My Guide To Anal Training & Stretching

Anal sex is as pleasurable to some (many) as standard, vaginal sex. This is, of course, the only option when it comes to gay male relationships, but many heterosexual and lesbian partners love engaging in anal sex as well. It’s different, it’s naughty, and it definitely has a kinky quality to it. 

However, it goes without saying that having anal sex is not as simple as having vaginal sex. The butt doesn’t self-lubricate and it takes a bit more warming up than what you might usually do. 

Not only that but before you actually decide to slide a penis (or a penis-like toy) into your ass or the ass of your partner, it would be best to go through some anal training first. 

I, as an anal sex connoisseur, would like to guide you through this.

In this post, I’m going to talk about what ass training is, what its benefits are, and how you should go about it. By the end, you will know everything you need to for safe anal play. 

What Is Anal Training?

Anal sex should never hurt and if it does then you need some training.

woman in blue lingerie bending over and showing off butt

Simply put, anal training is training you should go through to be able to take bigger dicks, dildos, and plugs in your butt. (And all other kinds of toys, if you’re so inclined.) 

It includes basically everything from using a douche to working your way up to big anal pleasure. The key here is to start small and gradually work your way up to avoid pain and even possible serious injury when you’re playing with your butt. (It doesn’t matter whether you are single or doing this with a partner.) 

I recommend that everyone who wants to have anal sex or to feel anal pleasure goes through this type of training.

My First Experience With Butt Play

woman with nice butt

The first time I had anal sex, I was young. Young and inexperienced and it was something I knew people did and I wanted to try it too! If all those over-the-top porn actors enjoyed anal sex in porn clips, I was bound to enjoy it as well, no? 

My boyfriend at the time didn’t have much experience in anal play either, but he was very much down to experimenting. So one night, we got a little tipsy – just enough to relax – and we started touching. 

It was easy and fun and we were excited to get to the butt. I don’t think the foreplay was very long because of how quickly we wanted to move on. Big mistake. 

We had lube – we had that much common sense at least – but we barely spent a minute on my butt, his lubed finger only dipping in for a moment before we decided we were ready. That I was ready.

Boy, was I not ready. 

First of all, because my boyfriend had spread lube over my entrance with his one finger, we figured that was enough. (It wasn’t enough.) Second of all, his dick was a lot bigger than his finger. And it was going in a lot harder. 

It wasn’t long before I actually started crying from how much it burned. It was by pure dumb luck that I didn’t get seriously hurt or started bleeding and that we immediately stopped when we realized this was not going to work. 

This experience put me off anal sex for a long, long time. It wasn’t until years later that I dared to try again, on my own, with plenty of research beforehand. 

My Simple Anal Training Guide

cartoon arrows pointing in different directions

If you want to avoid a painful, negative experience like my first anal sex, please take your time to learn how to training your ass to take dick the proper way. Learn what feels good and play with yourself (and/or with your partner), and most importantly, go slow. Don’t rush, be gentle, and breathe. Speed isn’t important here – comfort and safety are.

That being said, here are some key tips for you. Read through them and make a plan of how you’re going to get accustomed to anal penetration. Not all of these might work for you, but please consider them carefully before skipping to the next part. You must take it step by step and work your way up to the big things. 

Let’s begin.

If It Hurts Like Hell, STOP!

This is the number one rule! Sometimes anal penetration hurts a little in the beginning and that’s fine. As you get used to it (and possibly add even more lube), the pain should give way to nothing but sweet, sweet pleasure. 

But if it starts seriously hurting at any point, you should stop. Unbearable pain usually means you’re going too far and that you should dial it down. Listen to your body. It knows what’s good for it and what it can’t do yet. 

Keeping Things Clean (The Easy Way)

Hygiene is another important factor when it comes to anal play. Go to the toilet about 2 – 3 hours before your date, then have a shower before sex. You can use an anal douche if you didn’t go to the loo before and just put a finger in to get things really clean. 

Douching is usually overkill, but if you really want to be clean, it is the best way. (Not many people do this, however, so you don’t have to force yourself either. A trip to the bathroom and a thorough shower before meeting your partner should be just fine.) 

If you want to douche here’s a really good guide:

Get This Amazing Anal Lube

Lubes come in many different versions, like this water-based one and this oil-based one. There are also silicone lubricants. If you’re unsure which one to get, your best bet is always a water-based lube, preferably one that has a thicker consistency. 

If you’re planning to use a condom, definitely go for the water-based because that type of lube doesn’t degrade the latex of the condom (you can find out more about condoms here). If you’re not keen on applying additional lube during sex, opt for an oil- or silicone-based one as they are thicker and don’t need constant reapplying. Make sure you’re not allergic to any ingredients found in the lube you bought because that just creates unnecessary complications. 

