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Pushing Your Limits: The In’s and Out’s of Extreme Anal Play

by Trish Murray 20 Dec 2022 0 Comments

Ok, so this may be something you are familiar with or have thought about; or it may be one of those things where you are like “Nope, no way! Not a cat in hells chance!” But let me just throw some light on the fun and frivolity that is Extreme Anal Play!

As someone who has done this for years, I know what the do’s and don’ts are. I recall having a conversation with a friend a few years ago, and the talk got around to greedy boys, as it usually did with this friend. In a moment of jest, I said that I wasn’t greedy, I was accommodating; to which he quickly retorted, “More like accommodation!” And that was from a friend!

But he was right. I discovered the joy of extreme anal play years ago and have had many years of fun, stretching and seeing what I could fit in there. So, with this in mind I thought I would share some of my knowledge and tips, look at some of the myths around it, and give a little insight into the joys of Anal Stretching.

So where to start? Lets start at the bottom and work up, I guess!

What is Extreme Anal Play?

If you like the sensation of a toy or a dick in you anally, but want more, then this is for you!

Extreme Anal Play, or Anal Stretching, is the art of stretching the anal muscle, and allowing the cavity to accommodate bigger items. Be it 2 dick’s (DP), bigger butt plugs and dildos, or actual body parts, like someone’s fist and arm.

It’s a kink that some like to take to the extreme and it gives the used and the user more than just the physical sensation of the act.

Why do it?

There are a few reasons people do this. Some look at the stretching as an act of necessity because their partner is larger than they can comfortably accommodate, be it vaginally or anally, and the stretching is needed because if it wasn’t stretched it would be pain over pleasure.

Others want to be able to simply accommodate more, or they like the kink and feeling that is surrounded with DP’s, Fisting and Gaping. And please don’t think it’s just a guy thing, because I know men and women of all sexual fluidity that have the practiced and experienced the pleasure of extreme anal and vaginal play with bigger toys and loved it!

For me, being a gay man, I progressed to it after discovering the joy of anal play had been introduced to me with basic butt plugs, as well as the prostate stimulation from penetration. But being someone who’s not a fan of boundaries, I wanted to see what pleasure was to be had with different things, including larger toys and arms, so my journey into the pleasures of being a big ole’ bottom began, and I soon became a pro, with the challenge of what I could take next becoming part of my kink.

But the sensation of being stretched is not just a physical sensation, its also a mental one. Especially when it comes to someone using their hand and arm to play with you internally. Knowing someone is touching you inside is a sensation like no other. I still remember my first experience of this. It was with a chap who I fully trusted and who had previous experience of doing this, and was a vet, so he really did know the inside of an animal. We didn’t rush it and made an afternoon/evening of it, taking the play time slow, and keeping it clam. 4 hours later, and lots of pleasure and lube along the way, and there he was telling me what parts of the body he was playing with, and it Blew My Mind!

But why do the whole big toy thing? Well, apart from the challenge of it all, there is the whole fantasy and feeling of taking a big toy or a fist, the look of the toy in, or the opening after play, or the fact that you have such an incredible collection of toys. These are all part of the reason people do this. I will never forget taking someone home for the first time, opening the toy box, and laying the toys out from “small” to “large”. The look of shock, horror, admiration, lust, and sometimes confusion on their faces were all part of the joy for me.

Where to begin.

As with everything, remember the 3 P’s, Preparation, preparation, preparation! Make sure you have everything you need ready and you are prepared mentally and physically, so you will be in the best place to start.

Regardless on whether its anally or vaginally, LUBE will be your best friend. Make sure you have a good one, that’s suitable for the toys you use if needed, and long lasting, as you really do not want a lube that dries up quickly. There are a number of great “robust” lubes, with the majority being water based, like J-Lube , which reactivates with water. There are also oil based, which are not great with rubber or rubber toys, but perfect for skin on skin, and if you have never heard of Crisco, well it’s vegetable shortening that’s been used as a fisting lube for years!

A good selection of toys, in varying sizes, from ‘normal’ to ‘OH MY GOD’ are also a great to have ready, so you can seamlessly slide from one to the next. I gave all mine names, so I could tell where we were up to when I was face down in a world of bliss.

And for me, the key piece of equipment is the douche. Usually, a good call is to have an anal clean out 3 hours or so before you want to start to play, and use warm water with your douche, never hot and try to avoid cold. The rectum is a sensitive soul, and will clench more with cold water, and if its too hot it can burn your insides.

Ideally douche with a saline solution, as plain water strips the body of its natural electrolytes, the minerals that help regulate your pH levels and muscles and keeping you hydrated, basically an essential mineral for your body to function. You can make your own saline solution if needed, with half a teaspoon of salt per cup of water, making sure it is dissolved before using.

Make sure you prepare the area of play. It will be handy to have a spare towel or two, as it could get wet and messy. You may even decide to put down a waterproof sheet to protect the floor/bed/playspace.

The last, and most important thing to remember, is to relax. If you’re relaxed, your body is relaxed, including the all-important muscle(s). Try thinking of your most relaxing places, play your favourite chill music, do meditation, what ever it takes to get you calm and chilled before you start.

And so to start.

Its always a good call to start small and work your way up, until you are very well versed in the art. We were never taught to run before we could walk, and anal stretching and extreme anal play is the same. Don’t try to force something too big in straight away, work up to it, playing and teasing the opening, getting it used to taking one size, before you insert another.

If you have never done it before, a good way to start would with fingers; well lube’d

, well manicured fingers; and working them in one, then two, then three, you know where we are going with this don’t you! If you have experienced anal play, or know what you can take, then measure what you know you can manage, and look at something a little bigger, starting with the one you know, to get you ready for the next one.

