Post-Halloween party milestone

I went to this Halloween costume party (as the bellboy from Grand Budapest Hotel). Met this hot older guy (he wore a pilot uniform which really turned me on) and spent most of our time in the party together. Eventually, we went home to his place to hook up.After what seemed like half an hour of intense foreplay, he smoothly placed a condom on my dick. I actually wanted to get fucked by this hot older guy, but I just went with the course of events. He rode me like a cowboy and it felt AMAZING! Now, I have to say that I don't usually top, but this particular encounter made me want to fuck him in many positions.You might be wondering what the milestone is. As someone who's more used to getting fucked, I'm not that confident in my 'topping' skills. So we were in a cowboy position, and I wanted to try more positions with him. Suddenly, he said: "Oh shoot, I'm about to cum!" Indeed, when I looked at him bouncing on me, he was cumming HANDS FREE! It was my first time seeing that happen in real life, it was so surreal and amazing!I was very curious with how he felt, because when I bottom, my dick goes soft and I find it hard to cum. But this guy just exploded after a couple of minutes of fucking. Wow. So after our fuck session, I asked him how it felt and if it's usual for him to cum while bottoming. He said that it has happened to him a couple of times before, so I guess it was more of my milestone than his.TL;DR - I'm more bottom but suddenly tried being a top. Ended up making the guy cum hands free.