What I remember most about my first anal was that I had no doubts at the time whatsoever. I've described the scene on other threads but I've never mentioned my state of mind. I was with a guy who knew he was my first. He had built me up to it so slowly and patiently. There was one moment where I felt the head of his cock brush across my hole and that was when I knew it was time. I could feel myself rhythmically contracting, like uncontrolled kegels. He brushed across me and then around me several times more, and each time it felt like I was physically opening for him. I had only ever used toys on myself but had never experienced anything like this. By the time he pushed inside me I was yearning for it. Yes, there was a little pain at first, but still no doubt, and the pain soon gave way to a feeling of deep connection and trust. That first time was over twelve years ago now, still no regrets, and many more experiences.