundamentals

When it comes to anal sex, people develop their own style and preferences. Still, there are some ‘ground rules’ so to speak. You’ll have a much better time if you understand these anal sex basics.

Later, you can check out some more detailed information on different positions and other techniques. We’ll even cover the matter of hygiene. Learn how to clean for anal sex before you go any further. It’s time to learn how to do anal sex.

Starting With The Pros And Cons of Anal Sex

The process of discovering and mastering anal sex is definitely an exploratory one. You’ll learn quite a bit about your body and preferences, and your partner’s as well. You’ll also find that there are good and bad points to anal sex.

Anal Sex Pros

Pros Cons

The Best Anal sex is kinky and exciting.

Let's be honest, anal sex feels a bit forbidden. It's kinky, and a little dark. They are definitely associations between anal sex and the BDSM scene.

Also, it's just fun to try something new with your partner. Many men in particular are very turned on by the idea of their partner allow them to have anal sex with them.

Many people experience intense and different orgasms.

Your anus is full of nerve endings. In addition to this, engaging in anal sex is a great way to stimulate your G spot. You may have intense orgasms, like never before. Start by trying anal beads to feel the exuberant orgasmic impact that butt toys have to your pleasure. What are anal beads? All you need to know to start is that anal beads are WAY smaller than a male penis!

It gives you a new option for sex.

Simply put, anal sex allows you to add something new to your usual routine. It can even be used in role reversal, called pegging.

Nobody will get pregnant.

Obviously, there’s no risk of pregnancy here. For some people, this idea allows them to relax and enjoy sex a bit more.

Anal Sex Cons

You have to plan ahead.

You can have anal sex whenever you want. But, most people like to engage in some planning and preparation to ensure that they are physically and mentally ready for it.

You may feel pressured to have anal sex.

It’s difficult to imagine enjoying anal sex if you are only doing it for your partner. You might even feel resentful.

You might hate it.

Let’s be honest, this is a sex act that takes awhile to get used to. Some people just never learn to like anal sex. Unfortunately, you might try it, and simply hate it.

Do you want to have anal sex?


This is really something to consider. Many people, especially women, are particularly interested in anal sex. Instead, they agree to try it out in order to accommodate their partner's fantasies.

Here, it's important to find balance. it's wonderful to be kinky and to be willing to try new things, even if you aren't sure about them. On the other hand, you aren't going to enjoy anal if you do it begrudgingly or feel pressured. If that's the case, start with a vibrating anal dildo which is a smaller version of an erection making your experience more enjoyable.

Also, you may try anal and decide you absolutely hate it, and never want to do it again. That's fine as well. You might also find that you enjoy other types of anal play, but not full on anal intercourse.

You Need The Right Lube For Anal Sex

Anal sex and lube go hand in hand. In fact, you should never try anal without a great lube. Experiment a bit until you find what you want. For full details check out my list of best anal lubes but for a quicker summary to help you get started, here’s a breakdown:

Water-Based Lubes For Anal

Slippery water-based lubes work with condoms and sex toys. They are the easiest when it comes to clean-up. The only downside is that water-based lubes tend to run dry quickly making reapplication necessary, just when you’re in the zone. Rear entry anal lube is a water-based lube with a desensitizing agent. Consider combining it with a regular water-based  lube for ease of insertion without too much numbing.

Oil-Based Lubes For Anal

An oil-based lube tends to be thick. It will stay in place, and often gets slicker when friction increases. Of course, you cannot use oil-based lubes with a condom, and should only use them with a sex toy if the manufacturer says it’s okay to do that. Check out Petroleum anal lube.

Silicone-Based Lubes For Anal

Silicone lubes are slick, and they last a long time. That’s good, because you may need something that has endurance for your first time, when insertion will take awhile.  It’s also safe for condoms. If you decide to take the dive with a toy, stay away from silicone. A silicone-based lube will damage your sex toys. There are several silicone lubes made specifically for anal, including ID Backslide.

