Had this happen again yesterday. I was with a guy with a solid 9 and proportionally thick. I started off on top, and once my hole was relaxed enough for me to comfortably slide up and down most of his length we both acknowledged that his had reached the second ring. So he could definitely feel it just a few moments after I did.
He rolled us over so my legs were over his shoulders and told me he was going to get in me the whole way. It only took a couple thrusts, and we were working together like it was a joint challenge. I knew I could open up more and encouraged him, and he encouraged me to relax and open up. He was verbal through the whole process in a very hot way, which helped. Once he pushed through we both groaned. I entered my usual “bottom fugue state” (lol) and while he began to pump back and forth deeper to keep me deeply open he said that my hole was made to take cock, etc. I just made pleasure sounds and enjoyed a lengthy anal orgasm.
He fucked me almost non-stop 5 times in 3 hours. The first 3 he never had to pull out, he was so turned on that his cock stayed at least semi-hard in me after he came so he kept going. Brief breaks between the final 2, at which point he had me chest down ass up, but with my legs spread wide and my butt low so my hole was perfectly aligned with his cock. He waited until I was confidently, fully open for that position because he wanted to fuck me hard and deep without hurting me. I’d say it was a smart strategy given how blissed out I was taking his cock.
So yes he said he could feel it, and also he seemed very experienced with getting through it. It was one of the hottest fucks I’ve had in months.
never allowed to do anal 
