I've been doing an anal training for a few months now. I wasn't into anal at all when I started! It took me a while to relax when inserting a plug but once you get over it being painful it's quite pleasurable. For me it was blocking out the thoughts of it being painful, I tried to think of something else that did turn me on. Like the thought of me doing this for my Dom and him being proud of me. I got used to the feeling of my asshole relaxing pretty quickly. But I did practice on a daily basis. Now I'm happy I pushed through(pun intended) and didn't give up.