Hey there, IAmScared.
I'm going to get you started with some short answers first and some links, and we can take anything from here if you have further questions or want to dig in more.
1) Because "enjoyment" not only can cover a whole range of things, and because what people enjoy is so diverse but also because all orgasms aren't the same or don't feel the same, that's not something that can be answered the way you're asking. That's only something any one individual could tell you about for themselves, because people are going to have a wide range of answers. It might help to remember that orgasm is something that literally usually lasts only a few seconds, and while it can feel big and great, it's a very quick feeling, and in the grander scheme of an entire sexual experience -- physically, emotionally, interpersonally -- it isn't usually the only thing that people report is vital for them to feel satisfied. In studies on that, and when people talk about it honestly, things like creativity, expressed affection, and responsiveness to communication are usually either said to be as important and often more important.
2) Vaginal pain with sex usually isn't about how many times someone has had any given kind of sex: in other words, it's not something people necessarily will or will not experience with a first time and it isn't any more or less likely a first time than a 5th time or a 50th time, save that at some point people will usually figure out, if they have pain, what's causing it and how to correct for it. But here's some pieces on this kind of pain to give you more information, particularly since why someone is having pain matters, so the answers won't always be the same for this, depending on the cause of the pain:
• https://www.scarleteen.com/article/gend ... tercourse'
• https://www.scarleteen.com/article/bodi ... ps_for_sex
• https://www.scarleteen.com/article/bodi ... c-pain-101
• https://www.scarleteen.com/article/advi ... ed_to_hurt
3) "Kid inside your mind" isn't a general term for something universal, so I'm not sure what you mean by that. That said, someone's IQ isn't a determinant of if they can consent to sex or otherwise be ready for it or not. To be clear, people with low IQs or intellectual disabilities do sometimes have consensual sex lives they're ready for.
4) Having high levels of testosterone or high levels of sexual desire doesn't mean that we have to have orgasm, or even that orgasm will answer those things. But I hear you being clear that it seems to be causing you suffering. So, this sounds to me like a conversation to have with the prescribing physician for your T: talking to patients on T about managing how T can feel and sexuality, and figuring out if your levels are working for you or not, is a pretty common conversation many trans healthcare providers have. On the whole, especially once your body gets accustomed to T, it shouldn't make you feel the way you're expressing, so I think talking your provider is important. More on T is here: https://www.scarleteen.com/trans_summer ... stosterone