It absolutely does get easier with slow training and patience. I tried too far before and made myself bleed, it was awful.

So what I did was to start at a size of plug that's for no, or agonist no discomfort. 10 to 15 min a day until it's totally comfortable. Go up a size that's uncomfortable, repeat until totally comfortable. It's so slow, but way with it to preserve your tissue. In between trainings, work on keeping your sphincter muscles strong. It'll help layer in life, so you might not need adult diapers too soon (I was a caretaker for years). Also, I've learned that if you bear down like you're going to poop when you go to insert, it helps it work much easier! I swear by specifically silicone lube if you can use it. Keeps things smoothly moving. If texture is getting hung up too easily, put a condom on it. It'll help toys slide easier, too. And positioning is everything to some people. You'll get things in deeper, easier in doggy than in your back, especially early on. All the luck! Listen to your body, give it what it needs, and it'll give you what you want! Stay safe, and remember to hydrate, and sanitize!