There is no “second virginity” or “virginity by desire.” If there was, the word “virginity” wouldn’t mean anything. I’m really surprised to see that on a Catholic forum. You are a virgin or you are not. It doesn’t matter how renewed you are from your old life- there are no second chances there.
Virginity is huge going in to marriage. I agree that a woman’s virginity is of the most importance, but that does not diminish how important it is for a man to be a virgin when he marries.
There are temporal consequences for our actions, and losing your virginity before marriage is going to place unneeded strain on the marriage even if the man is repentant. When man and woman enter into marriage, a woman has to take very seriously the vow to respect her husband, and so too the husband to love his wife. Some women may not have as hard a time with it as others, but if his past mistakes are a bitter pill for her, she shouldn’t marry him.
When I became Catholic, a man who wasn’t a virgin was a deal breaker when considering a spouse. Even as a Protestant I understood how important virginity was, but becoming Catholic I understood better the spiritual aspect of it.
But circling back to the original question, I absolutely think each person should be forthcoming with the other about their sɛҳuąƖ history. It is for the best for both of them- there is no good reason not to.