Okay, I already see TWO 'how-do-I-tell-my-parents' topics, and I bet this question has been asked a BAZILLION times and is nearly impossible to answer, so I feel kinda reluctant to post mine.
But as of lately I'm getting REALLY frustrated with my physical body, the way people adress me, etc. In the past years, there always has been something that could 'distract' me from my dysphoria. Either it were my classmates, bullying, being excluded from the group, or school/work pressure, or both. Deep down I always knew I was trans, but I always fled into those other problems so I didn't have to face it. Later, in college (for half a year, lol!), I knew of myself I was trans, but was still a bit doubtful and VERY VERY scared, so I did it again. I told myself those other problems (like exams and feelings that I wanted to pursuit another career/study) were way more important than the 'transgender business', and put all my energy and focus on those instead.
Now I am having like half a year of holiday, not having a job, and a depressed and over-worrying mother (when I was little she worried for me, now she worries for herself and constantly feels like she 'doesn't belong with us' even though we ( = me and my dad) try to engage her in stuff really a lot. She does nothing all day but lie on the sofa and worry about her health, her life, everything. We tried to motivate her to do stuff, no avail, we got her to a psych, but all she does is complain it doesn't work and it makes her tired. Both me and my dad are going crazy from her!).
In the meantime my social anxiety and dysphoria are getting much worse, and I have no-where to flee to (for the better, probably). So I feel like I really HAVE to tell my parents. But I am 1) SCARED TO FCKING DEATH! and 2) worried my mom might not be able to take it (but I don't think she'll get 'better' within now and, say, a year)

So, okay, my mom won't get better in the time being, so I can best just come out to here asap anyway. It can go in two directions, either she cannot accept it and freaks out even more than she used to, and her mental state will worsen even more, OR her motherly love for me and desire for me to be happy is strong enough to let her accept it, and my troubles take her out of her ego-bubble-of-self-pity for a moment, and she'll focus all her negative and worry-energy on helping me, maybe even becoming an advocate for transpeople. How weird it might sound, both options are very much possible. But either way, it doesn't matter, because he situation right doesn't seem to improve anytime soon.

And then we have No 1... my freaking fear! Maybe the hardest to overcome. I am not a courageous person, but I never thought I was a real coward either, but now... I am doubting that. I have seriously NEVER been so scared before, and I don't even really know why! So many people come out, so many transpeople have walked this path before me, and succeeded. If they can do it, I should be able to do it too, right? But whenever I try, my stomach constricts into a tiny ball, and I feel like I'm going to pass out or vomit or both. Usually combined with crazy sweating, trembling, and loss of words. Farthest I came was like "Mom, dad, I gotto tell you something... *wave of fear passes* ... uhmmmm nevermind... what's for dinner?" :x
I even don't dare to just plain TALK about transpeople in general. Crap man! What is wrong with me! How can I GET MYSELF TOGETHER!? I have never felt such a goddamn coward before :s

(oh and sorry for the rant, I just had to let this out for a sec...)

I had a friend help me write a letter to my mom.  She is the easier to talk to one in my household.  Though, thankfully no one has many mental issues in my house and my dad is also very accepting ect. as well. 

Perhaps in your situation you should come out to your dad first, as he seems to be the most sane.  A letter helps prevent the fumbling/loss of words and going back on coming out halfway through.  You leave it in a place just for your dad, and then leave.  Leave so you can't go back and remove it, and leave to give him time to digest before you come back.  I just went and took a shower, but you can go where ever.  It may be better to leave more time then just a shower depending on how you feel.  That parts up to you really.  Well.... Its all up to you really.  Its going to be rough either way, but I think giving some time to digest before having any real discussion is a good idea - even if you do it in person.  Maybe just spit it out and say "I'm going to give you some time to think"  Give them some positive online resources or something as well, so they don't end up doing a random search and getting negative things. 

