Training and stretching your ass takes practice and patience. Whether you want to have anal sex, use bigger dildos, or you simply enjoy feeling stretched, the same principles apply. Follow these guidelines and you’ll cry out in pleasure rather than pain.
1. For anal beginners, a good rule of thumb is to start with a 1″-1.25″ diameter plug. But if you want a more exact idea of what size you should begin with, play with your fingers. Lube them up, see how many you can fit in your butt, then measure their circumference. Divide your measurement by pi and choose a plug with a diameter as close to this as possible.
2. I recommend sizing up in increments of up to 1″ in circumference, or 0.25″-0.3″ in diameter. This should give you a challenging, yet fun and doable stretch.
If you attempt an increment much bigger than this, either it won’t go in or you’ll hurt yourself. If you try a smaller increment, you may find it too easy and too similar to your previous toy.
I’ve only ever applied this rule to plugs, not dildos. I think it’s best to stretch yourself with plugs and let the girth of your dildos trail behind by about 1″ in circumference.
3. I think the easiest way to prepare yourself for a thicker toy is to wear your current largest plug long-term.
Once you can handle a plug for a few hours per session, you’re ready to size up.
But there’s no need to stop after only a few hours. Keep going as long as it’s comfortable. You can even sleep while plugged, though you’ll feel sore in the morning.
Increasing the duration of your plugging isn’t as helpful as increasing the girth of your plugs. But it’s still very helpful.
I have another article that focuses on long-term plugging tips.
4. Choose plugs with low bulb-to-neck ratios. A thick neck is your sphincters’ friend.
For example, I wouldn’t recommend b-Vibe’s Snug Plugs. Their necks are thin, so they’ll give your rectum a good stretch, but they’ll only stretch your sphincters during insertion and removal. Your sphincters are the tightest part of your ass—particularly your inner sphincter, which is incredibly difficult to relax consciously—so they need the bulk of your attention.
5. You will always be able to handle thicker plugs than dildos or penises, since thrusting is much more stressful on the body.
So before you ever attempt to take a penis, you need to be able to handle a plug that’s about 1″ in circumference thicker.
6. Don’t only practice with plugs. Use dildos, too.
Thrusting feels very different from plugging. Even if you could insert a giant 14″ circumference plug, I wouldn’t recommend anal sex until you’ve tried thrusting with a toy as thick as your partner.
7. Which means, if your partner is willing, you should measure the circumference of the thickest part of their penis.
You can’t eyeball a 0.25″ difference in circumference, but your ass will feel the difference. You don’t want to believe you’re ready for anal sex only to discover you underestimated your partner’s size.
8. Lube. Don’t forget lube. Too much is barely enough.
For plugging, I recommend coconut oil. It lasts longer than water-based lube and, unlike silicone-based lube, it won’t damage silicone toys.
But coconut oil isn’t the slipperiest lube, so there are better options for thrusting. My personal favourite is Sliquid’s Sassy, but this lube guide will help you find many more great lubes.
Also consult this lube compatibility chart before you buy anything. Some types of lube can ruin toys or break condoms.
9. Involve your partner in your stretching.
They need to learn what your butt enjoys and what pisses your butt off. If you wait to involve them in your anal play until you think you’re ready for sex, they’re going to be a crappy lover.
If they’re willing, you should also play with their ass. Even if it’s just a finger or a small plug, it will help them empathize with you and understand what pleasures and difficulties you’re going through.
Stretching yourself for anal sex is going to take several toys, and likely several months.
If you rush the process, you won’t enjoy it and you might hurt yourself. Keep it slow to keep it fun.
I’ll stick to plugs, since dildos have a lot more variety. I have a separate article dedicated to general butt plug recommendations, so I’ll focus on plugs that work well for stretching your ass.
Tantus’ Ringo is a big plug that doubles as an awesome stretcher. Its girth may intimidate you, but no worries: You’ll never need to insert the whole thing. The long, smooth taper makes it a great stretcher and foreplay tool. If you’re having difficulty with another toy because its head is blunt, Ringo will open you up. It can help at any stage of play, whether you’re pushing your girth limit or you’ve just pulled your pants down.
My favourite plugs are SquarePeg’s Egg Plugs. They’re wonderfully squishy and comfy in SuperSoft. They’re available in well-spaced sizes, so you can safely progress through their ranks. Best of all, their bulb-to-neck ratios are lower than most plugs, so they’re great at stretching sphincters. The only downside is the cost.
If you’d prefer less expensive plugs, check out Pipedream’s Anal Fantasy Collection Silicone Plugs. They come in six sizes: mini, small, medium, large, xl, and mega. The silicone is firmer than I personally prefer, but the shape is ergonomic. Unfortunately, their thin necks make them less than ideal for stretching sphincters. Still, if you’re on a budget, they’re worth it.
But fyi, these Pipedream plugs come with a small tube of Anal Eaze. Throw that shit out. Desensitizing your ass is a bad idea. You need to be able to feel pain. That’s how you know when something’s wrong.
The plugs with the lowest bulb-to-neck ratios I know of are SquarePeg’s Blunt Plugs and Vixen’s Tristan 1, 1.5, and 2. They’re first-rate sphincter stretchers. And if you wear one of the thicker ones right before anal sex, you may be able to jump right into things with minimal foreplay, since their neck circumferences are comparable to penis circumferences.
If you follow this guide, I’m confident that when you have anal sex, your butt will be well-prepared.
5 thoughts on “So You Wanna Get Your Butt Fucked? How to Train for Anal Sex”
My fiancé sent me this article to look over because he’s really excited about trying anal with me.. Problem is, I’m absolutely terrified of it. I enjoy when he rubs the outside of my asshole but it usually starts getting uncomfortable a little while after inserting his pinky, though sometimes I can handle 2 fingers. How can I relax and enjoy experimenting with this?
The most important thing is how you feel about it. If anal sex terrifies you and you only want to do it to please your partner, you’re going to have a bad time no matter how much you practice and prepare.
If you’re not interested in anal sex, I hope you feel secure telling your partner this. But if you are interested and you want to get over your fear, I have a couple tips that may help.
Play with your ass alone. I know #8 in the article says to involve your partner, but when you’re starting out, I think it’s less stressful to play alone. Without him there, you’ll feel less pressure, you’ll have more control, and you’ll be able to go at your own pace. I suspect you’ll find it easier to take one of your fingers than one of his.
The terror of anal play goes away with practice. It’s purely psychological, so the more you play with your ass, the less you’ll fear it. Even brief playing sessions will help you overcome your fear. Hell, if you’re alone, go ahead and massage the outside of your anus for a few seconds right now. Nothing bad will happen and all those concentrated nerve endings will make it feel good.
Whatever you decide to do, I hope you enjoy it.
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I want to eventually try anal sex with my partner. I have bought two beginner plugs before, both have a different bulb-to-neck ratios but I’ve had the same problem with both. They won’t stay in. They both eventually leave me after wearing them for a bit, doesn’t matter if it’s during intercourse or while wearing them while just being at home moving around the house. I don’t really know what to do about that, I read use less lube but even then it happens and is more painful at that. Also it isn’t exactly easy to put them in or particularly comfortable when just wearing them for practice. Any advice?
Take a look at my article on butt plug design: https://squirrelmunkwrites.wordpress.com/2017/11/26/the-elements-of-good-butt-plug-design/
The two most likely culprits are that the plug’s neck is too short or you’re just ready for a thicker plug. The two less likely culprits are that the taper from the bulb to the neck is too gradual or the bulb-to-neck ratio is too low.
Very helpful and very descriptive info thanks !!