This is a true story.
I wear diapers for urinary incontinence. The guy I’m with knows this and is OK with my diaper wearing. One evening as I came over to see him, he greeted me at the door completely nude with a hard dick. As I entered he gave me a hug from behind and I liked how his cock felt pressing against me.
As I undressed, he asked if I had any extra diapers with me. I always carry a few extra, I told him. He said he wanted to try wearing a diaper, so I pulled my pants back on and went out to my truck to get my diaper bag and came back to him.
He let me diaper him, so then we were both in diapers. We went out onto his back deck to relax and we sat out there drinking tea and talking in our diapers. It wasn’t long before he said he’d just peed in his diaper, so we went in so I could change him. As he lied there allowing me to remove his diaper, his dick was hard, so I went down on him sucking his dick; I could taste his pee and his manly taste.
After a bit he said I could stick a finger up in his ass; this was the first time he even mentioned anything like this. So one lubed finger went up in his asshole, then two fingers, then three fingers. Before long I had four fingers in him. I was enjoying sucking his dick and using my fingers on him, but it surprised me when he suggested I stick my dick up in his hole.
I looked at him and said, “You’re a virgin.”
“Not after tonight I won’t be,” he replied.
So as he lied there I spread his legs and got into position. I took my time penetrating him; I didn’t want to hurt his hole being the first time for him. Oh man, it felt so damn good! I felt like I was about to cum the instant I was fully in him! I held my composure as long as I could. I was fucking him slowly, letting it build, but I couldn’t hold it any longer and I thrust in and let loose a load of cum deep in his hole.
When I pulled out and collapsed on the bed next to him he said, “That was good, it didn’t hurt.”
We fell asleep and slept for about three hours.