Coming Out - Need Advice

So I want to come out as transgender (FtM) and gay to different people. I am out to all of my friends and my grandmother, but currently not out to my parents, the rest of my family or my future college roommate.

Let start with my background I was born as a only child into a conservative family. I never was girly growing up. I loved to hang out with the boys and I was a total tomboy. In 3rd grade puberty hit me super early and it freaked me out. I was suddenly forced to look more like a girl. I had to grow my hair long. I suddenly started to hate my body for being female. I even once told my bestfriend that I wanted to grow up as a boy and that I wanted a penis. She ended up calling me a freak. I freaked out so much that as a 3rd grade I was dignoised with depression. I never told any adults at that age what I was truly feeling because I thought they would react like my friend did. Middle school came around and 6th to 8th grade was any different. I started dressing more like a girl and wearing makeup, but I felt wrong in my body. I came out to my group of friends in 7th grade and well I caused me to loss a bunch of them. 8th grade wear I started wearing more guyish clothing without my parents knowning. I walked to school so I would hide some clothes my friend gave me in my back pack and would change at school. Only to change right before I went home. Well dreaded 9th grad hit and I was completely miserable. After experimenting with girls I found out I was completely and utterly attracted to guys. I had a boyfriend my freshman year and actually kind of came out to him. He was accepting and actually helped me give a label to want these feelings I had for years all meant. After doing soul searching for the whole year I knew I was ready. The summer following 9th grade I spent it divided between my grandparents house before my family took a trip to Florida. This is when I decided to I would come out to my grandmother. The woman who was where for me when I was little and the person I knew didn't judge others. The last night I was at her house I wrote a coming out letter. The next morning I felt literally sick and hid it in her bathroom. She ended up finding it and sent me a text saying she loved me and would always love me and that even though being transgender wasn't her personal belief she would accept me.

Now coming out to my parents. They are not practing Christians but when it comes to sexuality or gender topics in the media. They always seem to drag church into the subject. Okay to my mother the sad thing she has known since 6th grade. She first thought I was lesbian when I was experimenting with a few girls. Which make her absolutely furious to the point I couldn't be friends with the girls anymore and she took my phone. Then in 9th grade my iPhone accidentally connect my iMessages with her iPad and well she saw the messages of me coming out to my bestfriend. Well the week before 10 grade I couldn't take it anymore. After dinner one random day I plucked up the courage to come out to them. I asked them to sit down on the couch and I sat across them. I explained my feelings about my gender and how I want to be male. My father well he couldn't look at me and actually stormed out of the house crying and screaming. My mother freaked out at me and total me to look at what I had done and what would my grandparents or the rest of my family think. She also couldn't understand why I would think that because I work girls clothing and makeup. Then she told me to go to my room and think about my actions. A week later I was thrown into therapy I explained to the therapist what I was feeling and she even stated that she believed that I am transgender. My parents not liking that because they are hoping she would fix me took me out of therapy. So I started to deny that I was transgender for my parents sake so they would be happy. Because a couple months later I learned that they thought about throwing me out. So for the last three years I have been denying that I'm not transgender which honestly makes me sick. Because at school I have been out as transgender. A friend of mine even helped me obtain a packer, binder and a bunch of men's clothing that she hides in her car. For the last two years I have been living two different lives when it come to my school/work life and my home life. Next fall I am heading off to college. My parents and grandparents Are helping me pay for this.

This is where I ask for advice. How should I come out as transgender and gay to my parents again and possibly my grandparents?

Now my family they are a different story. My mom's side is the only real family members I have many are religious. Several of my cousins are gay but many of these cousins are in the closet or we don't speak of it. My one cousin was so terrified of my family finding out she ran away with her girlfriend and we haven't seen her since. I would like advice on how to come out to them? Would it be best over Facebook like most of my cousins have done?

Now my roommate is a big question mark. Umm we just became confirmed roommates two weeks ago. My future roommate is a straight girl that I really don't know what her opinions on Gay or transgender people are. I'm almost too afraid to ask. Now I would have roomed with a guy but since I'm not out to my parents or family I am unable to. Like I don't know how to ask her opinion on the subject or what I should even stay to her. Or if I should say anything at all.

Someone seriously help me please!