With my cousin for HIS first time.
I was fifteen and my cousin Billie was two years younger. Even though back then, two years was a large age difference for many things, it was not to us as we were together a lot back then. We lived relatively close and often spent weekends together either at his house or ours.
I had been masturbating to flowing orgasms since I was eleven and yes, Billie was often part of this pleasure. He too tried all the time to replicate what I was doing but was simply too young. We'd almost always masturbate with each other present or do each other simultaniously or just he'd do me and I'd do him or at least try. I'd usually cum in a couple of minutes back then and would work on him sometimes for ten or fifteen minutes when the sensations just got too great for him to continue and he'd make me stop. He just couldn't get over the edge.
It was a cold winter weekend when this finally happened. We had been ice skating and sledging on a hill nearby most of the day and had fun but Billie kept talking about what we would do that night as he felt he could finally squirt. Yeah, heard this a dozen or more times before. Probably about nine when we went to bed upstairs to my bedroom which was large but not fancy as it was just a converted attic space. My sisters shared a bedroom downstairs and parents had the other. Yet, this room gave me total privacy and was the room where I masturbated in the most.
During the past week, I somehow heard about using a lubricant from somebody. Not sure who but my dad often used lubricant on his hands which were always chapped from working outside. So, I liberated a partial jar as he had several. I told Billie about masturbating with the stuff and how it felt so different to me and he was very anxious to try it too.
In bed and off come our underwear in a flash. As usual, both had hard cocks albeit mine was probably twice the size of his which was about the size of my thumb in thickness and probably not much more than four inches long. He was just getting pubic hair while I had tons of hair for years already.
As he was so anxious to try it with a lube, I told him he would go first and took a large amount in my right palm and lubed his cock with it then slowly slid my hand up and down his cock. In a minute or so, his butt started coming up off the mattress and thrusting into my hand. His cock head would disappear into my palm then barely show itself with his thrust upward then disappear again only to reappear in a second or two.
I could see he was really into this but let go and had him kneel in front of me as I sat on the bed with my legs open and him in between them. I then again grasped his cock and had him thrust as we saw the porn pictures my dad had but this time, he would do all the work and literally fuck my hand. As his thrusts became faster, I squeezed a bit tighter. I don't know why but for some reason, I reached up and pinched his right breast which only made his face contort even more and a look of pain and pleasure was on him. His breath got quicker and it was at this point where he would always have me stop or he would stop. Yet, this time he didn't. His breath was coming out in little huffs and a look of terror came on his face and a sound kind of like a choked off scream and grunt all in one came from him as his cock was now slamming into my fist which was now against my body just above my cock which was getting rubbed with each forward thrust he made. I was fascinated looking at him and almost worried as he was moving so fast and making too much noise for my part when suddenly, his face got really red and his eyes seemed to bulge as he shot his first ejaculate on my stomach.
Oh, it wasn't all that much. Maybe three or four drops but it was the real thing. He put his head on my chest for a few moments as I felt his cock twitch between my hand then we were still. Lifting up, he was so happy to see what he finally did and for the moment, I think he was the happiest guy in the world. Trying for so long and for so often and finally getting there. Yes, he was so proud.
We had a mess though as I used too much lube for sure. It was all over both of our pubic regions and on our stomachs and well, just a lot of it. I still didn't cum yet so in a few minutes without any encouragement from me, Billy just got some of the excess lube on his hands and worked my shaft for maybe a minute and I shot well onto my chest and belly. Clean up was a chore but Billie was so happy that it didn't matter to either of us.
Yes, we did this a lot more as after that first time, it was a lot easier for Billie to cum, and often, without any lubricant we found like butter for instance, and yet nothing will replace the first time for Billie for either of us. No, neither of us are gay but just young and inquisitive as most guys are if they are honest. We did a lot together but this time was special.