I am very stressed out and I really do not like talking about it. He says he needs to know so that if anything comes up by surprise he will already know, but I do not think that is a good enough reason. How do I get him to leave this subject alone once and for all? Or should I just tell him some of my past so he will shut up?

I am not for revealing too much about one’s past. Number one, it invites comparison, and nobody gains by that. And then, where do you draw the line? Once this topic is in the open, it’s like Pandora’s Box. He’ll want to know their names. If they were good in bed. What you did with them. If you tell him the topic is off the board, then that’s that. Telling him a little is unlikely to satisfy him. Now if you’ve slept with half the men in town, or a good number of men that he knows and the subject is going to come up, you might have to tell him a few things in order to assure that he doesn’t get a nasty surprise. But if you’ve had relatively few lovers and they don’t travel in the same circle that he’s likely to meet, then that’s just not an issue. If you want, you can tell him that you asked me and I said that it’s like playing with fire and advised against it so that neither one of you gets burned.