Want to Start an Anal Training Schedule?

If you’re new to anal training, you’re not alone. Many beginners feel excited but also nervous about discomfort, safety, or simply not knowing where to start.

The good news is that anal training does not need to be painful or intimidating.

When approached slowly and comfortably, anal training can help your body gradually learn to relax and adjust to penetration in a way that feels safe, pleasurable, and confidence-building.

This guide will walk you through a beginner-friendly anal training schedule using a gradual progression of wands and plugs designed to help you train comfortably, never forcefully.

What Is Anal Training?

Anal training is the process of gradually helping the body become more comfortable with anal penetration over time.

Rather than rushing straight into anal sex, anal training focuses on:

relaxation
gradual progression
body awareness
comfort
consistency

The goal is not to “push through pain” or force stretching. In fact, discomfort is your body’s signal to slow down.

Comfortable anal training should feel gradual, controlled, and increasingly natural over time.

Why Most Anal Training Fails

Many beginners struggle with anal training because they:

move up in size too quickly
train inconsistently
rely on plugs alone- the narrow neck makes them inefficient for anal training
use toys with aggressive shapes
try to “tolerate” discomfort instead of listening to their body

One of the biggest misconceptions is that anal training should hurt. It shouldn’t.

That’s why Silolis Training Sets combine both tapered training wands and wearable plugs:

Wands actively train your body by allowing you to relax at the max girth of the toy while you to gradually adjust to insertion
Plugs passively train your body and help you maintain the progress of stretching with wands

Using both together creates a smoother, more comfortable progression than using plugs alone. Click here to learn more about what makes the Silolis design better than other training sets.

Before You Start

Before beginning your training schedule, keep these basics in mind:

Always use plenty of water-based lube
Go slowly and listen to your body
Never force insertion
Stop if you feel pain
Train when you feel relaxed and aroused
Clean all toys thoroughly after each use

Anal training is highly individual. Some people may progress through this schedule quickly, while others may need additional days at certain sizes. Both are completely normal.

The goal is comfort and consistency.

How Long Does Anal Training Take?

There is no “correct” timeline for anal training.

Some people may feel ready for larger sizes within a few days, while others may prefer taking several weeks. Your body’s comfort level matters more than any schedule.

The schedule below is best used as a comfort guide rather than a strict timeline.

Once you become familiar with your body and training technique, the process often becomes easier and more intuitive.

Beginner Anal Training Schedule

This schedule is based on a Medium Training Set (sizes 1-3).

Most importantly, plan to train slowly and regularly:

Day 1

Take time to relax physically and mentally before beginning.

Apply a generous amount of water-based lube to Wand 1 and begin with external stimulation and arousal before slowly inserting the wand. Spend time adjusting to the sensation and allow your body to relax around the toy naturally.

The experience should feel gradual and enjoyable, never rushed or painful.

Once Wand 1 feels fully comfortable, rest at its base for a few minutes and then remove it and insert Plug 1. It should slide in easily without resistance.

Wear Plug 1 for as long as it feels comfortable, up to about 2 hours. If discomfort develops, remove it and give your body a break or apply additional lube as needed.

You can also experiment with masturbation while wearing Plug 1 or using Wand 1 to help your body associate anal stimulation with pleasure and relaxation.

Day 2

Begin again with Wand 1 until comfortable.

Insert Plug 1 for 30–45 minutes before progressing to Wand 2. You may choose to briefly reinsert Wand 1 before moving up to loosen the sphincter a bit more.

Use the same approach:

lots of lube
slow progression
relaxation
arousal
patience

Gradually work on inserting Wand 2. You should be able to insert it fully within about 10 minutes with little discomfort and no pain. If you experience pain, stop and go back to Wand 1 for today. Once Wand 2 is inserted fully and comfortably, rest at the base for 5-10 minutes.

After removing Wand 2, wear Plug 2 for 1–3 hours as comfortable.

If it feels enjoyable, this can also be a good time to experiment with oral or vaginal sex while wearing Plug 1. This can help reinforce relaxation and pleasurable associations with anal stimulation.

Day 3

Begin with Wand 1 and then progress directly to Wand 2 once comfortable.

When Wand 2 feels easy and relaxed, insert Plug 2 and wear it for 1–3 hours, taking breaks and reapplying lube as needed.

Later in the day, repeat the training session again if your body feels comfortable doing so.

Consistency is often more important than speed.

Day 4

Using plenty of lube, begin with Wand 1 and progress comfortably to Wand 2.

Wear Plug 2 for 30–45 minutes before moving on to Wand 3. You may choose to briefly reinsert Wand 2 before moving up to loosen the sphincter a bit more.

Gradually work on inserting Wand 3. You should be able to insert it fully within about 10 minutes with little discomfort and no pain. Once Wand 3 is inserted fully and comfortably, rest at the base for 5-10 minutes.

If Wand 3 feels too intense today, that is completely okay. Return to Wand 2 and try again another day.

After relaxing comfortably at the base of Wand 3 for a few minutes, remove it and insert Plug 3. If its comfortable, wear Plug 3 for 1–3 hours.

At this point, many people begin feeling significantly more confident and relaxed with anal penetration.

If desired, you may also experiment with oral or vaginal sex while wearing Plug 2.

Days 5–7

Over the next several days, focus on comfortably working back up to Plug 3 at least once daily using the steps from Day 4.

Training should gradually begin feeling:

easier
quicker
more natural
more intuitive

Once you're able to comfortably and consistently stretch to level 3, you may feel ready to start experimenting with thrusting and possibly even anal sex (assuming size 3 corresponds to your partner's girth, read more about sizing here).

You may still prefer to take additional days at certain sizes, and that is completely normal.

ALWAYS CLEAN YOUR WANDS AND PLUGS IMMEDIATELY AFTER USE. PLEASE REVIEW OUR CARE AND CLEANING GUIDE.

When Are You Ready for Anal Sex?

You are likely ready to attempt anal sex once:

larger sizes feel consistently comfortable
insertion no longer creates anxiety or tension
your body can relax naturally during penetration
you can comfortably wear your goal size

When you do decide to try anal sex:

prioritize arousal
use plenty of lube
communicate openly with your partner
start slowly
keep expectations light and playful

It’s completely normal for the first few experience to involve adjustment and experimentation. Click here for more tips on having anal sex with a partner!

Common Beginner Mistakes

Moving Up Too Quickly

Progressing too aggressively often creates tension and discomfort. You should get very comfortable at your current size before moving up, and each step up should increase by no more than .3" diameter (1" circumference).

Training Through Pain

Pain is a signal to stop and slow down, not something to ignore.

Using Too Little Lube

More lube almost always improves comfort.

Training Inconsistently

Short, regular sessions are usually more effective than occasional intense sessions.

Using Unsafe Materials

Always choose body-safe, non-porous materials like platinum cure silicone for anal toys. Click here to read more about materials.

The goal of anal training is not to force your body to “handle” penetration. The goal is to create comfort, confidence, relaxation, and pleasure through gradual progression and patience. Go slowly, listen to your body, and celebrate progress.