Usually the eyes are too big for the ass when you're starting out, but don't worry the toys can always be used at a later stage and sometimes they seem too small then. You're experienced in anal play despite the lack of toys because three fingers and anal sex is quite advanced

The big end is an excellent plug and it's only a bit bigger than the Ryder which I consider as the best plug around (mostly because I don't feel comfortable with a "sharp" tip). The advantage of its shape is clear when it comes to training you gradually stretch your sphincter until you can get it all the way in.

In case you're looking for a plug for stretching that is variable in size, I'd suggest to loot at the Gapers Organic. Look through reviews, it's without doubt one of the best in that area.

Another very good and highly comfortable plug for wearing and intercourse is the Love Pacifier advanced and its smaller cousin Love Pacifier beginner. Those require a bit different approach to insertion as compared to the pointy ones. Of course there is the Pure plug medium - I don't posses this one so I have no educated opinion, but I love steel toys so I'd probably add it to my collection quite soon.

So it all depends what you want to do with the toy. The plugs are not really designed for penetration so you might look at something else, like the Ultra skin cock - it has some girth but due to the realistic material you get used to it very quickly. So as an addition to the plug it will do very well.

I hope I've given you some ideas for further exploration.