I will be moving into my college this weekend (horray!) and I have a female roommate who knows that I am trans and is comfortable with it. We were not assigned to each other, we talked while there was still time to chose a roommate, since I wanted to be sure I would be rooming with someone who was fine with a transman. She knows that I just started T and I've told her what changes I expect.
The pickle is that when she attempted to explain the situation to her parents (not in depth, just that I was a guy) it did not go well. I'm not sure 100% what happened, but essentially she started to test the waters, realised they were dangerous waters, and did not proceed further. Now we are stuck at her parents know I am not a straight girl (they came to the conclusion I'm a lesbian) and they're going to be helping at move in and move out. I don't see this being a problem at move in because my mom can't seem to get my preferred name right, and my roommate's family will be using a girl name, but it will definitely be a problem at move out and if her family comes to visit, since changes from T will start to become apparent. Her parents are already uncomfortable with her rooming with a lesbian and bother her about it, let alone with a guy, so we have both agreed telling them is sensitive. We're not really sure what to do when the time rolls around that we will have to tell them.
I've told her that it's all her decision, these are people she has to deal with every day, not me, these people are not important in my life but they are in hers, so I really don't care what they know. But she does take my thoughts into consideration and I'd like to try and help her as best I can.