I am on vacation for all of July. But I've invited Mistress Matisse to handle the Savage Love letters of the day. Mistress Matisse is a writer, a dominatrix and a sex worker’s rights activist. She has a blog here and twitter here. The archive of her Stranger column, Control Tower, is here. Mistress Matisse will be answering your questions all week.

My boyfriend and I have been off and on for a while. We met about four years ago, and casually dated off and on. I got pregnant a year and a half after we met, but we had almost no contact the whole pregnancy and the whole first year of my kiddo's life. 
He's since come back into the picture and we've had lots of rough patches. He's not working now and I'm letting him borrow some money until we get situated. I have many doubts about this. Recently, he asked me a strange question.
 We use condoms for birth control because I want to be as sure as possible I won't have a second child right now. Sometimes, I slip on the condom with my mouth. I also have a placard that I bought at an antique shop many years before I met him with a "License for Prostitution" from the 1900s 'cause I think it's awesome. 
So, the other night, we were sitting in bed chatting and he sort of backhandedly asked me if I've ever been a prostitute.
 I was kind of offended/weirded out by it, but I haven't and I said no. He didn't believe me! And he said, "I won't judge you or anything, you can tell me." And again, I said no, because it's the truth. We've talked about getting married and have been to a couple's counselor, but I still have a ton of doubts about this relationship.
 My main concern and reason for staying with him is that my kiddo does genuinely seem to love him and I don't want to rupture their relationship. I've also broken up with him before and he's threatened to sue me for custody every time I even mention my doubts about us working out as a couple. I am inclined to think he's abusive and I should leave him, but I don't know what to do.
His questioning me about my sexual past and not believing my true answer to his question concerns me, along with some other things I mentioned here. I've also seen him lie to others, and have felt he disregards my boundaries, however small.
 Any advice around this? We've been back together steadily not quite a whole year.

Don't Wanna Be Sued

Mistress Matisse's response after the jump...

Sister, you DO know what to do. You’re saying it right here in this letter! You should leave him, now.
But let’s go over why. Here’s what I’m reading in your letter: this guy is the biological father of your child, right? I’m inferring that from the “sue me for custody” part. He left you when you got pregnant and stayed away for a year. I’m assuming he offered you no financial support or any other assistance with the pregnancy/ baby? Now he’s come back around, he’s sleeping with you, and you’re loaning him money. (No, let’s actually say you’re giving him money, okay? Because I somehow doubt he’s going to pay it back.) It’s been less than a year, and you’re having “rough patches”. You feel like he disregards your boundaries. You’ve seen him lie to people. When you express doubts about the relationship, he threatens to take your child away. Yeah, I’d be pretty concerned by all this if I were you, too.
You are also right to be weirded out by the “have you ever been a prostitute?” question. I AM a sex worker, and there’s nothing wrong with doing sex work if you want to, but I find the way you’re describing that conversation extremely unsettling. There are only two reasons why I can think of that he would ask that in the manner that he did. Reason number one: he wants to have some incriminating information about you that he could use as leverage. If you had been a sex worker, and you’d told him so, he could then use the threat of revealing that - to family, friends, a judge in a custody battle - to keep you from breaking off the sweet little sex-and-money deal he’s got going on with you.
The other even-more-shitty-reason is that he thinks you should become a sex worker. I don’t know what you do for a living now, but my hunch is that he thinks if you did sex work, you could financially support him in a more luxurious manner. And - double bonus points - he’d still have the threat of outing you to keep you in line.
The more I think about this guy, the less I like him. And your main reason for staying with him is that your year-old baby seems to love him? That’s not a good reason for you to be in an intimate relationship with him. A baby is not a good judge of who should be in his/her life, much less yours. You say, “I’m inclined to think he’s abusive.” If that’s what your gut is telling you, then you need to end the relationship, because a mother being in an abusive relationship can cause stress and emotional damage to a child. Your baby depends on you to be strong and whole and functional.
The best-case scenario is that he takes the breakup gracefully, but still wants to be a father to his child. I don’t know anything about how child custody works, but I know who would: a family law attorney in your area. Find one – some of them have free consultations - and have a lawyer explain what your options are for things like: how to create a visitation schedule and a parenting plan with this man. That way, you’re all ready with accurate information when you talk to him.
This is the part that I hope is unnecessary, but which I just have to say: for a woman involved in an abusive relationship, the most dangerous time is when she leaves it. If you have any sense that this man might become physically violent, please take steps to keep yourself and your child safe. I can’t tell if you’re living with him or not, but right after you’ve told him you’re ending the relationship, try not to be alone with him or leave your baby alone with him. Make sure anyone who babysits for you knows not to give the child to him until you’re worked out a legal visitation schedule. Hopefully it won’t come to that, but a cooling-off period of a couple of weeks won’t hurt your baby’s relationship with him, and will give you both time to re-adjust to the new boundaries of your dealings with each other. I hope this all turns out as well as possible. Good luck!