I'll apologize in advance for what will surely be a long post.
I have a story for you all, and then some questions. Feel free to skip straight to the questions. The back story is what happened that brought the questions up, and the way back story (My attempt at humour, I know I suck

) will probably put the back story in perspective.
Way Back Story: Next year I'll be going to a high school on a college campus where I have to stay in a dorm. The school is really intent on making me room with a girl and use the girl's restrooms; the impression I got from them was that they were not at all willing to work with us on finding any other solution, and, the last time I talked to them, they were planning on just asking around and finding a girl that would be comfortable rooming with me. After getting some people from TYFA and the queer youth group I go to involved, I was told that they can't legally do that because my parents never gave them permission to disclose my trans status to anyone. In short, if they do we can sue them. At this point, they're not happy that we called TYFA, and they refuse to admit that the best option could possibly be giving me the single room that they already told me they had (they "don't want to give you [me] this room because we [they] don't want to give anyone a reason to hate you [me]." ). So, right now, I have no idea what housing or bathrooms will be like, and everyone I've talked to that will be going to school with me thinks that I'm a cisguy thanks to Facebook.
Back Story: One of the guys I'm going to school with, we'll call him R, was talking to me on facebook and texting me today. I originally though I wouldn't get along with him because he said something that I found offensive, but he apologized and I got over it; I think we might end up being pretty good friends. We were texting back and forth about doing parkour and my complete lack of upper body strength. This turned into him deciding that we should go to the gym at the college and be weight lifting partners. I sent him a text back saying that we should probably actually meet each other before we decided that for sure (this is my version of giving people a polite out if they decide they don't like me for being trans). Then my brother asked me who I was talking to; he only knew R as someone who was potentially a homophobe due to his offensive comment. I told him that R wanted to be weight lifting partners, and my brother asked me if R "knew". I told my brother that I hadn't told anyone at school that I was trans yet. He, more or less, yelled at me that I needed to tell R right now because otherwise I was lying and leading him on and that I shouldn't lie to people like that. He didn't seem to care that I made it clear several times that I intended to be openly trans at school, it's just not something I want to tell everyone through a text or over the internet.
Questions: Do you think that not disclosing (immediately or ever) is lying? Does it upset you when people say it is? Does it upset you when people say it isn't? Why do you feel that way?
Personally, I don't think it's lying at all. It's my choice whether or not I want to tell people. It annoys me when people say it is, because I associate it with what people say after they've hurt/killed a trans person. As in, "I only did it because they lied to me, it's their fault".