Hi, you have no idea how helpful your questions were.
Why didn't the doctors ask me such questions?

I don't understand, they just took my word for it. If they asked me some of the questions you asked me I think they would have had a better understand.
Anyway, to answer your questions.
1. All but the 1st doctor I saw were urologists, the first doctor I saw was a practitioner, he was by far the most helpful actually.
2. Natural medicine, I have thought about myself for days, but didn't know where to start, like who do I talk to? I tried googling some stuff ealier, like "natural pain cures" but of course in this day and age, you usually get stormed with fake sites that just want money.
** If you know anything more on how I can start looking into this, I would appreciate it allot!
3. The doctor said I had epidiymitis because one day I came in, told him what I was feeling then(pain was much worse at this time) he took an STD test, came out negative, but I had a fever, so he said I def. had some infection, gave me some antibiotics. Then I returned, told him, they worked, then stopped, then he gave me some more antibiotics, they didn't work at all this time, then he said, it can't be an infection then.
** It's as if they expected the antibiotics to work 100%. I also read some people's bodies become immune to antibiotics, but I am no doctor so maybe he was right.
4. The ultrasound, from what I know was to check for anything that wasn't suppose to be there, that's what the doctor told me, pretty much in those words. This was my first time with these things, call me stupid but I didn't really ask any questions, I just followed what ever they said. They called me few days later told me the results came out negative, they didnt' find anything unusual.
** I have no idea what a varicocele is, but since you mentioned it, I will look into it asap.
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5. Now that I really think about it, and feel my self out so to say, the pain is not actually in the testicles(the ball), but more on the skin or perhaps the nervers in the scrotum, near the bottom of the scrotum where the testicles usually lay if a man were to stand up straight.
6. I do find some difference in the support, when I wear loose boxers like I am now, usually* the pain/burning is not that bad. I can sit on the computer for a few hours and not really notice it too much. But, if I wear jeans, and I don't wear tight jeans at all, I can't sit anywhere with my jeans on for more than 30-40 minutes without my scrotum heating up it seems.
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Another thing, like when my left testicle's skin is touching my left thigh for more than 30 minutes, usually I feel some discomfort there as well, it seems like whatever my testicles touch for more than a short period of time, they can't stand it.
I'd also say the pain is more on the left side, like 70/30 ratio(70 on the left, 30 on the left) kinda thing.
Anyway, I really, really appreciate your reply, you have no idea what you just opened up in me. When I went to the doctors, it seemed like they were rushing me out the door, didn't really give me a chance to explain, just wrote me off some meds and set me off.
I really really appreciate this man, if you have more advice, please share.