I have the Bad Boy and although I like it a lot, I would say that it is probably not the best of the bunch for less experienced play. First, it is bigger than it looks online. Second, the texture can be a bit aggressive, especially if the user hasn't fully relaxed. Third, the stiff nature of the silicone equates to some very strong prostrate pressure. That last attribute took a little getting used to for me in the beginning and I have a fair amount of prostrate play experience.
Everybody's body is different, but I would start with the Rude Boy and upgrade if needed later on.