Some types of lube can ruin toys or break condoms. Start off with 10 or 15 minutes of plugging and of course be prepared to take it out sooner if it hurts. They come in nine well-spaced sizes, so you can safely progress through their ranks.
For anal play many folks myself included prefer lubes which are thicker and have more 'staying power. No matter how thrilling it sounds you probably won't be happy taking large objects in your bum on your first time out or rather, in. Start off small, with things like slimmer plugs, anal beads, and fingers. You may not be worried about the pain. Check it out here to learn how. Good anal toys have a flared base or handle for this purpose. You'll also learn the 5 dangerous mistakes that will ruin your sex life and relationship. This is actually where the 'training' comes in, because the third thing you need for really great buttsex is practice. One thing you don't need to be overly worried about when embarking on an anal adventure is poop. Choose plugs with low bulb-to-neck ratios. This is actually why anal sex feels so good for men. But be aware that many people find fingers to be more irritating than larger objects. Learn more about anal rimming here. Don't expect to be ready for vigorous thrusting right away. Oh yeah, and one last thing - anything you stick in your butt needs to be easily retrievable. You fill it with room temperate water — never hot or cold — and sit over the toilet while you squeeze the water from the bulb to your anal tract to clean out any fecal matter. Take things nice and slow; seduce your asshole. The second thing you need to have in abundance when embarking on a journey down the "Hershey Highway" is patience. The first rule of anal play is lube, lube, and more lube. Thrusting feels very different from plugging. Rectums do not produce their own lubricant the way vaginas do, so if you're going to be sticking anything up your bum you need to grease it up first. They need to learn what your butt enjoys and what pisses your butt off. It will thank you later. You might receive a sensual massage more on that here from your man to melt all your stress away. As your anus becomes used to the sensation, you can add a finger or increase toy size.
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