I recently decided that I'm going to transition so now the question changes from 'do I want to transition?' to 'how do I transition?'. At the moment I'm 21, unemployed, and financially dependent on my parents. While I don't doubt that my parents would accept me I'm still unsure when would be the best time to come out to them. I have a friend who's already a year (maybe more? I haven't asked) into her transition and she said that her only regret about transition was coming out to her family too soon so that makes me worried.

My parents are in town for a couple days (usually they're several hundred miles away) so part of me thinks that this would be a convenient time to come out to them. I'm in some therapy right now though it's a teaching clinic for psychology students at a local college (at $10 an hour the price was right) and I doubt they can write a letter for HRT. So I'll probably need another therapist who's likely far too expensive for me to afford. I also have no idea what costs insurance covers, how to charge things to insurance, etc. So I figure that my parents might be able to help me with those things.

On the other hand I think to myself "you're an adult, you should be able to figure this stuff out on your own." It's probably pride but also a fear of what they'd think of me if I come out but then change my mind. Part of me thinks that I should wait to tell my parents until I've already started transitioning so it's more of a heads up than asking for help/permission.

So I guess I have a few questions:
1) What, in your opinion, is the best time for a young adult to come out their parents? Before transition, after starting transition, after completing transition, etc.?

2) Should I maybe come out in 'stages'? Something like asking to see a therapist first, then mentioning gender issues later, then saying I want to transition?

3) Is it even possible to use their insurance to pay for HRT/therapy without them finding out? Or is there some kind of billing statement that shows what the insurance is being used for? (I have no idea how health insurance works but I don't see how I can afford things otherwise.)

I am 38 not that that should matter, other than I have been supressing my real self for decades. I too went from "I will stick to cross dressing and keep it to myself." to "I only came out to a girl friend or two because I was drunk." to "I finally have an appointment with the transition doctor, but I am going to transition with as little attention possible until just the right time" to "Mom, my entire life I have always wanted to be a girl and I am going to a doctor for 'treatment'"

Talk of sex change followed and I fell back to 'I don't have any foregone conclusions'

but I did it sober and I didn' plan to do it at all until it was pouring out.

i think you will start to embrace yourself without any control over it.

I told my parents before I started to physical transition but I was already well into therapy and knew I was trans. I decided the best way to help them deal with it was to make it seem as gentle a progress as possible. Rather then bursting in with hormones and operations all at once and frightening them half to death. So I told them I was unhappy with my gender and I told them I was seeing a therapist. They would ask about how it was going and what would happen next. Then I could ease them into hormone treatments and such. I found this approach (at least for me) also worked as because they were involved I could bring them to my sessions. Then my therapist could help explain things to them. I also felt them seeing a qualified professional, at a hospital, in a wing full of people dedicated to trans people helped them realise it was not just a fad. Or something people decided on a whim, this was a place full of medical people who treat it as seriously as any other medical condition.

I hope that helps you with the first two questions but as for the insurance....im afraid im as clueless as you. Im in my twentys too