I would have to say that the majority of what goes into this decision is your comfort level, as well as what is relevant. Personally, I am not comfortable with sharing much in the way of sexual history with a new partner. I have made my choices, and I stand by them. That being said, there are two people’s interpretations at play here. If there is one particular man you are considering dating and this subject comes up, allow him to ask the questions. Gage you gut reaction to his questions. Base your response on your instinct. If there is a question asked that raises your defenses, it may be best to inform your potential partner about how you feel so that you do not feel the need to provide those details. Just inform your partner that you are willing to let him know your health and relationship status, but that is all.
Alternately, if a question does not raise your defenses automatically, consider answering. If you are comfortable with all potential outcomes, then give the man some insight. Also remember that it appears that the men you are dating are operating under the assumption that asking these questions is OK. Perhaps before delving into all the dirty laundry, you two should have a more abstract conversation about what each of you expects to know, is comfortable sharing, and how to compromise. Sharing too little can leave suspicions and raise more questions; sharing too much can lead to thoughts of distrust and inadequacy if not handled appropriately.
This also leads back to relevancy. Determine if the information requested is necessary to the relationship’s health or forward movement. There is such a thing as just being nosy versus wanting to be informed. If I feel that a question is relevant for forward movement, I flat out ask what the purpose of knowing the answer will serve. When a partner inquires after details, I flat out lay out my boundaries. I will not share numbers. I will share test details. I will tell you what I like and don’t like. I will not tell you where I learned how to do that thing with my back that you seem to like so much. And never, ever ask a question if you are not prepared for any response that may follow. If questioning persists, I either answer or politely decline.