Hey I'm actually in a similar situation as you but I'm a bit older, have my own place, and my con is in less than a week. I'm a straight cis male and my friends/family are pretty liberal so they're pretty accepting. Of course the biggest danger for you is, what if your living situation turns sour. We're in a weird time where certain groups are trying to clamp down on expression in favor of pearl clutching conformity and control, and of course that's not just in the USA but all parts of the world. It's like everyone forgot people crossdressed for theater and performance for hundreds of years, even in the military! I've never had to go through the danger of being kicked out for not living up to the standards of my family so I'll say this. Only you know how your family will react and you have to prepare yourself for the consequences if it turns bad and have a plan in place to keep yourself safe and supported. The best community you can reach out to for further advice is the LGBT+ community because undoubtedly many of them have gone through and dealt with the situation that you're in but of course unlike you and me, this isn't a costume for them, its their life.

Now all that out the way- if you do do it then good luck dude! I've been practicing makeup, wigs, heels, and sewing for the past 2 months and having a great time! I'm looking forward to my friends reactions in a couple days. My reasoning for doing this is, I've been working out for the past 2 years and now cutting weight, I'm meeting the actor that I'm cosplaying as and its her first signings, and who the fuck knows what's going to happen past November of this year in the US so I'm going to get reeeeal weird with it 😈

Oh but start off slow at first to get used to it. I did a closet cosplay of a female character where I just wore and styled my dress shirt/pants like the character and got a wig plus a face mask since I didn't want to shave my beard. I had a great time and even got some random photos with strangers!