how was your first time?
was topping or bottoming what you expected?
I was topping soon after I came out. Was OK, but usually couldn't get off that way. Tried to bottom with my first BF, but I couldn't relax enough, we didn't get anywhere.
A few years later I chose a friend to finally "deflower" me. I'd blown him and knew he was very small, and I trusted him to go slow, and stop if I asked him.
With plenty of lube (and a condom) he didn't hurt at all, just some mild discomfort at first. He entered me doggy and within seconds I was slamming right back at him. He couldn't believe it was my first time, I was so into it, really great.
We did it 2 more times that night in other positions, and once again in the morning when we awoke, and I must admit when I finally went home it felt like he was still inside me. But no blood, no actual pain, no damage. I continued to go back for more.