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.

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.

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.

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.

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

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.

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.

You don’t want to believe you’re ready for anal sex only to discover you underestimated your partner’s size

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.