The Frisky Inflatable Stimulator

This is the ultimate beginner's inflatable toy!

At only .75 inches wide, even those new to anal can slide this in. Once you've got it in, every little squeeze on the bulb makes it a little bit bigger. It can slowly but surely grow to a whopping 3.5 inches wide. Of course in the confines of your ass it will grow while distributing pressure more evenly. It will work with your internal contours to slowly open you up. If you ever pump it even a little bit past where you're comfortable, you can just hit the pressure release button. It's a great toy to start out with before trying to insert something bigger and more aggressive.