I think there are some secrets that should always remain secrets. There is no reason any human being should know everything about any other.
BUT...and its a huge but....anything that would affect a persons decision to be with you must be told. If for example a person has HIV, you have to say it, that is not going to be a secret. Second, how a person reacts or feels or thinks about something you tell him is not your problem or responsibility. As it is, you are trying to do his thinking for him and you must not. Thats up to him. If he chooses to leave you because you were allegedly a prostitute, that his choice. Never deny a person their right to make a decision for themselves based on whats important to them. If you are not sure that a secret would be accepted the way you want it to be accepted, thats the test of what to tell someone or not. Clearly, you are very unsure how your secret would be taken and that means you have to tell it. If it breaks the relationship, relax and know that its OK. After all, you want someone who accepts the secret, yes? Of course we all do. So, free yourself for the next person who would accept.
Right now, turn the tables. If he had a similar charge from his past, would you want to know it? Do you have the kind of relationship in which nobody cares about things from the past? How about if he was in prison 25 years ago for incest or rape or armed robbery. Let bygones be bygones? Oh its OK, we dont care about things like that? And how would you feel when later when that old, buried fact pops up in a background check for a loan or license and you never knew about it?
Let me tell you two things from my life. The longer the time goes that you withhold important info, the harder it is to be accepted later. Many people think its better to let a relationship first build strength to withstand revelations later but it will likely backfire, make things worse and be harder to forgive. Second, dark and important secrets never stay buried forever, they come out in the saddest and oddest ways and at the worst possible times.
But this isnt Dear Abby. You are an adult and should know these answers without asking in here. Matters of the heart? Dont lie, period. After all, what are you going to build a future on, a flimsy foundation? Its up to you to get the habit of truth or the habit of lies and you dont need anyone to tell you the consequences of that.