hmm... for me it was hard, but a lot less hard because I knew, while there wasn't a guarantee of help, there was also no threat of disownment or discontinuance of support for school. My parents have always been very accepting kinds of people concerned mostly with me being a good, responsible, and intelligent person and to hell with the rest.
That being said the time I knew it was right to tell them was when I realized I needed their help to get where I wanted to be. Luckily, it worked and now here I am 5 years later on hormones and post-top op. Otherwise I didn't see it as much of any of their business, but thats just how I am. I also had a pretty good idea that they'd help me out. I guess I'd have come out eventually even if they were of a more ignorant ilk, but I can't say when really. I also tend to draw a stricter line than a lot of people about what is my business and what my family knows about me. I love them dearly, but not in my business. When I thought I was a lesbian I had no intention whatever of coming out to them (officially) even though I brought my gf over for holidays for years and we slept in the same bed (and they knew). It wasn't any source of shame.. it just merely wasn't any of their business. Its obviously different being gay than being called different pronouns and being treated as female in society... I guess I'm loosing myself on my point here... which is really if they don't like it that its your life in the end and not really any of their business.
I'm not at all trying to tell you to not come out. You may find unexpected support. A lot of times people will seem stubborn on a subject until they realize that their love breaks down those past ill conceptions. I know I have a lesbian friend whose mom would talk ->-bleeped-<- on gays and lesbians often. When she came out her mom almost immediately changed her tune, and allowed her long-distance gf come to stay with them for two weeks. I think her mom was just overjoyed to see my friend actually happy and in a relationship. That broke down her past feelings.
It may not come as readily as that for you. You may have to prove to your family that living your life in this way is the best thing for you (but do it for yourself, not for them). If they can't open their minds right off the bat then hopefully they'll see you become the man you are and become more comfortable with yourself as time goes by, and they'll come around to the idea.
As for when is the time right? Geez... when is it ever "right" I wrote a note for my mom... I had been on a month long trip and she picked me up at the airport at like 6AM.. we got home and I handed her the note before going up to get a shower. When I came down we talked it out. My dad was totally cool with it too, but I felt best just telling my mom first. She's the family coordinator. =p
I think notes are good because it allows a person to digest the information before coming out with a gut reaction. When someone gives you that kind of info and you're not expecting it who knows how one may react, but give the person an hour or two to calm down before you face them and you may find yourself with a much more cool-headed conversation. It also allows you to lay out your words carefully without being thrown off by interruptions or arguments. I'd say maybe towards the end of your 15 day break I'd hand them a note before heading out for the day or going to the store or something. It can be as short or as long as you like it. Maybe include some websites or something they could check out in your absence, and don't forget to tell them how much you love and appreciate them in your life.