Safety Rules For Anal Sex

Anal sex doesn’t need to be excruciating, and there shouldn’t be blood. If you do experience a bit of pain and tearing, that’s your sign to slow down. Try changing things up. Use more lube, or a different kind. Try a new position.

Also, it’s perfectly fine to give up, and try again another time. Don’t bear down and endure pain and discomfort just to get through your first time. Instead, follow the advice below to make even your first time pleasurable. Eventually, you’ll learn how to make anal sex less painful. Start solo - check out the list of the all-time best butt plugs for ideas on which have the best reviews and people like most. You'll certainly find your favorite here.


Relax And go Slowly to Avoid Pain

It’s time for some expectation management. The first time you have anal sex, insertion could take 30 minutes or longer. In addition to that, you may only get the first inch or so in on your first try. That is completely normal. What isn’t normal is painful anal sex. Apply lube with an anal lube injector first to make sure you targeted the entire rectal canal.

To make the best progress try to relax. Engage in lots of foreplay. Ask your partner to give you a massage. If you drink a glass of wine could take the edge off. Don’t get inebriated. That’s a bad idea during this delicate process.

Consider Anal Training

Buy an anal training toys set to get started on the right foot. It can take time to prepare yourself to accept the insertion of a penis. In fact, some people simply cannot take in something of that size the first time. Obviously, this is even more the case if your partner is well-endowed. You might consider anal training, try an anal toy first because they are smaller than your partner's erect penis. 

This is an anal sex technique where you physically prepare your body for anal sex. Basically, you begin by inserting something small, like a finger or a toy. Then, once you can accommodate that easily, you change over to something bigger. Anal training can take a couple of days, or a few weeks.

Some couples engage in anal training using the one finger, then two fingers method. You can also purchasestarter anal toys.

Anal Training Toy
One of my favorite toys for anal training.

Numb Very Carefully

It’s tempting to simply numb the anal area entirely to make your first time as painless as possible. Once again, please understand that this is a bad idea. Some numbing is a good thing. However, pain during anal sex is very important. It’s your signal to stop or slow down, and to check for any damage. Pain is an important signal, and you should pay very close attention to it.

Anal Sex Positions

There is no right or wrong position for anal sex. Yes, doggy style is quite popular, but it’s just one option. What works for you depends largely on your preferences. Here are some positions to consider as you explore the best way to have anal.

Cowgirl: When you are on top, you can control the angle and depth of insertion. There’s also no danger of your partner thrusting to deep or too hard. The downside is that you  have to focus on your balance and angle, while also taking on the job of insertion and thrusting.

Reverse Cowgirl: You’ll still have to handle balancing, moving, and insertion. However, you may feel a bit more stable in this position.

Flat Doggy Style: This position allows for penetration that isn’t so deep. This could help with your comfort levels during your first time. Just remember that this is a very passive position for you. So, be prepared to verbalize how you are feeling, and what you want your partner to do.

Classic Doggy Style: This is a classic for a reason. First, neither of you is bearing the weight of the other. From their position, your partner can see everything that’s going on back there. They can let you know when they are in, and how deep. This is also a great position for deep and fast thrusting, once you are ready for that.

Spooning: This is a wonderfully lazy, relaxed way to have vaginal intercourse. It’s also a nice alternative to anal sex. Here, you simply lay on your side, back to chest with your partner. Then, they left your upper leg with their arm, and penetrate you from behind. Because neither of you is bearing any weight, you can focus solely on penetration, thrusting, and how the experience feels.

Knees to Chest: Of course, if you are very flexible, this position might be called ‘ankles behind your ears’. This is a great position if you want to enjoy very deep penetration. Just know that it puts your partner in charge of insertion and thrusting. Again, be prepared to give plenty of feedback and anal sex instruction.

Finger Sleeves
The perfect (and cleanest) way to enhance anal sex.

