I think it is time to have the talk with them.

But I don't know how to go about it. My dad is old, more than 75 years old, so I don't know how he would react to it. My mother is 20 years younger and since I've always spoke with her about stuff first, I will go to her first. But they are SO complicated.

I don't know how to begin to communicate or what means of communication to use. I am considering either a letter or talking in person, however, I of course have no experience at coming out to parents so I am unsure of what would work better. My mother tends to overreact over things and make some VERY UNFAIR judgements based on preconceived views, which she changes after a while settling on a completely different opinion. Additionally, she oftens hits walls on conversations where she won't go forward, so talking to her can be fustrating as I have to repeat myself over and over only for her to not get things and twist my words around.

My dad doesn't overreacts, usually, but he will suffer quietly. If he really is opposed to something, he bursts out into anger and turns into Mr. Yell-a-Lot. Historically, he has used his money as a means to control me around,the "you in live in my house and eat my food" kind of stuff. As of now, I am away from both of them in another town at University, it is full time (including after midnight) so work is marginally a option. I managed to join a paid research project which provides me with some income, so I'm thankfuly not dependent on either of them for HRT as I got my expenses for the 'mones covered, but still, I'm not graduated yet, unable to work and study at the same time, and dependent on everything else.

So if I do this and things take a really bad turn, I'm screwed.

It will be nice to have them support me on this though, their financial and emotional support would be extremely welcome. I am using my female voice 100% of the time, with them included, my dad has seen me with nail polish and makeup, my mother as well, and they didn't berate me. I am yet to use female clothes around them, but my mother does knows I do it.

It seems to me like they all but know, I would just open a dialogue with them and let them know where you are with things and where you think you're going to go.  In coming out, its a process, I think many people are took quick to dump everything in one conversation when the truth is it's really an evolution and at least in the early stages you can't really talk accurately about timelines, outcomes, etc.

In short, just tell them what's been going on and where you think things are headed.  No more, no less.  I just told my mom (two days ago) that I was seeing a therapist, I didn't specifically mention the gender issues, but I talked about anxiety, depression, low self esteem.  Actually the funny thing is, I'm not even sure she fully heard me - we were walking on the beach at the time.  In any case, she didn't seem all that concerned - but for me its now an open dialogue I feel empowered to have with her.  So if I'm any example, start small, and work your way up from there.

Regan.

Thank you for your advice.

I'm actually pondering coming out to my dad first, since he is the most rational of the couple. I plan on doing this early august when I visit them.

If I were you I would start by writing a letter- this is what I (literally) just got done doing. While I haven't given them to my family yet (I'm starting with my aunt whom I'm very close to, then parents) I already feel a huge weight has been lifted. It really helps you organize your thoughts and how you feel, so even if you don't want to give them a letter or opt out of giving it to them, it can really help you know what you want to say if/when you talk to them.
I hope this helps.

I agree that you should write them a letter, or maybe a seperate one for each of them so you phrase things differently depending on how you might see them reacting.  I know for example, my dad reacts to big decisions best If I can present him plans I have made, connections and resources I have made, and prove that I have seriously thought the whole thing through, whereas my mom needs more assurance that I have really thought about other options and made sure its really what I want to do.  Its all emotional concern versus logistical with them.

Give them a week or so to process and think about the information, and be prepared on there end to really discuss it. 

The letter writing isn't a bad idea, but you have to approach each person on their level.  Like Jake said, write the letter and use it to organize your thoughts, you can read it to them then when you come out or you can let them read it to you.  Whatever you decide you need to give them the letter in person, calling them to say you've sent them a letter that you need them to read is just going to cause days of tension between the time you send the letter and they recieve it.  Again, I would suggest that what ever you decide, keep it short and too the point.  Things have a way of working out other then how we intended and if you start talking specifics now, it could hurt your credibility down the road when you start missing dates/milestones that you set out in your initial coming out or if you commit to one course and decide to follow another.