This is in part a rant, in part asking for advice, and in part giving advice

So I finally had another therapy appointment today- I'm doing family therapy with my dad, mom, and step-dad, not just individual therapy (She sits with my parents for the first half of the session, and me in the second half). I know for sure what I want, and the biggest incentive I had to go to therapy again was to help my family, not me. My previous appointment was several weeks ago, if not a couple of months ago, and I think we left that one with confusion about what our plan was. I'm not an assertive person and I struggle to have hard conversations. In therapy I tried to say that I want to be called Dean and male pronouns at home, but what my parents heard was that if I didn't correct them, I didn't care. My dad told me he wouldn't call me Dean or use male pronouns until I talked to my sister (which is a perfectly legitimate request, in my opinion). However, my sister has anxiety issues and so during school weeks she is not responsive enough to me to sit down and have a serious conversation and have her actually listen to what I'm saying. So my Dad never really started calling me Dean.
My mom and step-dad on the other hand were much more confused about what I wanted. Over the summer I met another transguy and somehow they decided that I only wanted to transition because of him, despite having brought it up long before I met him. (I think my dad felt this way too, at least a little). They never called me Dean and I think they assumed that since I never asked them to again, then I wasn't serious. I thought they were just trying to find answers to questions about what transition entailed, but really they were waiting for me to do something. 
I on the other hand took away from that appointment that they were going to be asking me questions about how I felt. I thought they would be coming to me. Whereas they thought I had to prove myself to them by initiating these conversations.

So today, I had to hear the hard truth that the past couple of months have had no progress, if not been steps backwards. I was under the assumption (based on conversations right after the previous appointment) that my parents were somewhat accepting, but just uneducated, which was wrong. My therapist asked me some questions and she made sure that I was serious about what I wanted. She asked the questions that let me be clear in what I wanted and how long I wanted it, and she told me that I can't wait for my parents to initiate anything. She made it clear to me that no matter what she tried to say to them, I am the one who needs to take FULL incentive to prove myself. She said it's not fair that I have to be SO straightforward and clear, SO demanding, that I have to deal with the full force of their ignorance and assumptions, but I do. They will not come around until I prove to them that this is long-thought-about and that I know the FULL consequences of what I'm doing. I cannot be unsure about things when I talk to them, which is very difficult when they ask about things like the long-term risks of hormones. I have to be very certain and deliberate with what I say and I cannot hesitate too long or sound unsure. This is really hard for me, as I'm a very passive, non-assertive person, but I HAVE to be assertive if I want them to believe me.
The implications behind this were also basically that I won't be starting T close to when I wanted. Originally (back several months ago at my first session), we were thinking about three weeks from now. That's definitely not going to happen now. I may not even get to start before my birthday (early August), which I was really hoping for. There's no endos near my college (the closest who treat transmen are 3-4 hours drive away) so I need to start this summer. But I have to battle to prove to my parents that I know what I'm doing and I know I want T, and who knows how long that will take.

The one good thing that happened was that my therapist told me that we're trying the best we can to make sure my family supports whatever I choose. But she also reassured me that, while it's nice, I don't NEED their support if I am of age. She did give me the informed consent documents to look over so that I had the information. It is comforting to know that I have those.

So basically at the end of the session we highlighted our 'game plan' so to speak. I want them to use male pronouns and Dean anytime except around school people since I'm not out there, keeping in mind that this cannot feasibly happen until I have a discussion with my sister. We outlined that we need to find a time when she isn't anxious or stressed, and I need to have someone there with me to make sure she behaves and doesn't start ignoring what I'm saying or arguing with me. Once that conversation happens, I expect them to call me Dean and use male pronouns. And then after that, it's all up to me to prove to them that I know what I'm doing before our next appointment. Who knows when that appointment will be, because I had to nag my mom to schedule this one for several weeks, but I should try to assure them that I'm confident in my decision by then.

So basically
The rant is that I screwed this up myself. I did something wrong to make them think I wasn't serious and now, since I couldn't bring myself to start that conversation with my sister, I'm off of my ideal timeline. I feel like it's my fault that I won't be starting T when I want to and originally planned.

The asking for advice is, what advice do you have for talking to my sister? How did you deal with people who had a tendency to be unresponsive or distant if you tried to have a serious conversation? And also, what are some tips for being more assertive about my feelings, thoughts, and wants? What are some ways for me to be assertive enough to show them that I'm serious about this?

And the advice I'm trying to give is for young people, when you come out to your parents, be very clear straight from the beginning that you have thought about this for a long time already, it's not a sudden decision. Make sure they know that you aren't telling them you want to transition on a whim. Be clear and straightforward right from the start.