Enhancing Anal Sex

Anal sex shouldn’t be an exercise in tolerance that  you endure for the benefit of your partner. It can and should be an amazing experience for both of you. Check out these tips for anal sex:

  • Try to orgasm first. Engage in oral sex or vaginal sex, or play with a vibrator before you start attempting anything anal. When you start, you’ll already feel relaxed and satisfied.
  • Use vaginal stimulation during the act. As your partner penetrates you, try to increase your pleasure by masturbating with your fingers or a sex toy at the same time.
  • Experiment with anal sex toys. There are great dildos and vibrators that you can use to increase your pleasure during anal play.
  • Engage in anal prep. If you’re worried that things aren’t as clean as they should be, you won’t enjoy the experience. You’ll just be worried about getting embarrassed. Employ some wet wipes, maybe even an anal douche for extra peace of mind.

Anal Sex Tips For Guys

Pegging Toy

What is pegging? It’s a sex act in which the male is penetrated anally by his female partner. Obviously, she would be donning a strap-on or using an anal dildo. Pegging dildos come in a variety of shapes and sizes. Guys can also enjoy anal play solo or on their own with anal dildos, vibrators, prostate massagers, and other toys.

It’s perfectly normal for a guy to engage in anal play. In fact, it makes quite a bit of sense, as anal sex stimulates the man’s prostate gland. This can lead to deep, intense orgasms.

The Final Breakdown

Anal sex can be absolutely amazing. The key is to go slow, use plenty of lube, and find what works for you. Also, it’s perfectly fine if you conclude that anal is simply not your thing.

Try different positions, use toys to enhance the experience, and start when you are relaxed and feeling positive. Finally, don’t be afraid to reverse roles if your partner decides they want to enjoy this experience, from the other side. Refer back to this anal sex tutorial whenever you have questions on how to enjoy anal sex.

Click to buy anal toys online.

Mayla Green

Mayla Green has been involved in the sex toy industry since 2004. Working behind the motto “Sex TOYS should be FUN”, Mayla provides unique tips & advice amassed from over a decade of hands on experience with adult products. She also coaches clients how to fully enjoy sexual pleasure and can be seen in major publications & magazines online.

Happily married since 2009, she knows firsthand how the sex life eventually becomes repetitive (which truthfully means boring), so if you're looking to spice things up in the bedroom, Mayla's your gal! Her literary pride & joy is covering topics for established couples needing inspiration to keep lovemaking exciting and fun.

Not in a relationship? Her other focus is teaching women how to properly handle the “little person in the canoe” to experience the best orgasms ever, no partner required! Her creative and innovative tips, techniques and advice is on par with a certified sex therapist or Sexologist, but with an extra advantage from her knowledge of the adult toy business.

View all articles published by Mayla Green exclusively for The Adult Toy Shop sex blog.

Follow me on Instagram.

Related Posts
  1. How to Use an Inflatable Butt Plug & What it Feels Like How to Use an Inflatable Butt Plug & What it Feels Like Watch videos of inflatable butt plugs inflate & deflate. What is an inflatable butt plug and why would a person want to try one? Expand your sexual horizons today! (Pun absolutely intended, of course).
  2. My Adventures With Anal Stretching Toys My Adventures With Anal Stretching Toys A fun diary with education in between the lines. The first step before enjoying anal sex is rectal stretching. This is the practice of relaxing the sphincter in order to have less painful (and safer) insertions. In this diary entry, I'll explain som
  3. 10 Best Pegging Toys & Dildos for Beginners 10 Best Pegging Toys & Dildos for Beginners The perfect small & thin pegging toys for beginners. Not just a "best pegging toys" list, this users guide offers useful tips on how to choose the best harness to fit a thin pegging toy. Most of these suggestions originate from the prostate toys cat
  4. Best Anal Lube: 6 Best Lubes for Anal Sex & Dildos Best Anal Lube: 6 Best Lubes for Anal Sex & Dildos Is thicker really better? Find out the truth now! Using the right anal lube makes all the difference in the world. This handy buyers guide lists my best anal lubes of all time. Also includes comparisons of their texture, viscosity and other features