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Not necessarily. 4.999... is a real number, which is a cope made up by mathematicians. For your penis to be 4.999... inches long, the error in saying your penis is 4.999... inches merely has to be less than any positive fraction of an inch. Note that this does not mean your penis is shorter than 5 inches. It could be equal to 5 inches or infinitesimally longer than 5 inches.
On the other hand, 5 is an integer, created by God Almighty. For your penis to be 5 inches, when you take an inch, an inch, an inch, an inch, and an inch, all perfect, and join them in a perfect straight line, they must be exactly the same length as your penis.