chillywillystretching your ass and getting your sphincter to allow penetration is very helpful if you are going to attempt to be bottom for anal sex. I had imagined anal penetration from when i was 12 years old and began to suck boys' dicks but i never acted on it. I got various toys which I inserted in my butt. I found one great rubber dildo which was hollow, yet firm so I could insert it with or without a vibrator in it. It was rather thick, tho and I could not get it in me but i kept trying. One night I sat on it and it popped right in and after that it was not at all difficult to insert it . when I finally did let a man fuck me, He was able to penetrate me with ease and I have been happy to accomodate anybody who will do me the favor and screw my asshole ;)