Yes I remember that feeling! And the slick cum soothing my sore anus.
I was in my 50's, and did it out of curiosity and to check off a bucket-list item. I looked for several months until I found a guy who said he had initiated several holes, and seemed to have a well thought-out approach to devirginizing an ass. He had several requirements: I would be kissed. I would be fucked "like a girl" - on my back, thighs open and legs up. In fact, he said that I would probably experience the same sensations - both physical and mental - of a young girl getting her hymen broke, and her pussy split by a cock for the very first time. His cock would be bare and would finish with a natural insemination. He was about average length but rather thick, so he said I should expect some pain.
It was all true. I hadn't thought about the comparison to a virgin girl's first time in her pussy - and especially the mental sensations - but it was right on target. I expected the kissing would be the worst part but it was actually very pleasurable and arousing. He prepared me very well. Eventually he eased me onto my back and folded some pillows under my hips. With my ass propped up in the air and my legs spread I felt so exposed and vulnerable! As I watched his thick cock approach me, and thought about what it was going to do, I had a VERY confusing mixture of anticipation, naughtiness, fear, excitement and nervousness. I understood what he said, that no virgin can truly relax when he or she gets popped and split for the first time. I allowed him to (respectfully and considerately) take my virginity, enjoy my tightness, take his pleasure from my most intimate and personal opening, and receive the essence of his manliness deep inside my body.
He laid out full-length on me, pinning my body under his. He started a long, deep, erotic kiss. I could feel his cock gently probing against my pucker and knew what it was going to do. After a while he started doing what had to be done in earnest.
There was gradually increasing pressure, and discomfort building to hurt, before his cock head broke through my sphincter. I vocalized the short, sharp pain. He pinned my body and held himself just inside my muscle ring while I tried to writhe, and said "Ouch!" (or maybe it was, "It hurts!") a few times. My cock went mostly soft. My anal muscles were still spasming a little when I got control of myself and took a deep breath. I think he used that as a signal to proceed. He finished the insertion with a controlled, steady stroke until he was all the way in. Toward the end of the stroke there was a dull but somewhat intense pain inside me. That's when I started to cry a little, but he paid no notice as he finished the insertion. He paused again, I was still sobbing a little when he started the fuck.
It was a very strange and new sensation to feel his erection sliding in and out of me. On some strokes it felt like he was going all the way up under my ribs. I should have asked for more lube, since my anus got rubbed a little raw but I didn't recognize that when it was happening. It was just starting to feel good when he pushed deep and hard - I cried out a little, again - and I felt his cock jerking inside me. At first I didn't know what it was but then I realized he was cumming in me. I didn't feel the actual squirts but I knew he was spilling his seed into my rectum. Instinctively I wrapped my arms and legs around him, clutching his body against mine and wanting to receive all of his cum.
After his first few contractions he made several long, slow strokes. I could tell that the texture inside me had changed. Then he pulled out, very quickly, a move he called "uncorking". I was still mostly soft but he immediately went down on me. Even though I wasn't hard, on the second stroke I exploded into his mouth. I had NO IDEA that I was THAT CLOSE to cumming!
