AOG, I know you don't think you are allowing it, but in a way you are, without realising it. The trouble is, his father got you into a pattern of letting a lot of this wash over you, then when you threw him out, you still haven't found the knack of turning it around so it simply is not permitted to happen. Plus, difficult child 1 got into bad habits too, which are very hard to break. In some way he is filling the niche left by his father (or at least, he is trying to.
I am speaking not from personal experience of being on the receiving end, but from personal experience of having watched my sister go through this first with her pig of a husband and then with her very wayward son. She didn't think she was allowing anything either and couldn't see it at the time. Years later though, she could. And years later, her son is cleaning up his act and is back in her life.
"Allowing it" doesn't mean "letting him say it with no reaction", but it DOES mean "not dealing with the problem in a way to strongly discourage repeat offences". You dole out punishments - clearly, it's not working. Besides, punishments can take a while to "bite" and frankly, he needs an IMMEDIATE consequence.
'The kid sits there and tells me "he wishes someone would come and rape me right now so he could laugh in my face" nice huh?'
You can't punish that with restrictions, with grounding, with a ban on the phone, with anything that limits his freedom, because what he has done isn't really connected with his freedom or otherwise - in short, forget trying to enforce any punishment. It's too hard to enforce (and make it stick); he's too old (and too big); you're too beaten down by it all already. And has it been working? Doesn't look like it.
But you have the upper hand, even though you haven't used it. Maybe years of abuse have blinded you to your opportunities.
Fran and MB were right, they had some very strong suggestions. I endorse them.
difficult child 1 needed you to drive him to this job. OK, you can't throw him out of the car and drive off, because that would violate his parole, it would provide him with the perfect excuse to not follow through on the job, etc.
But what you CAN do (and could have, here) - any time such foulness comes out of his mouth, ESPECIALLY while you are doing something for him - STOP THE CAR. REMOVE THE KEYS. Then tell him, clearly, "That was a really nasty, despicable, horrible thing to say. It was totally unwarranted - it is NEVER appropriate to say a vicious thing like that, not to anybody, not under any circumstances. You should be ashamed of yourself. And if that is how you're trying to persuade me to love you and to do nice things for you, you've got a darned funny way of going about things. I do not have to do a darned thing for you. I owe you absolutely nothing. But you, Boyo, owe me a great deal, beginning right now with one big fat apology."
Refuse to drive any further to his requested destination until he backs down. Instead, drive to the police station of your choice and dob him in, if in saying such things he has broken the terms of the arrangement.
If he gets physically abusive at all, stop the car again (it's safer, than trying to drive when a difficult child is grabbing at you or the wheel). And again, do not move off until he is keeping his hands to himself. If it gets to tat stage, call the cops from your cellphone. If he keeps grabbing at you, get out of the car (with the keys - do not leave them) and THEN call the cops, or flag down a passing car for assistance.
You have the upper hand. Use it TO THE HILT.
Do not feel guilty for doing this - a person who can say that to you, his mother, especially after what you experienced, has just blown all his chances in one fell swoop. If he doesn't get slapped down fast for it in this manner, then he will up the ante. If not with you, then with the next woman in his life.
Nobody deserves this sort of abuse. Not you, not the next woman he tries this crud with.
So even if you don't want to make too much fuss, or ANYONE even hints that you're not worth making such a fuss over, then at least tell yourself you are doing it for your prospective daughter-in-law.
(although you ARE definitely worth much more than this).
Forget any punishments. They won't have any impact. But an immediate "STOP!" and a pull of the emergency brake on the train wreck you're both riding, will NOT be what he expects.
I'd like to think that as you drive to the police station, he will be apologising (or backing down in some way). He'd have to back down a very long way, for me to not dob him right in, then and there. That creature is channeling his father and needs his PO to perform a radical 'exorcism'.
ANY stuff like that from him, do not accept it on board. Do not attack him personally in any way, instead attack what he says or does. Make it clear that his words or actions are not reducing you to tears but they ARE making you very angry. And then if this is happening at home, say your piece about how he just made a BIG mistake spouting such foulness, and then walk out.
You say your piece. Do not tack on any punishments (as in "apologise or else...") but just walk out. If he's under house arrest, you can leave but he may not. If you're supposed to stay on the premises also (as his jailer) then you should at least be able to sit across the road and watch the gate, while staying out of his physical reach. I would be approaching the court to have such a limitation changed, though (assuming there is any limitation on you because of him). Tell them what he is doing and saying, make it clear you need to be safe from this, or they need to provide you with a big stick with which to threaten him if he doesn't curb his tongue or his behaviour.
And if ANY of what he is doing or saying breaches his release conditions, REPORT HIM.
As for anything else you have been doing for him - stop. Don't cook for him. Don't wash his clothes. Do not clean his room. He should be able to supply his own needs. Do check up on what you can stop doing for him, because clearly if he's got restrictions on his movements he may not be able to do things like go shopping for groceries. But you do the absolute minimum you have to, live your own fulfilling life and do not let him impact your life more than the barest minimum. Also make sure he can't get his hands on any of your stuff (including your valuables & money) because if he is so disrespectful of you, then he will be just as disrespectful of your space and your possessions.
Marg