The first list - Yes, yes, and yes. All of it. Especially that you are an AMAZING boy, and that I will stay with you for as long as you'll have me.
The second list, I'll take point by point:
* Jason crossed lines, but it wasn't necessarily his fault because he didn't know better
That is no excuse. There is plenty of information in today's lifestyle culture, and plenty of people saying you need to learn what you're doing before you start practicing on other people.
* I made things worse by not saying no, and he might hurt more boys because of it
This bothers me. Objectively, it is true that he might hurt more boys, but...you'd been taught that you didn't say no to a Sir unless you were safewording. I think blaming yourself about any of this is erroneous and counter-productive. You did the best you could at the time.
* I made a lot of mistakes, and probably deserved some of those punishments
No, you didn't. I'm inclined to believe that he was looking for reasons to punish you, to the point of making them up out of whole cloth. And even the mistakes you made were not on purpose - I know this because I know you. When a boy makes honest mistakes, you correct him, yes. But I personally don't believe in punishing harshly for mistakes that weren't deliberate.
* If my friends knew all the details, they would probably feel differently
No, no, and a million times no.
* I should've left the relationship and I didn't
Objectively, it would have been best for you to have done so. But this kind of thing is never objective. Every person who's ever gotten out of an abusive relationship has felt this same way later, I think.
* Even if I was abused, it's kind of irrelevant now (starting to change mind on this one)
Good. If you don't change your mind, I'll have to change it for you.
* If Sir knew some of the things I asked Jason for, he'd be disgusted
Perhaps you should try telling Sir about them, instead of assuming how he'll react. Sir might or might not be into those things, but you can tell him and he will not be disgusted.
* You have to mind manners around a Sir because those are the rules of our culture
No, they're the rules of some Sirs and not others.
* You should trust a dominant unless they do something awful, like ignore safewords
No. You should trust a dominant until they prove they're not trustworthy, and ignoring a safeword is only one way they can do that.
* You should only tell a Sir when something's really really wrong (starting to change on this one)
Good, good, good. Change your mind again.
* I'm an okay boy, but I was a lot better when I'm younger and I'm still afraid of my decreasing relationship life expectancy
To put it bluntly, bullshit. If anything, you're a better boy because you've learned and grown and matured as a person.
* Sir believes that he wants to be with me for a long time, but if he sees my faults he might not feel the same way, or he might just get tired of me later (and he has every right)
You let Sir worry about that. Sir wants you with him for a long, long time, and if he does get tired of you, he'll be a gigantic wanker prick.
This is your assignment, boy. I want you to print out this email and put it on a mirror that you look into a lot. Twice a day I want you to read through my responses to that second list - out loud.
You are amazing and wonderful, and I'm damn lucky to have you.
I love you. You don't have to be so very patient with me, but you are, and I appreciate that so much.
I'll do my assignment, though since I'm supposed to say now if I don't like something instead of just doing it, I'll also admit that I don't like it very much. I guess I feel like everything you're saying should be obvious to me, and it bugs me that it's not, that I haven't internalized it, and that I have such silly beliefs. But I'll do it if you think it will help.
Thank you for letting me know how you feel about it, baby boy. And believe me, you are far from the only person who knows one thing but believes another. Every skinny girl who thinks she's fat even though she knows better, every smart person who fails one test and thinks he's an utter idiot...it's part of the human condition, I think. There's a saying that goes "Fake it till you make it" and in some cases, that's very true. If you keep telling yourself something long enough, you'll believe it, and it's time you stopped doing that with negative things and started doing it with positive things. I'm very proud of you.
I want to try. Not just because I love you, but I want to do better, I mean I really do. I want to be more relaxed about things and more secure, and I don't want things like my claustrophobia to get worse. I'll do my best.
Also, has anyone ever told you that you're very smart? Because you are. Not just book smart, but emotionally smart. I think maybe I knew that but the way you're handling all this is very impressive. You're good at explaining things to me. I think if you weren't an actor, you would be a good teacher.