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Yes, there are VERY REAL risks of taking it raw. Everybody says he is healthy, but get more of his details - like where he lives, his profession, etc. Then verify as much as you can. If he seems to be honest about that stuff, it increases the chances he's telling the truth about the other stuff.
When I got curious about getting my ass cherry popped I looked for a guy who had taken other anal virginities. I asked for descriptions of how he did it, what I should expect, etc. I found a guy who claimed to have initiated several young boys and seemed to know what he was talking about. It took me over 6 months of looking, and a week or so of emails with the top, before I met him.
I felt both physical and mental sensations of being naturally inseminated - and they were both very unique, very puzzling, and very intense. The top told me, beforehand, that I'd probably feel many of the same sensations - mental and physical - as a virgin girl getting her hymen broke and pussy split by a cock for the very first time. I think he was right. I have been with only one virgin girl, but after getting my ass fucked for the first time I think I understood why she cried through the whole first fuck, then wanted to do it again!