Toy Recommendations

Butt plugs can be good for beginner anal toy play. You can get kits with ones that come in different sizes.

For a bit more advanced play, FleshJack makes some good butt toys. They even vibrate.
 
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Butt plugs, prostate massagers and toys are a great way in! And if you have a certain male porn star you like, you could see if they have any dildos like Johnny Sins, Chad White etc :)
I'd recommend saving the Rocco Steele one for when you're a bit more comfortable. ;)