Tips on sizing up?

Nsaria05

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Tucson (Arizona, United States)
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100% Gay, 0% Straight
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Male
As the title says, I'm looking to go bigger, but I don't know how big to go. I've made mistakes before and assumed it would be fine and I was VERY wrong.

Currently the widest thing I have are the Master Series Black Baller Anal Beads that are 2.65 in wide.

I've also got the Doc Johnson John Holmes that is 2.5 in wide, but 12 in long.

Should I try to go all the way to 3? I've looked at options and I'm probably going to buy from Mr Hankeys, but I don't wanna go to big because they aren't cheap.

Any thoughts?