Your mother is a tough situation.  I think thats probably where the extra fear in the situation comes from.  Its tough enough when you know ahead of time that you probably have accepting parents, much less when you think that you could potentially push your mom off her rocker, over the edge, and into the deep end.  No one wants to be responsible for their mother going absolutely mad.  Especially when she's mad enough as it is.  I'm hoping that the second option happens, and she becomes almost too supportive.  I think maybe coming out to your dad, and seeing how he thinks you should deal with the situation with your mom. 

Also, maybe you and your dad should try going to a group therapy type situation with your mom?  Maybe once or twice before coming out.  That way if she freaks out its not something you haven't done before, and the therapist would already have a better idea of your relationship.  It sounds like she can't have too accurate of a description if its only by your moms telling. 

Hey GnomeKid, thanks for the reply!
I agree on coming out to my dad first, even if my mom would be mentally completely OK, he's still the one I have the best connection with. We share the same humour, and much more interests than me and my mom. He was always the one letting me go, while my mom tried to hold be back and protect me too much.

I'm not sure about the letter tho'. It used to be my staple method of telling something 'difficult' to my parents (though those difficult things look like a freaking joke now. Things like a game membership, or getting dreads. I don't even get what was the big deal with those things! LOL!), but that was always like "Is it allowed, yes or no?" and if they said yes I'd come over, give them a hug, be happy and never talk about it anymore.
With being trans it's completely different, I HAVE to talk about it, I HAVE to make clear to them I want to transition and I am SERIOUS as hell about it, and giving them ten pages of explaining the hows, whys, whens, etc. doesn't seem like a good way to do it, also because I have to overcome my fear of talking about trans stuff in general, AND waiting until your parents respond to the letter is HELL! I never dared to ask 'difficult' things directly, and that has to stop!
I think I WILL write a letter though, and take it with me in case I forget everything I want to say, etc. so he can still make sense of the message.

And my mom is a difficult case, yes. Her problem runs very deep and goes back all to her childhood. And even though she didn't seem to have it while I grew up, I think it was actually already lingering (in the way she protected me, tried to shelter me from everything, etc. and I think when she found out she couldn't do that and it would only harm me, something inside her just kinda broke, cause she gained her self worth from mothering and caring for me), I just beg hope and pray that my coming out will swing to the positive side. My hope is that she can accept me being trans, sees that's what I want and would make me happy, and THEN starts drawing her self worth from supporting me through my transition and once I'm 'done', with most of it, help OTHER parents of trans children or the transpeople themselves. But yeah, it could go either way... :/

I'll have to come out to my dad first tho', cause otherwise how do I explain the group therapy? I suggested it a couple times for HER (because she thinks all weird stuff about how we think about her, and maybe having a third party present would help), but she never felt like it was a good idea.
I'll just have to tell my dad...

When would be a good moment?

First before I forget, I just saw your last post...lol dude! I was scared of telling my parents I wanted dreads, too! Took me a week to tell them. Ah, I know the feeling.

But to the serious stuff, as you know from my post, I have the same fear. I'd say obviously telling your dad first is a good idea, and then maybe you can discuss with him how to tell your mother. With me, with my letter, I've explained that I'm transgender, what that means (in case they don't know), how I've come to realise it, what I plan on doing about it (I've left out hormones though because I don't want to bombard them with everything), and why it is that I need their support. I have no shame in admitting that I emphasised how unhappy I currently am, because I want them to get that it is making me unhappy to live as I am. Because I have depression and I'm suffering from a long-term illness, and they always say they just want me to be happy, so I wanted them to get that this is something that can help a bit. And the letter is only two pages long. So maybe you can write the letter and then see how long it is, see if it's something you want to give to them or if it's too long? Also, the wait is no doubt going to suck, so I guess leave the letter somewhere you know it'll be seen, and then going out for a walk or do something fun for a bit.

I'm sorry about your mother, though, it sounds like being stuck between two difficult choices. But the thing is, I guess she has depression? But you're not happy, either. So I'm sorry if this makes me sound like a terrible person, but I think one person being unhappy is better than two people being unhappy. You and your dad support your mother through her difficult problems, right? So maybe give her the opportunity to do the same. You need support, too.