Edited for personal information.

hi

Not so sure how much advice I can give you having not been in this situation but Ive read your post and guess would give you a few thoughts ...

you come across very well and clear in your writing and are clearly articulate so it really sucks that if u arent the kind of person with a dominant and forceful personality (a bit like me) that you are being forced to kind of assert yourself to get what you want you do always have the back up of being able to write the way you feel though and maybe if needs be u may have to utilise that and write letters to your parents and/or sister if you feel like you are not getting anywhere in person.

As far as the conversation with your sister its gunna be hard I guess and there will never be a right time but you could have everything you want to say  written down in a letter as back up and if u feel like u are struggling in the conversation then tell her I love you and i'm finding this conversation hard but I really need you to understand so can you please read this for me and even sit there with her while she does.

I think the thing with ure sister is the first hurdle and then you can move toward getting the things you want with your parents.

Dont worry about the timeline thing too much it will stress you out even more. As much as you can do it all by ureself when you are independent im sure you would much rather wait a month or two or whatever and have a better relationship with your parents and family supporting you than have to kind of go it alone.

I hope things will work out for you

J x

Edited for personal info.

I'm not sure you screwed up. You didn't know what you needed to do with your parents at that point. Now you do. It sucks but this is a process and you figure it out as you go.

I'm wondering, could you write your sister a letter? It could even have some bullet points so it's really clear for her to take in. That way she could maybe have time to process and it forces her to pay attention.

I agree with the sentiment that you shouldn't stress the timeline too bad, as long as you keep working at it, you ARE making progress.

I am not entirely certain on how you might properly assert your conversation with your sister.

I wish you luck in all of this!

It's difficult to assert yourself when you've been passive for so long. I should know; due to childhood trauma I used to be ridiculously passive to the extent that I could barely function. But to be honest, from your description I think the therapy session went better than you might think because it has given you the tools you need to formulate a game plan.

Here's what I got out of your post, with my thoughts in italics:

• Your family is willing to call you Dean and use male pronouns at home, but on the condition that you tell your sister. This means that you only have to do one tiny thing and they'll start trying to use the right name & pronouns. Hooray!
• Your parents don't realise that you mind them using the wrong name, because you're not correcting them. So start gently correcting them, every time they get it wrong. But keep it friendly if possible. A simple "actually, it's Dean" is a good way to respond when they use the wrong name. I also practise selective deafness: if anyone uses the wrong name or pronouns for me, I completely ignore them and if they ask why I haven't answered them I say "Oh, were you talking to me? Sorry, I didn't realise - I heard you say 'she' and I thought you must mean somebody else". 
• Your sister is highly stressed and anxious and there never seems to be a good time to talk to her. There never will be a 'right time'; everyone will always find some excuse. But you're just as important as she is, and your needs have to be met too. So either make an appointment with her - say Friday night at 7pm - or write her a letter/text/email. Or can she be invited to your next group therapy session?
• You're worried about how your sister might react to the news. So keep it simple. Just simply state that you love her and need to tell her something important: that you've been struggling with gender issues for X number of years and have made the decision to transition to male.... and that you'd appreciate her continued love and support. Then let the conversation evolve naturally from there.
• Your therapist is right: as uncomfortable as it seems, you need to start making tiny steps towards becoming more assertive. No offense, but that's part of becoming an adult. This is your transition. You have to own it and drive it forwards.
• You are of age and can make your own medical decisions (although I'm not sure about whether you can pay for your own treatment). So take charge. If you are of age, you don't need your parents' consent or permission to start T; you can start it any time you choose. Book your own appointments (apart from group therapy) and then just tell whoever pays for them that you'll be going on that date. The worst that can happen is that you might have to cancel it if they refuse to pay, but then you're no worse off than you currently are. Or can you get an appointment at your nearest Planned Parenthood instead?
• You have the informed consent documents. So what's the next step? Can you sign them and hand them to someone to start treatment? Just asking this question of your therapist would indicate to her that you're serious.

You haven't done anything wrong, and you haven't screwed anything up. You're just going through what we all go through: that difficult cusp between teenagehood and adulthood, when we have to get behind the wheel and start driving our own lives forward. It's not easy, especially if you're trans... but what is necessary is rarely easy.

Your folks are probably like everyone else's folks: they just want what's best for you and they want to make sure you don't make any big mistakes. So show them that you've done your research and are taking charge of your life, and they'll catch up with you. Eventually.

Good luck.

You might want to write to your sister (even in the same household). Also I agree that your parents won't know if you are quiet. Good luck, sounds complicated to me anyway.

--Jay