Anal play is not supposed to be uncomfortable! 

1. Create a Comfortable, Relaxing Environment

Your mindset plays a much bigger role than many people realize. If you’re anxious, embarrassed, or feeling rushed and uncomfortable, your body naturally tenses up, including the muscles around the anus. This can make insertion uncomfortable, even when you’re doing everything else correctly.

Instead, treat the experience as self-care rather than something you need to “get over with.”

Before you begin, try some (or one) of the following and start to get your body ACTUALLY prepared to have some fun! Try: 

• Taking a warm shower or bath to help your muscles relax.
• Cleaning the area if it helps you feel more confident. 
• Putting fresh towels or clean sheets on the bed.
• Choosing a private, quiet space where you won’t be interrupted. Maybe put on a playlist that you enjoy or that relaxes you!
• Taking a few deep breaths before starting.
• Setting aside plenty of time so you don’t feel rushed.

Some people also like to incorporate massage, calming music, or a warm heating pad beforehand to help release tension; there is no wrong answer to exploring yourself comfortably. 

Remember, there’s no prize for rushing. The more relaxed you are, the more easily your body will respond.

2. What Anal Play Should Not Feel Like

Some people believe that pain is just a part of the experience. 

It isn’t.

While you may feel pressure, fullness, or a new sensation that takes a little getting used to, sharp pain, burning, or intense discomfort are signs to stop immediately and reassess/add/change things up. 

If something hurts:

• Slow down.
• Add more lubricant.
• Relax your breathing.
• Try a different position.
• Use a smaller toy or finger.
• Stop completely if the discomfort doesn’t improve.

Your body is very good at telling you when something isn’t right, and this is NOT a self-lubricating part of the body. Listen to those signals!

Patience almost always leads to a better experience than trying to force things. 

3. Start Small: Fingers, Lubricant, and Comfortable Positions

When you’re first exploring anal play, less is more.

Starting with a single lubricated finger helps you become familiar with the sensations before introducing any toys.

Lubricant is absolutely essential.

Unlike the vagina, the anus does not produce natural lubrication, so using a generous amount of high-quality lubricant helps reduce friction and improves comfort. Don’t be afraid to reapply throughout your session if needed. There is no such thing as too much lube!

Beginner-Friendly Positions

Everyone’s body is different, but these positions are often the most comfortable for first-time exploration:

• Lying on your side with your knees bent.
• Lying on your back with your knees drawn toward your chest.
• Kneeling on all fours.
• Standing with one foot elevated on a stool or bathtub edge.

Experiment slowly to find what feels most natural for your body. These positions also help you completely control the speed, depth, and angle at which you are penetrating yourself or being penetrated. 

There’s no “correct” position, only the one that allows you to stay relaxed and comfortable the most.

4. Beginner Anal Toys Worth Considering

Once you’re comfortable with finger exploration, you may decide to try a small beginner-friendly anal toy to slowly increase the width of penetration to your preference – whether you are working up to simple plugs, dildos, or a penis. 

The best toys for beginners are:

• Slim and narrow or tapered.
• Made from body-safe silicone.
• Flexible enough to move comfortably with your body.
• Equipped with a flared base for safety.

Starting with a toy specifically designed for beginners can make the learning process much easier than choosing something larger right away. Seriously, take your time. 

Recommended Beginner Toys

Here are some of my favorite beginner kits to get you started:

3-Plug Anal Trainer Kit  – This kit has 3 tapered silicone plugs that are flexible and perfect for those who are JUST getting started. Beyond that, you don’t have to keep purchasing plugs to move up. It’s comfortable, easy to insert, and perfect for longer-term wear if you prefer.

Climb Anal Trainer Kit – If you want to add vibration, this kit is perfect! The plugs are slightly less tapered than the first kit mentioned, and there is a vibrating option in the largest size! Adding vibration can really assist with additional anal pleasure, and the more rounded shapes do help with a feeling of fullness. Beyond that, there are still three different sizes in this kit!

5. Why Gradually Sizing Up Matters

One of the most common mistakes beginners make is progressing too quickly in size, which can hurt you.

The muscles surrounding the anus are designed to stay closed and protective. They naturally adapt over time with gentle, gradual stretching, but they don’t respond well to force!

Think of it like stretching before exercise.

You wouldn’t attempt the deepest stretch possible without warming up first, and the same principle applies here with anal play and sex toys.

Many experienced enthusiasts own toys in several sizes and continue to use smaller options depending on how their body feels that day.

There’s absolutely nothing wrong with staying at a size that feels comfortable. Bigger isn’t automatically better. You can switch between your preferences as long as you are safe! 

6. The Benefits of Anal Play When Done Correctly

When approached safely and patiently, anal play can become an enjoyable part of your solo and partner play. There are plenty of benefits that go beyond simple pleasure. 

Increased Body Awareness

Exploring new sensations helps many people better understand what feels pleasurable and how their body responds to different types of stimulation. This also helps you better navigate your partner in the bedroom and your preferences with them.

Enhanced Pleasure

The area contains numerous sensitive nerve endings, and gentle stimulation can create pleasurable sensations for people of all genders.

Prostate Stimulation

For individuals with a prostate, anal play can stimulate what’s often referred to as the “P-spot.” Many people describe prostate stimulation as producing unique sensations that differ from traditional penile stimulation and may enhance overall sexual pleasure.

If prostate exploration is something you’re interested in, purpose-built prostate plugs and massagers are specifically shaped to comfortably target this area.

One of my personal favorites: Xara Stroke

It’s time to explore! Ensure you are going slow, using lots of lubrication, finding a safe space to play, and above all: HAVE FUN!