You can also watch this amazing guide on various things you can use as sexual lubrication and check out this guide we did on our favorite anal lube:

Start With Your Fingers (Have a Play Around)

Your first anal experience should be with your fingers. They’re readily available and relatively thin and easy to control (since they’re yours, obviously). Have a play around, try putting one finger in and then maybe two.

Feel yourself out. To start with, you don’t need any fancy toys. You can do a lot with just your fingers and it’s always the best place to start. (Use your partner’s fingers as well!)

Before Anything Goes In Your Butt

It’s always a good idea to massage your butt with your fingers. Insert a finger or two and warm yourself up; this in itself can take away a lot of discomforts. Do this a few times for a week or two. Relax, tease yourself, make a game of it. Use toys on other parts of yourself and let loose. Reach an orgasm – it’s always a lot easier to insert things in your butt when you’re aroused. 

Let The Stretching Begin With A Butt Plug

Butt plugs are the easiest toy to use to stretch you out. They’re small and you can even leave them in for longer periods.

You want to start with a beginner butt plug (smaller in size) and then slowly work your way up to bigger plugs. After that, let your anal dildos follow.

Leave your butt plug in for a while. During this time, your partner can go down on you or you can masturbate or do something else that’s fun. (You can even have regular sex with the butt plug in!) The longer the plug is in, the more stretched out you’ll become.

If you are serious about anal stretching, then you could also get an inflatable butt plug. This is the type that’s relatively small as you slide it in, but that you can then expand (inflate) when it’s 

already inside for a very freaky yet very intense sensation.

Make it kinky! I like to walk around with my butt plug in, to go out to my garden, to sunbathe… It adds a little extra thrill to my everyday activities.

Next, You Need A Beautiful Anal Dildo

Once you’re used to butt plugs, get yourself an anal dildo. You’ll be able to thrust and simulate penetration with a real penis, plus it feels absolutely amazing. 

Thrusting adds a little more stress to the body and that’s why it’s best to use a dildo after you’ve used a butt plug. It stretches you out even more and gets you prepared for actual anal sex somewhere down the line. 

If you’re a guy, the Aneros range is unreal and great for unlocking your prostate. It’s ergonomically designed and made from hypoallergenic silicone for a smooth feel. It has about 4 inches of insertable length, making it perfect for beginners, too. Don’t be surprised if you cry out when you hit that P-spot!

Suction cup dildos can be good for trying different anal sex positions too. 

This anal dildo is shaped like a real penis, complete with a tapered head and a pair of balls. It has texture alongside the shaft in the form of veins for additional pleasure. It is also quite bendable, so it curves along with your body no matter what position you’re in. Suction cup dildos are great for a hands-free ride. 

Get Yourself A Beginner Anal Kit (Saves Time & Money)

A good rule of thumb is to start with an anal kit like this. It saves you money and effort you’d spend looking for all these individual tools and toys.

This kit will not stretch you out too much but will get you ready for anal sex with an average-sized dick. It has a butt plug, a vibrating butt plug, vibrating anal beads, a vibrating P-spot massager, and an anal douche for keeping things clean. 

Plus, these toys are a must-have for anyone’s collection.

Time To Start Really Stretching Your Ass Out

This kit is by far the best dilator kit. It is relatively simple, made from five identical butt plugs that vary in size. When you’re just starting out, you should begin with the smallest one, then work your way through them until you can take in the biggest. 

Go slow! If you’re not a complete beginner, start at the level you’re on and gradually increase the size. Don’t forget to use a lot of lube and don’t push yourself if it’s not working. Take a break, let it go, and come back to it some other time. This isn’t a race, and all that matters is that you are comfortable. 

Keep Things Going Regular, But Go Slow

Wear butt plugs for long periods of time. Technically, you can wear them for as long as you want, just make sure they don’t interfere with your regular physiological needs.  

Try anal play daily, but don’t overdo it. Use smaller toys and then maybe a few times a week try upgrading to a bigger plug/dildo. If you don’t have time for this, do it when you can, but try not to go a week without playing with your butt at least a little bit. 

The Big Moment

Finally! You feel like you’re ready to try actual anal sex! You (and possibly your partner) have been playing with toys for a long time and you think your ass can finally take a whole dick. Well, there are some things to keep in mind here as well. 

First, foreplay. The better and longer the foreplay is, the more you’ll be able to fit. I’ve said this before – how relaxed and aroused you are is directly related to how much you can take in your ass. At this point, it’s all about long sex sessions, patience, and experimenting. 

Remember that this is supposed to be fun! So keep it light, let your partner please you, touch and kiss you, and don’t stress over whether or not it will work the first time. If it doesn’t, it will work another time for sure. 

