I’m a top. Entry is usually pretty intense, as I am trying to gauge the bottom’s level of comfort with the pressure I’m feeling all around my cock. Inexperienced bottoms or ones that took a bit of a break are usually so tight that the squeeze almost feels painful, but the intense sensation tends to make my cock even harder. I try not to throb, as it tends to be a bit much for the btm at the moment. Once I gingerly ease my cock all the way in by going 1 inch forward 0.5 inch back, all while kissing and caressing the bottom, I stay still for a while, feeling the sphincter muscle melt around my cock. Then I pull most of the way out and ease back in again, this time with less difficulty, hopefully, and more pleasure for the bottom, as the pressure becomes less a quivering death grip and more a submissive “holding on” to my cock. This “submission” signals to me that the hole is ready for a bit more thrusting.
Towards the anus end, especially when I’m very stoned, I can almost visualise my cockhead sliding past or pushing against the prostate. As I slowly move my hips and carefully angle my cock, the pressure change causes the prostate to tighten into sort of a knot that I can massage and tease and push against.
Past the prostate, the passage is a bit wider, and looser without the powerful sphincter muscles. The texture of the walls feels similar to the underside of the tongue sliding on my cockhead, slick, every so slightly rippling, and warm. The deeper you go, the warmer it gets.
As I thrust to the deepest that I can push, my pubic bone firmly presses against the bottom’s warm perianal area and ass cheeks. The more muscular the bottom is, the more intense this pressure feels, while fat provides a softer embrace. It can hurt with very skinny (read: boney) bottoms. This tends to cause the bottom to first tighten, then relax, further loosening the grip.
Bu this point, most bottoms are ready for ruthless ramming and jackhammering, which can create friction on the cockhead. This isn’t particularly my jam, as it could easy become overwhelming and is very likely irritating the bottom’s linings, making longer sessions uncomfortable for them. Though, it can be the fast track to cumming, so many bottoms habitually just seem to take it and get ready for breeding.
I often don’t even cum during sex, so these days I mostly try to stay in the prostate massage while peppering some deeper strokes here and there to keep the bottoms on their toes, either til I get them til they cum, or they get overwhelmed with the prostate pressure and ask for a break.
Edit: this is all referring to the missionary position, where I feel I reach the deepest. Positions like doggy or cowgirl usually feels quite different, the former feeling less tight and less deep, and the latter feeling a bit cock-bendy/breaky when the bottom moves forwards and backwards.