Here's what I can offer from coming out to my family as trans/crossdressing:

First of all, I had a feeling that my family would be pretty supportive. They are all pretty socially liberal and generally cool with LGBTQ things, but you never know when it's you and not just a group as a whole. So...while I did come out to them, I didn't come out to them until I was partway through college, had come out to my partner (who is still my partner now!), and had really reached a place where I was comfortable with myself.

For me I came out via email. I know it's a little impersonal, but I wrote a really thought out, long, and detailed email about sharing that particular part of me to them. I felt like it would give them the most space to respond as they needed/wanted. Their response was pretty much "we love you no matter what, but let's talk about this more."

So we took the conversation from there, talked on the phone, talked a bit in person the next time I had time to spend with them and it all went really well.

Which, unfortunately may not work for everyone...

But, I would say that giving them the space to process things, and then formulate a good set of questions, at least for my parents, helped out a lot. Just springing it on them in a conversation might have made it more uncomfortable for all involved. But no matter what I would say, know yourself, be confident that you are happy, healthy, and stable with who you are and want to be, and present it to your parents/family as your true self. If they truly love you they will understand. And make sure to have a good support network if things are a little rough. Most family can come around given time, but no matter what your family is like coming out can be a difficult process.

Hope for your sake it's not, my family was/is awesome.

I did it in a letter, because I feel that it gives them the time to process and react and absorb things without having to react right then and there on the spot.

Also, because I didn't care what my family thought, but we barely have a relationship in the first place.

ETA: The first question, I think, is do you live with your parents/family that you want to come out to, and the next would be, can you see a therapist and talk to someone about it?

I wrote my parents a very long letter. I wanted to have time to explain everything to them so that they would better be able to understand. I also wanted to give them time to process the information. Sometimes, I get to emotional to say everything I want to say. This way, I was able to.

the letter is a good option for some guys. i really just told my mom one day. she had browsed my search history and started asking. the rest of my family, i came out to all at once through myspace. but that's because i wasn't really seeing them or part of their lives. it's been 6 years since i came out to everybody. since then, most of them have shut me out of their lives.

the thing with parents is that they feel like they failed when their child comes out and says "i don't feel like i'm really a girl." they take it personally and assume you're rebelling. go into it with your facts right. explain that you've been reading about this medical condition, that you feel like it applies to you because you share the same feelings as others with it do, and then to the best of your ability say something like "this is nobody's fault. i'm not choosing this. if i had an option, i wouldn't feel this way. but i feel like a guy, and i have for (insert length of time). i'm miserable in my own body. i suffer from severe emotional pain called dysphoria because i look down and the skin i'm in doesn't match the way i feel inside. i love you, i'm the same person. and i hope you'll accept this so we can work through it together." at least, that's how i would do it if i had the chance to come out again. if you choose to put it in a letter (or maybe even a video?), be sure you're ready to have a real life conversation with them after. good luck, bro

I'm just kind of skipping along, ignoring the fact that I have to actually come out one day

I didn't come out to my family on purpose as an adult (I tried as a kid and got no results. Just mostly ignored and called a "tomboy").

This time around, my family saw what was going on- me dressing masculine, shaving my head, having friends call me Max, and they asked about it. Well now they know, and it's not going great but it's going alright. They didn't disown me or anything.

As for me, I don't have much in the way of tips other than that showing you're serious and letting them know you care what they think but this is your only life and you cannot live it being someone else.

I used to have a lot of issues when I was younger and my family sees I am driven and strive not just to stay alive but improve my life and sees I have come a long way since when I was younger, so I think that helped.

One thing i advise, is go slowly. If you're anything like i was? I'd been running things over in my mind for months and months, and felt how i had for years. My feelings were old and i knew them back to front. When i told my parents, it all came out 100MPH, and they were as confused as anything.

This information you're going to be giving them is new, very new. To you it may seem like the most obvious thing, but they really have no idea.

Take it slow and tell the truth

One of the best pieces of advice I've ever received was to never accuse anyone. It's better to say "I feel like you mean this when you say that" but never to say "You mean that!"