I think there are TWO valid ways for a top to gain experience.
1.) A top can learn by getting fucked and learning from experienced tops.
2.) A top can learn by fucking bottoms who are willing to coach him on what works.
Personally, I learned to top by bottoming first. It made me realize how important it is to feel for the ass muscles to relax, etc.
Also, I recently taught a top how to fuck after he almost killed me the first time. Since he wanted to get together again, I told him the only way I would do it is if he was willing to listen and learn. He turned out to be a great student and has told me that he has started to ask other bottoms what they like and dislike. He appears to be developing his skills quite quickly.
In think that any guy can eventually strech his asshole to painlessly accomodate any sized dick. This doesn't mean they will be sexually turned on by it -- it may feel like a medical procedure -- but it won't be painful if the guy has spent enough time (years in some cases) training his hole.
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