Shady past,how much do I have to share?

That's why it's the past.. Live the present. Why try to fix something thats not broken? Personally if your current relationship is going well why try and bring up your past it'll only bring him insecurities and cause him not to trust you.

Your past is just that, *yours*

Your past is never anyone else's business. Don't concern yourself with what idiots in your town think or what they think they know about you. If you personally feel like your boyfriend has the right to know (psst... he doesn't) about your past, then by all means, go ahead and tell him.

A person's past should never be an issue for anything as long as you have changed yourself. People make mistakes all the time when they are young. I've made plenty. I'm not gonna spoil my happiness and my spouse's happiness with unnecessary information about myself. Your boyfriend has probably made plenty of mistakes too, you don't see him stressing over it do ya??

Be as honest ASAP. I just got done dating a girl who told me straight off the bat that she's an alcoholic, used to be addicted to crack, used to get raped (her sister being one of the offenders), was beaten daily, had 4 abortions, and had no teeth. The only reason I gave her a chance was because she was honest. And in my opinion, honesty is #1. But I broke up with her because the actions and thoughts her baggage left behind became far too much to handle. What I'm trying to say is... Nobody wants to date a liar.

unless its life-threatening, you should never have to share anything unless you feel comfortable sharing it. so if he really cares about you, he'll wait for you to be ready to talk about it.