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Written by: Monique from The Anal Sex Toys Shop
Publish on 22/06/2026
If you're learning how to train for anal, let me save you from one of the most common mistakes: trying to rush the process.
Anal training isn't a race. It's not about seeing how quickly you can move up to a bigger toy or proving that you can handle more. The people who have the best experiences with anal play are usually the ones who take their time.
Your body responds much better to patience than pressure.
Safe anal training is built on a few simple principles: start smaller than you think you need to, use plenty of lubricant, keep sessions manageable, and increase size gradually. When you do that, each session becomes more comfortable instead of more intimidating.
In this guide, I'll walk you through how to start, how often to train, when to move up in size, and how to tell whether you're making progress without pushing your body too far.
If you'd like a complete overview of toys, lube, safety, and training stages, check out our Anal Training Guide.
And if you're looking for toys specifically designed for gradual progression, our Anal Trainers collection includes beginner-friendly plugs, dilators, and training sets that make the process much easier.
Starting Small
When it comes to anal training, starting small isn't being cautious — it's being smart.
One of the biggest reasons people struggle with anal play is that they choose a toy that's technically "beginner-friendly" but still larger than what their body is ready for. A toy can look tiny on a product page and feel surprisingly substantial once it's actually inserted.
Starting with a smaller toy gives your body time to get familiar with the sensations of insertion, pressure, and fullness without overwhelming you.
For your first trainer, look for:
- A slim diameter
- A smooth surface
- A tapered tip
- A secure flared base
- Some flexibility or softness
- A shape that feels approachable rather than intimidating
Your first few sessions aren't about stretching as much as possible.
They're about learning how to relax.
That's the skill that makes everything else easier.
Small anal trainers, beginner plugs, and slim dilators are excellent choices because they allow you to focus on comfort instead of size. Once a toy feels easy to insert and wear, that's when you can start thinking about progression.
And please — use more lube than you think you need.
If insertion starts feeling sticky, draggy, or uncomfortable, stop and add more. Lubricant is one of the simplest ways to make anal training safer and more enjoyable.
If you're still deciding where to begin, our Anal Trainers collection includes several smaller options specifically designed for gradual anal training.
Frequency of Training
Let desire set the rhythm, not the calendar. You do not need to train every day or hit a weekly target. Some weeks you may want more; other weeks your body may simply say, “Not tonight.”
If you feel sore or irritated, leave penetration for another day. A planned session is never a reason to push through discomfort.
Wondering how long the journey might take? Our Anal Training Timeline talks about pace without giving you a deadline. If you have pain or bleeding, stop and read Can You Stretch Too Fast in Anal Training? for the warning signs and when to get medical help.
Size Progression
Moving up is optional. A familiar toy can still feel incredible, and every session does not need to become a test of how much more you can take.
One good experience with one size does not promise that a bigger toy will feel the same. A different shape, firmness or curve can change the feeling completely.
Stay where pleasure feels easy. If curiosity pulls you towards something fuller, save it for a day when you are not sore or irritated. If it hurts, stop—do not switch to a smaller toy and keep going.
Not sure whether to stay with your favourite or try another size? Our Anal Training Progression guide looks at that choice without giving you a target to reach.
Tracking Progress
Most people are better at remembering their frustrations than their successes.
That's why tracking your progress can be surprisingly helpful.
You don't need a spreadsheet or a complicated journal. A simple note on your phone works perfectly.
After each session, consider recording:
- The toy you used
- The size
- How much lube you needed
- How easy insertion felt
- Whether you felt relaxed or tense
- Session length
- Any soreness afterward
- Whether the toy felt easier than last time
Over time, patterns start to emerge.
You might discover that certain sizes feel easier after an extra rest day. You might notice that spending five additional minutes relaxing beforehand makes a huge difference.
You may also catch yourself trying to move up too quickly.
And remember: progress isn't only about size.
Real progress often looks like:
- Feeling less nervous
- Relaxing more easily
- Using less effort during insertion
- Recovering faster afterward
- Feeling more confident
- Knowing when to stop
Those improvements matter just as much as moving up to a larger toy.
Sometimes more.
FAQ
How long does anal training usually take?
There is no fixed timeline.
Some people feel comfortable progressing after a few weeks, while others prefer a slower pace over several months. Consistency, comfort, and recovery matter more than speed.
Do you need lubricant every time?
Yes. The anus does not self-lubricate, so using a quality lubricant is one of the most important parts of safe anal training.
Reapply whenever things start to feel dry or resistant.
Should you stop if you feel sore afterward?
Yes. Give penetration a break while you feel sore or irritated. Do not test another size just to see whether it feels better.
Get medical advice for severe or persistent pain, or bleeding. Heavy or non-stop bleeding needs urgent medical attention.
Is it normal to stay at the same size for a while?
Absolutely. Many people spend multiple sessions — or even weeks — using the same trainer before moving up.
Staying comfortable at one size is often a sign of good progress, not a lack of progress.
What's more important: size or comfort?
Comfort. Successful anal training is about building confidence, relaxation, and consistency. Moving up in size should happen naturally once your current size feels easy and predictable.
Where to Go Next
-If you're building a gradual anal training routine, these resources can help:
- Anal Training Guide — a complete overview of toys, safety, lube, and progression
- Anal Trainers — beginner-friendly trainers, plugs, dilators, and training sets
- Anal Lube Guide — choosing the right lubricant for smoother training sessions
- What Size Butt Plug Should I Start With — understanding beginner-friendly sizing
- How to Use a Butt Plug Correctly — insertion, wear time, and removal tips
- Small Butt Plugs vs Medium — understanding how fullness changes as size increases
The best anal training advice I can give is simple: go slower than you think you need to.
Your body will tell you when it's ready for more.
Listen to that, use plenty of lube, take rest days when needed, and let comfort — not impatience — guide your progress.
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