This is going to require some backstory. Tw for abuse, rape, suicide mentions. 

I had a bad childhood. Divorced parents, physically and mentally abusive mother, sexual abuse from a friend of the family...the list is pretty long. 
More recently, around the beginning of 2016 I found out that my older best friend that I met when I was 15 and he was 25 raped a five year old girl and was arrested. I started dating a few different guys casually for a distraction. About three weeks ago, a guy that I had been flirting with for a while and was starting to develop serious feelings for committed suicide. Cue feeling abandoned and guilty.

One of the other guys I was casually sleeping with (26m) became my boyfriend. I meant for it to be a one night stand, but he kept texting and calling until I felt that he actually seemed like he wanted to get to know me. I agreed to hang out with him more. Then he asked me to be his girlfriend, and I didn't want to turn him down just because I felt bitter and distrustful of people, and I was enjoying the way he treated me. So now we're official. 
He's been as perfect as a boyfriend can be, although I'm aware that I could be glossing over some of his less than amazing points out of wanting to feel cared about and attached to someone. 
I'm a sex worker, and he's never acted squeamish or jealous about my job. The sex is great, he asks me about myself a lot--everything feels great. 
My problem is that I haven't told him about the not so great things that have happened to me or around me yet. I don't know if I should, and if I should then I don't know when would be appropriate. There's no natural segue into "So my mom used to beat the shit out of me when I was a kid and I still cry about it sometimes". I'm also afraid that he'll run screaming once he realizes how much of a handful I am, and I desperately want to continue receiving his affection and attention. The closest I've gotten to telling him about the crappy parts have been just glossing over it then changing the subject ("My parents and I aren't very close. Anyway, do you want to go see this movie sometime?").  

I guess my questions are these two things: Should I even bring up my weird past? 
If I do, when is it okay to start talking about such serious subjects? A few months? Longer? When he brings up something that happened with him first? Is there any indication of an appropriate time?
I don't want to feel like I'm hiding things from him, but I also really don't want to scare him off. 