Great question. As a bottom, I've often wondered the same. I do know that if I'm getting butt fucked frequently with a long and thick one (8", 20cm) I can work that cock to the point where it doesn't hurt so he can just bang away all he wants. But, for instance, I hadn't had any anal sex with a hung guy for 4 months, and last week, I did and it really hurt when he went in deep. He was fucking me doggy style and It hurt to the point I was yelping and jerking forward when he plunged in deep, so ya, he knew when he was hitting that second ring,But, could he feel it? That is the question.
Tops.... Please answer this as I'm sure that there are a lot of bottoms out there like me that would like to know.
You have to remember that everyone is a bit different. Some guys have deep asses and I can go as deep as I want. They love it, not uncomfortable for them and love the feeling of me so far in them. But I never hit that second hole.
Then there is the majority of guys with not so deep of asses. Usually two things happen. The most common is that if I push too hard, it hurts them, so I have to back off. Some get more used to it, like you and after a bit of careful pounding seem to like me banging on that wall. And some from the very beginning love for me to go deep and hit that wall as hard as I can. I feel incredible pressure when my dick hits that back wall, and that feels really good. But there is more.
Then there is a totally different experience. And that is when my dickhead feels like it is getting through a very tight hole as it makes that corner. Then the deeper I go the more the guy loves it. They want me to never leave that spot. And as a top it is fuckin amazing. It is like you are fucking a guy and someone decides that this just isn't feeling good enough all ready so they start to work not only the entire length of your dick, but they start to pay special attention to the head of your cock. It is so incredibly stimulating that I can't do it for very long. I have to pull back a little, bite my lip to keep from coming and just relax a little. But as soon as I regain control, I am back in that second hole for as long as I can hold on. It is amazing for both me and the bottom. I love looking at them with their eyeballs rolled back in their heads like they have never felt anything like this in their lives. I know that day, I have created a size queen. lol
I also have to say, experience doesn't have much to do with it. I remember fucking a 18 year old kid. He was pretty new to all this, and was eager to have his first big dick. After taking my time for the normal beginning, I slowly slide my dick all the way in. Yeah no problem. I was in that second hole and we were both feeling pretty amazing. I saw him a lot in the next couple of weeks. lol.