I can give a perspective from a well hung versatile guy.
Bottom: I have been in a few situations as a bottom where I couldn't take a fuck because the top insisted on fucking me harder than I could take it or in a position where he is hitting spots that cause me pain instead of pleasure. This has little to do with the size of the dick once you are talking about average size cocks, but the technique of the top. If a guy has a really huge cock I usually like to sit on it 1st and find my comfort zone, then the guy can usually take me in any position with only a few limitations and most big guys are willing, it's usually the ones with average endowments that cause the problem.
Top: I have had a lot of guys have some difficulty taking me I'm 8.5" and moderately thick. I usually try to get the bottom to try what works for me as a bottom if they are having a problem, but I have come across a couple of guys that just couldn't take it no matter what we tried. I've had a lot more guys back out when they see it hard than have tried to take it and couldn't. Since I top a lot more than I bottom, and almost have guys lining up for me to fuck them when I go to the bath's I would tend to think my technique is pretty good.
So in answer to your question CollegeFlyBoi22 I believe that he would benefit from switching positions regardless of the tops cock size.
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