Hi can I please get a little help here? This is a bit long by the way. Sorry.

To make a long story short, I realized (when I knew what the word meant) I was transgender about two years or a yr and a half back. Go in reverse and thinking back to my childhood everything seems to make a lot, and I mean a LOT of sense. Now fast forward back to the present and I'm presented with the issue of telling my family this. A family who, according to my mother and grandmother, has people who still don't even know I'm not straight. A family with members who still think I'm bi (went through a bi thing 7th-8th grade, not pleasant). So to be fair to family, I gotta tell them the truth but how is the question. My moms side is not that much of an issue cause we closer so I'm hoping our bond keeps us good even though I know this'll be strange to them, heck took me a few years it's only right to give them that as well. Now I do have an aunt who tells me, every time my grandmother brings up my sexuality and thinks its funny that I'm single and identify as lesbian, that my choice, its a choice to her, is nasty and wrong. She assumes it a (now 3 year) phase and thinks the whole 'homosexual thing' is a (5 year) phase. I laughed a bit one time simply because I doubt a phase like this lasts a few years.

Anyway, besides her I have a few other family members who's religion is seemingly why they talk about homosexuality like its a disease. I was forced to hear, when younger, very homophobic conversations with my mom, grandmother, aunties, uncles, and cousins. I'm even told by my other cousin to not tell anyone she's a lesbian cause of that fact we both are aware of. So I doubt they handle transsexual news kindly.

Now thats not ALL of my moms side, but unfortunately many of them are actually the ones I'm closest to, been raised by even. But my dads side? Well many of them have pretty much dismissed me after I told them, over Thanksgiving dinner when I was going home, that the reason I don't have a boyfriend is because I'm interested in the same sex and at the time had a crush on a girl. I got that awkward, 'Oh.' and haven't talked to them since. And that was about 3 years ago. My dads mom and a few cousins and I still talk, but his mother is like my aunt and doesn't like hearing any of 'that gay s___' after an altercation we had when I simply was telling my DAD about a girl he saw me chatting with.

So I got a few problems here and want to, to be fair to my family, let them know that their 'lil baby cousin'  not only does not like, but doesn't want to be a female anymore. How can I tell them that? I told my mom and that was a painful conversation along with my grandmother which was just hurtful because she laughed at me. I just told my dad and he acted the way he did when I came out as a lesbian and said, 'as long as you're comfortable and if it's what you want to do'. I don't even know how to APPROACH the subject! Say, 'hey I know we haven't talked in a while, just calling to say I'm transgender, google it?' I don't know! Can anyone help me? Heck should I even tell them at all?

Just tell the people closest to you for now. If it ever comes up in conversation with a relative then release the info. If not, no reason to randomly call a relative to say you are trans. Of course this is my opinion on the topic.

My father and I don't talk often so I won't bother telling him for now since he lives in another state and I haven't seen him in 5 years. I'm thinking about coming out to my mother, I know she will freak out. I did write a letter but have not given it to her yet. My sibling thinks its best to not say any thing and "naturally transition". If the conversation comes up, then I'll have to tell her. If not, then she can continue to ignore the transition and deny anything is happening. I'm due to start HRT in October.

Good Luck!

First of all congratulations on coming out to your mom and dad I still have that conversation ahead of me (oh, joy ).

I'd say, focus on telling those people who are really important to you, so they don't hear it through the grapevine. I prefer telling people in person, but it doesn't have to be that way.
You don't have to come out to everyone and to everyone at the same time.  Mikah, the author of the neutrois.me blog has a post titled "disclosure is a spectrum". It's about being stealth, not coming out, and the nb situation is different from mtf/ftm, but I still think there is an important point there: you decide when and how much you disclose to people.

I decided to start with my husband and close friends. I'll face the family situation before Christmas because I can't imagine surviving this when I have to pretend I am someone I'm not.

I read so much about the struggles with family that I only now realize how lucky I am with the people around me. All I would suggest is to not focus on telling your partners at first. Find someone whom you trust and talk about it with him/her. Have someone support you trough thick and thin so that in case anyone in your family makes a problem of it. You will have someone to lean on.

Thanks for advice I'll try it. I'm just having problems because I've pretended to be bi at least until my sophomore year and really let go at that point. I'm comfortable as who I am now, but I'm afraid of pretending to be a female when I want to be seen as, or at least addressed as, a male. I don't know what to do, or how to even do it.

On the bright side my best friend knows, has been for over a year, and first thing she said was, 'Are you sure?' When I said yes, she then said (and this made me laugh) 'okay. We need to find you a boyish name then.' She calls me Latrell now haha . My mother said if I were a boy she'd actually name me Kody so I'm thinking on male names at least.

I just sort of skimmed through the other posts so I'm not sure if anyone has mentioned this yet but if you think your parents will react really negatively to you coming out then it might be better to wait until you're financially independent to tell them. That way if things do go badly you can give them some space until they come to terms with it.