The Beginner’s Guide to Anal Masturbation

If you have never experimented with anal masturbation, you might be missing out on the greatest anal play yet! Sure, anal play may feel intimidating at first, but we can promise you that once you discover the world of anal play and pleasure, you can never go back. 

However, not enough people are talking about what anal masturbation is, how to do it, or why exactly you’ll want it in your life. Sometimes talking about anything other than heteronormative, penetrative sex can feel taboo. 

If you’ve been toying with the idea of anal masturbation and are still on the fence, there are many reasons to take the plunge, bum-first. 

Some of the best reasons include: 

  • Experiencing intense orgasms
  • Bringing an element of naughtiness that can kick your arousal level into high gear
  • Enjoying new ways to explore your sexual desires
  • Introducing new sex toys into the mix
  • Experience prostate pleasure and wellness
  • Building intimacy with yourself and with a partner

At GIDDI, we are here to help you ditch the stigmas around anal play, and guide you to the world of anal masturbation and stimulation. No matter how excited you are to jump into this new sexual experience, jumping right into something new could lead to discomfort or injury. 

Read on buttercup, and get all the critical need-to-know info on pleasuring your behind!

Why Anal Masturbation

First things first, why should you incorporate anal play into your life? Maybe you have no problem reaching orgasm after penile stimulation. But what if we told you that exploring anal masturbation may lead to the most intense, pleasurable orgasm you’ve ever had??

What Is the Prostate?

illustration of a man using an anal sex toy

The prostate is an organ that is crucial for reproduction purposes. The prostate makes prostatic fluid, which is one of the main components of semen. Located below the bladder and in front of the rectum, the prostate can be accessed internally or externally, depending on what you are trying to achieve.

It is located just a few inches inside the anus, making it easily accessible once you know the ropes! 

Besides being a crucial part of the creation and expulsion of semen, the prostate, or P-Spot, is also your go-to spot for intense pleasure. Because it is loaded with nerve endings, it is incredibly sensitive (in the best way)

The prostate gland swells when you are aroused, and many people find that putting direct or indirect pressure on it during sex creates a mind-blowing orgasm.

Switch It Up

Besides leading to an intense, mind-blowing orgasm, incorporating anal masturbation into your life might be the perfect way to spice up your sex life. If you have never tapped into the potential of your prostate, it’s time to discover your pleasure center!

How To Prepare for Anal Masturbation

doggy 1

Like all new sexual experiences, you shouldn’t jump right in — you may want to go slowly and prepare yourself as best as possible. Luckily, there are a few things you can do to make sure you feel ready and relaxed.


Even though the butt might seem like a messy place to approach when pleasuring yourself, that's not necessarily true! If you want to introduce anal play into your bedroom routine, start with taking a look at your diet. A healthy diet can be the secret to healthy anal sex. 

Here are a few easy ways to adjust your diet to keep your fun mess-free:

Maintaining the right amounts of protein and fiber in your diet is important. Protein hardens your poop, and fiber makes pushing it out easy and painless. This combo can lead to regular bowel movements, eliminating the risk of non-serendipitous surprises in the bedroom, if you know what we mean. 

Don’t forget to skip on the coffee, caffeinated drinks, and excessive alcohol before anal play. 


Another easy way to reduce stress about a mess is to ensure that you are properly cleaned. After going to the bathroom anywhere from 30 minutes to an hour before anal play, be sure to wash with warm water and hypoallergenic soap. 

You can wash up in the shower, over the toilet, standing up in the tub, or over a towel. Just wash the anus and the surrounding tissue and rinse with water. It’s as easy as that! You can repeat this process as many times as you need until you feel comfortable and ready to get down to business.

Pro Tip: When you become a regular participant of anal play, you might even consider installing a bidet to make washing you behind easier than ever!

Set the Tone

If you are new to anal masturbation, we understand you might be a little nervous. The best way to combat this is to get yourself in the mood. Dim the lights, light some candles, put on a sexy playlist, and dress or undress in a way that makes you feel confident and comfortable. 