Never rush it, it is supposed to be enjoyable, and things that you enjoy need to be savoured and not rushed!

Long-term stretching and anal play.

There is a preconception that some believe, that once it’s stretched out it will never go back. Well, it’s a lie! I should know after everything that I’ve put mine through!

The human body is an incredible piece of machinery, and the muscles within it are designed to stretch and contract, and these muscles are no different. Both the vaginal and anal muscle is strong, elastic, and great at repairing its strength. If you play regularly, you will keep some elasticity in the muscle, so it will be easier to go back to the toys you get used to quicker, so you can go larger, easier. But if you stop playing or stretching the muscle will heal itself, regaining its grip, and within a few weeks its likely that you will be as tight as you were before, so you will be able to start the fun all over again!

If you’re looking at doing this to accommodate more on a regular basis, then you need to “stretch” a couple of times a week. If your lucky enough to have a partner with a porn-star dick; and trust me when I say they are very few and far between, then fucking a couple of times a week will keep the muscle where you need it. And if you decide want to stretch for more, the ideal time would be when the one you have regular doesn’t hurt when it goes in!

But if I were to only give you one bit of advice, then that would be listen to your body, as it will tell you what’s right. Don’t get me wrong, there will be pain, but it should always be manageable pain. I know people that use numbing lubes, but I would never advocate this. Relaxing ones yes, numbing no! At the end of it all, part of the fun is feeling it, fighting with your inner saboteur to stop, and allowing your body to work through the pain (and sphincter wall) to create a feeling like no other. Using numbing lube will take away this fun, but it will also take away your ability to know when its too much; when someone is pushing too hard; or trying to get something too big in; ultimatly causing you damage.

I’m a safety girl!

As with all kinks there are do’s and don’ts and extreme anal play and stretching comes with its own risk assessment. Don’t fret, I don’t mean you can’t, or that its unsafe, I just mean you need to know some things that will help you, long term!

Any anal play can cause internal microtears in the tissue, which in turn can lead to bacteria and infection, so its uber important to make sure you clean your toys before and after use with a good ant-bacterial cleaner.  And as already mentioned at the beginning of this read, LUBE! The tears are generally caused by friction, and a good dollop of lube will ease the friction. We have all had friction burns on our knees from the carpet, just imagine what they would feel like in your bum...!

Stretching you ass may lead to haemorrhoids too. The act of anal sex done right wont, but as with everything, if you don’t treat your bottom with the love it deserves, it will rebel! Haemorrhoids are the result of pushing you ass muscle beyond its limits, so as always LISTEN TO YOUR BODY. The ass isn’t designed to take all the toys together, it’s not a suitcase.

So, the simple rule is really to stop when you feel pain. Just STOP. Let your body have a minute or two to relax a little, then start again. If there’s still pain, it’s time to call it a day, and let your body do what it needs to do to recover.

If you have soreness too that lasts, then stop, and give it chance to heal. If you are going for larger, then there will be soreness for a couple of days, but it will subside, if it doesn’t then it may be time to have a full rest, and don’t play until the pain has gone completely. And when you go back, don’t go back to the same size; go smaller and start to stretch again, gradually!


You may have seen films where the guys or girls are just popping in a traffic cone or dropping onto a closed fist in the first scene. But I can assure you; they have been preparing for this scene well in advance of the word ‘action’.

Knowing what you are capable of will come with time and you will learn how to relax quicker; what positions are best for you to be in to take what is being offered and the time your body needs to recover! Just don’t rush it, lie back and enjoy it.

If playing with a partner, make sure there is trust between you, and make sure you have your safe word, so when you say stop, they know its stop! My safe word was rabbit, but whatever you choose, make sure it’s not No, Stop, or Fuck! It must be something you wouldn’t normally say in the throes of passion!

I’ve been into extreme anal play for years, and in my time, I was a very willing receiver and could manage a lot, easily. I knew what the best position my body needed to be in for what I was about to receive, which lube was best for what practice, and how long I needed to recover between sessions.

It was not something that was achieved in 5 minutes. I’d been bottoming for 12 months before the bigger toys started, and it was a gradual climb. I still have all my toys, in a big box under the bed, but haven’t used the big stuff for a year or two, and I know, when I go back to them, I’m going to start slow and build up again!

The Best Toys for the Job

Butt Plugs are great for stretching the cavity, more than the muscle, as the muscle will close around the neck of the toy, it's thinnest point. But you can increase the size of the plugs as you get used to them, and a well designed one should stay in on its own. Just remember to pop it out when it starts to become uncomfortable.

Dildos are good for length and girth, and a great beginners one would be something with a taper, as it will open you as it widens. For hands free, it is better to go with a suction cup one. But remember, which ever dildo you choose, they are not designed to stay in on there own like a butt plug.

Anal Beads are fun and come in two styles. The ones that grow in size that are close together, so you close around one and another is trying to get in, and then the ones with space between each one. The first sort is generally smaller in size overall but are a great way of getting used to something anally, before moving on to the others. I once had an ex who called me greedy because I wanted the big set of beads and him at the same time, which he said felt strange as he could feel himself moving them as he went in and out, I though it was fantastatic! Needless to say he didn’t last as long as the balls have!

Whatever toy you decide on, just remember to keep them nice and clean, and anti-back'd! Silicone is the best material in the “bendy” toys, as it is non-porous and super hygienic, but not always the biggest! Glass and metal are also super hygienic, but not bendy.

So, have fun however you choose to play, stay safe, and stay lube’d!


Check out Nice ‘n’ Naughty’s range of Large and Extreme Anal Toys here

Check out Nice ‘n’ Naughty’s range of Fisting Lubes here

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