So I sucked him off 4 times in a row this morning until he was breathless and his foreskin was thoroughly stretched. After the last blowjob he said he was ready so I got his VR and brought it over to him and he said "have fun" then he stood up, crossed his arms, and gave me access to his dick. I was already hard as steel and he was 100% floppy. I peeled his skin back and it was still wet and slimy from the remnants of his precum, cum and spit from my blowjobs. I touched my tip to his tip and rolled his skin back over his tip, then stretched it to start covering my tip. It must have hurt him because he jerked away and grunted in pain. He told me to do it slower and be more gentle but after 2 or 3 more attempts, it hurt him too much for me to stretch it over my tip. He took off his VR and saw that I was really sad that we couldn't dock so he said we could try one more time, but he would stretch his skin since he knew when it would hurt. He went over to his side table, grabbed some lube, squirted it inside his foreskin, held the end open with his fingers, and told me to put his VR back on him and to stick my tip inside his foreskin. With how he was holding it, we were able to cover most of my tip with his foreskin. When he said it was hurting, I stopped and just enjoyed our tips buried together inside his wet foreskin. I started to wiggle my dick and he said "just stop moving, I'll take care of it" and he pushed his skin over my tip as far as he could and wrapped his hand around the end ofmy dick covered in his skin and gently squeezed and loosened, squeezed and loosened for about a minute until I lost it. I exploded inside his foreskin and as my orgasm hit he realized it and squeezed harder while I reached around his sweaty body and held on as my knees nearly gave out. We stood there for another minute as i softened and caught my breath. When I was finally soft he loosened his grip and I watched my dick drop from inside his foreskin and my (now watery) cum just dropped out everywhere. He took his VR off, looked down at our docks, and said "you realize that my dick needs cleaning, right?" I replied "mhm" and he sat down at the edge of his bed and I got down onto my knees I looked up at him, I said "thank you", he nodded, and I got to work cleaning up my mess. After a few licks he started getting hard and, realizing what he just did for me, I asked if he wanted to throat fuck me instead of a normal BJ. He declined and just said "just pleasure my dick the way you like to do it" and he laid back and I did just that. The taste of my cum mixing in with his precum and ultimately the mixture of both our cum was hot. When I finished we cuddled and watched some shows in his bed for the entire day. Every so often I reached down and played with Mr softie, his low hangers, and his bush. It was a wonderful day.