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The largest plug I have is 3.3 inches in diameter (833mm)
It took a lot of practice to work up to that size, but when I finally managed it, it did hurt quite a lot, and it hurt as well getting it back out past the widest part.
I eventually got used to it, even though it still hurt getting it passed the widest part.
It holds itself in really well, and I have been to the local shops with it inside a few times.
I have even gone to sleep at night with it inside.
I really only use that when I'm extremely horny, and my usual day to day plug, is a prostate massaging plug that I wear all day.
I do have a 14 inch long steel dildo with a 50mm wide head that I use now and then..I can just get 12 inches inside before it cums to a stop.
It was bought for my wife originally, but one night, I let her try it on me..
I told her to take it very slowly and carefully.
She lubed up both my butt hole and the dildo, and started pressing..It would only go in so far.
She decided a good hard push might work, and the neighbours must have heard my scream.
I had never felt such pain, but she laughed and said at least its inside now.
so clearly, I need to get back to sitting on it 2-3 times a week.
As far as stretching your hole. Try to find a tapered dildo and use it frequently. The more you use it and the deeper you get it inthe more you will stretch. Of course, there are limits to how much one will stretch.
I don't have a problem with stretching enough, but my bone structure back there seems to limit the size I can take. I've seen guys using huge items and I just can't get anything over about 2" to 2 1/4", and then it needs to be squishable. No bottles, cans or ball bats for me, unfortunately. Hope this helps