For All The Size Queens

woman taking off lingerie

Some of you are here not to make anal sex easier, but to fill yourself up with a nice big toy, which is admirable in itself. Size queens are people (of any gender identity) who prefer to have sex with someone who has a dick that’s larger than average. 

This preference can come from anything; they can enjoy the feeling of a huge cock in their throat; they can enjoy being stretched open by the large dick; they can even simply admire the visual aesthetic of it. 

Stretching yourself out for a massive penis is mostly the same as doing it for an average-sized one. However, instead of stopping at traditionally-sized toys, you could go further and reach for some that are bigger than average. To take in a huge dick, you need to play with a similarly huge toy. 

All the same rules apply: lots of lube and a slow pace. Massive stretching can lead to tearing and bleeding, so be extra careful when you’re playing with something a lot bigger. 

How To Anal Gape

There are a lot of people who love the look of anal gaping. This is when your butt or vagina (but mostly the butt) doesn’t close up right away after sex. 

Here’s how to make it happen:

  • Get thoroughly cleaned beforehand (a douche is preferable here).
  • Make sure you are intensely aroused (like after a couple of orgasms, at least).
  • Assume the position of having your head and your body on the bed and your ass high up in the air (on your knees). Spread your legs a little to open yourself up as much as you can.
  • Use a LOT of lube. And I mean A LOT.
  • Stretch yourself open with toys. Be slow and thorough. Move on to bigger toys.
  • Have anal sex. Deep thrusts, moving side to side, make that hole huge and gaping!
  • To keep your hole open, use gaping butt plugs! These are larger than your average ones and they’ll feel out of this world. 

Before And After

woman laying on bed in blue panties, wearing orange top

After I’ve done all my research and applied all of the techniques I outlined here – used my fingers, then a butt plug, then an anal dildo – I was finally ready to have anal sex again. This time, I was older and a lot more experienced (and a lot more comfortable with my sexuality) and I had a boyfriend who helped me train for this moment. 

It was so much better. It was so great, in fact, that I almost achieved an anal orgasm! We had a little wine after dinner, then we played with each other for a long time before actual penetration came about. My boyfriend went down on me, made me climax twice before he ever even touched my ass.

This helped me not only relax but practically melt into the bed. By the time we moved on to the actual anal play, I was almost desperate for it. Through my training, I had already learned what it felt like to have something in my ass and how good it can be, and I knew what to expect. 

It didn’t hurt at all when my boyfriend slid his finger inside me. He used a butt plug to warm me up as well, and then his cock went in without any effort. 

It was still big. It still took a little getting used to. But none of this was even close to the searing pain I had felt the first time I clumsily tried anal sex. 

I loved it when he started thrusting. I loved it when he climaxed into my ass. It is a type of ecstasy that you need to open yourself up to because it is worth every damn moment. 

Questions About Stretching Your Butt You Need To Know

questions about anal stretching

Will I Get A Loose Butthole?

Opinions are mixed in this case. If you’re engaging in regular anal play, with regular toys and regular penises, you shouldn’t be too concerned about this. The sphincter (the butt opening) is a powerful muscle, and it should have no problems coming back to its original state after anal sex.

However, if you’re into more extreme kinks, like fisting or using gigantic toys or plugs (if you like gaping, too!) this could, potentially, become a problem. So make sure you take breaks of at least a couple of weeks between these more hardcore sessions. 

Is Anal Play Dangerous?

Yes, anal play can be dangerous, especially if you put things in your butt that are not made to go in the butt. (Please don’t use fruit, vegetables, bottles, or similar. It’s incredibly dangerous to your health for many reasons.)

It’s also dangerous if you overreach and put something too big in your butt. You can cause splitting and maybe even bowel rupture, so listen to your body! Do as much research as you can and don’t overdo it.

How Long Does It Take Before You See Results?

Not too long. Stretch yourself little by little and relatively often (at least every couple of days) for optimal results. The longer breaks you take, the longer it will be before you can take in a toy bigger in size. 

Is Desensitizer A Good Idea?

I’ve used a few desensitizers and they can be good, but personally, I avoid them.

It’s important to be able to feel any pain since that stops you from over-stretching yourself and causing injury. Even though desensitizers work and there are times when they’re useful, I wouldn’t recommend them while stretching.

Is There A Difference Between Male And Female Butts? (Can men fit more?) 

There is a theory that male butts can take in more (because men are larger overall), but this is false. Male anal sphincters are the same size as female sphincters and anal training should work exactly the same for both. 

However, in terms of experiencing pleasure, there’s actually no way to determine whether anal sex is more pleasurable for men or for women. (Because there would have to be one person to experience both, which inherently makes it impossible. It’s the old ‘What’s worse: the pain of getting hit in the nuts or the pain of childbirth?’ conundrum.)

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