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"Waiting" isn't the solution. I was waiting, and curious about it for years - decades, even - before I finally got up the nerve to just DO IT, and offer up my ass cherry. Took a couple months of ads and email before I found a top who seemed to know a lot about initiating a virgin bottom. He had never taken a cherry from a guy in his 50's, and was a little surprised that I reacted about the same as a teen.