Find a soft surface that allows you to move enough to find what position feels best. This can be a bed, a couch, or a carpeted area. It might even be helpful to lay a towel down on the surface for easy clean-up (not to mention an easy way to reduce anxiety about making a mess).

Similarly, you might find it helpful to have another towel nearby to hold any sex toys or lube.


Speaking of lube, this is going to be the most important part of your solo play! The anus is not self-lubricating, and the tissues around the anus are especially sensitive. If you do not use a sufficient amount of lube, you risk tearing the tissues down there, which can be extremely painful. 

Similarly, having a sufficient amount of lube can make the entire process easier and more enjoyable.

There are so many different types of lube to choose from. However, for any anal play, you’ll want a lube that is thick, long-lasting, and compatible with any toys you might use. We know that’s a lot to consider!

Thankfully, we have a lube specifically for anal. 

The Wicked Jelle Water Based Anal Lube address the specific needs of anal play. This lube is very viscous, long-lasting, and never sticky. This lube stays put and provides extra cushion and superior glide. 

This carefully-crafted formula is free from desensitizers to ensure optimal safety, sensation, and pleasure.

There is no such thing as “too much lube,” so apply generously to your hand or toy and the exterior of your anus. 

The Best Techniques for Anal Masturbation

illustration of a man using an anal sex toy

Now that you have the perfect setup and the proper lube in hand, you are ready to get started. There are a few different ways to stimulate your prostate; just remember to start slow and do whatever feels pleasurable and comfortable. 


The easiest way to warm up or try out anal masturbation for the first time is to use your fingers. Once you have lube on your finger and your anus, you can start by massaging the external muscle and surrounding area. 

There is no need to jam your finger in; start off slowly and massage the area until you feel ready. 

Then, slowly insert a finger or two while taking deep breaths. Once they are fully inserted, point your fingers toward your belly button and feel for the prostate. Look for a fleshy bulge that feels different from the surrounding areas. 

Once you find the prostate, you can stimulate it with your fingers in a few different ways, including:

  • Stroking: Use your index finger to push towards the navel in a “come-hither” motion. Start by moving slowly and only increase the speed or pressure when you or your partner feel comfortable. 
  • Circling: If you struggle to keep the motions constant, try using the circling technique. Use the pad of your index finger to make circles around the entirety of the prostate. If it feels too intense, you can widen your circles even more. 
  • Pressing: This is a good introductory technique — it’s easy and gentle. Once again, use the pad of your index finger to press down repeatedly on the prostate, as if ringing a doorbell. We love this technique because it allows for many different speeds and pressures, depending on what feels best. 

You can stimulate your prostate with a finger until you reach an orgasm. It may feel strange at first, but if it feels uncomfortable or too intense, take a break and try again later. 


illustration of a man using an anal sex toy

Once you feel fully comfortable using your fingers to stimulate your prostate, you might want to move on to using toys. Perhaps you’re ready for a vibrating prostate massager. These are toys designed specifically for prostate stimulation, and those toy designers know exactly what they’re doing!

To insert a prostate massager, first apply a generous amount of lube to the head and shaft of the prostate massager and your anus. Then, you can slowly insert the head’s tip until the widest point is at the external muscle. Slowly rock the massager back and forth until the entire head is inside the anus. 

Don't force it if you experience any pain or discomfort during insertion. Forcing insertion can only cause your muscles to tighten up more, making penetration and climax much more difficult. 


When you know more about your body and how anal pleasure feels, it’ll be easier to try anal masturbation with a partner. Plus, you might just discover how much you enjoy anal stimulation during anal masturbation. In the end, anal masturbation is all about feeling good. 

Visit GIDDI and let us help you find which prostate massager is right for you! 


The Best Diet for Digestion and Anal Sex! | Gay Male Journal

Anal fissure - Symptoms and causes | Mayo Clinic

Nerve endings in the human prostate | PubMed

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