If he is your first it will be pleasurable, more so the second time and later. Your first time having sex will not be the best, but the second time will be better. What matters is once you are with a certain size, then others with smaller ones would feel less pleasurable. Think of it like a rubber-band that can slowly be stretched. It doesn't fit so well eventually if it has been stretched too much. That's why women that have been with many guys need bigger ones, where as women that haven't are more satisfied if they can stay with their first. If someone could somehow stay a virgin until they were sure they found the one person they would always be with, that sex would feel the best for them.
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