I started with my fingers and a good lube. Be sure you learn how to clean out your ass before you do any anal play, even if it's with your self. Find a few objects or dildos and explore, see what hurts and what feels good. As I got older, I found places that men (tops and bottoms) love to visit, places like adult video stores with gloryholes and sex clubs with rooms and/pools with nude tanning. Being a petite, cute young Latino man, not very masculine looking....it wasn't difficult finding a man that wanted to fuck my ass. I am grateful that the first five or so were not well hung men. I would say they were about five to six inches in length and normal girth. It gave my ass a chance to be accepting of cock and a man that just kept pounding away in my ass, even those first five were slightly painful.
I was about twenty-one or so when I encountered my first large cock, married guy looking for a lil more than what he was getting at home. Probably a good 9 inches and thick as fuck. We needed lots of lube and patience, the pain was unbearable at first, I remember making loud whimpers, he had to cover my mouth. This went on for about five minutes before he started working it deeper and harder. After that my hole body had a rush of pleasure. Took him a good 30-40 minutes to shoot his load. From that point on, my ass was broken in, and any other big cock wasn't as hard to accept, even though this gentlemen and I developed a sexual relationship over a year or two, he broke my ass in real nice. I never had to worry about someone being too big for my ass.