Despite repeated forays, all of my previous attempts to train my ass have led to failure. I used to believe that this was due to, ah, insurmountable problems of a medical/anatomical nature, if you catch my drift. However, I am coming to realize that it may in fact be due to a lack of proper tools.
My jelly plug had been touted as a great beginner plug; I didn't want to spend much money on a toy I'd quickly grow out of, and I didn't know the issues of jelly. Little did I know that it was probably the worst design I could have tried. It was jelly, first off. It was long and pointy. It didn't taper to the neck, it cut in almost horizontally. All I can say is that I didn't know any better. My next toy was a vibrating jelly (again) probe. It was rather long, and had a series of bulges from tip to base. The first time I worked myself up to it, I managed to take the entire length; after losing ground, I never was able to do it again. My third butt toy, silicone this time (see, I do learn eventually), has yet to see my ass; it's not even a dedicate ass tool, it's a multi-purpose dildo that happens to be small enough.
I need some serious butt toys. Ergonomically designed, safe material, high quality ass candy. I'd settle for safe materials, moderately high quality toys that at least take ergonomics into account. Because honestly, toys made from the molds of other people's colons squick me a little bit.
Two very different baubles share the top of my wishlist.
At the very top is the gorgeous, glorious Romp by NobEssence. A hardwood work of art, this is designed to work equally well for play and for long-term wear. It's small, but reviews rave about how it is still filling because of the design. It's outside my price range for the time being, but it still beckons and tells me I don't really need to eat for a little while...
The other toy highest on the list is FunFactory's Bootie. Another toy reviewed as perfect for both beginners and extended wear, this one is made of FunFactory's safe, lovely silicone. The curve looks wonderful, and the flange is substantial, but narrow enough to hide unseen between the cheeks. It's also affordable, which is of great importance on a college budget.
New as I am (returning) to anal play, the give to the Bootie will probably be a better place to start than hardwood, but the Romp is so gorgeous, and has such an amazing shape. I'd love to play with both eventually.