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Hello Danger Zone, I completely understand where you are coming from. I do not teach in Japan (yet), but I have taught ESL in the US for international students. My last year's class was all Japanese. Having gone to school in the US and worked in a US public school before this, I knew that teachers and students had very strict barriers that they could not cross.
I had one male student who was similar to yours and it did make me quite nervous. He would always find me during school hours to talk. At first it was English related, but then it went to casual conversation such as what to do in the area since he was new to it. I didn't mind at first because I assumed he was just lonely and homesick since he didn't have very many friends yet.
He began to spend more time with me than other students though and the his conversation topics were more personal (do you have a boyfriend, do you go out at night, do you party, etc). I thought he might have a crush on me so I began to distance myself from him.
I set aside a time after class that students could come to me for English tutoring. It was always in an open room. I didn't want anything small or private. I wanted it to be open and public.
When he would see me at lunch or anywhere else in the school, I would have polite conversation with him, but if he tried to make it more than that I would say, "I'm very busy, but if you need any help with English or on your homework feel free to visit me during my tutoring hours!"
Like your situation, he was usually the only one to show up during the tutoring hours. When he would show up I would ask him what he needed help with and when he said nothing, I would then create things for him to do. Usually more English work because if I didn't do that he would try to talk about personal topics again that shouldn't be discussed between teachers and students. He once kept asking me how much I drink, how much it takes me to get drunk, who do I party with, would I party with people like him, etc. I politely, but sternly said that topic isn't appropriate for us to discuss. Fortunately this prevented it from going any further.
Since the people you work with aren't taking you concern seriously, I think you should be very stern with him. Set aside time in an open space for tutoring. If he is the only one that comes in for it, but has no work, give him work. Direct the conversation so inappropriate topics don't come up. And if they do, you really should tell him it's inappropriate. It's not to embarrass him. It's to make him aware of the boundaries. If he continues to try and see you outside of class or tutoring hours, have a quick conversation, but then end on a happy note, "Stop by during tutoring hours if you need help! I am more than happy to help you with your English!"
Even if the JTE or other people you work with were to say/do something, sometimes it's better for the student to hear it directly from you. I know in another class when there was an awkward/inappropriate situation, my supervisor addressed it without me around. When my supervisor wasn't around, the students would keep up with their inappropriate behavior. I had to let them know my rules and my limits. Hearing it from me made a big difference.
Of course I am not saying be mean, but take control of the conversation and times you see him. Easier said than done, I know.
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