Maybe it was because he was used to guys who liked that kind of stuff. It does not excuse him but remember his last partner. Some people would do anything to het easy money so they can buy nonsence. Dan was not like this but Joo had the impression. I say it from the start that if Dan was honest, jaekyung would treat him differently.
If he had that impression, then just don't make a contract? He was not mistreated by his old partners, he never wanted to actually respect them to begin with. He never wanted to know about Dan or whatever his motives really were, he just needed a hole and treated it like shit because he gets off insulting people to feel better about himself.
He literally helped Dan every time he needed help. Every time he learned about his situation, he was nicer to him about that and treated him better. He also asked him if he ever did it. If he knew Dan was virgin and told him from start why he need the money, jaekyung would treet him differently but i guess, because he had such a hard childhood and had to earn everything basically by himself, he was kinda disgusted with guys who just whoored themselves for money and treated them like that. Like "if you want money and dont want to work hard for it, i will make you".
Bro, even with ALL of this that you said... he did so many messed up things that "being nicer" to him SOMETIMES doesn't make up for the horrible shit he did like exposing him to someone else without his consent or knowledge If he was so disgusted by people who whored themselves, why would he even hire one??? He clearly enjoys making people feel worthless, he needs to reassure himself that he's better than everyone by making others feel like shit. No amount of pity or motives can excuse that behavior

"What have I done " Like, bro... even if he had experience before he is still a human being, does his body count measures how much value he has as a human being??? you were an asshole regardless of the circumstances, it's not a "misunderstanding" cuz you probably would've still treated him like shit if you knew from the start wth