Before I moved in with my 2 roommates I told one of them, and he took it really well seeing as we have been friends for years. my other roommate I haven't told cause I don't think he will take it well. but my other roommate is like my best friend and we have grown to be really good friends over the past couple of years and he doesn't mind me dressing up in front of him and one of the reasons he doesn't care is cause his sister is a tomboy and she likes dressing in guys clothes and I have been reluctant to dress up in front of him but he doesn't mind it at all. so for the few past weekends where my other roommate isn't home on the weekends I dress up and it feels amazing to be free and not have to worry about being embarrassed in front of him which makes me happy. it's good to have friends who are trusting and understanding.