Telling a parent isn't easy because we worry about the rejection.  Honestly, I was in my forties before I told my mother because I was really at my wits end and needed to tell somebody.  I had to tell her over the phone since we were, and still are in different states.  Surprisingly, though she cried when I told her, she took it well.  She sent me a letter very soon afterwords giving me her full support.  I didn't expect that.  I think it is natural to expect the worst outcome.  I know that some parents have not been at all supportive.  It's really a crap shoot and you won't know until you finally tell her.  At some point in time you will come out to her, whether it be now or later.  In my case it was much later and I have some regrets about that.  Perhaps if I'd come out to her sooner, I'd be living as a woman now, I don't know, but it's a good guess that I would be. It's easy to tell someone to take that step to tell her.  I've been there and I know how frightening that is, but she has to know sooner or later, and perhaps sooner is really better in the long run for you.  Sometimes we magnify our fears to something far more than what they should be.  I say this in hindsight since it did take me such a very long time.  Don't make the same mistake I did.  Come out and begin to live as your true self.  Whether she is negative or positive, you will have taken an important step to beginning your new life.

Over coming fears is never the same for each individual. I know someone who came out to her parents that she was gay by coming home with a pamphlet about what it was being gay. (I know Trans is a bit different) She did that because she knew no matter what she would say, they would not listen. So, instead she left that and the number for the local LGBT community here in Iceland that offer free counseling session for those having ether a hard time coming out or accepting someone who has.
Then is my story, the best way I did it was to call my dad and ask him to come over and told him the reason was, was because I wanted to tell him something important but not over the phone. So, I set myself in the position, started the conversation knowing well I would have to get to the end when my dad came over cause I knew if I wouldn't I would back out on the last minute. I will be doing something similar with my grandparents when I will be coming out to them in the next week or two.
Another person I know always has someone with them when confronting their fears of telling someone something. So, you could ask a friend being there. It can help, even though the person says absolutely nothing and just stands there.

So, you could perhaps find a good time to talk to your dad, and then perhaps try to get him to talk with you to your mother.

I hope things will go well for you Erik, if there is ever anything, you can always send me a PM

Thanks guys, I hope I can get the courage to tell him the first moment we have some alone time, without my mom hanging around and possibly barging in.
I decided to write it as well, because I probably cannot get a word out of my mouth of anxiety, lol, and that way I can structure my thoughts better, etc.
Stuff is really going to happen this week and the next, cause I told my friends at LARP and have a LARP event next weekend, and a few days after I'll have my selection day at art academy, where I am also signed up as Erik and the school staff knows of me being trans. So excited! But also a bit nervous! Like... what if people don't respect it, or keep treating me as a girl, etc. or don't believe I'm a guy (at art academy), or if I don't tell my parents before that date, and they find out through another source than me, etc. etc. it's like the whole life I thought I had comes crumbling down upon me. I hated that life, because I lived like playing a role in a play, but you can even get attached to a role you hate. For the security and certainty it gives. But you know what they say; good things never came from comfort zones.

You could try my plan, which consists of avoiding the issue and never telling them because I moved far, far away from where they live.  It also involves never seeing them either, so there's some downsides...

Thanks for asking the question, because it's the next big thing I have to deal with (or avoid, as the case may be).

Hi Erik, I don't know if you have told your parents yet but I thought I would give you my opinion. Wheather face to face or with a letter you don't have to do this by yourself you can have a friend with you. Secondary with parents don't sugar coat this the truth while painful is the best way to show them how serious you are, (this is your chance to be as blunt as you want). If they have a tendency to get emotional I would suggest telling them outside it forces them to control their emotions (yes it can be unfair but you want to keep things as calm as possible). Good luck

This vid is what me just do it.    http://www.upworthy.com/a-4-year-old-girl-asked-a-lesbian-if-shes-a-boy-she-responded-the-awesomest-way-possible?g=2&c=ufb2